Acetaminophen

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Identification

Summary

Acetaminophen is an analgesic drug used alone or in combination with opioids for pain management, and as an antipyretic agent.

Brand Names

Acephen, Acetadryl, Allzital, Apadaz, Arthriten Inflammatory Pain, Bupap, Butapap, Cetafen, Children's Silapap, Combogesic, Coricidin Hbp Cold & Flu, Darvocet-N, Dayquil Sinex, Diphen, Dolofin, Dologen, Dologesic Reformulated Jun 2016, Duralgina, Dvorah, Endocet, Esgic, Exaprin, Excedrin, Excedrin PM Triple Action, Excedrin Tension Headache, Feverall, Fioricet, Fioricet With Codeine, Goody's Back & Body Pain Relief, Goody's Body Pain, Goody's Extra Strength, Goody's Headache Relief Shot, Goody's PM, Hycet, Legatrin PM, Little Fevers, Lorcet, Lortab, Mapap, Mersyndol, Midol Complete, Midol Cramps & Bodyaches, Nalocet, Norco, Orbivan, Pamprin Max Formula, Pamprin Multi-symptom, Panadol, Pediacare Children's Fever Reducer Pain Reliever, Percocet, Percogesic Reformulated Jan 2011, Pharbetol, Premsyn Pms, Prolate, Rivacocet, Robaxacet, Robaxacet-8, Roxicet, Sudafed PE Sinus Headache, Tactinal, Tencon, Trezix, Triatec, Triatec-30, Triatec-8, Tylenol, Tylenol PM, Tylenol With Codeine, Ultracet, Vanatol, Vanatol S, Vanquish, Xodol, Xolox, Zamicet, Zflex, Zydone

Generic Name

Acetaminophen

DrugBank Accession Number

DB00316

Background

Acetaminophen (paracetamol), also commonly known as Tylenol, is the most commonly taken analgesic worldwide and is recommended as first-line therapy in pain conditions by the World Health Organization (WHO).¹⁰ It is also used for its antipyretic effects, helping to reduce fever.²³ This drug was initially approved by the U.S. FDA in 1951 and is available in a variety of forms including syrup form, regular tablets, effervescent tablets, injection, suppository, and other forms.^{15,16,23,Label}

Acetaminophen is often found combined with other drugs in more than 600 over the counter (OTC) allergy medications, cold medications, sleep medications, pain relievers, and other products.¹⁹ Confusion about dosing of this drug may be caused by the availability of different formulas, strengths, and dosage instructions for children of different ages.¹⁹ Due to the possibility of fatal overdose and liver failure associated with the incorrect use of acetaminophen, it is important to follow current and available national and manufacturer dosing guidelines while this drug is taken or prescribed.^20,21,Label

Type

Small Molecule

Groups

Approved

Structure

Similar Structures

Weight: Average: 151.1626
Monoisotopic: 151.063328537
Chemical Formula: C₈H₉NO₂

Synonyms

4-(Acetylamino)phenol
4-acetamidophenol
4'-hydroxyacetanilide
Acenol
Acetaminofén
Acetaminophen
Acétaminophène
APAP
N-acetyl-p-aminophenol
p-acetamidophenol
p-acetaminophenol
p-Acetylaminophenol
p-hydroxy-acetanilid
p-hydroxyacetanilide
p-hydroxyphenolacetamide
Paracetamol
Paracétamol
Paracetamolum

External IDs

NSC-109028
NSC-3991

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Pharmacology

Indication

In general, acetaminophen is used for the treatment of mild to moderate pain and reduction of fever.²³ It is available over the counter in various forms, the most common being oral forms.

Acetaminophen injection is indicated for the management of mild to moderate pain, the management of moderate to severe pain with adjunctive opioid analgesics, and the reduction of fever.^Label

Because of its low risk of causing allergic reactions, this drug can be administered in patients who are intolerant to salicylates and those with allergic tendencies, including bronchial asthmatics.²³ Specific dosing guidelines should be followed when administering acetaminophen to children.¹⁸

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Dose Form
Used in combination for symptomatic treatment of	Acute gouty arthritis	Combination Product in combination with: Etodolac (DB00749)	••••••••••••	••••••• ••••••
Used as adjunct in combination to treat	Acute gouty arthritis	Combination Product in combination with: Lornoxicam (DB06725)	••••••••••••	••••••• ••••••••••••
Used in combination for symptomatic treatment of	Acute musculoskeletal pain	Combination Product in combination with: Etodolac (DB00749)	••••••••••••	••••••• ••••••
Used in combination for symptomatic treatment of	Allergies	Combination Product in combination with: Dextromethorphan (DB00514), Guaifenesin (DB00874), Chlorpheniramine (DB01114), Pseudoephedrine (DB00852)	••• •••	•••••••
Used in combination for symptomatic treatment of	Allergies	Combination Product in combination with: Brompheniramine (DB00835), Dextromethorphan (DB00514)	••••••••••••

Associated Therapies

Contraindications & Blackbox Warnings

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Pharmacodynamics

Animal and clinical studies have determined that acetaminophen has both antipyretic and analgesic effects. This drug has been shown to lack anti-inflammatory effects. As opposed to the salicylate drug class, acetaminophen does not disrupt tubular secretion of uric acid and does not affect acid-base balance if taken at the recommended doses.²³ Acetaminophen does not disrupt hemostasis and does not have inhibitory activities against platelet aggregation.^Label,23 Allergic reactions are rare occurrences following acetaminophen use.²³

Mechanism of action

According to its FDA labeling, acetaminophen's exact mechanism of action has not been fully established^Label - despite this, it is often categorized alongside NSAIDs (nonsteroidal anti-inflammatory drugs) due to its ability to inhibit the cyclooxygenase (COX) pathways.¹⁴ It is thought to exert central actions which ultimately lead to the alleviation of pain symptoms.¹⁴

One theory is that acetaminophen increases the pain threshold by inhibiting two isoforms of cyclooxygenase, COX-1 and COX-2, which are involved in prostaglandin (PG) synthesis. Prostaglandins are responsible for eliciting pain sensations.¹³ Acetaminophen does not inhibit cyclooxygenase in peripheral tissues and, therefore, has no peripheral anti-inflammatory effects. Though acetylsalicylic acid (aspirin) is an irreversible inhibitor of COX and directly blocks the active site of this enzyme, studies have shown that acetaminophen (paracetamol) blocks COX indirectly.²⁴ Studies also suggest that acetaminophen selectively blocks a variant type of the COX enzyme that is unique from the known variants COX-1 and COX-2.⁶ This enzyme has been referred to as COX-3. The antipyretic actions of acetaminophen are likely attributed to direct action on heat-regulating centers in the brain, resulting in peripheral vasodilation, sweating, and loss of body heat.²⁴ The exact mechanism of action of this drug is not fully understood at this time, but future research may contribute to deeper knowledge.²⁴

Target	Actions	Organism
AProstaglandin G/H synthase 2	inhibitor	Humans
ASodium-dependent serotonin transporter	inhibitor	Humans
ASodium-dependent noradrenaline transporter	inhibitor	Humans
AProstaglandin G/H synthase 1	inhibitor	Humans
UProstaglandin E synthase 3	inhibitor	Humans
UTransient receptor potential cation channel subfamily V member 1	activator	Humans

Absorption

Acetaminophen has 88% oral bioavailability and reaches its highest plasma concentration 90 minutes after ingestion.⁹ Peak blood levels of free acetaminophen are not reached until 3 hours after rectal administration of the suppository form of acetaminophen and the peak blood concentration is approximately 50% of the observed concentration after the ingestion of an equivalent oral dose (10-20 mcg/mL).²³

The percentage of a systemically absorbed rectal dose of acetaminophen is inconsistent, demonstrated by major differences in the bioavailability of acetaminophen after a dose administered rectally. Higher rectal doses or an increased frequency of administration may be used to attain blood concentrations of acetaminophen similar to those attained after oral acetaminophen administration.^Label

Volume of distribution

Volume of distribution is about 0.9L/kg. 10 to 20% of the drug is bound to red blood cells.¹¹ Acetaminophen appears to be widely distributed throughout most body tissues except in fat.^Label

Protein binding

The binding of acetaminophen to plasma proteins is low (ranging from 10% to 25%), when given at therapeutic doses.^Label

Metabolism

Acetaminophen is the major metabolite of phenacetin and acetanilid.²³ Acetaminophen is mainly metabolized in the liver by first-order kinetics and its metabolism of comprised of 3 pathways: conjugation with glucuronide, conjugation with sulfate, and oxidation through the cytochrome P450 enzyme pathway, mainly CYP2E1, to produce a reactive metabolite (N-acetyl-p-benzoquinone imine or NAPQI). At normal therapeutic doses, NAPQI undergoes fast conjugation with glutathione and is subsequently metabolized to produce both cysteine and mercapturic acid conjugates.^Label

High doses of acetaminophen (overdoses) can lead to hepatic necrosis due to the depletion of glutathione and of binding of high levels of reactive metabolite (NAPQI) to important parts of liver cells. The abovementioned damage to the liver can be prevented by the early administration of sulfhydryl compounds, for example, methionine and N-acetylcysteine.¹²

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Acetaminophen

Route of elimination

Acetaminophen metabolites are mainly excreted in the urine. Less than 5% is excreted in the urine as free (unconjugated) acetaminophen and at least 90% of the administered dose is excreted within 24 hours.²³

Half-life

The half-life for adults is 2.5 h after an intravenous dose of 15 mg/kg.^Label After an overdose, the half-life can range from 4 to 8 hours depending on the severity of injury to the liver, as it heavily metabolizes acetaminophen.⁹

Clearance

Adults: 0.27 L/h/kg following a 15 mg/kg intravenous (IV) dose.^Label Children: 0.34 L/h/kg following a 15 mg/kg intravenous (IV dose).^Label

Adverse Effects

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Toxicity

LD50 = 338 mg/kg (oral, mouse); LD50 = 1944 mg/kg (oral, rat)²⁴

Overdose and liver toxicity

Acetaminophen overdose may be manifested by renal tubular necrosis, hypoglycemic coma, and thrombocytopenia. Sometimes, liver necrosis can occur as well as liver failure. Death and the requirement of a liver transplant may also occur.^Label Metabolism by the CYP2E1 pathway releases a toxic acetaminophen metabolite known as N-acetyl-p-benzoquinoneimine(NAPQI). The toxic effects caused by this drug are attributed to NAPQI, not acetaminophen alone.²⁴

Carcinogenesis

Long-term studies in mice and rats have been completed by the National Toxicology Program to study the carcinogenic risk of acetaminophen. In 2-year feeding studies, F344/N rats and B6C3F1 mice consumed a diet containing acetaminophen up to 6,000 ppm. Female rats showed evidence of carcinogenic activity demonstrated by a higher incidence of mononuclear cell leukemia at doses 0.8 times the maximum human daily dose (MHDD). No evidence of carcinogenesis in male rats (0.7 times) or mice (1.2 to 1.4 times the MHDD) was noted.^Label The clinical relevance of this finding in humans is unknown.

Mutagenesis

Acetaminophen was not found to be mutagenic in the bacterial reverse mutation assay (Ames test). Despite this finding, acetaminophen tested positive in the in vitro mouse lymphoma assay as well as the in vitro chromosomal aberration assay using human lymphocytes. In published studies, acetaminophen has been reported to be clastogenic (disrupting chromosomes) when given a high dose of 1,500 mg/kg/day to the rat model (3.6 times the MHDD). No clastogenicity was observed at a dose of 750 mg/kg/day (1.8 times the MHDD), indicating that this drug has a threshold before it may cause mutagenesis.^Label The clinical relevance of this finding in humans is unknown.

Impairment of Fertility

In studies conducted by the National Toxicology Program, fertility assessments have been performed in Swiss mice in a continuous breeding study. No effects on fertility were seen.^Label

Use in pregnancy and nursing

The FDA label for acetaminophen considers it a pregnancy category C drug, meaning this drug has demonstrated adverse effects in animal studies. No human clinical studies in pregnancy have been done to this date for intravenous acetaminophen.^Label Use acetaminophen only when necessary during pregnancy.^Label Epidemiological data on oral acetaminophen use in pregnant women demonstrate no increase in the risk of major congenital malformations.^Label While prospective clinical studies examining the results of nursing with acetaminophen use have not been conducted, acetaminophen is found secreted in human milk at low concentrations after oral administration. Data from more than 15 nursing mothers taking acetaminophen was obtained, and the calculated daily dose of acetaminophen that reaches the infant is about 1 to 2% of the maternal dose. Caution should be observed when acetaminophen is taken by a nursing woman.^Label

Pathways

Pathway	Category
Acetaminophen Metabolism Pathway	Drug metabolism
Acetaminophen Action Pathway	Drug action

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Drug	Interaction
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Abacavir	Acetaminophen may decrease the excretion rate of Abacavir which could result in a higher serum level.
Abametapir	The serum concentration of Acetaminophen can be increased when it is combined with Abametapir.
Abatacept	The metabolism of Acetaminophen can be increased when combined with Abatacept.
Abemaciclib	The metabolism of Abemaciclib can be increased when combined with Acetaminophen.
Abiraterone	The serum concentration of Acetaminophen can be increased when it is combined with Abiraterone.

Food Interactions

Avoid alcohol. Alcohol may increase the risk of hepatotoxicity.
Take with or without food. The absorption is unaffected by food.

Products

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Product Images

International/Other Brands

Acamol (Teva) / Aceta Elixir / Aceta Tablets / Acetalgin / Actamin / Actimol / Algotropyl / Alvedon / Aminofen / Anacin-3 / Anhiba / Apacet / Banesin / Calpol / Conacetol / Dafalgan / Dapa X-S / Disprol / Dolprone / Dymadon / Dypap / Enelfa / Febridol / Febrilix / Finimal / Gelocatil / Genapap / Genebs / Injectapap / Liquiprin / Napafen / Oraphen-PD / Paldesic / Panofen / Paraspen / Parmol / Redutemp / Rounox / Salzone / Snaplets-FR / St. Joseph Fever Reducer / Suppap / Tapanol / Valorin

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
7T Gummy ES	Tablet, chewable	500 mg/1	Oral	7T Pharma LLC	2019-09-01	Not applicable
Acetaminophen	Injection	1000 mg/100mL	Intravenous	Hikma Pharmaceuticals USA Inc.	2022-06-03	Not applicable
Acetaminophen	Injection	10 mg/1mL	Intravenous	Fresenius Kabi Italia S.R.L.	2020-12-06	Not applicable
Acetaminophen	Injection	10 mg/1mL	Intravenous	B. Braun Medical Inc.	2021-02-18	Not applicable
Acetaminophen	Injection	10 mg/1mL	Intravenous	B. Braun Medical Inc.	2021-02-18	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Acephen	Suppository	325 mg/1	Rectal	Remedy Repack	2015-01-16	2016-01-16
Acetaminophen	Injection, solution	10 mg/1mL	Intravenous	Hikma Pharmaceuticals USA Inc.	2023-03-01	Not applicable
Acetaminophen	Injection, solution	10 mg/1mL	Intravenous	Camber Pharmaceuticals, Inc.	2022-07-27	Not applicable
Acetaminophen	Injection, solution	10 mg/1mL	Intravenous	Baxter Healthcare Corporation	2021-09-17	Not applicable
Acetaminophen	Injection, solution	10 mg/1mL	Intravenous	Hikma Pharmaceuticals USA Inc.	2020-12-07	Not applicable

Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
222 AF Extra Strength Caplet (500mg)	Tablet	500 mg	Oral	Merck Frosst Canada & Cie, Merck Frosst Canada & Co.	1992-12-31	1997-08-14
222 AF Regular Strength Caplet (325mg)	Tablet	325 mg	Oral	Merck Frosst Canada & Cie, Merck Frosst Canada & Co.	1992-12-31	1997-08-14
222af Extra Strength 500mg	Tablet	500 mg	Oral	Merck Frosst Canada & Cie, Merck Frosst Canada & Co.	1978-12-31	1997-08-14
222af Regular Strength 325mg	Tablet	325 mg	Oral	Merck Frosst Canada & Cie, Merck Frosst Canada & Co.	1977-12-31	1997-08-14
24 / 7 Life Extra Strength Pain Reliever	Tablet	500 mg/1	Oral	Lil' Drug Store Products, Inc.	2021-01-05	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
(extra Strength) Acetaminophen, Caffeine & 8mg Codeine Phosphate Caplets	Acetaminophen (500 mg) + Caffeine (15 mg) + Codeine phosphate (8 mg)	Tablet	Oral	Stanley Pharmaceuticals, A Division Of Vita Health Products Inc.	1998-07-22	2002-07-31
10 Person ANSI	Acetaminophen (325 mg/1) + Acetylsalicylic acid (325 mg/1) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (0.13 g/100g) + Benzalkonium chloride (0.40 mL/100mL) + Benzocaine (6 mL/100mL) + Ethanol (60 mL/100mL) + Ibuprofen (200 mg/1) + Lidocaine (0.5 1/100g) + Neomycin sulfate (5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Water (98.6 mL/100mL)	Kit	Ophthalmic; Oral; Topical	Genuine First Aid	2010-04-24	Not applicable
24 / 7 Life Extra Strength Pain Reliever PM	Acetaminophen (500 mg/1) + Diphenhydramine hydrochloride (25 mg/1)	Tablet, film coated	Oral	Lil' Drug Store Products, Inc.	2020-12-17	Not applicable
24/7 Life Cold and Flu DayTime Severe	Acetaminophen (325 mg/1) + Dextromethorphan hydrobromide monohydrate (10 mg/1) + Guaifenesin (200 mg/1) + Phenylephrine hydrochloride (5 mg/1)	Tablet, film coated	Oral	Lil' Drug Store Products, Inc.	2021-10-27	Not applicable
25 Person ANSI	Acetaminophen (325 mg/1) + Acetylsalicylic acid (325 mg/1) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (0.13 g/100g) + Benzalkonium chloride (0.40 mL/100mL) + Benzocaine (6 mL/100mL) + Ethanol (60 mL/100mL) + Ethanol (62 g/100g) + Ibuprofen (200 mg/1) + Isopropyl alcohol (70 mL/100mL) + Lidocaine (0.5 g/100g) + Neomycin sulfate (5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Water (98.6 mL/100mL)	Kit	Ophthalmic; Oral; Topical	Genuine First Aid	2010-04-25	Not applicable

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
4017 First Aid Kit	Acetaminophen (325 mg/1) + Benzalkonium chloride (0.13 g/100g) + Benzalkonium chloride (1.3 mg/1mL) + Ethanol (0.5 mL/1mL) + Lidocaine hydrochloride (20 mg/1mL) + Lidocaine hydrochloride (0.5 g/100g) + Neomycin sulfate (3.5 mg/1g) + Water (98.6 mL/100mL)	Cream; Kit; Liquid; Ointment; Swab; Tablet	Ophthalmic; Oral; Topical	Honeywell Safety Products USA, Inc	2018-10-18	Not applicable
4022 First Aid Kit	Acetaminophen (325 mg/1) + Benzalkonium chloride (0.13 g/100g) + Benzalkonium chloride (1.3 mg/1mL) + Ethanol (0.5 mL/1mL) + Lidocaine hydrochloride (20 mg/1mL) + Lidocaine hydrochloride (0.5 g/100g) + Neomycin sulfate (3.5 mg/1g) + Water (98.6 mL/100mL)	Cream; Kit; Liquid; Ointment; Swab; Tablet	Ophthalmic; Oral; Topical	Honeywell Safety Products USA, Inc	2018-10-18	Not applicable
4056 First Aid Kit	Acetaminophen (325 mg/1) + Benzalkonium chloride (0.13 g/100g) + Benzalkonium chloride (1.3 mg/1mL) + Ethanol (0.5 mL/1mL) + Lidocaine hydrochloride (20 mg/1mL) + Lidocaine hydrochloride (0.5 g/100g) + Neomycin sulfate (3.5 mg/1g) + Water (98.6 mL/100mL)	Kit	Ophthalmic; Oral; Topical	Honeywell Safety Products USA, Inc	2018-10-18	2019-10-18
4068 First Aid Kit	Acetaminophen (325 mg/1) + Benzalkonium chloride (0.13 g/100g) + Benzalkonium chloride (1.3 mg/1mL) + Ethanol (0.5 mL/1mL) + Lidocaine hydrochloride (20 mg/1mL) + Lidocaine hydrochloride (0.5 g/100g) + Neomycin sulfate (3.5 mg/1g) + Water (98.6 mL/100mL)	Kit	Ophthalmic; Oral; Topical	Honeywell Safety Products USA, Inc	2018-10-18	Not applicable
4069 First Aid Kit	Acetaminophen (325 mg/1) + Benzalkonium chloride (0.13 g/100g) + Benzalkonium chloride (1.3 mg/1mL) + Ethanol (0.5 mL/1mL) + Lidocaine hydrochloride (20 mg/1mL) + Lidocaine hydrochloride (0.5 g/100g) + Neomycin sulfate (3.5 mg/1g) + Water (98.6 mL/100mL)	Kit	Topical	Honeywell Safety Products USA, Inc	2018-10-18	2019-03-10

Chemical Identifiers

UNII: 362O9ITL9D
CAS number: 103-90-2
InChI Key: RZVAJINKPMORJF-UHFFFAOYSA-N
InChI: InChI=1S/C8H9NO2/c1-6(10)9-7-2-4-8(11)5-3-7/h2-5,11H,1H3,(H,9,10)
IUPAC Name: N-(4-hydroxyphenyl)acetamide
SMILES: CC(=O)NC1=CC=C(O)C=C1

References

Synthesis Reference

Jeffrey L. Finnan, Rudolph E. Lisa, Douglass N. Schmidt, "Process for preparing spray dried acetaminophen powder and the powder prepared thereby." U.S. Patent US4710519, issued October, 1975.

US4710519

General References

Kis B, Snipes JA, Busija DW: Acetaminophen and the cyclooxygenase-3 puzzle: sorting out facts, fictions, and uncertainties. J Pharmacol Exp Ther. 2005 Oct;315(1):1-7. Epub 2005 May 6. [Article]
Aronoff DM, Oates JA, Boutaud O: New insights into the mechanism of action of acetaminophen: Its clinical pharmacologic characteristics reflect its inhibition of the two prostaglandin H2 synthases. Clin Pharmacol Ther. 2006 Jan;79(1):9-19. [Article]
Bertolini A, Ferrari A, Ottani A, Guerzoni S, Tacchi R, Leone S: Paracetamol: new vistas of an old drug. CNS Drug Rev. 2006 Fall-Winter;12(3-4):250-75. [Article]
Graham GG, Scott KF: Mechanism of action of paracetamol. Am J Ther. 2005 Jan-Feb;12(1):46-55. [Article]
Ohki S, Ogino N, Yamamoto S, Hayaishi O: Prostaglandin hydroperoxidase, an integral part of prostaglandin endoperoxide synthetase from bovine vesicular gland microsomes. J Biol Chem. 1979 Feb 10;254(3):829-36. [Article]
Chandrasekharan NV, Dai H, Roos KL, Evanson NK, Tomsik J, Elton TS, Simmons DL: COX-3, a cyclooxygenase-1 variant inhibited by acetaminophen and other analgesic/antipyretic drugs: cloning, structure, and expression. Proc Natl Acad Sci U S A. 2002 Oct 15;99(21):13926-31. Epub 2002 Sep 19. [Article]
Adjei AA, Gaedigk A, Simon SD, Weinshilboum RM, Leeder JS: Interindividual variability in acetaminophen sulfation by human fetal liver: implications for pharmacogenetic investigations of drug-induced birth defects. Birth Defects Res A Clin Mol Teratol. 2008 Mar;82(3):155-65. doi: 10.1002/bdra.20535. [Article]
Hazai E, Vereczkey L, Monostory K: Reduction of toxic metabolite formation of acetaminophen. Biochem Biophys Res Commun. 2002 Mar 8;291(4):1089-94. [Article]
Mazaleuskaya LL, Sangkuhl K, Thorn CF, FitzGerald GA, Altman RB, Klein TE: PharmGKB summary: pathways of acetaminophen metabolism at the therapeutic versus toxic doses. Pharmacogenet Genomics. 2015 Aug;25(8):416-26. doi: 10.1097/FPC.0000000000000150. [Article]
Ennis ZN, Dideriksen D, Vaegter HB, Handberg G, Pottegard A: Acetaminophen for Chronic Pain: A Systematic Review on Efficacy. Basic Clin Pharmacol Toxicol. 2016 Mar;118(3):184-9. doi: 10.1111/bcpt.12527. Epub 2015 Dec 28. [Article]
Bannwarth B, Pehourcq F: [Pharmacologic basis for using paracetamol: pharmacokinetic and pharmacodynamic issues]. Drugs. 2003;63 Spec No 2:5-13. [Article]
Forrest JA, Clements JA, Prescott LF: Clinical pharmacokinetics of paracetamol. Clin Pharmacokinet. 1982 Mar-Apr;7(2):93-107. [Article]
Ricciotti E, FitzGerald GA: Prostaglandins and inflammation. Arterioscler Thromb Vasc Biol. 2011 May;31(5):986-1000. doi: 10.1161/ATVBAHA.110.207449. [Article]
Valerie Gerriets; Thomas M. Nappe (2019). Acetaminophen. StatPearls publishing.
Acetaminophen tablet, DailyMed [Link]
Acetaminophen effervescent tablets, Cleveland Clinic [Link]
FDA safety communication: FDA has reviewed possible risks of pain medicine use during pregnancy [Link]
U.S. National Medical Library: MedlinePlus- Acetaminophen dosing for children [Link]
FDA consumer health information: Acetaminophen [Link]
FDA : Acetaminophen Information [Link]
Using Acetaminophen and Nonsteroidal Anti-inflammatory Drugs Safely [Link]
FDA Approved Drug Products: Acetaminophen solution for intravenous injection [Link]
Acetaminophen monograph, suppository [File]
Acetaminophen data sheet, ebi.ac.uk [File]
Tylenol arthritis pain label, OTC [File]

External Links

Human Metabolome Database: HMDB0001859
KEGG Drug: D00217
KEGG Compound: C06804
PubChem Compound: 1983
PubChem Substance: 46506142
ChemSpider: 1906
BindingDB: 26197
RxNav: 161
ChEBI: 46195
ChEMBL: CHEMBL112
ZINC: ZINC000013550868
Therapeutic Targets Database: DAP001436
PharmGKB: PA448015
PDBe Ligand: TYL
RxList: RxList Drug Page
Drugs.com: Drugs.com Drug Page
Wikipedia: Paracetamol

PDB Entries

1tyl / 1tym / 2dpz / 2ocu / 3py4 / 4a9j / 4a9k / 4cut / 4yji / 5pbe

FDA label

Download (392 KB)

MSDS

Download (71.9 KB)

Clinical Trials

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Phase	Status	Purpose	Conditions	Count	Start Date	Why Stopped	100+ additional columns
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Not Available	Active Not Recruiting	Not Available	Acute Respiratory Viral Infections	1	somestatus	stop reason	just information to hide
Not Available	Active Not Recruiting	Not Available	Transgendered Persons	1	somestatus	stop reason	just information to hide
Not Available	Active Not Recruiting	Prevention	Opioid Misuse / Opioids Use / Pain / Postoperative pain	1	somestatus	stop reason	just information to hide
Not Available	Active Not Recruiting	Treatment	Patent Ductus Arteriosus in Preterm Infants	1	somestatus	stop reason	just information to hide
Not Available	Completed	Not Available	AAT Deficiency / AATD / Alpha-1 Anti-trypsin Deficiency / Liver Fibrosis	1	somestatus	stop reason	just information to hide

Pharmacoeconomics

Manufacturers

Ortho mcneil pharmaceutical inc
G and w laboratories inc
Able laboratories inc
Actavis mid atlantic llc
Perrigo new york inc
Roxane laboratories inc
Polymedica industries inc
Mcneil consumer healthcare
Ohm laboratories inc
L perrigo co
Ranbaxy inc

Packagers

Actavis Group
Advent Pharmaceuticals Inc.
Amneal Pharmaceuticals
Aristos Pharmaceuticals
A-S Medication Solutions LLC
Bergen Brunswig
Chain Drug
Concord Labs
CVS Pharmacy
DRX Pharmaceuticals
Equaline Vitamins
G & W Labs
International Ethical Labs Inc.
Ivax Pharmaceuticals
Kroger Co.
Letco Medical Inc.
Longs Drug Store
Major Pharmaceuticals
Mallinckrodt Inc.
Maneesh Pharmaceuticals Ltd.
McNeil Laboratories
Medique Products
Medtech Labs
Nexgen Pharma Inc.
Novartis AG
Nucare Pharmaceuticals Inc.
PCA LLC
Perrigo Co.
Pharmpak Inc.
Physicians Total Care Inc.
Prepackage Specialists
Prescript Pharmaceuticals
Qualitest
Quality Care
Rite Aid Corp.
S&P Healthcare
Schwarz Pharma Inc.
Teva Pharmaceutical Industries Ltd.
Valeant Ltd.
Walgreen Co.
Watson Pharmaceuticals
Xanodyne Pharmaceuticals Inc.

Dosage Forms

Form	Route	Strength
Cream; kit; liquid; ointment; swab; tablet	Ophthalmic; Oral; Topical
Kit	Ophthalmic; Oral; Respiratory (inhalation); Topical
Kit; liquid; ointment; spray; swab; tablet	Ophthalmic; Oral; Topical
Kit; liquid; lozenge; ointment; spray; swab; tablet	Ophthalmic; Oral; Topical
Kit	Oral; Respiratory (inhalation); Topical
Kit; liquid; ointment; tablet	Ophthalmic; Oral; Topical
Inhalant; kit; liquid; ointment; spray; swab; tablet	Ophthalmic; Oral; Respiratory (inhalation); Topical
Kit; liquid; ointment; swab; tablet	Ophthalmic; Oral; Topical
Kit; liquid; ointment; swab; tablet	Oral; Topical
Kit; liquid; ointment; spray; tablet	Ophthalmic; Oral; Topical
Gel; kit; liquid; ointment; swab; tablet	Oral; Topical
Cream; kit; liquid; ointment; swab; tablet	Oral; Topical
Cream; kit; liquid; swab; tablet	Oral; Topical
Kit	Ophthalmic; Oral; Topical
Tablet, chewable	Oral	500 mg/1
Capsule, coated	Oral	500 mg/1U
Suppository	Rectal	325 mg/1
Suppository	Rectal	160 mg
Suppository	Rectal	650 mg
Tablet, effervescent	Oral	500 mg/1
Tablet, chewable	Oral	100 mg
Solution	Oral	3000 mg
Solution	Oral	200 mg
Syrup	Oral	320000 g
Tablet	Oral	50000000 mg
Solution	Oral	0.1 g
Solution	Oral	10 mg
Solution	Oral	10 g
Solution	Oral	320000 g
Syrup	Oral	3.02 g
Syrup	Oral	3.33 g
Syrup	Oral	300000 g
Syrup	Oral	3.2 g
Capsule, liquid filled	Oral	50000000 mg
Tablet	Oral	500 mg
Tablet	Oral	555.56 mg
Tablet, film coated	Oral	50000000 mg
Solution	Buccal; Oral	10 g
Bar, chewable	Oral	160 mg/1
Injection	Intravenous	10 mg/1mL
Injection	Intravenous	1000 mg/100mL
Injection, solution	Intravenous	1000 mg/100mL
Solution	Oral	1000 mg/30mL
Suppository	Rectal	120 mg/1
Suppository	Rectal	650 mg / sup
Suspension	Oral	160 mg/100mL
Syrup	Oral	500 mg/15mL
Tablet	Not applicable	650 mg/1
Tablet	Oral	0.325 g/1g
Tablet	Oral	0.5 g/1g
Tablet	Oral	325 mg/1
Tablet	Oral	500 mg/5001
Tablet, chewable	Oral	325 mg/1
Tablet, coated	Oral	325 mg/1
Tablet, extended release	Oral	650 mg/1
Tablet, film coated	Oral	500 mg/1
Solution	Oral
Tablet	Not applicable
Tablet	Oral	160 mg / tab
Tablet	Oral	500.0 mg
Solution	Oral	500 mg/15mL
Tablet	Oral	500.4 mg/556mg
Solution	Oral	3.333 g/100mL
Suspension / drops	Oral	80 mg/0.8mL
Solution	Intravenous	100 mg / 10 mL
Solution	Intravenous	1000 mg / 100 mL
Solution	Intravenous	500 mg / 50 mL
Solution	Oral	325 mg/10.15mL
Solution	Oral	650 mg/20.3mL
Elixir	Oral	32 mg / mL
Solution	Oral	80 mg / 5 mL
Solution	Oral	80 mg / mL
Solution	Oral	160 mg / 5 mL
Suppository	Rectal	650 mg/1
Capsule, gelatin coated		499.5 mg/1
Tablet	Oral	324.9 mg/361mg
Syrup	Oral	160 mg / 5 mL
Solution	Intravenous	100 mg
Tablet; tablet, film coated	Oral	325 mg
Syrup	Oral	2 g
Tablet, film coated	Oral	518 mg
Tablet, chewable	Buccal	100 mg
Solution	Oral	100.0000 mg
Elixir	Oral	3.33 g
Suspension	Oral	3 g
Kit	Oral; Topical
Kit	Topical
Suspension	Oral	250 MG
Tablet	Oral	4.000 mg
Powder	Oral	500 mg
Capsule	Oral	200 mg
Powder, for solution	Oral	500 mg
Capsule, liquid filled	Not applicable
Granule, effervescent	Oral
Tablet, orally disintegrating	Oral	325 mg/1
Capsule, gelatin coated	Oral
Syrup	Oral	3 g
Solution	Intravenous	1.000 g
Tablet	Oral	500.00 mg
Syrup	Oral	3.04 g
Tablet, sugar coated	Oral	1 mg
Tablet; tablet, film coated	Oral
Tablet	Oral	35 mg
Tablet	Oral	3.000 mg
Solution	Oral	500 mg/5mL
Capsule	Oral	500 mg/1
Solution	Oral	100 MG/ML
Tablet, extended release	Oral	650.0 mg
Capsule, gelatin coated	Oral	325 mg/1
Tablet	Oral	325.00 mg
Syrup	Oral	120 mg
Capsule	Oral	650 mg
Syrup	Oral	100 MG/ML
Tablet	Oral
Suppository	Rectal
Suppository	Rectal	75 MG
Granule	Oral	1000 MG
Granule	Oral	250 MG
Granule	Oral	500 MG
Syrup	Oral
Syrup	Oral	200 mg/5mL
Tablet	Oral	555.000 mg
Tablet		10 mg
Tablet; tablet, multilayer	Oral	500 mg
Tablet		400 mg
Solution / drops; suspension / drops		60 MG/0.6ML
Syrup	Oral	2 mg/5mL
Solution	Oral	500.000 mg
Tablet	Oral	5.000 mg
Tablet, coated	Oral	500 MG
Tablet, film coated	Oral	10 mg
Liquid	Topical
Suspension	Oral	150 ml
Capsule	Oral	250.0000 mg
Suspension	Oral	5 g
Tablet, chewable	Oral	10000000 mg
Tablet	Oral	25 mg
Elixir	Oral	160 mg / 5 mL
Elixir	Oral	80 mg / mL
Liquid	Oral	160 mg / 5 mL
Suspension	Oral	160 mg / 5 mL
Syrup	Oral	80 mg / 5 mL
Tablet	Oral	80 mg / tab
Tablet, chewable	Oral	80 mg
Powder	Oral	250 mg
Syrup	Oral	1 mg/5ml
Powder	Oral	160 mg / sachet
Elixir	Oral	160 mg/5mL
Suspension	Oral	32 mg/1mL
Suspension	Oral	320 mg/10mL
Suspension	Oral	325 mg/10.15mL
Suspension	Oral	650 mg/20.3mL
Tablet, orally disintegrating	Oral	80 mg/1
Solution	Oral	160 mg/5mL
Tablet	Oral	80 mg/1
Solution	Oral	160 mg/10.15mL
Liquid	Oral	160 mg/5mL
Liquid	Oral	80 mg/2.5mL
Kit; suspension; tablet, chewable	Oral
Powder	Oral	160 mg/1
Suspension	Oral
Tablet	Oral	2 mg
Suspension
Solution	Oral	2.500 g
Kit; tablet, coated	Oral
Capsule, gelatin coated	Oral	10.50 mg
Injection	Intravenous
Solution	Intravenous
Powder	Not applicable
Powder		90 mg/100mg
Powder	Not applicable	90 mg/100mg
Powder	Not applicable	89.605 mg/89.605mg
Powder	Not applicable	90 mg/90mg
Kit; tablet	Oral
Tablet	Oral	4.00 mg
Capsule, gelatin coated; kit; tablet	Oral
Tablet	Oral	833.333 mg
Tablet	Oral	200.00 mg
Solution	Intravenous	1000 mg
Solution	Intravenous	500 mg
Kit; liquid; solution	Oral
Kit; tablet; tablet, coated	Oral
Capsule; kit	Oral
Capsule, gelatin coated; capsule, liquid filled; kit	Oral
Suspension	Oral	80 mg/0.8mL
Tablet	Oral	300 mg
Tablet, chewable	Oral
Cream; kit; liquid; ointment; tablet; tablet, chewable; tablet, film coated	Oral; Topical
Syrup	Oral	3200 mg
Capsule, liquid filled	Oral	500 mg
Syrup	Oral	3000 mg
Tablet	Oral	32500000 mg
Tablet, orally disintegrating	Oral
Solution	Oral	100.00 mg
Tablet	Oral	500.000 mg
Syrup	Oral	2.400 g
Suppository	Rectal	120 mg / sup
Suppository	Rectal	325 mg / sup
Bar, chewable	Oral	80 mg/1
Enema	Rectal	125 mg
Enema	Rectal	250 mg
Tablet	Oral	75.000 mg
Suppository	Rectal	300 MG
Tablet, effervescent	Oral	1000 MG
Tablet, effervescent	Oral	500 MG
Tablet		2 mg
Tablet, coated
Granule	Oral	650.00 mg
Kit; tablet, film coated	Oral
Tablet, delayed release	Oral	650 mg/1
Tablet, delayed release	Oral	500 mg/1
Liquid	Oral	500 mg/5mL
Tablet	Oral	500 mg/1
Capsule	Oral	500 mg / cap
Tablet, orally disintegrating	Oral	500 mg
Capsule, gelatin coated	Oral	500 mg/1
Suspension	Oral	500 mg/15mL
Capsule, liquid filled	Oral	500 mg/1
Tablet, chewable	Oral	500.0 mg
Powder	Oral	500 mg / sachet
Solution	Oral	500 mg / 15 mL
Syrup	Oral	160 mg
Suspension		1 mg/5mL
Suspension		1.067 mg/5mL
Tablet	Oral	500.000 mg
Tablet		7.6 mg
Suppository	Rectal	80 mg/1
Tablet, effervescent	Oral
Capsule	Oral
Powder, for suspension	Oral
Capsule	Oral	15 mg
Syrup	Oral	0.500 g
Syrup	Oral	160 mg/5mL
Solution	Oral	55.000 mg
Granule	Oral
Tablet, film coated	Oral	500 mg
Liquid	Oral	675 mg/15mL
Tablet, film coated	Oral
Capsule, coated	Oral	500 mg/1
Powder	Oral
Liquid	Oral	1000 mg/60mL
Capsule, coated	Oral
Tablet	Oral	50000000 mg
Powder	Parenteral	600 mg
Powder, for solution	Oral
Tablet	Oral	750.000 mg
Tablet, film coated	Topical
Powder, for solution	Oral	250 mg
Liquid	Oral	650 mg/50mL
Tablet	Oral	15 mg
Tablet	Oral	325.000 mg
Kit; powder	Oral
Injection	Intravenous	150 mg/ml
Injection	Intravenous	600 mg/4ml
Solution / drops; suspension / drops		60 mg
Suspension		0.5 mg/60mL
Elixir	Oral
Tablet	Oral
Syrup	Oral	50 mg/5mL
Suspension	Oral	80 mg / mL
Suspension	Oral	200 mg/2mL
Suspension	Oral	160 mg/1.6mL
Solution / drops	Oral	80 mg/0.8mL
Solution	Intravenous	10.00 mg
Cream; kit; tablet, film coated	Oral; Topical
Tablet, chewable	Oral	160 mg/1
Tablet, orally disintegrating	Oral	160 mg/1
Tablet, chewable	Oral	160 mg
Tablet	Oral	160 mg/1
Solution / drops; suspension / drops		100 mg
Tablet, effervescent	Oral	120 mg
Capsule, delayed release pellets	Oral
Syrup	Oral	150 mg/5mL
Capsule	Oral	25 mg
Powder, for solution	Oral	1000 mg
Solution	Intravenous	1.0000 g
Solution		1 % w/v
Liquid	Oral	.8 mL/1mL
Cream; kit; liquid	Oral; Topical
Tablet		1 mg
Suppository	Rectal
Syrup	Oral
Granule, effervescent	Oral	1000 MG
Tablet, film coated, extended release	Oral	650 mg/1
Tablet	Oral	125 mg
Solution	Oral	3.2 g
Tablet, chewable	Oral	80 mg/1
Tablet	Oral	80.000 mg
Powder	Not applicable	1 kg/1kg
Capsule	Oral
Kit; solution; suspension	Oral
Kit; tablet, coated; tablet, film coated	Oral
Capsule, liquid filled; kit; solution	Nasal; Oral
Kit; liquid	Oral
Capsule, liquid filled	Oral
Powder, for solution	Oral	125 mg
Powder, for solution	Oral	50 mg
Capsule	Oral	325 mg/1570mg
Syrup	Oral	135 mg/5mL
Syrup	Oral	40 mg/5mL
Tablet	Oral	350 mg
Tablet	Oral	375.000 mg
Solution / drops; suspension / drops
Granule, for solution	Oral	500 MG
Solution	Intravenous	500.000 mg
Tablet	Oral	500 1/1
Tablet, multilayer	Oral
Capsule, coated	Oral	500 mg
Tablet, film coated	Oral	200 mg
Powder
Powder		150 MG
Syrup	Oral	16.7 mg/5mL
Solution	Oral	3200 mg
Injection, solution	Intravenous	10 mg/1mL
Solution	Intravenous	10 mg / mL
Granule, for solution	Oral
Suspension	Oral	160 mg/5mL
Tablet, coated	Oral
Tablet, effervescent	Oral
Tablet	Oral	9 mg
Tablet	Oral	1 G
Tablet, for solution	Oral	500 mg
Syrup	Oral	60 mg/0.6ml
Tablet, film coated	Oral	665 mg
Capsule	Oral	665 mg
Tablet	Oral	500 mg
Tablet, effervescent	Oral	65 mg
Tablet, film coated	Oral	2 mg
Tablet, film coated	Oral	25 mg
Capsule	Oral	500.04 mg
Suspension	Oral	100 ml
Suspension	Oral	120 mg
Tablet	Oral	325 mg / tab
Tablet	Oral	500 mg / tab
Tablet, film coated	Oral	1 g
Capsule	Oral	250 MG
Tablet, soluble	Oral
Tablet	Oral	665 MG
Tablet, film coated	Oral	160 mg
Injection	Intravenous	1 g
Injection	Intravenous	1 g/100ml
Injection	Intravenous	10 mg/ml
Solution / drops; suspension / drops
Solution / drops; suspension / drops		100 MG/ML
Solution, concentrate	Intravenous	1 g
Solution	Intravenous	10 mg
Solution	Parenteral	10 mg/ml
Solution	Parenteral
Injection, solution	Intravenous	10 mg/ ml
Solution	Intravenous	1.00 g/100ml
Suspension	Oral
Elixir	Oral	120 mg/5ml
Solution	Intravenous
Solution	Oral	40 mg/ml
Solution	Oral	200 mg/5mL
Solution	Intravenous	10 MG/ML
Elixir	Oral
Granule, effervescent	Oral
Solution / drops	Oral	100 MG/ML
Suppository	Rectal	1000 MG
Injection, solution	Intravenous
Tablet	Oral	1000 MG
Injection, solution	Intravenous	10 MG/ML
Tablet	Dental
Solution	Oral
Tablet, film coated	Oral	1000 MG
Solution	Intravenous	50000000 mg
Granule	Oral
Tablet	Oral	8 mg
Tablet		50 mg
Tablet, extended release	Oral	665 mg
Tablet, film coated, extended release	Oral	665 mg
Suppository	Rectal	200 mg
Solution		150 mg/1ml
Injection, solution	Intravenous	1 g/100ml
Liquid	Oral	80 mg/0.8mL
Syrup	Oral	250 g
Liquid; solution / drops	Oral	80 mg / mL
Solution / drops	Oral	80 mg / mL
Syrup	Oral	125 mg/5ml
Solution	Oral	10.00 g
Solution	Oral	0.1000 g
Injection	Intravenous
Syrup	Oral	150 ml
Syrup	Oral	2.4 G/100ML
Suppository	Rectal	160 mg / sup
Tablet, chewable	Oral	120 MG
Suppository	Rectal	125 mg
Suspension	Oral	50 mg/ml
Tablet	Oral	650 mg/1
Solution	Oral	0.1000 g
Tablet	Oral	15.000 mg
Tablet	Oral	300.000 mg
Solution	Oral	3 g
Capsule	Oral	325 mg
Tablet, film coated	Oral
Solution / drops	Oral
Syrup	Oral	80 mg/0.8mL
Tablet, film coated	Oral	325 mg/1
Injection	Parenteral	10 mg/ml
Tablet	Oral	500.00 mg
Capsule, liquid filled; kit	Oral
Tablet	Oral	250 MG
Liquid	Oral	80 mg / 5 mL
Solution	Oral	100 mg
Syrup	Oral	120 mg/5mL
Suppository	Rectal	150 MG
Suppository	Rectal	600 MG
Syrup	Oral	2.4 g
Solution	Intravenous	1000.000 mg
Tablet	Oral	750 mg/1
Tablet, film coated	Oral	37.5 mg
Kit; tablet; tablet, film coated	Oral
Liquid	Oral	80 mg / mL
Tablet	Oral	500 mg/583mg
Tablet	Oral	12.5 mg
Suppository
Tablet, film coated	Oral	150 mg
Syrup	Oral	3.200 g
Solution	Oral	100.000 mg
Tablet	Oral	600 MG
Solution	Intravenous	1 g
Tablet	Oral	162.00 mg
Granule, effervescent	Oral	125 MG
Granule, effervescent	Oral	500 MG
Granule, for solution	Oral	1000 MG
Suppository	Rectal	5 mg
Tablet, for suspension
Tablet, orally disintegrating	Oral
Suppository	Rectal	350 mg
Solution / drops	Oral	15 ml
Tablet	Oral	0.5 gr
Solution / drops	Oral	30 ml
Liquid	Oral	100 mg/1mL
Suppository	Rectal	80.000 mg
Solution / drops; suspension / drops		80 mg
Tablet	Oral	650.000 mg
Syrup	Oral	250 mg
Tablet	Oral	400.000 mg
Suppository	Rectal	100 mg
Syrup	Oral	0.5 mg/5mL
Granule	Oral	6.28 g
Kit; solution	Oral
Kit; powder, for solution	Oral
Kit	Oral
Solution	Intramuscular; Intravenous	300 mg
Solution	Intravenous	1000000 mg
Syrup	Oral	160 mg/5mL
Tablet, extended release	Oral
Suppository	Rectal	300 mg/1
Kit; syrup	Oral
Suspension	Oral	100.000 mg
Tablet, extended release	Oral	650 mg
Tablet, film coated	Oral	650 mg/1
Suspension	Oral	3.2 g
Tablet, extended release	Oral	650 mg / tab
Liquid	Oral	500 mg/15mL
Powder	Oral	500 mg/0.95g
Tablet, coated	Oral	500 mg/1
Capsule, liquid filled	Oral	325 mg/1
Tablet, delayed release	Oral	1000 mg/1
Tablet, delayed release	Oral
Suppository	Rectal	120 mg
Powder		125 mg
Powder		250 mg
Powder		500 mg
Suppository	Rectal	240 mg
Solution	Oral	1000.000 mg
Solution	Oral	10.000 g
Tablet, film coated	Oral	325 mg
Tablet	Oral	30 mg
Suspension	Oral	1000 mg/1
Kit; suspension	Oral
Powder, for solution	Oral
Powder, for solution	Oral	1000 mg
Solution	Oral	650 mg / 15 mL
Granule	Oral	500.000 mg
Kit; tablet, chewable	Oral; Topical
Tablet, soluble	Oral	250 mg
Tablet, soluble	Oral	500 mg
Solution	Oral	120 mg / 5 mL
Capsule	Oral	450 mg
Injection, solution, concentrate	Intravenous	10 mg/ml
Capsule	Oral	10.00 mg
Tablet, sugar coated	Oral	30 mg
Capsule	Oral	250.000 mg
Liquid	Oral
Solution	Parenteral	500 mg
Tablet, film coated
Capsule
Solution / drops	Oral	500 mg/5ml
Tablet, film coated	Oral	500 mg
Syrup	Oral	150 mg/5mL
Suspension	Oral	250 mg/5mL
Syrup	Oral	500 mg/5ml
Tablet	Oral	325 mg
Solution		120 mg/5ml
Syrup	Oral	120 mg/5ml
Syrup	Oral	250 mg/5mL
Solution	Oral	120 mg/5ml
Tablet, coated	Oral	325 mg
Suspension	Oral	500 mg/5ml
Tablet	Oral	300 mg
Suppository	Rectal	80 mg
Suppository	Rectal	325 mg
Capsule	Oral	500 mg
Tablet	Oral	120 mg
Tablet, sugar coated	Oral
Solution		10 mg/1ml
Solution		500 mg/5ml
Solution
Elixir
Tablet	Oral	650 mg
Tablet, coated	Oral	500 mg
Suspension	Oral	120 mg/5mL
Tablet
Syrup	Oral	240 mg/5mL
Suppository	Rectal	250 mg
Suppository	Rectal	500 mg
Syrup
Tablet	Oral	160 mg
Tablet	Oral	80 mg

Prices

Unit description	Cost	Unit
Tylenol 100 325 mg tablet Bottle	16.98USD	bottle
Phrenilin Forte 50-650 mg capsule	5.24USD	capsule
Phrenilin forte capsule	4.46USD	capsule
Norco 7.5-325 tablet	2.77USD	tablet
Norco 10-325 tablet	2.76USD	tablet
Propoxyphen-apap 100-325 mg tablet	2.66USD	tablet
Darvocet-N 100 100-650 mg tablet	2.33USD	tablet
Norco 10-325 mg tablet	2.14USD	tablet
Ultracet 37.5-325 mg tablet	1.95USD	tablet
Propoxyphen-apap 100-500 mg tablet	1.85USD	tablet
Ultracet tablet	1.79USD	tablet
Darvocet-n 100 tablet	1.72USD	tablet
Tylenol with Codeine #4 300-60 mg tablet	1.65USD	tablet
Phrenilin 50-325 mg tablet	1.63USD	tablet
Norco 7.5-325 mg tablet	1.61USD	tablet
Darvocet a500 tablet	1.5USD	tablet
Norco 5-325 mg tablet	1.43USD	tablet
Darvocet A500 100-500 mg tablet	1.38USD	tablet
Phrenilin tablet	1.32USD	tablet
Norco 5-325 tablet	1.19USD	tablet
Darvocet-n 50 tablet	1.14USD	tablet
Hydrocodone-apap 10-750 tablet	1.12USD	tablet
Tylenol with Codeine #3 300-30 mg tablet	1.1USD	tablet
Tencon tablet	1.01USD	tablet
Hydrocodone-apap 7.5-650 tablet	0.93USD	tablet
Propoxyphene-apap 50-325 mg tablet	0.93USD	tablet
Co-gesic 5-500 tablet	0.92USD	each
Sedapap 50-650 mg tablet	0.92USD	tablet
Clemastine fum 2.68 mg tablet	0.86USD	tablet
Feverall 120 mg suppository	0.8USD	suppository
Feverall 325 mg suppository	0.8USD	suppository
Feverall 80 mg suppository	0.8USD	suppository
Tavist nd 10 mg tablet	0.74USD	tablet
Darvocet-N 50 50-325 mg tablet	0.73USD	tablet
Hydrocodone-apap 10-325 tablet	0.7USD	tablet
Hydrocodone-apap 7.5-325 tablet	0.62USD	tablet
Hydrocodone-apap 10-660 tablet	0.61USD	tablet
Acephen 650 mg suppository	0.55USD	suppository
Propoxyphen-apap 100-650 mg tablet	0.55USD	tablet
Acephen 120 mg suppository	0.54USD	suppository
Acephen 325 mg suppository	0.54USD	suppository
Hydrocodone-apap 5-325 tablet	0.54USD	tablet
Hydrocodone-apap 10-500 tablet	0.53USD	tablet
Tavist-1 1.34 mg tablet	0.5USD	tablet
Acetaminophen 325 mg suppository	0.44USD	suppository
Feverall 650 mg suppository	0.43USD	suppository
Drixoral cold & allergy tablet sa	0.4USD	tablet
Acetaminophen 650 mg suppository	0.39USD	suppository
Acetaminophen 120 mg suppository	0.38USD	suppository
Apap-butalbital 325-50 tablet	0.38USD	tablet
Hydrocodone-apap 10-650 tablet	0.37USD	each
Hydrocodone-apap 2.5-500 tablet	0.33USD	tablet
Tylenol flu max-strn gelcap	0.24USD	capsule
Momentum caplet	0.23USD	caplet
Tylenol cold gelcap	0.23USD	capsule
Tylenol cold head congestion	0.23USD	each
Tylenol cold multi-symp gelcap	0.23USD	capsule
Tylenol allergy m-s caplet	0.22USD	caplet
Tylenol cold multi-symptom caplet	0.22USD	caplet
Tylenol cold head cong caplet	0.21USD	caplet
Tylenol cold multi-symp caplet	0.21USD	caplet
Tylenol cold severe congestion	0.21USD	each
Tylenol sinus caplet	0.21USD	caplet
Excedrin quicktabs	0.2USD	tablet
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Tylenol allergy complete caplet	0.19USD	caplet
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Tylenol flu nighttime gelcap	0.19USD	capsule
Tylenol sinus congest-pain caplet	0.19USD	caplet
Tylenol sinus gelcap	0.19USD	capsule
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Childrens apap 80 mg tablet chew	0.17USD	tablet
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Tylenol allergy sinus caplet	0.17USD	caplet
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Tylenol ex-str 500 mg geltab	0.09USD	tablet
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Pain reliever 160 mg tablet	0.08USD	tablet
Tylenol es for arthritis pain	0.08USD	each
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Tylenol pm ex-strength geltab	0.08USD	tablet
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Acetaminophen powder dense	0.07USD	g
Apap 325 mg tablet	0.07USD	tablet
Apap child's 80 mg tablet chew	0.07USD	tablet
Soba pain rel xs 500 mg tablet	0.07USD	tablet
Tylenol 325 mg tablet	0.07USD	tablet
Acetaminophen 500 mg gelcap	0.06USD	tablet
CVS Pharmacy non-aspirin 500 mg caplet	0.06USD	caplet
CVS Pharmacy non-aspirin 500 mg tablet	0.06USD	tablet
CVS Pharmacy pain relief 500 mg gelcap	0.06USD	capsule
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Eql pain relief 325 mg tablet	0.06USD	tablet
Pain relief 500 mg caplet	0.06USD	caplet
Pain reliever 325 mg tablet	0.06USD	tablet
Soba pain reliever 500 mg tablet	0.06USD	tablet
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Child tylenol cough-sore thrt	0.05USD	ml
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Non-aspirin 500 mg geltab	0.05USD	tablet
Pain relief without asa tablet	0.05USD	tablet
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Non-aspirin 500 mg tablet	0.04USD	tablet
Pain reliever 500 mg geltab	0.04USD	tablet
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Ra acetaminophen pm caplet	0.04USD	caplet
Acetaminophen 325 mg tablet	0.03USD	tablet
Acetaminophen 500 mg caplet	0.03USD	caplet
Genapap 325 mg tablet	0.03USD	tablet
Genapap 500 mg tablet	0.03USD	tablet
Pain relief 500 mg tablet	0.03USD	each
Pain reliever 500 mg gelcap	0.03USD	capsule
Pain reliever 500 mg tablet	0.03USD	tablet
Pain relief 325 mg tablet	0.02USD	tablet
Pain reliever w-o asa 325 mg	0.02USD	each
Tylenol cold & flu severe liq	0.02USD	ml
Tylenol cold m-s severe day liquid	0.02USD	ml
Tylenol cough & sore throat lq	0.02USD	ml
Tylenol nighttime liquid	0.02USD	ml
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Maxapap 500 mg tablet	0.01USD	tablet

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Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
USRE39221	No	2006-08-01	2011-08-09
US5972916	No	1999-10-26	2017-07-14
US6488962	No	2002-12-03	2020-06-20
US6028222	Yes	2000-02-22	2018-02-05
US6992218	Yes	2006-01-31	2021-12-06
US8372432	No	2013-02-12	2029-03-11
US8668929	No	2014-03-11	2029-03-11
US8377453	No	2013-02-19	2029-11-19
US7976870	No	2011-07-12	2027-06-01
US8741885	No	2014-06-03	2032-05-16
US8992975	No	2015-03-31	2032-05-16
US8597681	No	2013-12-03	2030-12-21
US8980319	No	2015-03-17	2030-12-21
US8394408	No	2013-03-12	2029-03-11
US9050335	No	2015-06-09	2032-05-16
US8658631	No	2014-02-25	2032-05-16
US9399012	Yes	2016-07-26	2032-03-11
US9610265	Yes	2017-04-04	2029-05-13
US9468636	No	2016-10-18	2032-05-16
US9132125	No	2015-09-15	2030-07-01
US8828978	No	2014-09-09	2030-07-01
US9549923	No	2017-01-24	2030-07-01
US8748413	No	2014-06-10	2030-07-01
US8461137	No	2013-06-11	2031-02-22
US9987238	Yes	2018-06-05	2029-05-13
US10383834	No	2019-08-20	2028-11-13
US8741959	No	2014-06-03	2030-04-19
US10532036	No	2020-01-14	2025-09-22
US11197830	No	2021-12-14	2039-02-27
US11534407	No	2019-02-27	2039-02-27
US11446266	No	2011-10-26	2031-10-26
US11213498	No	2016-01-14	2036-01-14
US11389416	No	2015-07-17	2035-07-17
US11896567	No	2011-10-26	2031-10-26
US11918693	No	2021-07-09	2041-07-09

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	168-172	https://www.medisca.com/NDC_SPECS/MUS/0409/MSDS/0409.pdf
boiling point (°C)	>500	http://www.inchem.org/documents/icsc/icsc/eics1330.htm
water solubility	very slightly soluble in cold water but greater solubility in hot water	http://www.inchem.org/documents/pims/pharm/pim396.htm
logP	0.46	https://www.medisca.com/NDC_SPECS/MUS/0409/MSDS/0409.pdf

Predicted Properties

Property	Value	Source
Water Solubility	4.15 mg/mL	ALOGPS
logP	0.51	ALOGPS
logP	0.91	Chemaxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	9.46	Chemaxon
pKa (Strongest Basic)	-4.4	Chemaxon
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	2	Chemaxon
Hydrogen Donor Count	2	Chemaxon
Polar Surface Area	49.33 Å²	Chemaxon
Rotatable Bond Count	1	Chemaxon
Refractivity	42.9 m³·mol^-1	Chemaxon
Polarizability	15.52 Å³	Chemaxon
Number of Rings	1	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.9921
Blood Brain Barrier	+	0.9544
Caco-2 permeable	+	0.8285
P-glycoprotein substrate	Non-substrate	0.8202
P-glycoprotein inhibitor I	Non-inhibitor	0.982
P-glycoprotein inhibitor II	Non-inhibitor	0.9781
Renal organic cation transporter	Non-inhibitor	0.9292
CYP450 2C9 substrate	Non-substrate	0.7259
CYP450 2D6 substrate	Substrate	0.8918
CYP450 3A4 substrate	Non-substrate	0.5554
CYP450 1A2 substrate	Non-inhibitor	0.9045
CYP450 2C9 inhibitor	Non-inhibitor	0.907
CYP450 2D6 inhibitor	Non-inhibitor	0.9755
CYP450 2C19 inhibitor	Non-inhibitor	0.9161
CYP450 3A4 inhibitor	Non-inhibitor	0.8496
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.8842
Ames test	Non AMES toxic	0.8767
Carcinogenicity	Non-carcinogens	0.7654
Biodegradation	Ready biodegradable	0.6342
Rat acute toxicity	1.8596 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9717
hERG inhibition (predictor II)	Non-inhibitor	0.9597

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Download (7.63 KB)

Spectra

Spectrum	Spectrum Type	Splash Key
GC-MS Spectrum - GC-MS (2 TMS)	GC-MS	splash10-0a4i-4971200000-17e6e1373f10ba4ec138
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-0a4i-3900000000-070b8ab49f93898e0aa4
GC-MS Spectrum - EI-B	GC-MS	splash10-0a4i-1900000000-df97f74a81da3a46a697
GC-MS Spectrum - EI-B	GC-MS	splash10-0a4i-4900000000-ef277124e1b50b5f010e
GC-MS Spectrum - CI-B	GC-MS	splash10-0udi-0900000000-7aa6a54b74b345d91e37
GC-MS Spectrum - GC-MS	GC-MS	splash10-0a4i-4971200000-17e6e1373f10ba4ec138
Mass Spectrum (Electron Ionization)	MS	splash10-0a4i-4900000000-ffdd0f8a1e6e450fc162
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	LC-MS/MS	splash10-0w29-3900000000-97741eddc3be9c7eaea8
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	LC-MS/MS	splash10-0ik9-1900000000-1ddd59340d1db920fa66
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	LC-MS/MS	splash10-00kf-9000000000-148fa91ce08e13165712
MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	LC-MS/MS	splash10-0a4i-1900000000-5997c3f6cdebc5326b65
MS/MS Spectrum - EI-B (Unknown) , Positive	LC-MS/MS	splash10-0a4i-4900000000-ef277124e1b50b5f010e
MS/MS Spectrum - CI-B (Unknown) , Positive	LC-MS/MS	splash10-0udi-0900000000-7aa6a54b74b345d91e37
LC-MS/MS Spectrum - LC-ESI-ITFT , negative	LC-MS/MS	splash10-0zfr-0900000000-125e44ce332576a1e155
LC-MS/MS Spectrum - LC-ESI-ITFT , negative	LC-MS/MS	splash10-0udi-0900000000-7e46df4b4b653c90c258
LC-MS/MS Spectrum - LC-ESI-ITFT , negative	LC-MS/MS	splash10-0udi-0900000000-bb6e34d2d574a249d721
LC-MS/MS Spectrum - LC-ESI-ITFT , negative	LC-MS/MS	splash10-0udi-0900000000-2f45dd7efce38361f806
LC-MS/MS Spectrum - LC-ESI-ITFT , negative	LC-MS/MS	splash10-0pb9-0900000000-e48b48d64b6b985ab455
LC-MS/MS Spectrum - LC-ESI-ITFT , negative	LC-MS/MS	splash10-0a4i-0900000000-b72b0e33fd35512fe6de
LC-MS/MS Spectrum - LC-ESI-ITFT , negative	LC-MS/MS	splash10-0a4i-0900000000-97bcaa95f26159307d03
LC-MS/MS Spectrum - LC-ESI-ITFT , negative	LC-MS/MS	splash10-0udi-0900000000-c50b4b79792e2c2e68f9
LC-MS/MS Spectrum - LC-ESI-ITFT , negative	LC-MS/MS	splash10-0udi-0900000000-7e46df4b4b653c90c258
LC-MS/MS Spectrum - LC-ESI-ITFT , negative	LC-MS/MS	splash10-0udi-0900000000-2b07cd2813d3f23e88f1
LC-MS/MS Spectrum - LC-ESI-ITFT , negative	LC-MS/MS	splash10-0pb9-0900000000-5b92f09589afe838f23a
LC-MS/MS Spectrum - LC-ESI-ITFT , negative	LC-MS/MS	splash10-0a4i-0900000000-f0ca5ff6526b9f005034
LC-MS/MS Spectrum - LC-ESI-ITFT , negative	LC-MS/MS	splash10-0udi-0900000000-7e45ef71674dcdde9068
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-0w29-1900000000-38d21a339e82f461beac
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0udi-0900000000-d953f92b362e4b262210
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0udi-0900000000-3170dca3f927500ea230
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0udi-0900000000-f835e92fb0bae0c7b8bc
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0w29-0900000000-4e01c7ff07665fcdb218
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-03di-0900000000-a3c279c288bb690496b3
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-03di-2900000000-4435e0230105d5d28a94
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-03di-6900000000-76671cc7ad1df1b5983d
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0udi-0900000000-9895c5f2b10912092523
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0udi-0900000000-d73797c93a4ef79ea79e
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0w29-0900000000-22d62a7732ed3d99e87d
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-03di-0900000000-c652f4f179daa6465678
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-03di-2900000000-0e7e745540d8ec7b99f4
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-03di-6900000000-2a4263b38fa30bc64dd0
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0w29-0900000000-cf0ac615ec636ce7a253
LC-MS/MS Spectrum - LC-ESI-IT , positive	LC-MS/MS	splash10-03di-0900000000-428d8023ee5761fed84c
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-03di-0900000000-ed26fb95b6aea6986085
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-03di-1900000000-5b942e17f1e66a3832b8
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-03di-0900000000-d6a7498b8d87d4e00028
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-03di-0900000000-9ff40d4cd8c0f46836c2
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0w29-0900000000-fcf8e62537bd6db11b3a
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0w29-0900000000-c27e8f1522f41492aae3
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0udi-3900000000-c3de1f2edf14ef295993
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0udi-0900000000-6874d104043a8fbbf727
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-01q9-7900000000-959439ab2edc9a9713cd
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0006-9500000000-148bf88bb72dad07125e
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-05o0-9600000000-cc9ad880bc57639a06f5
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0cgl-9700000000-ec41f7290fa179181ef6
1H NMR Spectrum	1D NMR	Not Applicable
1H NMR Spectrum	1D NMR	Not Applicable
13C NMR Spectrum	1D NMR	Not Applicable
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable
[1H,13C] 2D NMR Spectrum	2D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	134.6437896	predicted	DarkChem Lite v0.1.0
[M-H]-	134.8657896	predicted	DarkChem Lite v0.1.0
[M-H]-	134.8702896	predicted	DarkChem Lite v0.1.0
[M-H]-	134.8689896	predicted	DarkChem Lite v0.1.0
[M-H]-	130.27197	predicted	DeepCCS 1.0 (2019)
[M+H]+	135.9129896	predicted	DarkChem Lite v0.1.0
[M+H]+	136.2496896	predicted	DarkChem Lite v0.1.0
[M+H]+	136.7223896	predicted	DarkChem Lite v0.1.0
[M+H]+	136.1651896	predicted	DarkChem Lite v0.1.0
[M+H]+	133.95085	predicted	DeepCCS 1.0 (2019)
[M+Na]+	135.9491896	predicted	DarkChem Lite v0.1.0
[M+Na]+	135.6949896	predicted	DarkChem Lite v0.1.0
[M+Na]+	136.1131896	predicted	DarkChem Lite v0.1.0
[M+Na]+	135.5634896	predicted	DarkChem Lite v0.1.0
[M+Na]+	143.3404	predicted	DeepCCS 1.0 (2019)

Targets

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Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	141000	N/A	N/A	A27736
Ki (nM)	>10000	N/A	N/A	A5629 / A27471

Details1. Prostaglandin G/H synthase 2

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Inhibitor

General Function: Dual cyclooxygenase and peroxidase in the biosynthesis pathway of prostanoids, a class of C20 oxylipins mainly derived from arachidonate ((5Z,8Z,11Z,14Z)-eicosatetraenoate, AA, C20:4(n-6)), with a particular role in the inflammatory response (PubMed:11939906, PubMed:16373578, PubMed:19540099, PubMed:22942274, PubMed:26859324, PubMed:27226593, PubMed:7592599, PubMed:7947975, PubMed:9261177). The cyclooxygenase activity oxygenates AA to the hydroperoxy endoperoxide prostaglandin G2 (PGG2), and the peroxidase activity reduces PGG2 to the hydroxy endoperoxide prostaglandin H2 (PGH2), the precursor of all 2-series prostaglandins and thromboxanes (PubMed:16373578, PubMed:22942274, PubMed:26859324, PubMed:27226593, PubMed:7592599, PubMed:7947975, PubMed:9261177). This complex transformation is initiated by abstraction of hydrogen at carbon 13 (with S-stereochemistry), followed by insertion of molecular O2 to form the endoperoxide bridge between carbon 9 and 11 that defines prostaglandins. The insertion of a second molecule of O2 (bis-oxygenase activity) yields a hydroperoxy group in PGG2 that is then reduced to PGH2 by two electrons (PubMed:16373578, PubMed:22942274, PubMed:26859324, PubMed:27226593, PubMed:7592599, PubMed:7947975, PubMed:9261177). Similarly catalyzes successive cyclooxygenation and peroxidation of dihomo-gamma-linoleate (DGLA, C20:3(n-6)) and eicosapentaenoate (EPA, C20:5(n-3)) to corresponding PGH1 and PGH3, the precursors of 1- and 3-series prostaglandins (PubMed:11939906, PubMed:19540099). In an alternative pathway of prostanoid biosynthesis, converts 2-arachidonoyl lysophopholipids to prostanoid lysophopholipids, which are then hydrolyzed by intracellular phospholipases to release free prostanoids (PubMed:27642067). Metabolizes 2-arachidonoyl glycerol yielding the glyceryl ester of PGH2, a process that can contribute to pain response (PubMed:22942274). Generates lipid mediators from n-3 and n-6 polyunsaturated fatty acids (PUFAs) via a lipoxygenase-type mechanism. Oxygenates PUFAs to hydroperoxy compounds and then reduces them to corresponding alcohols (PubMed:11034610, PubMed:11192938, PubMed:9048568, PubMed:9261177). Plays a role in the generation of resolution phase interaction products (resolvins) during both sterile and infectious inflammation (PubMed:12391014). Metabolizes docosahexaenoate (DHA, C22:6(n-3)) to 17R-HDHA, a precursor of the D-series resolvins (RvDs) (PubMed:12391014). As a component of the biosynthetic pathway of E-series resolvins (RvEs), converts eicosapentaenoate (EPA, C20:5(n-3)) primarily to 18S-HEPE that is further metabolized by ALOX5 and LTA4H to generate 18S-RvE1 and 18S-RvE2 (PubMed:21206090). In vascular endothelial cells, converts docosapentaenoate (DPA, C22:5(n-3)) to 13R-HDPA, a precursor for 13-series resolvins (RvTs) shown to activate macrophage phagocytosis during bacterial infection (PubMed:26236990). In activated leukocytes, contributes to oxygenation of hydroxyeicosatetraenoates (HETE) to diHETES (5,15-diHETE and 5,11-diHETE) (PubMed:22068350, PubMed:26282205). Can also use linoleate (LA, (9Z,12Z)-octadecadienoate, C18:2(n-6)) as substrate and produce hydroxyoctadecadienoates (HODEs) in a regio- and stereospecific manner, being (9R)-HODE ((9R)-hydroxy-(10E,12Z)-octadecadienoate) and (13S)-HODE ((13S)-hydroxy-(9Z,11E)-octadecadienoate) its major products (By similarity). During neuroinflammation, plays a role in neuronal secretion of specialized preresolving mediators (SPMs) 15R-lipoxin A4 that regulates phagocytic microglia (By similarity)
Specific Function: enzyme binding
Gene Name: PTGS2
Uniprot ID: P35354
Uniprot Name: Prostaglandin G/H synthase 2
Molecular Weight: 68995.625 Da

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Lee YS, Kim H, Brahim JS, Rowan J, Lee G, Dionne RA: Acetaminophen selectively suppresses peripheral prostaglandin E2 release and increases COX-2 gene expression in a clinical model of acute inflammation. Pain. 2007 Jun;129(3):279-86. Epub 2006 Dec 18. [Article]
Hinz B, Cheremina O, Brune K: Acetaminophen (paracetamol) is a selective cyclooxygenase-2 inhibitor in man. FASEB J. 2008 Feb;22(2):383-90. Epub 2007 Sep 20. [Article]
Weinheimer EM, Jemiolo B, Carroll CC, Harber MP, Haus JM, Burd NA, LeMoine JK, Trappe SW, Trappe TA: Resistance exercise and cyclooxygenase (COX) expression in human skeletal muscle: implications for COX-inhibiting drugs and protein synthesis. Am J Physiol Regul Integr Comp Physiol. 2007 Jun;292(6):R2241-8. Epub 2007 Feb 22. [Article]
Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]

Details2. Sodium-dependent serotonin transporter

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Inhibitor

General Function: Serotonin transporter that cotransports serotonin with one Na(+) ion in exchange for one K(+) ion and possibly one proton in an overall electroneutral transport cycle. Transports serotonin across the plasma membrane from the extracellular compartment to the cytosol thus limiting serotonin intercellular signaling (PubMed:10407194, PubMed:12869649, PubMed:21730057, PubMed:27049939, PubMed:27756841, PubMed:34851672). Essential for serotonin homeostasis in the central nervous system. In the developing somatosensory cortex, acts in glutamatergic neurons to control serotonin uptake and its trophic functions accounting for proper spatial organization of cortical neurons and elaboration of sensory circuits. In the mature cortex, acts primarily in brainstem raphe neurons to mediate serotonin uptake from the synaptic cleft back into the pre-synaptic terminal thus terminating serotonin signaling at the synapse (By similarity). Modulates mucosal serotonin levels in the gastrointestinal tract through uptake and clearance of serotonin in enterocytes. Required for enteric neurogenesis and gastrointestinal reflexes (By similarity). Regulates blood serotonin levels by ensuring rapid high affinity uptake of serotonin from plasma to platelets, where it is further stored in dense granules via vesicular monoamine transporters and then released upon stimulation (PubMed:17506858, PubMed:18317590). Mechanistically, the transport cycle starts with an outward-open conformation having Na1(+) and Cl(-) sites occupied. The binding of a second extracellular Na2(+) ion and serotonin substrate leads to structural changes to outward-occluded to inward-occluded to inward-open, where the Na2(+) ion and serotonin are released into the cytosol. Binding of intracellular K(+) ion induces conformational transitions to inward-occluded to outward-open and completes the cycle by releasing K(+) possibly together with a proton bound to Asp-98 into the extracellular compartment. Na1(+) and Cl(-) ions remain bound throughout the transport cycle (PubMed:10407194, PubMed:12869649, PubMed:21730057, PubMed:27049939, PubMed:27756841, PubMed:34851672). Additionally, displays serotonin-induced channel-like conductance for monovalent cations, mainly Na(+) ions. The channel activity is uncoupled from the transport cycle and may contribute to the membrane resting potential or excitability (By similarity)
Specific Function: actin filament binding
Gene Name: SLC6A4
Uniprot ID: P31645
Uniprot Name: Sodium-dependent serotonin transporter
Molecular Weight: 70324.165 Da

References

Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]

Details3. Sodium-dependent noradrenaline transporter

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Inhibitor

General Function: Mediates sodium- and chloride-dependent transport of norepinephrine (also known as noradrenaline) (PubMed:2008212, PubMed:8125921). Can also mediate sodium- and chloride-dependent transport of dopamine (PubMed:11093780, PubMed:8125921)
Specific Function: actin binding
Gene Name: SLC6A2
Uniprot ID: P23975
Uniprot Name: Sodium-dependent noradrenaline transporter
Molecular Weight: 69331.42 Da

References

Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]

Details4. Prostaglandin G/H synthase 1

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Inhibitor

General Function: Dual cyclooxygenase and peroxidase that plays an important role in the biosynthesis pathway of prostanoids, a class of C20 oxylipins mainly derived from arachidonate ((5Z,8Z,11Z,14Z)-eicosatetraenoate, AA, C20:4(n-6)), with a particular role in the inflammatory response. The cyclooxygenase activity oxygenates AA to the hydroperoxy endoperoxide prostaglandin G2 (PGG2), and the peroxidase activity reduces PGG2 to the hydroxy endoperoxide prostaglandin H2 (PGH2), the precursor of all 2-series prostaglandins and thromboxanes. This complex transformation is initiated by abstraction of hydrogen at carbon 13 (with S-stereochemistry), followed by insertion of molecular O2 to form the endoperoxide bridge between carbon 9 and 11 that defines prostaglandins. The insertion of a second molecule of O2 (bis-oxygenase activity) yields a hydroperoxy group in PGG2 that is then reduced to PGH2 by two electrons (PubMed:7947975). Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gastric epithelial cells, it is a key step in the generation of prostaglandins, such as prostaglandin E2 (PGE2), which plays an important role in cytoprotection. In platelets, it is involved in the generation of thromboxane A2 (TXA2), which promotes platelet activation and aggregation, vasoconstriction and proliferation of vascular smooth muscle cells (Probable). Can also use linoleate (LA, (9Z,12Z)-octadecadienoate, C18:2(n-6)) as substrate and produce hydroxyoctadecadienoates (HODEs) in a regio- and stereospecific manner, being (9R)-HODE ((9R)-hydroxy-(10E,12Z)-octadecadienoate) and (13S)-HODE ((13S)-hydroxy-(9Z,11E)-octadecadienoate) its major products (By similarity)
Specific Function: heme binding
Gene Name: PTGS1
Uniprot ID: P23219
Uniprot Name: Prostaglandin G/H synthase 1
Molecular Weight: 68685.82 Da

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Hinz B, Cheremina O, Brune K: Acetaminophen (paracetamol) is a selective cyclooxygenase-2 inhibitor in man. FASEB J. 2008 Feb;22(2):383-90. Epub 2007 Sep 20. [Article]
Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]

Details5. Prostaglandin E synthase 3

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Cytosolic prostaglandin synthase that catalyzes the oxidoreduction of prostaglandin endoperoxide H2 (PGH2) to prostaglandin E2 (PGE2) (PubMed:10922363). Molecular chaperone that localizes to genomic response elements in a hormone-dependent manner and disrupts receptor-mediated transcriptional activation, by promoting disassembly of transcriptional regulatory complexes (PubMed:11274138, PubMed:12077419). Facilitates HIF alpha proteins hydroxylation via interaction with EGLN1/PHD2, leading to recruit EGLN1/PHD2 to the HSP90 pathway (PubMed:24711448)
Specific Function: DNA polymerase binding
Gene Name: PTGES3
Uniprot ID: Q15185
Uniprot Name: Prostaglandin E synthase 3
Molecular Weight: 18697.195 Da

References

Botting R, Ayoub SS: COX-3 and the mechanism of action of paracetamol/acetaminophen. Prostaglandins Leukot Essent Fatty Acids. 2005 Feb;72(2):85-7. [Article]
Chandrasekharan NV, Dai H, Roos KL, Evanson NK, Tomsik J, Elton TS, Simmons DL: COX-3, a cyclooxygenase-1 variant inhibited by acetaminophen and other analgesic/antipyretic drugs: cloning, structure, and expression. Proc Natl Acad Sci U S A. 2002 Oct 15;99(21):13926-31. Epub 2002 Sep 19. [Article]
Data sheet, Acetaminophen, ebi.ac.uk [File]

Details6. Transient receptor potential cation channel subfamily V member 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Activator

General Function: Ligand-activated non-selective calcium permeant cation channel involved in detection of noxious chemical and thermal stimuli. Seems to mediate proton influx and may be involved in intracellular acidosis in nociceptive neurons. Involved in mediation of inflammatory pain and hyperalgesia. Sensitized by a phosphatidylinositol second messenger system activated by receptor tyrosine kinases, which involves PKC isozymes and PCL. Activation by vanilloids, like capsaicin, and temperatures higher than 42 degrees Celsius, exhibits a time- and Ca(2+)-dependent outward rectification, followed by a long-lasting refractory state. Mild extracellular acidic pH (6.5) potentiates channel activation by noxious heat and vanilloids, whereas acidic conditions (pH <6) directly activate the channel. Can be activated by endogenous compounds, including 12-hydroperoxytetraenoic acid and bradykinin. Acts as ionotropic endocannabinoid receptor with central neuromodulatory effects. Triggers a form of long-term depression (TRPV1-LTD) mediated by the endocannabinoid anandamine in the hippocampus and nucleus accumbens by affecting AMPA receptors endocytosis
Specific Function: ATP binding
Gene Name: TRPV1
Uniprot ID: Q8NER1
Uniprot Name: Transient receptor potential cation channel subfamily V member 1
Molecular Weight: 94955.33 Da

References

Hogestatt ED, Jonsson BA, Ermund A, Andersson DA, Bjork H, Alexander JP, Cravatt BF, Basbaum AI, Zygmunt PM: Conversion of acetaminophen to the bioactive N-acylphenolamine AM404 via fatty acid amide hydrolase-dependent arachidonic acid conjugation in the nervous system. J Biol Chem. 2005 Sep 9;280(36):31405-12. Epub 2005 Jun 29. [Article]
Mallet C, Barriere DA, Ermund A, Jonsson BA, Eschalier A, Zygmunt PM, Hogestatt ED: TRPV1 in brain is involved in acetaminophen-induced antinociception. PLoS One. 2010 Sep 17;5(9). pii: e12748. doi: 10.1371/journal.pone.0012748. [Article]

Enzymes

Details1. Cytochrome P450 2E1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: A cytochrome P450 monooxygenase involved in the metabolism of fatty acids (PubMed:10553002, PubMed:18577768). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:10553002, PubMed:18577768). Catalyzes the hydroxylation of carbon-hydrogen bonds. Hydroxylates fatty acids specifically at the omega-1 position displaying the highest catalytic activity for saturated fatty acids (PubMed:10553002, PubMed:18577768). May be involved in the oxidative metabolism of xenobiotics (Probable)
Specific Function: 4-nitrophenol 2-monooxygenase activity
Gene Name: CYP2E1
Uniprot ID: P05181
Uniprot Name: Cytochrome P450 2E1
Molecular Weight: 56848.42 Da

References

Dong H, Haining RL, Thummel KE, Rettie AE, Nelson SD: Involvement of human cytochrome P450 2D6 in the bioactivation of acetaminophen. Drug Metab Dispos. 2000 Dec;28(12):1397-400. [Article]
Manyike PT, Kharasch ED, Kalhorn TF, Slattery JT: Contribution of CYP2E1 and CYP3A to acetaminophen reactive metabolite formation. Clin Pharmacol Ther. 2000 Mar;67(3):275-82. doi: 10.1067/mcp.2000.104736. [Article]
Flockhart Table of Drug Interactions [Link]
Acetaminophen FDA label [File]

Details2. Cytochrome P450 1A2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:19965576, PubMed:9435160). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:19965576, PubMed:9435160). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:11555828, PubMed:12865317). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2 (PubMed:11555828, PubMed:12865317). Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). May act as a major enzyme for all-trans retinoic acid biosynthesis in the liver. Catalyzes two successive oxidative transformation of all-trans retinol to all-trans retinal and then to the active form all-trans retinoic acid (PubMed:10681376). Primarily catalyzes stereoselective epoxidation of the last double bond of polyunsaturated fatty acids (PUFA), displaying a strong preference for the (R,S) stereoisomer (PubMed:19965576). Catalyzes bisallylic hydroxylation and omega-1 hydroxylation of PUFA (PubMed:9435160). May also participate in eicosanoids metabolism by converting hydroperoxide species into oxo metabolites (lipoxygenase-like reaction, NADPH-independent) (PubMed:21068195). Plays a role in the oxidative metabolism of xenobiotics. Catalyzes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin (PubMed:14725854). Metabolizes caffeine via N3-demethylation (Probable)
Specific Function: aromatase activity
Gene Name: CYP1A2
Uniprot ID: P05177
Uniprot Name: Cytochrome P450 1A2
Molecular Weight: 58406.915 Da

References

Raucy JL, Lasker JM, Lieber CS, Black M: Acetaminophen activation by human liver cytochromes P450IIE1 and P450IA2. Arch Biochem Biophys. 1989 Jun;271(2):270-83. [Article]
Patten CJ, Thomas PE, Guy RL, Lee M, Gonzalez FJ, Guengerich FP, Yang CS: Cytochrome P450 enzymes involved in acetaminophen activation by rat and human liver microsomes and their kinetics. Chem Res Toxicol. 1993 Jul-Aug;6(4):511-8. [Article]
Li Y, Wang E, Patten CJ, Chen L, Yang CS: Effects of flavonoids on cytochrome P450-dependent acetaminophen metabolism in rats and human liver microsomes. Drug Metab Dispos. 1994 Jul-Aug;22(4):566-71. [Article]
Tassaneeyakul W, Birkett DJ, Veronese ME, McManus ME, Tukey RH, Quattrochi LC, Gelboin HV, Miners JO: Specificity of substrate and inhibitor probes for human cytochromes P450 1A1 and 1A2. J Pharmacol Exp Ther. 1993 Apr;265(1):401-7. [Article]
Mazaleuskaya LL, Sangkuhl K, Thorn CF, FitzGerald GA, Altman RB, Klein TE: PharmGKB summary: pathways of acetaminophen metabolism at the therapeutic versus toxic doses. Pharmacogenet Genomics. 2015 Aug;25(8):416-26. doi: 10.1097/FPC.0000000000000150. [Article]
Flockhart Table of Drug Interactions [Link]

Details3. Cytochrome P450 3A4

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate
Inducer

General Function: A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981)
Specific Function: 1,8-cineole 2-exo-monooxygenase activity
Gene Name: CYP3A4
Uniprot ID: P08684
Uniprot Name: Cytochrome P450 3A4
Molecular Weight: 57342.67 Da

References

Feierman DE, Melnikov Z, Zhang J: The paradoxical effect of acetaminophen on CYP3A4 activity and content in transfected HepG2 cells. Arch Biochem Biophys. 2002 Feb 1;398(1):109-17. doi: 10.1006/abbi.2001.2677. [Article]
Cao L, Kwara A, Greenblatt DJ: Metabolic interactions between acetaminophen (paracetamol) and two flavonoids, luteolin and quercetin, through in-vitro inhibition studies. J Pharm Pharmacol. 2017 Dec;69(12):1762-1772. doi: 10.1111/jphp.12812. Epub 2017 Sep 5. [Article]
Laine JE, Auriola S, Pasanen M, Juvonen RO: Acetaminophen bioactivation by human cytochrome P450 enzymes and animal microsomes. Xenobiotica. 2009 Jan;39(1):11-21. doi: 10.1080/00498250802512830 . [Article]

Details4. Cytochrome P450 2D6

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: A cytochrome P450 monooxygenase involved in the metabolism of fatty acids, steroids and retinoids (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:19965576, PubMed:20972997). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 20-hydroxyeicosatetraenoic acid ethanolamide (20-HETE-EA) and 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:18698000, PubMed:21289075). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Catalyzes the oxidative transformations of all-trans retinol to all-trans retinal, a precursor for the active form all-trans-retinoic acid (PubMed:10681376). Also involved in the oxidative metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants
Specific Function: anandamide 11,12 epoxidase activity
Gene Name: CYP2D6
Uniprot ID: P10635
Uniprot Name: Cytochrome P450 2D6
Molecular Weight: 55768.94 Da

References

Dong H, Haining RL, Thummel KE, Rettie AE, Nelson SD: Involvement of human cytochrome P450 2D6 in the bioactivation of acetaminophen. Drug Metab Dispos. 2000 Dec;28(12):1397-400. [Article]
Cao L, Kwara A, Greenblatt DJ: Metabolic interactions between acetaminophen (paracetamol) and two flavonoids, luteolin and quercetin, through in-vitro inhibition studies. J Pharm Pharmacol. 2017 Dec;69(12):1762-1772. doi: 10.1111/jphp.12812. Epub 2017 Sep 5. [Article]

Details5. Cytochrome P450 2A6

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity
Specific Function: arachidonic acid epoxygenase activity
Gene Name: CYP2A6
Uniprot ID: P11509
Uniprot Name: Cytochrome P450 2A6
Molecular Weight: 56517.005 Da

References

Cao L, Kwara A, Greenblatt DJ: Metabolic interactions between acetaminophen (paracetamol) and two flavonoids, luteolin and quercetin, through in-vitro inhibition studies. J Pharm Pharmacol. 2017 Dec;69(12):1762-1772. doi: 10.1111/jphp.12812. Epub 2017 Sep 5. [Article]
Kalsi SS, Wood DM, Waring WS, Dargan PI: Does cytochrome P450 liver isoenzyme induction increase the risk of liver toxicity after paracetamol overdose? Open Access Emerg Med. 2011 Oct 13;3:69-76. doi: 10.2147/OAEM.S24962. eCollection 2011. [Article]

Details6. UDP-glucuronosyltransferase 1-6

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols. Isoform 3 lacks transferase activity but acts as a negative regulator of isoform 1 (By similarity)
Specific Function: enzyme binding
Gene Name: UGT1A6
Uniprot ID: P19224
Uniprot Name: UDP-glucuronosyltransferase 1-6
Molecular Weight: 60750.215 Da

References

Court MH, Duan SX, von Moltke LL, Greenblatt DJ, Patten CJ, Miners JO, Mackenzie PI: Interindividual variability in acetaminophen glucuronidation by human liver microsomes: identification of relevant acetaminophen UDP-glucuronosyltransferase isoforms. J Pharmacol Exp Ther. 2001 Dec;299(3):998-1006. [Article]
Nagar S, Zalatoris JJ, Blanchard RL: Human UGT1A6 pharmacogenetics: identification of a novel SNP, characterization of allele frequencies and functional analysis of recombinant allozymes in human liver tissue and in cultured cells. Pharmacogenetics. 2004 Aug;14(8):487-99. [Article]
Navarro SL, Chen Y, Li L, Li SS, Chang JL, Schwarz Y, King IB, Potter JD, Bigler J, Lampe JW: UGT1A6 and UGT2B15 polymorphisms and acetaminophen conjugation in response to a randomized, controlled diet of select fruits and vegetables. Drug Metab Dispos. 2011 Sep;39(9):1650-7. doi: 10.1124/dmd.111.039149. Epub 2011 Jun 10. [Article]

Details7. UDP-glucuronosyltransferase 1A1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: UDP-glucuronosyltransferase (UGT) that catalyzes phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase the metabolite's water solubility, thereby facilitating excretion into either the urine or bile (PubMed:12181437, PubMed:15472229, PubMed:18004206, PubMed:18004212, PubMed:18719240, PubMed:19830808, PubMed:23288867). Essential for the elimination and detoxification of drugs, xenobiotics and endogenous compounds (PubMed:12181437, PubMed:18004206, PubMed:18004212). Catalyzes the glucuronidation of endogenous estrogen hormones such as estradiol, estrone and estriol (PubMed:15472229, PubMed:18719240, PubMed:23288867). Involved in the glucuronidation of bilirubin, a degradation product occurring in the normal catabolic pathway that breaks down heme in vertebrates (PubMed:17187418, PubMed:18004206, PubMed:19830808, PubMed:24525562). Also catalyzes the glucuronidation the isoflavones genistein, daidzein, glycitein, formononetin, biochanin A and prunetin, which are phytoestrogens with anticancer and cardiovascular properties (PubMed:18052087, PubMed:19545173). Involved in the glucuronidation of the AGTR1 angiotensin receptor antagonist losartan, a drug which can inhibit the effect of angiotensin II (PubMed:18674515). Involved in the biotransformation of 7-ethyl-10-hydroxycamptothecin (SN-38), the pharmacologically active metabolite of the anticancer drug irinotecan (PubMed:12181437, PubMed:18004212, PubMed:20610558)
Specific Function: enzyme binding
Gene Name: UGT1A1
Uniprot ID: P22309
Uniprot Name: UDP-glucuronosyltransferase 1A1
Molecular Weight: 59590.91 Da

References

Bock KW, Forster A, Gschaidmeier H, Bruck M, Munzel P, Schareck W, Fournel-Gigleux S, Burchell B: Paracetamol glucuronidation by recombinant rat and human phenol UDP-glucuronosyltransferases. Biochem Pharmacol. 1993 May 5;45(9):1809-14. [Article]
Tankanitlert J, Morales NP, Howard TA, Fucharoen P, Ware RE, Fucharoen S, Chantharaksri U: Effects of combined UDP-glucuronosyltransferase (UGT) 1A1*28 and 1A6*2 on paracetamol pharmacokinetics in beta-thalassemia/HbE. Pharmacology. 2007;79(2):97-103. doi: 10.1159/000097908. Epub 2006 Dec 12. [Article]
Mehboob H, Tahir IM, Iqbal T, Saleem S, Perveen S, Farooqi A: Effect of UDP-Glucuronosyltransferase (UGT) 1A Polymorphism (rs8330 and rs10929303) on Glucuronidation Status of Acetaminophen. Dose Response. 2017 Sep 11;15(3):1559325817723731. doi: 10.1177/1559325817723731. eCollection 2017 Jul-Sep. [Article]
Court MH, Duan SX, von Moltke LL, Greenblatt DJ, Patten CJ, Miners JO, Mackenzie PI: Interindividual variability in acetaminophen glucuronidation by human liver microsomes: identification of relevant acetaminophen UDP-glucuronosyltransferase isoforms. J Pharmacol Exp Ther. 2001 Dec;299(3):998-1006. [Article]

Details8. UDP-glucuronosyltransferase 1A9

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: UDP-glucuronosyltransferase (UGT) that catalyzes phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase the metabolite's water solubility, thereby facilitating excretion into either the urine or bile (PubMed:12181437, PubMed:15470161, PubMed:15472229, PubMed:18004212, PubMed:18052087, PubMed:18674515, PubMed:19545173). Essential for the elimination and detoxification of drugs, xenobiotics and endogenous compounds (PubMed:12181437, PubMed:18004212). Catalyzes the glucuronidation of endogenous estrogen hormones such as estradiol and estrone (PubMed:15472229). Also catalyzes the glucuronidation of the isoflavones genistein, daidzein, glycitein, formononetin, biochanin A and prunetin, which are phytoestrogens with anticancer and cardiovascular properties (PubMed:18052087, PubMed:19545173). Involved in the glucuronidation of the AGTR1 angiotensin receptor antagonist caderastan, a drug which can inhibit the effect of angiotensin II (PubMed:18674515). Involved in the biotransformation of 7-ethyl-10-hydroxycamptothecin (SN-38), the pharmacologically active metabolite of the anticancer drug irinotecan (PubMed:12181437, PubMed:20610558). Also metabolizes mycophenolate, an immunosuppressive agent (PubMed:15470161, PubMed:18004212)
Specific Function: enzyme binding
Gene Name: UGT1A9
Uniprot ID: O60656
Uniprot Name: UDP-glucuronosyltransferase 1A9
Molecular Weight: 59940.495 Da

References

Court MH, Duan SX, von Moltke LL, Greenblatt DJ, Patten CJ, Miners JO, Mackenzie PI: Interindividual variability in acetaminophen glucuronidation by human liver microsomes: identification of relevant acetaminophen UDP-glucuronosyltransferase isoforms. J Pharmacol Exp Ther. 2001 Dec;299(3):998-1006. [Article]
Linakis MW, Cook SF, Kumar SS, Liu X, Wilkins DG, Gaedigk R, Gaedigk A, Sherwin CMT, van den Anker JN: Polymorphic Expression of UGT1A9 is Associated with Variable Acetaminophen Glucuronidation in Neonates: A Population Pharmacokinetic and Pharmacogenetic Study. Clin Pharmacokinet. 2018 Apr 13. pii: 10.1007/s40262-018-0634-9. doi: 10.1007/s40262-018-0634-9. [Article]

Details9. UDP-glucuronosyltransferase 2B15

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: UDP-glucuronosyltransferase (UGT) that catalyzes phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase the metabolite's water solubility, thereby facilitating excretion into either the urine or bile (PubMed:16595710, PubMed:18719240, PubMed:23288867, PubMed:7835232, PubMed:9295060). Essential for the elimination and detoxification of drugs, xenobiotics and endogenous compounds (PubMed:7835232). Catalyzes the glucuronidation of endogenous steroid hormones such as androgens (testosterone, androsterone) and estrogens (estradiol, epiestradiol, estriol, catechol estrogens) (PubMed:16595710, PubMed:18719240, PubMed:23288867, PubMed:7835232, PubMed:9295060). Displays glucuronidation activity toward several classes of xenobiotic substrates, including phenolic compounds (eugenol, 4-nitrophenol, 4-hydroxybiphenyl) and phenylpropanoids (naringenin, coumarins) (PubMed:7835232). Catalyzes the glucuronidation of monoterpenoid alcohols such as borneol, menthol and isomenthol, a class of natural compounds used in essential oils (By similarity)
Specific Function: glucuronosyltransferase activity
Gene Name: UGT2B15
Uniprot ID: P54855
Uniprot Name: UDP-glucuronosyltransferase 2B15
Molecular Weight: 61035.815 Da

References

Navarro SL, Chen Y, Li L, Li SS, Chang JL, Schwarz Y, King IB, Potter JD, Bigler J, Lampe JW: UGT1A6 and UGT2B15 polymorphisms and acetaminophen conjugation in response to a randomized, controlled diet of select fruits and vegetables. Drug Metab Dispos. 2011 Sep;39(9):1650-7. doi: 10.1124/dmd.111.039149. Epub 2011 Jun 10. [Article]
Mutlib AE, Goosen TC, Bauman JN, Williams JA, Kulkarni S, Kostrubsky S: Kinetics of acetaminophen glucuronidation by UDP-glucuronosyltransferases 1A1, 1A6, 1A9 and 2B15. Potential implications in acetaminophen-induced hepatotoxicity. Chem Res Toxicol. 2006 May;19(5):701-9. doi: 10.1021/tx050317i. [Article]

Details10. Sulfotransferase 1A1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of a wide variety of acceptor molecules bearing a hydroxyl or an amine groupe. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Displays broad substrate specificity for small phenolic compounds. Plays an important role in the sulfonation of endogenous molecules such as steroid hormones and 3,3'-diiodothyronin (PubMed:10199779, PubMed:12471039, PubMed:16221673, PubMed:21723874, PubMed:22069470, PubMed:7834621). Mediates the sulfate conjugation of a variety of xenobiotics, including the drugs acetaminophen and minoxidil (By similarity). Mediates also the metabolic activation of carcinogenic N-hydroxyarylamines leading to highly reactive intermediates capable of forming DNA adducts, potentially resulting in mutagenesis (PubMed:7834621). May play a role in gut microbiota-host metabolic interaction. O-sulfonates 4-ethylphenol (4-EP), a dietary tyrosine-derived metabolite produced by gut bacteria. The product 4-EPS crosses the blood-brain barrier and may negatively regulate oligodendrocyte maturation and myelination, affecting the functional connectivity of different brain regions associated with the limbic system
Specific Function: 3'-phosphoadenosine 5'-phosphosulfate binding
Gene Name: SULT1A1
Uniprot ID: P50225
Uniprot Name: Sulfotransferase 1A1
Molecular Weight: 34165.13 Da

References

Adjei AA, Gaedigk A, Simon SD, Weinshilboum RM, Leeder JS: Interindividual variability in acetaminophen sulfation by human fetal liver: implications for pharmacogenetic investigations of drug-induced birth defects. Birth Defects Res A Clin Mol Teratol. 2008 Mar;82(3):155-65. doi: 10.1002/bdra.20535. [Article]
Yamamoto A, Liu MY, Kurogi K, Sakakibara Y, Saeki Y, Suiko M, Liu MC: Sulphation of acetaminophen by the human cytosolic sulfotransferases: a systematic analysis. J Biochem. 2015 Dec;158(6):497-504. doi: 10.1093/jb/mvv062. Epub 2015 Jun 11. [Article]
Cohen IV, Cirulli ET, Mitchell MW, Jonsson TJ, Yu J, Shah N, Spector TD, Guo L, Venter JC, Telenti A: Acetaminophen (Paracetamol) Use Modifies the Sulfation of Sex Hormones. EBioMedicine. 2018 Feb;28:316-323. doi: 10.1016/j.ebiom.2018.01.033. Epub 2018 Feb 15. [Article]

Details11. Sulfotransferase 1A3

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs
Specific Function: amine sulfotransferase activity
Gene Name: SULT1A3
Uniprot ID: P0DMM9
Uniprot Name: Sulfotransferase 1A3
Molecular Weight: 34195.96 Da

References

Adjei AA, Gaedigk A, Simon SD, Weinshilboum RM, Leeder JS: Interindividual variability in acetaminophen sulfation by human fetal liver: implications for pharmacogenetic investigations of drug-induced birth defects. Birth Defects Res A Clin Mol Teratol. 2008 Mar;82(3):155-65. doi: 10.1002/bdra.20535. [Article]
Yamamoto A, Liu MY, Kurogi K, Sakakibara Y, Saeki Y, Suiko M, Liu MC: Sulphation of acetaminophen by the human cytosolic sulfotransferases: a systematic analysis. J Biochem. 2015 Dec;158(6):497-504. doi: 10.1093/jb/mvv062. Epub 2015 Jun 11. [Article]
Bairam AF, Rasool MI, Alherz FA, Abunnaja MS, El Daibani AA, Kurogi K, Liu MC: Effects of human SULT1A3/SULT1A4 genetic polymorphisms on the sulfation of acetaminophen and opioid drugs by the cytosolic sulfotransferase SULT1A3. Arch Biochem Biophys. 2018 Jun 15;648:44-52. doi: 10.1016/j.abb.2018.04.019. Epub 2018 Apr 26. [Article]

Details12. Arylamine N-acetyltransferase 2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Catalyzes the N- or O-acetylation of various arylamine and heterocyclic amine substrates (PubMed:12222688, PubMed:7915226). Participates in the detoxification of a plethora of hydrazine and arylamine drugs, and is able to bioactivate several known carcinogens
Specific Function: arylamine N-acetyltransferase activity
Gene Name: NAT2
Uniprot ID: P11245
Uniprot Name: Arylamine N-acetyltransferase 2
Molecular Weight: 33570.245 Da

References

Rothen JP, Haefeli WE, Meyer UA, Todesco L, Wenk M: Acetaminophen is an inhibitor of hepatic N-acetyltransferase 2 in vitro and in vivo. Pharmacogenetics. 1998 Dec;8(6):553-9. [Article]
Tahir IM, Iqbal T, Saleem S, Mehboob H, Akhter N, Riaz M: Effect of acetaminophen on sulfamethazine acetylation in male volunteers. Int J Immunopathol Pharmacol. 2016 Mar;29(1):17-22. doi: 10.1177/0394632015593238. Epub 2015 Oct 30. [Article]

Details13. Fatty-acid amide hydrolase 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Catalyzes the hydrolysis of endogenous amidated lipids like the sleep-inducing lipid oleamide ((9Z)-octadecenamide), the endocannabinoid anandamide (N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine), as well as other fatty amides, to their corresponding fatty acids, thereby regulating the signaling functions of these molecules (PubMed:17015445, PubMed:19926788, PubMed:9122178). Hydrolyzes polyunsaturated substrate anandamide preferentially as compared to monounsaturated substrates (PubMed:17015445, PubMed:9122178). It can also catalyze the hydrolysis of the endocannabinoid 2-arachidonoylglycerol (2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol) (PubMed:21049984). FAAH cooperates with PM20D1 in the hydrolysis of amino acid-conjugated fatty acids such as N-fatty acyl glycine and N-fatty acyl-L-serine, thereby acting as a physiological regulator of specific subsets of intracellular, but not of extracellular, N-fatty acyl amino acids (By similarity)
Specific Function: acylglycerol lipase activity
Gene Name: FAAH
Uniprot ID: O00519
Uniprot Name: Fatty-acid amide hydrolase 1
Molecular Weight: 63065.28 Da

References

Hogestatt ED, Jonsson BA, Ermund A, Andersson DA, Bjork H, Alexander JP, Cravatt BF, Basbaum AI, Zygmunt PM: Conversion of acetaminophen to the bioactive N-acylphenolamine AM404 via fatty acid amide hydrolase-dependent arachidonic acid conjugation in the nervous system. J Biol Chem. 2005 Sep 9;280(36):31405-12. Epub 2005 Jun 29. [Article]
Zaitone SA, El-Wakeil AF, Abou-El-Ela SH: Inhibition of fatty acid amide hydrolase by URB597 attenuates the anxiolytic-like effect of acetaminophen in the mouse elevated plus-maze test. Behav Pharmacol. 2012 Aug;23(4):417-25. doi: 10.1097/FBP.0b013e3283566065. [Article]
Bertolini A, Ferrari A, Ottani A, Guerzoni S, Tacchi R, Leone S: Paracetamol: new vistas of an old drug. CNS Drug Rev. 2006 Fall-Winter;12(3-4):250-75. [Article]
Muramatsu S, Shiraishi S, Miyano K, Sudo Y, Toda A, Mogi M, Hara M, Yokoyama A, Kawasaki Y, Taniguchi M, Uezono Y: Metabolism of AM404 From Acetaminophen at Human Therapeutic Dosages in the Rat Brain. Anesth Pain Med. 2016 Jan 17;6(1):e32873. doi: 10.5812/aapm.32873. eCollection 2016 Feb. [Article]

Details14. Glutathione S-transferase P

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. Involved in the formation of glutathione conjugates of both prostaglandin A2 (PGA2) and prostaglandin J2 (PGJ2) (PubMed:9084911). Participates in the formation of novel hepoxilin regioisomers (PubMed:21046276). Negatively regulates CDK5 activity via p25/p35 translocation to prevent neurodegeneration
Specific Function: dinitrosyl-iron complex binding
Gene Name: GSTP1
Uniprot ID: P09211
Uniprot Name: Glutathione S-transferase P
Molecular Weight: 23355.625 Da

References

Boerma JS, Vermeulen NP, Commandeur JN: Application of CYP102A1M11H as a tool for the generation of protein adducts of reactive drug metabolites. Chem Res Toxicol. 2011 Aug 15;24(8):1263-74. doi: 10.1021/tx2001515. Epub 2011 Jun 16. [Article]

Details15. Glutathione S-transferase Mu 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. Involved in the formation of glutathione conjugates of both prostaglandin A2 (PGA2) and prostaglandin J2 (PGJ2) (PubMed:9084911). Participates in the formation of novel hepoxilin regioisomers (PubMed:21046276)
Specific Function: enzyme binding
Gene Name: GSTM1
Uniprot ID: P09488
Uniprot Name: Glutathione S-transferase Mu 1
Molecular Weight: 25711.555 Da

References

Arakawa S, Maejima T, Fujimoto K, Yamaguchi T, Yagi M, Sugiura T, Atsumi R, Yamazoe Y: Resistance to acetaminophen-induced hepatotoxicity in glutathione S-transferase Mu 1-null mice. J Toxicol Sci. 2012;37(3):595-605. [Article]

Carriers

Details1. Albumin

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Binder

General Function: Binds water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs (Probable). Its main function is the regulation of the colloidal osmotic pressure of blood (Probable). Major zinc transporter in plasma, typically binds about 80% of all plasma zinc (PubMed:19021548). Major calcium and magnesium transporter in plasma, binds approximately 45% of circulating calcium and magnesium in plasma (By similarity). Potentially has more than two calcium-binding sites and might additionally bind calcium in a non-specific manner (By similarity). The shared binding site between zinc and calcium at residue Asp-273 suggests a crosstalk between zinc and calcium transport in the blood (By similarity). The rank order of affinity is zinc > calcium > magnesium (By similarity). Binds to the bacterial siderophore enterobactin and inhibits enterobactin-mediated iron uptake of E.coli from ferric transferrin, and may thereby limit the utilization of iron and growth of enteric bacteria such as E.coli (PubMed:6234017). Does not prevent iron uptake by the bacterial siderophore aerobactin (PubMed:6234017)
Specific Function: antioxidant activity
Gene Name: ALB
Uniprot ID: P02768
Uniprot Name: Albumin
Molecular Weight: 69365.94 Da

References

Morris ME, Levy G: Renal clearance and serum protein binding of acetaminophen and its major conjugates in humans. J Pharm Sci. 1984 Aug;73(8):1038-41. doi: 10.1002/jps.2600730806. [Article]

Transporters

Details1. ATP-dependent translocase ABCB1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate
Inhibitor

General Function: Translocates drugs and phospholipids across the membrane (PubMed:2897240, PubMed:35970996, PubMed:8898203, PubMed:9038218). Catalyzes the flop of phospholipids from the cytoplasmic to the exoplasmic leaflet of the apical membrane. Participates mainly to the flop of phosphatidylcholine, phosphatidylethanolamine, beta-D-glucosylceramides and sphingomyelins (PubMed:8898203). Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells (PubMed:2897240, PubMed:35970996, PubMed:9038218)
Specific Function: ABC-type xenobiotic transporter activity
Gene Name: ABCB1
Uniprot ID: P08183
Uniprot Name: ATP-dependent translocase ABCB1
Molecular Weight: 141477.255 Da

References

Wang E, Lew K, Barecki M, Casciano CN, Clement RP, Johnson WW: Quantitative distinctions of active site molecular recognition by P-glycoprotein and cytochrome P450 3A4. Chem Res Toxicol. 2001 Dec;14(12):1596-603. [Article]
Faassen F, Vogel G, Spanings H, Vromans H: Caco-2 permeability, P-glycoprotein transport ratios and brain penetration of heterocyclic drugs. Int J Pharm. 2003 Sep 16;263(1-2):113-22. [Article]
Novak A, Carpini GD, Ruiz ML, Luquita MG, Rubio MC, Mottino AD, Ghanem CI: Acetaminophen inhibits intestinal p-glycoprotein transport activity. J Pharm Sci. 2013 Oct;102(10):3830-7. doi: 10.1002/jps.23673. Epub 2013 Jul 29. [Article]
Manov I, Bashenko Y, Hirsh M, Iancu TC: Involvement of the multidrug resistance P-glycoprotein in acetaminophen-induced toxicity in hepatoma-derived HepG2 and Hep3B cells. Basic Clin Pharmacol Toxicol. 2006 Sep;99(3):213-24. doi: 10.1111/j.1742-7843.2006.pto_443.x. [Article]

Drug created at June 13, 2005 13:24 / Updated at October 11, 2024 18:19

Acetaminophen

Identification

Structure for Acetaminophen (DB00316)

Pharmacology

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Chemical Identifiers

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Clinical Trials

Clinical Trial & Rare Diseases Add-on Data Package

Pharmacoeconomics

Properties

Spectra

Collision Cross Sections (CCS)

Targets

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Enzymes

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Carriers

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Transporters

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