Identification

Name
Acetaminophen
Accession Number
DB00316
Description

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
Thumb
Weight
Average: 151.1626
Monoisotopic: 151.063328537
Chemical Formula
C8H9NO2
Synonyms
  • 4-(Acetylamino)phenol
  • 4-acetamidophenol
  • 4'-hydroxyacetanilide
  • Acenol
  • Acetaminofén
  • 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

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

Associated Conditions
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 establishedLabel - 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

TargetActionsOrganism
UProstaglandin E synthase 3
inhibitor
Humans
AProstaglandin G/H synthase 2
inhibitor
Humans
AProstaglandin G/H synthase 1
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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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

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Acetaminophen Metabolism PathwayDrug metabolism
Acetaminophen Action PathwayDrug 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.
DrugInteraction
AbacavirAcetaminophen may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbametapirThe serum concentration of Acetaminophen can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Acetaminophen can be increased when combined with Abatacept.
AbirateroneThe serum concentration of Acetaminophen can be increased when it is combined with Abiraterone.
AcalabrutinibThe metabolism of Acetaminophen can be increased when combined with Acalabrutinib.
AcarboseAcarbose may decrease the excretion rate of Acetaminophen which could result in a higher serum level.
AcebutololThe metabolism of Acetaminophen can be decreased when combined with Acebutolol.
AceclofenacThe risk or severity of adverse effects can be increased when Acetaminophen is combined with Aceclofenac.
AcemetacinThe risk or severity of adverse effects can be increased when Acetaminophen is combined with Acemetacin.
AcenocoumarolThe metabolism of Acenocoumarol can be increased when combined with Acetaminophen.
Additional Data Available
  • Extended Description
    Extended Description

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

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  • Action
    Action

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

Products

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
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
7T Gummy ESTablet, chewable500 mg/1Oral7T Pharma LLC2019-09-01Not applicableUS flag
AcetaminophenTablet325 mg/1OralRemedy Repack2011-03-092012-08-16US flag
Acetaminophen InjectionSolutionIntravenousAvir Pharma Inc2019-09-13Not applicableCanada flag
Childrens SilapapLiquid160 mg/5mLOralbryant ranch prepack1994-09-05Not applicableUS flag
OfirmevInjection, solution10 mg/1mLIntravenousCardinal Health2010-11-082019-02-28US flag
OfirmevSolution10 mgIntravenousMallinckrodt Hospital Products IncNot applicableNot applicableCanada flag
OfirmevInjection, solution10 mg/1mLIntravenousMallinckrodt Hospital Products Inc.2010-11-08Not applicableUS flag
Ofirmev (acetaminophen)Injection, solution10 mg/1mLIntravenousHF Acquisition Co LLC, DBA HealthFirst2019-12-21Not applicableUS flag
Regular Strength QPAPTablet325 mg/1Oralbryant ranch prepack1996-02-01Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AcephenSuppository325 mg/1RectalRemedy Repack2015-01-162016-01-16US flag
Good Neighbor Pharmacy Pain ReliefTablet, film coated, extended release650 mg/1Oralbryant ranch prepack2008-11-03Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
222 AF Extra Strength Caplet (500mg)TabletOralMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1992-12-311997-08-14Canada flag
222 AF Regular Strength Caplet (325mg)TabletOralMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1992-12-311997-08-14Canada flag
222af Extra Strength 500mgTabletOralMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1978-12-311997-08-14Canada flag
222af Regular Strength 325mgTabletOralMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1977-12-311997-08-14Canada flag
365 Everyday Value AcetaminophenTablet500 mg/1OralWhole Foods Market, Inc.2018-08-23Not applicableUS flag
365 Everyday Value AcetaminophenTablet500 mg/1OralWhole Foods Market, Inc.2020-08-23Not applicableUS flag
7 Select AcetaminophenTablet500 mg/1Oral7-Eleven2014-05-142021-03-31US flag
7 Select Childrens Pain ReliefSuspension160 mg/5mLOral7-Eleven2014-08-132021-02-28US flag
8 Hour Arthritis PainTablet, extended release650 mg/1OralAmerisource Bergen2019-11-01Not applicableUS flag
8 Hour Arthritis PainTablet, extended release650 mg/1OralValu Merchandisers Company2020-01-01Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
(extra Strength) Acetaminophen, Caffeine & 8mg Codeine Phosphate CapletsAcetaminophen (500 mg) + Caffeine (15 mg) + Codeine phosphate (8 mg)TabletOralStanley Pharmaceuticals, A Division Of Vita Health Products Inc.1998-07-222002-07-31Canada flag
10 Person ANSIAcetaminophen (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)KitOphthalmic; Oral; TopicalGenuine First Aid2010-04-24Not applicableUS flag
25 Person ANSIAcetaminophen (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)KitOphthalmic; Oral; TopicalGenuine First Aid2010-04-25Not applicableUS flag
4017 First Aid KitAcetaminophen (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)KitOphthalmic; Oral; TopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUS flag
4022 First Aid KitAcetaminophen (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)KitOphthalmic; Oral; TopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUS flag
4056 First Aid KitAcetaminophen (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)KitOphthalmic; Oral; TopicalHoneywell Safety Products USA, Inc2018-10-182019-10-18US flag
4068 First Aid KitAcetaminophen (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)KitOphthalmic; Oral; TopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUS flag
4069 First Aid KitAcetaminophen (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)KitTopicalHoneywell Safety Products USA, Inc2018-10-182019-03-10US flag
4076 First Aid KitAcetaminophen (325 mg/1) + Ammonia (0.045 g/0.3mL) + 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)KitTopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUS flag
4081 First Aid KitAcetaminophen (325 mg/1) + Benzalkonium chloride (0.13 g/100g) + Benzalkonium chloride (1.3 mg/1mL) + Ethanol (0.5 mL/1mL) + Lidocaine hydrochloride (0.5 g/100g) + Lidocaine hydrochloride (20 mg/1mL) + Neomycin sulfate (3.5 mg/1g) + Water (98.6 mL/100mL)KitOphthalmic; Oral; TopicalHoneywell Safety Products USA, Inc2018-10-182019-10-18US flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
4017 First Aid KitAcetaminophen (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)KitOphthalmic; Oral; TopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUS flag
4022 First Aid KitAcetaminophen (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)KitOphthalmic; Oral; TopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUS flag
4056 First Aid KitAcetaminophen (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)KitOphthalmic; Oral; TopicalHoneywell Safety Products USA, Inc2018-10-182019-10-18US flag
4068 First Aid KitAcetaminophen (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)KitOphthalmic; Oral; TopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUS flag
4069 First Aid KitAcetaminophen (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)KitTopicalHoneywell Safety Products USA, Inc2018-10-182019-03-10US flag
4076 First Aid KitAcetaminophen (325 mg/1) + Ammonia (0.045 g/0.3mL) + 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)KitTopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUS flag
4081 First Aid KitAcetaminophen (325 mg/1) + Benzalkonium chloride (0.13 g/100g) + Benzalkonium chloride (1.3 mg/1mL) + Ethanol (0.5 mL/1mL) + Lidocaine hydrochloride (0.5 g/100g) + Lidocaine hydrochloride (20 mg/1mL) + Neomycin sulfate (3.5 mg/1g) + Water (98.6 mL/100mL)KitOphthalmic; Oral; TopicalHoneywell Safety Products USA, Inc2018-10-182019-10-18US flag
4082 First Aid KitAcetaminophen (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)KitOphthalmic; Oral; TopicalHoneywell Safety Products USA, Inc2018-10-182019-10-18US flag
4083 First Aid KitAcetaminophen (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)KitOphthalmic; Oral; TopicalHoneywell Safety Products USA, Inc2018-10-182019-10-18US flag
4084 First Aid KitAcetaminophen (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)KitOphthalmic; Oral; TopicalHoneywell Safety Products USA, Inc2018-10-182019-10-18US flag

Categories

ATC Codes
N02BE71 — Paracetamol, combinations with psycholepticsN02BE01 — ParacetamolN02AJ13 — Tramadol and paracetamolN02AJ17 — Oxycodone and paracetamolN02BE51 — Paracetamol, combinations excl. psycholepticsN02AJ06 — Codeine and paracetamolN02AJ01 — Dihydrocodeine and paracetamol
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that a unsubstituted at the 2-position.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Phenols
Sub Class
1-hydroxy-2-unsubstituted benzenoids
Direct Parent
1-hydroxy-2-unsubstituted benzenoids
Alternative Parents
Benzene and substituted derivatives / Propargyl-type 1,3-dipolar organic compounds / Carboximidic acids / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Hydrocarbon derivatives
Substituents
1-hydroxy-2-unsubstituted benzenoid / Aromatic homomonocyclic compound / Carboximidic acid / Carboximidic acid derivative / Hydrocarbon derivative / Monocyclic benzene moiety / Organic 1,3-dipolar compound / Organic nitrogen compound / Organic oxygen compound / Organonitrogen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
phenols, acetamides (CHEBI:46195) / a small molecule (CPD-7669)

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
  1. 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. [PubMed:15879007]
  2. 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. [PubMed:16413237]
  3. 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. [PubMed:17227290]
  4. Graham GG, Scott KF: Mechanism of action of paracetamol. Am J Ther. 2005 Jan-Feb;12(1):46-55. [PubMed:15662292]
  5. 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. [PubMed:104998]
  6. 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. [PubMed:12242329]
  7. 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. [PubMed:18232020]
  8. Hazai E, Vereczkey L, Monostory K: Reduction of toxic metabolite formation of acetaminophen. Biochem Biophys Res Commun. 2002 Mar 8;291(4):1089-94. [PubMed:11866476]
  9. 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. [PubMed:26049587]
  10. 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. [PubMed:26572078]
  11. Bannwarth B, Pehourcq F: [Pharmacologic basis for using paracetamol: pharmacokinetic and pharmacodynamic issues]. Drugs. 2003;63 Spec No 2:5-13. [PubMed:14758786]
  12. Forrest JA, Clements JA, Prescott LF: Clinical pharmacokinetics of paracetamol. Clin Pharmacokinet. 1982 Mar-Apr;7(2):93-107. [PubMed:7039926]
  13. Ricciotti E, FitzGerald GA: Prostaglandins and inflammation. Arterioscler Thromb Vasc Biol. 2011 May;31(5):986-1000. doi: 10.1161/ATVBAHA.110.207449. [PubMed:21508345]
  14. Valerie Gerriets; Thomas M. Nappe (2019). Acetaminophen. StatPearls publishing.
  15. Acetaminophen tablet, DailyMed [Link]
  16. Acetaminophen effervescent tablets, Cleveland Clinic [Link]
  17. FDA safety communication: FDA has reviewed possible risks of pain medicine use during pregnancy [Link]
  18. U.S. National Medical Library: MedlinePlus- Acetaminophen dosing for children [Link]
  19. FDA consumer health information: Acetaminophen [Link]
  20. FDA : Acetaminophen Information [Link]
  21. Using Acetaminophen and Nonsteroidal Anti-inflammatory Drugs Safely [Link]
  22. Acetaminophen FDA Label [Link]
  23. Acetaminophen monograph, suppository [File]
  24. Acetaminophen data sheet, ebi.ac.uk [File]
  25. Tylenol arthritis pain label, OTC [File]
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
AHFS Codes
  • 28:08.92 — Miscellaneous Analgesics and Antipyretics
PDB Entries
1tyl / 1tym / 2dpz / 2ocu / 3py4 / 4a9j / 4a9k / 4cut / 4gn6 / 4yji
show 1 more
FDA label
Download (392 KB)
MSDS
Download (71.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingPreventionAcetaminophen Toxicity1
4Active Not RecruitingSupportive CareCarpal Tunnel1
4Active Not RecruitingSupportive CareNeoplasms, Thyroid / Parathyroid Adenomas / Parathyroid Diseases / Parathyroid Hyperplasia / Thyroid Cancers / Thyroid Diseases / Thyroid Goitre / Thyroid Nodules1
4Active Not RecruitingTreatmentAbdominal Wall Hernia / Bowel Diseases / Gastric Diseases / Gastric Outlet Obstruction / Pancreatic Diseases1
4Active Not RecruitingTreatmentChronic Disease of Musculoskeletal System / High Blood Pressure (Hypertension)1
4Active Not RecruitingTreatmentEclampsia / HELLP Syndrome / Prophylaxis of preeclampsia1
4Active Not RecruitingTreatmentImmunosuppression / Neoplasms, Lung / Pain1
4Active Not RecruitingTreatmentLumbar Disc Disease / Lumbar Radiculopathy / Prolapsed Lumbar Disc1
4Active Not RecruitingTreatmentMigraine1
4Active Not RecruitingTreatmentOocyte Retrieval / Postoperative pain1

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
FormRouteStrength
KitOphthalmic; Oral; Respiratory (inhalation); Topical
KitOral; Respiratory (inhalation); Topical
KitOphthalmic; Oral; Topical
Tablet, chewableOral500 mg/1
CapsuleOral300 mg
Tablet, coatedOral650 mg
PowderOral500 mg/6g
SyrupOral120 mg/5ml
SuppositoryRectal325 mg/1
SuppositoryRectal
Tablet, effervescentOral500 mg/1
Tablet, coatedOral1000 mg
TabletOral500 mg
SolutionOral10 g
Bar, chewableOral160 mg/1
SolutionOral160 mg
SolutionOral80 mg
Solution / dropsOral80 mg
SuppositoryRectal120 mg/1
SuppositoryRectal120 mg
SuppositoryRectal160 mg
SuppositoryRectal325 mg
SuppositoryRectal650 mg
SuspensionOral160 mg/100mL
TabletNot applicable650 mg/1
TabletOral0.325 g/1g
TabletOral0.5 g/1g
TabletOral325 mg/1
Tablet, chewableOral160 mg
Tablet, chewableOral325 mg/1
Tablet, chewableOral80 mg
Tablet, coatedOral325 mg/1
Tablet, extended releaseOral650 mg/1
Tablet, film coatedOral500 mg/1
SolutionOral
Tablet, extended releaseOral650 mg
TabletOral500.4 mg/556mg
SolutionOral3.333 g/100mL
Suspension / dropsOral80 mg/0.8mL
SolutionIntravenous
SolutionOral325 mg/10.15mL
SolutionOral650 mg/20.3mL
SuppositoryRectal650 mg/1
TabletOral324.9 mg/361mg
TabletOral
KitOral; Topical
KitTopical
TabletOral200 mg
TabletOral650 mg
TabletOral300 mg
Capsule, liquid filledNot applicable
Granule, effervescentOral
Tablet, orally disintegratingOral325 mg/1
Capsule, gelatin coatedOral
SolutionOral100 mg
SolutionOral500 mg/5mL
CapsuleOral500 mg/1
SolutionOral100 MG/ML
Tablet, extended releaseOral650.0 mg
Elixir120 mg/5ml
PowderOral600 mg
Capsule, gelatin coatedOral325 mg/1
SyrupOral3 g
Tablet0.75 mg
Tablet1000 MG
Suppository1000 MG
Suppository125 MG
Suppository250 MG
CapsuleOral500 MG
Tablet500 MG
Suppository75 MG
GranuleOral250 MG
GranuleOral500 MG
SyrupOral200 mg/5mL
Tablet, film coatedOral500 mg
SuppositoryRectal125 mg
TabletOral30 mg
Tablet, film coatedOral10 mg
LiquidTopical
SuspensionOral250 mg/5ml
SuspensionOral120 mg/5ml
Suspension150 ml
Capsule, liquid filledOral500 mg
ElixirOral
SyrupOral
ElixirOral160 mg/5mL
SuspensionOral32 mg/1mL
SuspensionOral325 mg/10.15mL
SuspensionOral650 mg/20.3mL
Tablet, orally disintegratingOral80 mg/1
SolutionOral160 mg/5mL
TabletOral80 mg/1
LiquidOral160 mg/5mL
LiquidOral80 mg/2.5mL
PowderOral160 mg/1
SuspensionOral
Tablet400 mg
Capsule; kitOral
Kit; tabletOral
CapsuleOral325 mg
PowderNot applicable90 mg/100mg
GranuleOral20 mg
Capsule, coatedOral250 mg
Capsule5 mg
SyrupOral5 mg/5ml
Kit; powder, for solutionOral
Tablet, effervescentOral200 mg
SuspensionOral80 mg/0.8mL
Tablet, chewableOral
PowderOral300 mg
Tablet, coated25 mg
Tablet, coatedOral25 mg
Tablet, coatedOral50 mg
Tablet, effervescentOral25 mg
Tablet, effervescentOral50 mg
Tablet500 mg/1
SyrupOral3.2 g
SyrupOral3200 mg
Tablet, chewableOral100 mg
SuspensionOral5 g
Tablet, coatedOral500 mg
Capsule, coatedOral500 mg
SolutionOral3 g
Tablet, coatedOral10 mg
Tablet, orally disintegratingOral325 mg
TabletOral250 mg
Tablet200 mg
Tablet, effervescentOral325 mg
Capsule, liquid filledOral325 mg
Suppository500 MG
Tablet, coated10 mg
Tablet, delayed releaseOral650 mg/1
Tablet, delayed releaseOral500 mg/1
LiquidOral500 mg/5mL
TabletOral500 mg/1
Tablet, orally disintegratingOral
Capsule, gelatin coatedOral500 mg/1
SuspensionOral500 mg/15mL
Capsule, liquid filledOral500 mg/1
SuppositoryRectal80 mg/1
Tablet, film coatedOral250 mg
Powder, for suspensionOral
GranuleOral
GranuleOral500.25 mg
SyrupOral160 mg
LiquidOral675 mg/675mL
Capsule, coatedOral500 mg/1
PowderOral
LiquidOral1000 mg/60mL
Capsule, coatedOral
PowderOral250 mg
PowderOral10 mg
PowderOral11 mg
CapsuleOral250 mg
Tablet, film coatedOral650 mg
PowderParenteral600 mg
Tablet, film coatedTopical
SuspensionOral
Kit; powderOral
Injection
Suspension
Syrup
ElixirOral
TabletOral
Injection, solutionIntravenous
Tablet, coatedOral75 mg
SuspensionOral200 mg/2mL
SuspensionOral160 mg/1.6mL
Solution / dropsOral80 mg/0.8mL
Solution / drops15 ml
Tablet, chewableOral160 mg/1
Tablet, orally disintegratingOral160 mg/1
TabletOral160 mg/1
SyrupOral120 mg
Tablet, effervescent120 mg
Capsule, delayed release pelletsOral
Tablet, film coatedOral200 mg
LiquidOral.8 mL/1mL
Tablet, effervescentOral8 mg
SyrupOral
Granule1000 MG
Tablet325 mg
Tablet650 mg
Tablet, film coated, extended releaseOral650 mg/1
SolutionOral6.5 g
SolutionOral3.2 g
Tablet, chewableOral80 mg/1
PowderNot applicable1 kg/1kg
Tablet, coatedOral250 mg
CapsuleOral
Capsule, liquid filledOral
Solution100 ml
TabletOral500 1/1
Powder, for solutionOral500 mg
PowderOral500 mg
Tablet, multilayerOral
Powder, for solutionOral0.5 g
Powder, for solutionOral325 mg
SolutionOral3200 mg
Injection, solutionIntravenous10 mg/1mL
Granule, effervescentOral500 mg
Granule, for solutionOral
SyrupOral6.5 g
Tablet, coatedOral30 mg
SuspensionOral160 mg
SuspensionOral160 mg/5mL
Tablet, coatedOral
Tablet, effervescentOral
Tablet, coated500 mg
Tablet, film coated500 mg
CapsuleOral
Suspension100 ml
Tablet
Injection, solutionIntravenous10 mg/ml
SolutionIntravenous10 mg
Powder
Solution
Tablet, effervescentOral500 MG
SolutionOral40 mg/ml
SolutionOral200 mg/5mL
SolutionOral
Tablet250 MG
Tablet, coated1000 MG
Suppository150 MG
Suppository300 MG
Suppository600 MG
SolutionIntravenous500 mg
SolutionIntravenous1000 mg
Injection10 mg/ml
LiquidOral80 mg/0.8mL
SyrupOral250 g
Liquid; solution / dropsOral
Solution / dropsOral
Suspension120 mg/5ml
Suspension250 mg/5ml
Injection, solution10 MG/ML
Syrup150 ml
Syrup2.4 G/100ML
Tablet, chewableOral
TabletOral650 mg/1
Tablet, film coatedOral
SyrupOral80 mg/0.8mL
Tablet, film coatedOral325 mg/1
Tablet, coatedOral325 mg
LiquidOral
Tablet, coated150 mg
SolutionOral120 MG/5ML
Syrup120 mg
Syrup120 mg/5ml
TabletOral750 mg/1
TabletOral325 mg
TabletOral350 mg
TabletOral500 mg/583mg
Tablet, film coated10 mg
SolutionIntravenous1 g
Granule125 MG
Granule500 MG
Granule, for solutionOral1000 MG
Solution / dropsOral100 MG/ML
Tablet0.5 gr
Solution / drops30 ml
LiquidOral100 mg/1mL
Suppository100 mg
Tablet, coatedOral350 mg
Tablet, film coatedOral325 mg
TabletOral37.5 mg
KitOral
SolutionIntramuscular; Intravenous300 mg
Tablet, coatedOral277.77 mg
SyrupOral160 mg/5mL
Tablet, extended releaseOral
Tablet, film coatedOral650 mg/1
Tablet, extended releaseOral
SolutionOral500 mg/15mL
LiquidOral500 mg/15mL
PowderOral500 mg/0.95g
Tablet, coatedOral500 mg/1
Capsule, liquid filledOral325 mg/1
Tablet, delayed releaseOral1000 mg/1
Tablet, delayed releaseOral
Suppository120 mg
Suppository240 mg
Powder, for solution400 mg
SuspensionOral1000 mg/1
Powder, for solutionOral
SyrupOral3000 mg
Tablet, effervescent500 mg
SyrupOral12.5 mg/30mL
SuppositoryRectal500 mg
Injection, solution, concentrateIntravenous10 mg/ml
Tablet, film coatedOral37.5 mg
SyrupOral6500 mg
LiquidOral
Capsule, liquid filledOral250 mg
Prices
Unit descriptionCostUnit
Tylenol 100 325 mg tablet Bottle16.98USD bottle
Phrenilin Forte 50-650 mg capsule5.24USD capsule
Phrenilin forte capsule4.46USD capsule
Norco 7.5-325 tablet2.77USD tablet
Norco 10-325 tablet2.76USD tablet
Propoxyphen-apap 100-325 mg tablet2.66USD tablet
Darvocet-N 100 100-650 mg tablet2.33USD tablet
Norco 10-325 mg tablet2.14USD tablet
Ultracet 37.5-325 mg tablet1.95USD tablet
Propoxyphen-apap 100-500 mg tablet1.85USD tablet
Ultracet tablet1.79USD tablet
Darvocet-n 100 tablet1.72USD tablet
Tylenol with Codeine #4 300-60 mg tablet1.65USD tablet
Phrenilin 50-325 mg tablet1.63USD tablet
Norco 7.5-325 mg tablet1.61USD tablet
Darvocet a500 tablet1.5USD tablet
Norco 5-325 mg tablet1.43USD tablet
Darvocet A500 100-500 mg tablet1.38USD tablet
Phrenilin tablet1.32USD tablet
Norco 5-325 tablet1.19USD tablet
Darvocet-n 50 tablet1.14USD tablet
Hydrocodone-apap 10-750 tablet1.12USD tablet
Tylenol with Codeine #3 300-30 mg tablet1.1USD tablet
Tencon tablet1.01USD tablet
Hydrocodone-apap 7.5-650 tablet0.93USD tablet
Propoxyphene-apap 50-325 mg tablet0.93USD tablet
Co-gesic 5-500 tablet0.92USD each
Sedapap 50-650 mg tablet0.92USD tablet
Clemastine fum 2.68 mg tablet0.86USD tablet
Feverall 120 mg suppository0.8USD suppository
Feverall 325 mg suppository0.8USD suppository
Feverall 80 mg suppository0.8USD suppository
Tavist nd 10 mg tablet0.74USD tablet
Darvocet-N 50 50-325 mg tablet0.73USD tablet
Hydrocodone-apap 10-325 tablet0.7USD tablet
Hydrocodone-apap 7.5-325 tablet0.62USD tablet
Hydrocodone-apap 10-660 tablet0.61USD tablet
Acephen 650 mg suppository0.55USD suppository
Propoxyphen-apap 100-650 mg tablet0.55USD tablet
Acephen 120 mg suppository0.54USD suppository
Acephen 325 mg suppository0.54USD suppository
Hydrocodone-apap 5-325 tablet0.54USD tablet
Hydrocodone-apap 10-500 tablet0.53USD tablet
Tavist-1 1.34 mg tablet0.5USD tablet
Acetaminophen 325 mg suppository0.44USD suppository
Feverall 650 mg suppository0.43USD suppository
Drixoral cold & allergy tablet sa0.4USD tablet
Acetaminophen 650 mg suppository0.39USD suppository
Acetaminophen 120 mg suppository0.38USD suppository
Apap-butalbital 325-50 tablet0.38USD tablet
Hydrocodone-apap 10-650 tablet0.37USD each
Hydrocodone-apap 2.5-500 tablet0.33USD tablet
Tylenol flu max-strn gelcap0.24USD capsule
Momentum caplet0.23USD caplet
Tylenol cold gelcap0.23USD capsule
Tylenol cold head congestion0.23USD each
Tylenol cold multi-symp gelcap0.23USD capsule
Tylenol allergy m-s caplet0.22USD caplet
Tylenol cold multi-symptom caplet0.22USD caplet
Tylenol cold head cong caplet0.21USD caplet
Tylenol cold multi-symp caplet0.21USD caplet
Tylenol cold severe congestion0.21USD each
Tylenol sinus caplet0.21USD caplet
Excedrin quicktabs0.2USD tablet
Tylenol allergy m-s night caplet0.2USD caplet
Tylenol chest congestion caplet0.2USD caplet
Tylenol cold head congest caplet0.2USD caplet
Tylenol sinus congestion&pain0.2USD each
Excedrin menstrual cmplt gelcap0.19USD capsule
Jr. tylenol 160 mg meltaways0.19USD each
Tylenol allergy complete caplet0.19USD caplet
Tylenol allergy complete gelcap0.19USD capsule
Tylenol allergy sinus gelcap0.19USD capsule
Tylenol allergy sinus geltab0.19USD tablet
Tylenol flu nighttime gelcap0.19USD capsule
Tylenol sinus congest-pain caplet0.19USD caplet
Tylenol sinus gelcap0.19USD capsule
Tylenol sinus geltab0.19USD tablet
Tylenol sinus nighttime caplet0.19USD caplet
Tylenol arthritis geltab0.18USD tablet
Child tylenol cold/cough tablet0.17USD tablet
Childrens apap 80 mg tablet chew0.17USD tablet
Tavist max-str sinus caplet0.17USD caplet
Tylenol allergy sinus caplet0.17USD caplet
Tylenol cold caplet0.17USD caplet
Tylenol severe allergy caplet0.17USD caplet
Tylenol allergy multi-symptom0.16USD each
Tylenol cold relief nightime0.16USD each
Tylenol pm ex-strength gelcap0.16USD capsule
Women's tylenol 500-25 capsule0.16USD capsule
Excedrin migraine geltabs0.15USD tablet
Tylenol cold relief caplet0.15USD caplet
Excedrin extra strength caplet0.14USD caplet
Excedrin migraine caplet0.14USD caplet
Excedrin sinus headache tablet0.14USD tablet
Excedrin tension headache tablet0.14USD tablet
Hydrocodone-apap 7.5-750 tablet0.13USD tablet
Tylenol arthritis caplet sa0.13USD caplet
Tylenol ex-str 500 mg tablet0.13USD tablet
Acetaminophen 650 mg caplet0.12USD caplet
Apap jr str 160 mg tablet chew0.12USD tablet
Hydrocodone-apap 7.5-500 tablet0.12USD tablet
Tylenol day & night value pack0.12USD each
Acetaminophen 500 mg geltab0.11USD tablet
Acetaminophen 500 mg tablet0.11USD tablet
Child's tylenol 80 mg meltaway0.11USD each
Eql pain relief 500 mg caplet0.1USD caplet
Eql pain relief 500 mg geltab0.1USD tablet
Excedrin back & body caplet0.1USD caplet
Excedrin sinus headache caplet0.1USD caplet
Excedrin tension headache caplet0.1USD caplet
Soba pain rel 500 mg gelcap0.1USD capsule
Tylenol 8 hour 650 mg caplet0.1USD caplet
Tylenol p.m. ex-str geltab0.1USD tablet
Tylenol pm ex-strength caplet0.1USD caplet
Acetaminophen 160 mg tablet chw0.09USD tablet
Pain reliever 500 mg caplet0.09USD caplet
Tylenol ex-str 500 mg geltab0.09USD tablet
Acetaminophen pm caplet0.08USD caplet
Excedrin pm 500-38 mg tablet0.08USD tablet
Pain reliever 160 mg tablet0.08USD tablet
Tylenol es for arthritis pain0.08USD each
Tylenol ex-str 500 mg caplet0.08USD caplet
Tylenol pm ex-strength geltab0.08USD tablet
Acetaminophen 80 mg tablet chew0.07USD tablet
Acetaminophen powder dense0.07USD g
Apap 325 mg tablet0.07USD tablet
Apap child's 80 mg tablet chew0.07USD tablet
Soba pain rel xs 500 mg tablet0.07USD tablet
Tylenol 325 mg tablet0.07USD tablet
Acetaminophen 500 mg gelcap0.06USD tablet
CVS Pharmacy non-aspirin 500 mg caplet0.06USD caplet
CVS Pharmacy non-aspirin 500 mg tablet0.06USD tablet
CVS Pharmacy pain relief 500 mg gelcap0.06USD capsule
CVS Pharmacy pain rlf cool ice caplet0.06USD caplet
Eql pain relief 325 mg tablet0.06USD tablet
Pain relief 500 mg caplet0.06USD caplet
Pain reliever 325 mg tablet0.06USD tablet
Soba pain reliever 500 mg tablet0.06USD tablet
Child tylenol cough-runny nose0.05USD ml
Child tylenol cough-sore thrt0.05USD ml
Childs tylenol cold-cough susp0.05USD ml
Mapap 325 mg tablet0.05USD tablet
Non-aspirin 500 mg geltab0.05USD tablet
Pain relief without asa tablet0.05USD tablet
Tylenol ex-str 500 mg gelcap0.05USD capsule
Childs tylenol cold-aller susp0.04USD ml
Childs tylenol plus cold susp0.04USD ml
Childs tylenol plus flu susp0.04USD ml
CVS Pharmacy acetaminophen 325 mg tablet0.04USD tablet
Non-aspirin 500 mg tablet0.04USD tablet
Pain reliever 500 mg geltab0.04USD tablet
Q-pap ex-str 500 mg tablet0.04USD tablet
Ra acetaminophen pm caplet0.04USD caplet
Acetaminophen 325 mg tablet0.03USD tablet
Acetaminophen 500 mg caplet0.03USD caplet
Genapap 325 mg tablet0.03USD tablet
Genapap 500 mg tablet0.03USD tablet
Pain relief 500 mg tablet0.03USD each
Pain reliever 500 mg gelcap0.03USD capsule
Pain reliever 500 mg tablet0.03USD tablet
Pain relief 325 mg tablet0.02USD tablet
Pain reliever w-o asa 325 mg0.02USD each
Tylenol cold & flu severe liq0.02USD ml
Tylenol cold m-s severe day liquid0.02USD ml
Tylenol cough & sore throat lq0.02USD ml
Tylenol nighttime liquid0.02USD ml
Tylenol pm liquid0.02USD ml
Tylenol sore throat liquid0.02USD ml
Maxapap 325 mg tablet0.01USD tablet
Maxapap 500 mg caplet0.01USD each
Maxapap 500 mg tablet0.01USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
USRE39221No2006-08-012011-08-09US flag
US5972916No1999-10-262017-07-14US flag
US6488962No2002-12-032020-06-20US flag
US6028222Yes2000-02-222018-02-05US flag
US6992218Yes2006-01-312021-12-06US flag
US8372432No2013-02-122029-03-11US flag
US8668929No2014-03-112029-03-11US flag
US8377453No2013-02-192029-11-19US flag
US7976870No2011-07-122027-06-01US flag
US8741885No2014-06-032032-05-16US flag
US8992975No2015-03-312032-05-16US flag
US8597681No2013-12-032030-12-21US flag
US8980319No2015-03-172030-12-21US flag
US8394408No2013-03-122029-03-11US flag
US9050335No2015-06-092032-05-16US flag
US8658631No2014-02-252032-05-16US flag
US9399012Yes2016-07-262032-03-11US flag
US9610265Yes2017-04-042029-05-13US flag
US9468636No2016-10-182032-05-16US flag
US9132125No2015-09-152030-07-01US flag
US8828978No2014-09-092030-07-01US flag
US9549923No2017-01-242030-07-01US flag
US8748413No2014-06-102030-07-01US flag
US8461137No2013-06-112031-02-22US flag
US9987238Yes2018-06-052029-05-13US flag
US10383834No2019-08-202028-11-13US flag
US8741959No2014-06-032030-04-19US flag
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)170MSDS
boiling point (°C)>500http://www.inchem.org/documents/icsc/icsc/eics1330.htm
water solubilityvery slightly soluble in cold water but greater solubility in hot waterhttp://www.inchem.org/documents/pims/pharm/pim396.htm
logP0.91http://www.t3db.ca/toxins/T3D2571
logS-1.6http://www.t3db.ca/toxins/T3D2571
pKa-4.4 (strongest basic)http://www.t3db.ca/toxins/T3D2571
Predicted Properties
PropertyValueSource
Water Solubility4.15 mg/mLALOGPS
logP0.51ALOGPS
logP0.91ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)9.46ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.33 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity42.9 m3·mol-1ChemAxon
Polarizability15.52 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9921
Blood Brain Barrier+0.9544
Caco-2 permeable+0.8285
P-glycoprotein substrateNon-substrate0.8202
P-glycoprotein inhibitor INon-inhibitor0.982
P-glycoprotein inhibitor IINon-inhibitor0.9781
Renal organic cation transporterNon-inhibitor0.9292
CYP450 2C9 substrateNon-substrate0.7259
CYP450 2D6 substrateSubstrate0.8918
CYP450 3A4 substrateNon-substrate0.5554
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9755
CYP450 2C19 inhibitorNon-inhibitor0.9161
CYP450 3A4 inhibitorNon-inhibitor0.8496
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8842
Ames testNon AMES toxic0.8767
CarcinogenicityNon-carcinogens0.7654
BiodegradationReady biodegradable0.6342
Rat acute toxicity1.8596 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9717
hERG inhibition (predictor II)Non-inhibitor0.9597
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (7.63 KB)
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-0a4i-4971200000-17e6e1373f10ba4ec138
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0a4i-1900000000-df97f74a81da3a46a697
GC-MS Spectrum - EI-BGC-MSsplash10-0a4i-4900000000-ef277124e1b50b5f010e
GC-MS Spectrum - CI-BGC-MSsplash10-0udi-0900000000-7aa6a54b74b345d91e37
GC-MS Spectrum - GC-MSGC-MSsplash10-0a4i-4971200000-17e6e1373f10ba4ec138
Mass Spectrum (Electron Ionization)MSsplash10-0a4i-4900000000-ffdd0f8a1e6e450fc162
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-0w29-3900000000-97741eddc3be9c7eaea8
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-0ik9-1900000000-1ddd59340d1db920fa66
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-00kf-9000000000-148fa91ce08e13165712
MS/MS Spectrum - EI-B (HITACHI M-80) , PositiveLC-MS/MSsplash10-0a4i-1900000000-5997c3f6cdebc5326b65
MS/MS Spectrum - EI-B (Unknown) , PositiveLC-MS/MSsplash10-0a4i-4900000000-ef277124e1b50b5f010e
MS/MS Spectrum - CI-B (Unknown) , PositiveLC-MS/MSsplash10-0udi-0900000000-7aa6a54b74b345d91e37
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0zfr-0900000000-125e44ce332576a1e155
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0udi-0900000000-7e46df4b4b653c90c258
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0udi-0900000000-bb6e34d2d574a249d721
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0udi-0900000000-2f45dd7efce38361f806
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0pb9-0900000000-e48b48d64b6b985ab455
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0a4i-0900000000-b72b0e33fd35512fe6de
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0a4i-0900000000-97bcaa95f26159307d03
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0udi-0900000000-c50b4b79792e2c2e68f9
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0udi-0900000000-7e46df4b4b653c90c258
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0udi-0900000000-2b07cd2813d3f23e88f1
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0pb9-0900000000-5b92f09589afe838f23a
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0a4i-0900000000-f0ca5ff6526b9f005034
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0udi-0900000000-7e45ef71674dcdde9068
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0w29-1900000000-38d21a339e82f461beac
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-0900000000-d953f92b362e4b262210
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-0900000000-3170dca3f927500ea230
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-0900000000-f835e92fb0bae0c7b8bc
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0w29-0900000000-4e01c7ff07665fcdb218
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03di-0900000000-a3c279c288bb690496b3
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03di-2900000000-4435e0230105d5d28a94
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03di-6900000000-76671cc7ad1df1b5983d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-0900000000-9895c5f2b10912092523
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-0900000000-d73797c93a4ef79ea79e
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0w29-0900000000-22d62a7732ed3d99e87d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03di-0900000000-c652f4f179daa6465678
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03di-2900000000-0e7e745540d8ec7b99f4
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03di-6900000000-2a4263b38fa30bc64dd0
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0w29-0900000000-cf0ac615ec636ce7a253
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-03di-0900000000-428d8023ee5761fed84c
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03di-0900000000-ed26fb95b6aea6986085
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03di-1900000000-5b942e17f1e66a3832b8
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03di-0900000000-d6a7498b8d87d4e00028
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03di-0900000000-9ff40d4cd8c0f46836c2
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0w29-0900000000-fcf8e62537bd6db11b3a
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0w29-0900000000-c27e8f1522f41492aae3
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Unfolded protein binding
Specific Function
Cytosolic prostaglandin synthase that catalyzes the oxidoreduction of prostaglandin endoperoxide H2 (PGH2) to prostaglandin E2 (PGE2) (PubMed:10922363). Molecular chaperone that localizes to genomi...
Gene Name
PTGES3
Uniprot ID
Q15185
Uniprot Name
Prostaglandin E synthase 3
Molecular Weight
18697.195 Da
References
  1. 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. [PubMed:15626590]
  2. 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. [PubMed:12242329]
  3. Data sheet, Acetaminophen, ebi.ac.uk [File]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and...
Gene Name
PTGS2
Uniprot ID
P35354
Uniprot Name
Prostaglandin G/H synthase 2
Molecular Weight
68995.625 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  2. 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. [PubMed:17175104]
  3. 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. [PubMed:17884974]
  4. 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. [PubMed:17322116]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gas...
Gene Name
PTGS1
Uniprot ID
P23219
Uniprot Name
Prostaglandin G/H synthase 1
Molecular Weight
68685.82 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  2. 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. [PubMed:17884974]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Activator
General Function
Transmembrane signaling receptor activity
Specific 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 aci...
Gene Name
TRPV1
Uniprot ID
Q8NER1
Uniprot Name
Transient receptor potential cation channel subfamily V member 1
Molecular Weight
94955.33 Da
References
  1. 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. [PubMed:15987694]
  2. 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. [PubMed:20862299]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
Gene Name
CYP2E1
Uniprot ID
P05181
Uniprot Name
Cytochrome P450 2E1
Molecular Weight
56848.42 Da
References
  1. 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. [PubMed:11095574]
  2. 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. [PubMed:10741631]
  3. Flockhart Table of Drug Interactions [Link]
  4. Acetaminophen FDA label [File]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. 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. [PubMed:2729995]
  2. 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. [PubMed:8374050]
  3. 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. [PubMed:7956731]
  4. 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. [PubMed:8474022]
  5. 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. [PubMed:26049587]
  6. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inducer
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. 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. [PubMed:11811955]
  2. 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. [PubMed:28872689]
  3. 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 . [PubMed:19219744]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. 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. [PubMed:11095574]
  2. 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. [PubMed:28872689]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific 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. Const...
Gene Name
CYP2A6
Uniprot ID
P11509
Uniprot Name
Cytochrome P450 2A6
Molecular Weight
56501.005 Da
References
  1. 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. [PubMed:28872689]
  2. 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. [PubMed:27147854]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Protein homodimerization activity
Specific 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 trans...
Gene Name
UGT1A6
Uniprot ID
P19224
Uniprot Name
UDP-glucuronosyltransferase 1-6
Molecular Weight
60750.215 Da
References
  1. 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. [PubMed:11714888]
  2. 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. [PubMed:15284531]
  3. 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. [PubMed:21666065]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...
Gene Name
UGT1A1
Uniprot ID
P22309
Uniprot Name
UDP-glucuronosyltransferase 1-1
Molecular Weight
59590.91 Da
References
  1. 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. [PubMed:8494539]
  2. 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. [PubMed:17164591]
  3. 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. [PubMed:28932176]
  4. 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. [PubMed:11714888]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Retinoic acid binding
Specific 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 2 lacks trans...
Gene Name
UGT1A9
Uniprot ID
O60656
Uniprot Name
UDP-glucuronosyltransferase 1-9
Molecular Weight
59940.495 Da
References
  1. 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. [PubMed:11714888]
  2. 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. [PubMed:29654492]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Glucuronosyltransferase activity
Specific Function
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme displays activity toward several classes of xeno...
Gene Name
UGT2B15
Uniprot ID
P54855
Uniprot Name
UDP-glucuronosyltransferase 2B15
Molecular Weight
61035.815 Da
References
  1. 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. [PubMed:21666065]
  2. 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. [PubMed:16696573]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Sulfotransferase activity
Specific Function
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of catecholamines, phenolic drugs and neurotransmitters. Has also estroge...
Gene Name
SULT1A1
Uniprot ID
P50225
Uniprot Name
Sulfotransferase 1A1
Molecular Weight
34165.13 Da
References
  1. 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. [PubMed:18232020]
  2. 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. [PubMed:26067475]
  3. 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. [PubMed:29398597]
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
  1. 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. [PubMed:18232020]
  2. 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. [PubMed:26067475]
  3. 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. [PubMed:29705271]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Arylamine n-acetyltransferase activity
Specific Function
Participates in the detoxification of a plethora of hydrazine and arylamine drugs. Catalyzes the N- or O-acetylation of various arylamine and heterocyclic amine substrates and is able to bioactivat...
Gene Name
NAT2
Uniprot ID
P11245
Uniprot Name
Arylamine N-acetyltransferase 2
Molecular Weight
33542.235 Da
References
  1. 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. [PubMed:9918139]
  2. 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. [PubMed:26519524]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Fatty acid amide hydrolase activity
Specific Function
Degrades bioactive fatty acid amides like oleamide, the endogenous cannabinoid, anandamide and myristic amide to their corresponding acids, thereby serving to terminate the signaling functions of t...
Gene Name
FAAH
Uniprot ID
O00519
Uniprot Name
Fatty-acid amide hydrolase 1
Molecular Weight
63065.28 Da
References
  1. 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. [PubMed:15987694]
  2. 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. [PubMed:22750843]
  3. 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. [PubMed:17227290]
  4. 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. [PubMed:27110534]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
S-nitrosoglutathione binding
Specific Function
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. Regulates negatively CDK5 activity via p25/p35 translocation to prevent neurodegeneration.
Gene Name
GSTP1
Uniprot ID
P09211
Uniprot Name
Glutathione S-transferase P
Molecular Weight
23355.625 Da
References
  1. 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. [PubMed:21639118]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Protein homodimerization activity
Specific Function
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
Gene Name
GSTM1
Uniprot ID
P09488
Uniprot Name
Glutathione S-transferase Mu 1
Molecular Weight
25711.555 Da
References
  1. 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. [PubMed:22687999]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. 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. [PubMed:6491906]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. 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. [PubMed:11743742]
  2. 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. [PubMed:12954186]
  3. 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. [PubMed:23897240]
  4. 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. [PubMed:16930294]

Drug created on June 13, 2005 07:24 / Updated on September 19, 2020 16:48

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