Naproxen

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Identification

Summary

Naproxen is an NSAID used to treat rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, polyarticular juvenile idiopathic arthritis, tendinitis, bursitis, acute gout, primary dysmenorrhea, and mild to moderate pain.

Brand Names

Aleve, Aleve PM, Aleve-D, Anaprox, Naprelan, Naprosyn, Sallus, Sudafed Sinus & Pain, Treximet, Vimovo

Generic Name

Naproxen

DrugBank Accession Number

DB00788

Background

Naproxen is classified as a nonsteroidal anti-inflammatory dug (NSAID) and was initially approved for prescription use in 1976 and then for over-the-counter (OTC) use in 1994.³ It can effectively manage acute pain as well as pain related to rheumatic diseases, and has a well studied adverse effect profile.⁵ Given its overall tolerability and effectiveness, naproxen can be considered a first line treatment for a variety of clinical situations requiring analgesia.⁵ Naproxen is available in both immediate and delayed release formulations, in combination with sumatriptan to treat migraines, and in combination with esomeprazole to lower the risk of developing gastric ulcers.^12131516

Type

Small Molecule

Groups

Approved, Vet approved

Structure

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Naproxen (DB00788)

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Weight

Average: 230.2592
Monoisotopic: 230.094294314

Chemical Formula

C₁₄H₁₄O₃

Synonyms

• (+)-(S)-6-Methoxy-α-methyl-2-naphthaleneacetic acid
• (+)-(S)-Naproxen
• (+)-2-(6-Methoxy-2-naphthyl)propionic acid
• (+)-2-(Methoxy-2-naphthyl)-propionic acid
• (+)-2-(Methoxy-2-naphthyl)-propionsäure
• (+)-Naproxen
• (S)-(+)-2-(6-Methoxy-2-naphthyl)propionic acid
• (S)-(+)-Naproxen
• (S)-2-(6-Methoxy-2-naphthyl)propanoic acid
• (S)-2-(6-Methoxy-2-naphthyl)propionic acid
• (S)-6-Methoxy-alpha-methyl-2-naphthaleneacetic acid
• (S)-Naproxen
• Naprolag
• Naproxen
• Naproxène
• Naproxeno
• Naproxenum

External IDs

• RS 3540
• RS 3650
• RS-3540

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Pharmacology

Indication

Naproxen is indicated for the management of rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, polyarticular juvenile idiopathic arthritis, tendinitis, bursitis, acute gout, primary dysmenorrhea, and for the relief of mild to moderate pain.¹²¹³³ Further, it is first-line therapy for osteoarthritis, acute gouty arthritis, dysmenorrhea, and musculoskeletal inflammation and pain.³

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Symptomatic treatment of	Acute gouty arthritis		••••••••••••			••••••• •••••••• ••••••• ••••••• ••••••• •••• ••••••
Treatment of	Acute migraine		••• •••••
Used in combination to treat	Acute migraine	Combination Product in combination with: Sumatriptan (DB00669)	••••••••••••
Used in combination for symptomatic treatment of	Ankylosing spondylitis	Combination Product in combination with: Esomeprazole (DB00736)	••••••••••••	•••••
Symptomatic treatment of	Ankylosing spondylitis		••••••••••••			••••••• ••••••• •••••••• ••••••• •••••••• ••••••• ••••••• ••••••• •••• ••••••

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Pharmacodynamics

Naproxen is an established non-selective NSAID and is useful as an analgesic, anti-inflammatory and antipyretic.⁵ Similar to other NSAIDs, the pharmacological activity of naproxen can be attributed to the inhibition of cyclo-oxygenase, which in turn reduces prostaglandin synthesis in various tissues and fluids including the synovial fluid, gastric mucosa, and the blood.⁵

Although naproxen is an effective analgesic, it can have unintended deleterious effects in the patient. For instance, naproxen can adversely affect blood pressure control.¹⁰ A study found that use of naproxen induced an increase in blood pressure, although the increase was not as significant as that found with ibuprofen use.¹⁰

Further, studies have found that the risk of upper gastrointestinal bleeding is on average four-fold higher for individuals taking NSAIDs.¹¹ Other factors that increase the risk of upper gastrointestinal bleeding include concurrent use of corticosteroids or anticoagulants, and a history of gastrointestinal ulcers.¹¹

Mechanism of action

As with other non-selective NSAIDs, naproxen exerts it's clinical effects by blocking COX-1 and COX-2 enzymes leading to decreased prostaglandin synthesis.³ Although both enzymes contribute to prostaglandin production, they have unique functional differences.³ The COX-1 enzymes is constitutively active and can be found in normal tissues such as the stomach lining, while the COX-2 enzyme is inducible and produces prostaglandins that mediate pain, fever and inflammation.⁴ The COX-2 enzyme mediates the desired antipyretic, analgesic and anti-inflammatory properties offered by Naproxen, while undesired adverse effects such as gastrointestinal upset and renal toxicities are linked to the COX-1 enzyme.⁴

Target	Actions	Organism
APancreatic triacylglycerol lipase	inhibitor	Humans
AProstaglandin G/H synthase 1	inhibitor	Humans
AProstaglandin G/H synthase 2	inhibitor	Humans
UPeptostreptococcal albumin-binding protein	Not Available	Peptostreptococcus magnus

Absorption

Naproxen is available as a free acid and sodium salt.⁵ At comparable doses, (naproxen 500 mg = naproxen sodium 550 mg) they differ slightly in their rates of absorption, but otherwise they are therapeutically and pharmacologically equivalent.⁵ Naproxen sodium achieves a peak plasma concentration after 1 hour, while peak plasma concentration is observed after 2 hours with naproxen (free acid).⁵ There are no differences between the 2 forms in the post-absorption phase pharmacokinetics.⁵ The difference in initial absorption should be considered when treating acute pain, since naproxen sodium may offer a quicker onset of action.⁵

The mean Cmax for the various formulations (immediate release, enteric coated, controlled release etc.) of naproxen are comparable and range from 94 mcg/mL to 97.4 mcg/mL.¹²¹³ In one pharmacokinetic study, the mean Tmax of naproxen 500 mg (immediate release) given every 12 hours over 5 days was 3 hours, compared to a mean Tmax of 5 hours for Naprelan 1000 mg (controlled release) given every 24 hours over 5 days.¹² In this same study, the AUC_0-24hr was 1446mcgxhr/mL for naproxen immediate release and 1448 mcgxhr/mL for the controlled release formulation.¹² A separate study comparing the pharmacokinetics of Naprosyn tablets and EC-Naprosyn observed the following values: Tmax and AUC_0-12hrs of EC-Naprosyn were 4 hours and 845 mcgxhr/mL respectively, and Tmax and AUC_0-12hrs values of Naprosyn were 1.9 hours and 767 mcgxhr/mL respectively.¹³

When given in combination with sumatriptan the Cmax of naproxen is roughly 36% lower compared to naproxen sodium 550 mg tablets, and the median Tmax is 5 hours.¹⁵

Based on the AUC and Cmax of naproxen, Vimovo (naproxen/esomeprazole combination product) and enteric-coated naproxen may be considered bioequivalent.¹⁶

Overall, naproxen is rapidly and completely absorbed when administered orally and rectally.⁶⁵ Food may contribute to a delay in the absorption of orally administered naproxen, but will not affect the extent of absorption.⁵

Volume of distribution

Naproxen has a volume of distribution of 0.16 L/kg.¹²¹³

Protein binding

Naproxen is highly protein bound with >99% of the drug bound to albumin at therapeutic levels.¹²¹³

Metabolism

Naproxen is heavily metabolized in the liver and undergoes both Phase I and Phase II metabolism.¹²¹³⁷ The first step involves demethylation of naproxen via CYP 1A2, 2C8, and 2C9⁸⁹. Both naproxen and desmethylnaproxen proceed to Phase II metabolism; however, desmethylnaproxen can form both acyl and phenolic glucoronide products, while naproxen only produces the acyl glucuronide.⁸⁷ The acyl glucuronidation process involves UGT 1A1, 1A3, 1A6, 1A7, 1A9, 1A10 and 2B7, while phenolic glucuronidation is catalyzed by UGT 1A1, 1A7,1A9, and 1A10.⁸ Desmethylnaproxen also undergoes sulphation which is mediated by SULT 1A1, 1B1 and 1E1.⁷

Hover over products below to view reaction partners

• Naproxen
  • O-Desmethylnaproxen
    • O-Desmethylnaproxen O-glucuronide
    • O-Desmethylnaproxen acyl glucuronide
    • O-Desmethylnaproxen sulfate
  • Naproxen O-glucuronide

Route of elimination

After oral administration, about 95% of naproxen and it's metabolites can be recovered in the urine with 66-92% recovered as conjugated metabolite and less than 1% recovered as naproxen or desmethylnaproxen.⁷¹²¹³ Less than 5% of naproxen is excreted in the feces.¹²¹³

Half-life

The elimination half-life of naproxen is reported to be 12-17 hours.³¹³

Clearance

Naproxen is cleared at a rate of 0.13 mL/min/kg.¹²¹³

Adverse Effects

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Toxicity

Although the over-the-counter (OTC) availability of naproxen provides convenience to patients, it also increases the likelihood of overdose.³ Thankfully, the extent of overdose is typically mild with adverse effects normally limited to drowsiness, lethargy, epigastric pain, nausea and vomiting.³¹²¹³ Although there is no antidote for naproxen overdose, symptoms will typically subside with appropriate supportive care.¹²¹³³

Naproxen is classified as Category B during the first 2 trimesters of pregnancy, and as Category D during the third trimester.¹⁴ Naproxen is contraindicated in the 3rd trimester since it increases the risk of premature closure of the fetal ductus arteriosus and should be avoided in pregnant women starting at 30 weeks gestation.¹²¹³

Pathways

Pathway	Category
Naproxen 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.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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Abacavir	Naproxen may decrease the excretion rate of Abacavir which could result in a higher serum level.
Abametapir	The serum concentration of Naproxen can be increased when it is combined with Abametapir.
Abatacept	The metabolism of Naproxen can be increased when combined with Abatacept.
Abciximab	The risk or severity of bleeding and hemorrhage can be increased when Naproxen is combined with Abciximab.
Abiraterone	The serum concentration of Naproxen can be increased when it is combined with Abiraterone.

Food Interactions

• Take with food. Food reduces GI irritation.

Products

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Naproxen sodium	9TN87S3A3C	26159-34-2	CDBRNDSHEYLDJV-FVGYRXGTSA-M

Product Images

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International/Other Brands

Alidase (Laboratorios) / Alpoxen (Actavis) / Alpron (Aldril) / Apain (Marvic) / Apranax (Roche) / Apronax (Bayer) / Bonyl (Orion) / Bruproxen (Bruluart) / Bumaflex N (Nycomed) / Congex (Buxton) / Debril (Monserrat) / Deproxen (Drug International) / Dysmenalgit (Krewel Meuselbach) / Emox (Emo-Farm) / Emoxen (EMO) / Eurogesic (Saval) / Fabralgina (Fabra) / Feminax Ultra (Bayer) / Flogotone (Interpharma) / Gerinap (Gerard) / Honlow (Panion & BF) / Improstan (Farmacoop) / Inflamax (Farmaceutica) / Inza (Alphapharm) / Iraxen (Quilab) / Jinkangpuli (Conba) / Lexinax (Brisafarma) / Melgar (Hexa) / Messelxen (Biomep) / Mobilat (STADA) / Naprometin (Roche) / Naprosyn CR (Abdi Ibrahim) / Naprosyn EC (Roche) / Naprosyn Entero (Roche) / Naprosyn SR (Roche) / Naprosyne (Roche) / Naproval (Labinco) / Naprux (Andromaco) / Neuralprona (Lba) / Noflam (Mylan) / Nopain (Medicef) / Prexan (New Research) / Priaxen (Remedica) / Princeps (Laser ) / Pronaxen (Orion) / Proxen (Grünenthal) / Proxen S (Roche) / Proxen SR (Roche) / Releve (General Pharma) / Repro (Doctor's Chemical Works) / Reuxen (Helcor) / Riproxen (BioGenet) / Sanaprox (Perumed) / Seladin (YSP) / Servinaprox (Novartis) / Tarproxen (Polfa Tarchomin) / Ticoflex (Incepta) / Tundra (Frasca) / Xenar (Elder) / Xenar-CR (Elder)

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Anaprox	Tablet	275 mg/1	Oral	Roche Laboratories Inc.	2006-05-17	2006-05-17
Anaprox	Tablet	275 mg	Oral	Atnahs Pharma Uk Limited	1995-12-31	Not applicable
Anaprox	Tablet	275 mg/1	Oral	Physicians Total Care, Inc.	1980-09-04	2011-06-30
Anaprox	Tablet	275 mg	Oral	Syntex Inc.	1980-12-31	1996-09-30
Anaprox DS	Tablet	550 mg/1	Oral	Canton Laboratories	2016-06-01	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
All Day Relief	Tablet	220 mg/1	Oral	Remedy Repack	2015-02-02	2017-03-10
Anaprox	Tablet	550 mg/1	Oral	Direct Rx	2016-07-11	Not applicable
Apo Naproxen Tab 125mg	Tablet	125 mg	Oral	Apotex Corporation	1982-12-31	Not applicable
Apo-napro-NA	Tablet	275 mg	Oral	Apotex Corporation	1989-12-31	Not applicable
Apo-napro-NA DS	Tablet	550 mg	Oral	Apotex Corporation	1993-12-31	Not applicable

Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
7 Select Naproxen Sodium	Tablet, film coated	220 mg/1	Oral	7 Eleven	2014-08-05	2016-06-19
7 Select Naproxen Sodium	Tablet, film coated	220 mg/1	Oral	7-Eleven	2014-08-11	2020-12-31
Aleve	Tablet	220 mg/1	Oral	Lil' Drug Store Products, Inc	2006-11-16	Not applicable
Aleve	Tablet	220 mg/1	Oral	R J General Corporation	2014-02-26	Not applicable
Aleve	Tablet	220 mg/1	Oral	Cardinal Health	1994-01-11	2011-03-31

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
AFLIXDOL® FORTE TABLETAS	Naproxen sodium (220 mg) + Acetaminophen (250 mg) + Caffeine (65 mg)	Tablet	Oral	COASPHARMA S.A.S. (PLANTA PALOQUEMAO)	2023-10-09	Not applicable
AINEDAP® FORTE	Naproxen sodium (550 mg) + Caffeine (65 mg)	Tablet, coated	Oral	QUIBI S.A. EN REESTRUCTURACION	2023-03-22	Not applicable
Aleve Nighttime	Naproxen sodium (220 mg) + Diphenhydramine hydrochloride (25 mg)	Tablet	Oral	Bayer	2016-02-24	Not applicable
Aleve PM	Naproxen sodium (220 mg/1) + Diphenhydramine hydrochloride (25 mg/1)	Tablet, film coated	Oral	Bayer Healthcare Llc.	2014-09-09	Not applicable
Aleve-D Sinus and Cold	Naproxen sodium (220 mg/1) + Pseudoephedrine hydrochloride (120 mg/1)	Tablet	Oral	Bayer Healthcare Llc.	2014-01-01	Not applicable

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Cold FAid	Naproxen sodium (220 mg/1) + Chlorpheniramine maleate (4 mg/1) + Phenylephrine hydrochloride (10 mg/1)	Kit	Oral	Cold FAid	2020-03-24	2022-03-31
Cold FAid	Naproxen sodium (220 mg/1) + Chlorpheniramine maleate (12 mg/1) + Phenylephrine hydrochloride (10 mg/1)	Kit	Oral	Cold FAid	2019-05-06	2021-01-31
Cold FAid	Naproxen sodium (220 mg/1) + Chlorpheniramine maleate (4 mg/1) + Phenylephrine hydrochloride (10 mg/1)	Kit	Oral	Cold FAid	2021-02-01	Not applicable
Equipto - Naproxen External Cream Compounding Kit	Naproxen (1 g/1g)	Kit	Topical	Alvix Laboratories	2015-01-20	2018-03-08
NaproPax	Naproxen (500 mg/1) + Capsaicin (0.0375 g/100g) + Menthol (5 1/100g)	Kit	Oral; Topical	Basiem	2015-08-30	2016-03-04

Categories

ATC Codes

M01AE02 — Naproxen

• M01AE — Propionic acid derivatives
• M01A — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS
• M01 — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
• M — MUSCULO-SKELETAL SYSTEM

M01AE57 — Naproxen and diphenhydramine

• M01AE — Propionic acid derivatives
• M01A — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS
• M01 — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
• M — MUSCULO-SKELETAL SYSTEM

G02CC02 — Naproxen

• G02CC — Antiinflammatory products for vaginal administration
• G02C — OTHER GYNECOLOGICALS
• G02 — OTHER GYNECOLOGICALS
• G — GENITO URINARY SYSTEM AND SEX HORMONES

M02AA12 — Naproxen

• M02AA — Antiinflammatory preparations, non-steroids for topical use
• M02A — TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN
• M02 — TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN
• M — MUSCULO-SKELETAL SYSTEM

M01AE56 — Naproxen and misoprostol

• M01AE — Propionic acid derivatives
• M01A — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS
• M01 — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
• M — MUSCULO-SKELETAL SYSTEM

M01AE52 — Naproxen and esomeprazole

• M01AE — Propionic acid derivatives
• M01A — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS
• M01 — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
• M — MUSCULO-SKELETAL SYSTEM

N02CC51 — Sumatriptan and naproxen

• N02CC — Selective serotonin (5HT1) agonists
• N02C — ANTIMIGRAINE PREPARATIONS
• N02 — ANALGESICS
• N — NERVOUS SYSTEM

Drug Categories

• Agents causing hyperkalemia
• Agents that produce hypertension
• Analgesics
• Analgesics, Non-Narcotic
• Anti-Inflammatory Agents
• Anti-Inflammatory Agents, Non-Steroidal
• Anti-Inflammatory Agents, Non-Steroidal (Non-Selective)
• Antigout Preparations
• Antiinflammatory and Antirheumatic Products
• Antiinflammatory and Antirheumatic Products, Non-Steroids
• Antiinflammatory Preparations, Non-Steroids for Topical Use
• Antiinflammatory Products for Vaginal Administration
• Antimigraine Preparations
• Antirheumatic Agents
• Arylpropionic acid NSAIDS
• BSEP/ABCB11 Substrates
• Central Nervous System Agents
• Cyclooxygenase Inhibitors
• Cytochrome P-450 CYP1A2 Substrates
• Cytochrome P-450 CYP2C8 Substrates
• Cytochrome P-450 CYP2C9 Substrates
• Cytochrome P-450 Substrates
• Drugs causing inadvertant photosensitivity
• Enzyme Inhibitors
• Genito Urinary System and Sex Hormones
• Musculo-Skeletal System
• Naphthaleneacetic Acids
• Naphthalenes
• Nephrotoxic agents
• Nervous System
• Non COX-2 selective NSAIDS
• OAT1/SLC22A6 inhibitors
• Other Nonsteroidal Anti-inflammatory Agents
• P-glycoprotein inhibitors
• Peripheral Nervous System Agents
• Photosensitizing Agents
• Propionates
• Sensory System Agents
• Topical Products for Joint and Muscular Pain
• UGT1A1 Substrates
• UGT1A3 substrates
• UGT1A6 substrate
• UGT1A9 Substrates
• UGT2B7 substrates

Chemical TaxonomyProvided by Classyfire

Description

This compound belongs to the class of organic compounds known as naphthalenes. These are compounds containing a naphthalene moiety, which consists of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Not Available

Direct Parent

Naphthalenes

Alternative Parents

Anisoles / Alkyl aryl ethers / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds

Substituents

Alkyl aryl ether / Anisole / Aromatic homopolycyclic compound / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Ether / Hydrocarbon derivative / Monocarboxylic acid or derivatives / Naphthalene

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

monocarboxylic acid, methoxynaphthalene (CHEBI:7476)

Affected organisms

• Humans and other mammals

Chemical Identifiers

UNII

57Y76R9ATQ

CAS number

22204-53-1

InChI Key

CMWTZPSULFXXJA-VIFPVBQESA-N

InChI

InChI=1S/C14H14O3/c1-9(14(15)16)10-3-4-12-8-13(17-2)6-5-11(12)7-10/h3-9H,1-2H3,(H,15,16)/t9-/m0/s1

IUPAC Name

(2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid

SMILES

COC1=CC2=C(C=C1)C=C(C=C2)[C@H](C)C(O)=O

References

Synthesis Reference

US4009197

General References

1. Kearney PM, Baigent C, Godwin J, Halls H, Emberson JR, Patrono C: Do selective cyclo-oxygenase-2 inhibitors and traditional non-steroidal anti-inflammatory drugs increase the risk of atherothrombosis? Meta-analysis of randomised trials. BMJ. 2006 Jun 3;332(7553):1302-8. [Article]
2. Zhang J, Ding EL, Song Y: Adverse effects of cyclooxygenase 2 inhibitors on renal and arrhythmia events: meta-analysis of randomized trials. JAMA. 2006 Oct 4;296(13):1619-32. Epub 2006 Sep 12. [Article]
3. Brutzkus JC, Varacallo M: Naproxen . [Article]
4. Wongrakpanich S, Wongrakpanich A, Melhado K, Rangaswami J: A Comprehensive Review of Non-Steroidal Anti-Inflammatory Drug Use in The Elderly. Aging Dis. 2018 Feb 1;9(1):143-150. doi: 10.14336/AD.2017.0306. eCollection 2018 Feb. [Article]
5. Todd PA, Clissold SP: Naproxen. A reappraisal of its pharmacology, and therapeutic use in rheumatic diseases and pain states. Drugs. 1990 Jul;40(1):91-137. doi: 10.2165/00003495-199040010-00006. [Article]
6. Davies NM, Anderson KE: Clinical pharmacokinetics of naproxen. Clin Pharmacokinet. 1997 Apr;32(4):268-93. doi: 10.2165/00003088-199732040-00002. [Article]
7. Falany CN, Strom P, Swedmark S: Sulphation of o-desmethylnaproxen and related compounds by human cytosolic sulfotransferases. Br J Clin Pharmacol. 2005 Dec;60(6):632-40. doi: 10.1111/j.1365-2125.2005.02506.x. [Article]
8. Bowalgaha K, Elliot DJ, Mackenzie PI, Knights KM, Swedmark S, Miners JO: S-Naproxen and desmethylnaproxen glucuronidation by human liver microsomes and recombinant human UDP-glucuronosyltransferases (UGT): role of UGT2B7 in the elimination of naproxen. Br J Clin Pharmacol. 2005 Oct;60(4):423-33. doi: 10.1111/j.1365-2125.2005.02446.x. [Article]
9. Tracy TS, Marra C, Wrighton SA, Gonzalez FJ, Korzekwa KR: Involvement of multiple cytochrome P450 isoforms in naproxen O-demethylation. Eur J Clin Pharmacol. 1997;52(4):293-8. [Article]
10. Ruschitzka F, Borer JS, Krum H, Flammer AJ, Yeomans ND, Libby P, Luscher TF, Solomon DH, Husni ME, Graham DY, Davey DA, Wisniewski LM, Menon V, Fayyad R, Beckerman B, Iorga D, Lincoff AM, Nissen SE: Differential blood pressure effects of ibuprofen, naproxen, and celecoxib in patients with arthritis: the PRECISION-ABPM (Prospective Randomized Evaluation of Celecoxib Integrated Safety Versus Ibuprofen or Naproxen Ambulatory Blood Pressure Measurement) Trial. Eur Heart J. 2017 Nov 21;38(44):3282-3292. doi: 10.1093/eurheartj/ehx508. [Article]
11. Mellemkjaer L, Blot WJ, Sorensen HT, Thomassen L, McLaughlin JK, Nielsen GL, Olsen JH: Upper gastrointestinal bleeding among users of NSAIDs: a population-based cohort study in Denmark. Br J Clin Pharmacol. 2002 Feb;53(2):173-81. doi: 10.1046/j.0306-5251.2001.01220.x. [Article]
12. Naprelan FDA Label [Link]
13. Naprosyn FDA Label [Link]
14. Over-the-counter Medications in Pregnancy [Link]
15. Treximet FDA Label [Link]
16. Vimovo FDA Label [Link]

External Links

Human Metabolome Database

HMDB0001923

KEGG Drug

D00118

KEGG Compound

C01517

PubChem Compound

156391

PubChem Substance

46505508

ChemSpider

137720

BindingDB

50339185

RxNav

7258

ChEBI

7476

ChEMBL

CHEMBL154

ZINC

ZINC000000105216

Therapeutic Targets Database

DAP000968

PharmGKB

PA450595

PDBe Ligand

NPS

RxList

RxList Drug Page

Drugs.com

Drugs.com Drug Page

PDRhealth

PDRhealth Drug Page

Wikipedia

Naproxen

PDB Entries

2vdb / 3nt1 / 3r58 / 4fjp / 4jq1 / 4or0 / 4ot2 / 4po0 / 4zbr / 5dby …

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MSDS

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Clinical Trials

Clinical Trials

Clinical Trial & Rare Diseases Add-on Data Package

Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package

Phase	Status	Purpose	Conditions	Count	Start Date	Why Stopped	100+ additional columns
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Not Available	Completed	Not Available	Efficacy of Clarithromycin-Naproxen-Oseltamivir Combination Therapy vs. Oseltamivir Alone for Hospitalised Paediatric Influenza Patients	1	somestatus	stop reason	just information to hide
Not Available	Completed	Not Available	Migraine	5	somestatus	stop reason	just information to hide
Not Available	Completed	Basic Science	Achilles Tendinopathy / Inflammation / Tendon Injuries	1	somestatus	stop reason	just information to hide
Not Available	Completed	Basic Science	Healthy Volunteers (HV)	1	somestatus	stop reason	just information to hide
Not Available	Completed	Basic Science	Treatment of Sweet Taste Receptors Without or With an Oral Rinse of Ibuprofen Solution in Healthy Participants / Treatment of Sweet Taste Receptors Without or With an Oral Rinse of Naproxen Solution in Healthy Participants	1	somestatus	stop reason	just information to hide

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Pharmacoeconomics

Manufacturers

• Roche palo alto llc
• Roxane laboratories inc
• Actavis elizabeth llc
• Alphapharm party ltd
• Pliva inc
• Sandoz inc
• Teva pharmaceuticals usa inc
• Amneal pharmaceuticals ny llc
• Baxter healthcare corp anesthesia and critical care
• Dava pharmaceuticals inc
• Glenmark generics ltd
• Hamilton pharmaceuticals ltd
• Ivax pharmaceuticals inc sub teva pharmaceuticals usa
• Mylan pharmaceuticals inc
• Perrigo r and d co
• Purepac pharmaceutical co
• Teva pharmaceuticals usa
• Watson laboratories inc
• Westward pharmaceutical corp
• Zydus pharmaceuticals usa inc
• Banner pharmacaps inc
• Stat trade inc
• Watson laboratories inc florida
• Bayer healthcare llc
• Able laboratories inc
• Contract pharmacal corp
• Dr reddys laboratories inc
• Dr reddys laboratories ltd
• Hikma pharmaceuticals
• L perrigo co

Packagers

• Advanced Pharmaceutical Services Inc.
• Aidarex Pharmacuticals LLC
• Altura Pharmaceuticals Inc.
• Amerisource Health Services Corp.
• Amneal Pharmaceuticals
• Apotheca Inc.
• Apothecary Shop Wholesale
• A-S Medication Solutions LLC
• AstraZeneca Inc.
• Atlantic Biologicals Corporation
• Avkare Incorporated
• Bayer Healthcare
• Blenheim Pharmacal
• Bryant Ranch Prepack
• Cardinal Health
• Chain Drug
• Comprehensive Consultant Services Inc.
• Corepharma LLC
• Coupler Enterprises Inc.
• CVS Pharmacy
• DAVA Pharmaceuticals
• Dept Health Central Pharmacy
• DHHS Program Support Center Supply Service Center
• Direct Dispensing Inc.
• Dispensing Solutions
• Diversified Healthcare Services Inc.
• Doctor Reddys Laboratories Ltd.
• Elan Pharmaceuticals Inc.
• Ethex Corp.
• F Hoffmann-La Roche Ltd.
• Glenmark Generics Ltd.
• Golden State Medical Supply Inc.
• Group Health Cooperative
• H.J. Harkins Co. Inc.
• Heartland Repack Services LLC
• Hikma Pharmaceuticals
• Innovative Manufacturing and Distribution Services Inc.
• Innoviant Pharmacy Inc.
• International Ethical Labs Inc.
• Ivax Pharmaceuticals
• Kaiser Foundation Hospital
• Keltman Pharmaceuticals Inc.
• Lake Erie Medical and Surgical Supply
• Legacy Pharmaceuticals Packaging LLC
• Liberty Pharmaceuticals
• Major Pharmaceuticals
• Medique Products
• Medisca Inc.
• Medvantx Inc.
• Murfreesboro Pharmaceutical Nursing Supply
• Mylan
• Novopharm Ltd.
• Nucare Pharmaceuticals Inc.
• Palmetto Pharmaceuticals Inc.
• Patheon Inc.
• Patient First Corp.
• PCA LLC
• PD-Rx Pharmaceuticals Inc.
• Perrigo Co.
• Pharmaceutical Utilization Management Program VA Inc.
• Pharmedix
• Pharmpak Inc.
• Physician Partners Ltd.
• Physicians Total Care Inc.
• Pliva Inc.
• Preferred Pharmaceuticals Inc.
• Prepackage Specialists
• Prepak Systems Inc.
• Prescription Dispensing Service Inc.
• Quality Pharmaceuticals Services Inc.
• Rebel Distributors Corp.
• Redpharm Drug
• Remedy Repack
• Resource Optimization and Innovation LLC
• Roxane Labs
• Sandhills Packaging Inc.
• Sandoz
• Southwood Pharmaceuticals
• St Mary's Medical Park Pharmacy
• Stat Rx Usa
• Talbert Medical Management Corp.
• Teva Pharmaceutical Industries Ltd.
• Tya Pharmaceuticals
• UDL Laboratories
• Va Cmop Dallas
• Vangard Labs Inc.
• Victory Pharma
• Walgreen Co.
• Watson Pharmaceuticals
• West-Ward Pharmaceuticals

Dosage Forms

Form	Route	Strength
Tablet	Oral	550 mg
Tablet, film coated	Oral	220 MG
Gel	Cutaneous	10.00000 g
Gel	Cutaneous
Tablet	Oral	125 mg
Tablet	Oral	375 mg
Tablet, coated	Oral
Tablet, film coated	Oral	100 mg
Capsule, liquid filled	Oral	275 mg
Tablet, coated	Oral	275 mg
Tablet	Oral	275 mg
Suspension	Oral
Tablet	Oral	250.00 mg
Capsule	Oral	220 mg/1
Tablet, film coated	Oral	242 mg
Kit; tablet	Oral	500 mg/1
Suspension	Oral	2.500 g
Tablet	Oral	550.0000 mg
Tablet, coated	Oral	20 mg
Capsule, liquid filled	Oral	250 mg
Capsule, liquid filled	Oral	500 mg
Capsule, liquid filled	Oral	50000000 mg
Capsule, liquid filled	Oral
Tablet	Oral	200 mg/1
Kit	Topical	1 g/1g
Tablet, delayed release	Oral	250 mg
Gel	Topical	5.500 g
Tablet	Oral	660.000 mg
Tablet	Oral	250.000 mg
Tablet	Oral	275.000 mg
Capsule, liquid filled	Oral	550 mg
Injection, powder, for solution	Intramuscular
Granule, for solution	Oral
Tablet, film coated	Oral	220 mg/1
Solution	Vaginal
Gel	Topical	50 gr
Tablet	Oral	550.000 mg
Tablet, coated	Oral	100 mg
Powder, for suspension	Oral	2 g
Tablet	Oral	750 MG
Tablet	Oral	660 MG
Granule, for solution	Oral	220 MG
Gel	Topical	1000000 g
Gel	Topical	5 %
Injection, solution	Intramuscular	275 mg
Tablet, coated	Oral	220 MG
Tablet, film coated	Oral
Gel	Topical	5 mg
Tablet, extended release	Oral	375 mg
Tablet, extended release	Oral	500 mg
Tablet, film coated, extended release	Oral	375 mg/1
Tablet, film coated, extended release	Oral	500 mg/1
Tablet, film coated, extended release	Oral	750 mg/1
Injection, solution	Intramuscular
Gel	Topical	10 g
Injection, powder, for suspension	Parenteral	2.5 g
Suspension	Oral
Kit	Oral; Topical
Granule, for suspension	Oral	500 MG
Tablet, delayed release	Oral
Tablet, extended release	Oral
Capsule	Oral	220 MG
Tablet, film coated	Oral	500 MG
Granule, for suspension	Oral	250 MG
Injection, powder, for solution	Intramuscular	250 MG
Injection, powder, for solution	Intramuscular	500 MG
Suspension	Oral	250 mg/10mL
Suspension	Oral	500 mg/20mL
Tablet	Oral	500 MG
Tablet	Oral	250 mg / tab
Suppository	Rectal	500 mg / sup
Gel	Topical
Suspension	Oral	25 mg / mL
Tablet, extended release	Oral	750 mg
Cream; kit; tablet	Oral; Topical
Suspension	Oral	2500 mg
Suspension	Oral	125 mg/5mL
Suspension	Oral	25 mg/1mL
Tablet	Oral	220 mg
Tablet	Oral	250 mg/1
Tablet	Oral	375 mg/1
Tablet	Oral	500 mg/1
Tablet	Oral	500 mg/500mg
Tablet, delayed release	Oral	375 mg/1
Tablet, delayed release	Oral	500 mg/1
Capsule	Oral
Tablet	Oral
Suspension	Oral	50 mg/ml
Solution	Oral
Capsule, liquid filled	Oral	220 mg/1
Powder	Not applicable	25 kg/25kg
Tablet	Oral	200 1/1
Tablet	Oral	220 mg/1
Tablet	Oral	275 mg/1
Tablet	Oral	550 mg/1
Tablet, coated	Oral	220 mg/1
Tablet, film coated	Not applicable	220 mg/1
Tablet, film coated	Oral	200 mg/1
Tablet, film coated	Oral	275 mg/1
Tablet, film coated	Oral	550 mg/1
Tablet, film coated, extended release	Oral	220 1/1
Tablet, film coated, extended release	Oral	220 mg/1
Tablet, extended release	Oral
Tablet	Oral
Tablet, film coated	Oral	750 MG
Gel	Topical	10 %
Suppository	Rectal	250 mg
Capsule	Oral	550 MG
Injection, powder, for solution	Intramuscular	275 mg
Solution	Intramuscular	550 mg/5ml
Suppository	Rectal	550 MG
Powder, for solution	Oral	2.5 g
Suspension	Oral	2.5 g
Tablet	Oral	25000000 mg
Tablet	Oral	273.864 mg
Tablet, coated	Oral	250 mg
Powder, for suspension	Oral	3 g
Tablet	Oral	50000000 mg
Capsule, coated	Oral	250 mg
Solution	Parenteral	500 mg
Powder, for suspension	Oral	250000 g
Tablet, coated	Oral	550 mg
Tablet	Oral	100 mg
Tablet, coated	Oral	50000000 mg
Tablet, coated	Oral	547.729 mg
Tablet, film coated		275 mg
Tablet, film coated		550 mg
Tablet	Oral	500.00 mg
Suppository	Rectal
Suspension	Oral	3 g
Suppository	Rectal	500 mg
Kit	Oral
Granule
Tablet, coated	Oral
Gel	Topical	50 g
Tablet, film coated	Oral	275 mg
Tablet, film coated	Oral	550 mg
Suppository	Rectal	50 mg
Gel	Topical	0.1 g/50g
Tablet, coated	Oral	250 mg
Tablet, coated	Oral	500 mg
Kit	Oral	500 mg/1
Tablet, multilayer, extended release	Oral
Tablet, film coated, extended release	Oral
Tablet	Oral	680 MG
Granule, for suspension	Oral	550 MG
Injection, solution	Intramuscular	550 MG
Suppository	Rectal	275 MG
Tablet, delayed release	Oral	375 mg
Tablet, delayed release	Oral	500 mg
Tablet, film coated	Oral	200 MG
Tablet, film coated	Oral
Tablet, delayed release	Oral
Powder, for suspension	Oral	2.5 g
Capsule	Oral
Cream	Topical
Gel	Topical
Granule, for suspension	Oral
Suppository	Rectal
Capsule	Oral	200 mg
Tablet	Oral	250 mg
Tablet, film coated	Oral	250 mg
Capsule	Oral	250 mg
Capsule	Oral	275 mg

Prices

Unit description	Cost	Unit
Naproxen 125 mg/5ml Suspension 500ml Bottle	51.5USD	bottle
Naprelan 750 mg 24 Hour tablet	8.87USD	tablet
Naprelan cr 500 mg tablet	8.5USD	tablet
Naprelan cr 750 mg tablet	8.02USD	tablet
Naprelan cr dosecrd 500-750 mg	5.98USD	each
Naprelan 375 mg 24 Hour tablet	4.34USD	tablet
Anaprox ds 550 mg tablet	3.66USD	tablet
Naprelan 500 mg 24 Hour tablet	3.63USD	tablet
Naprelan cr 375 mg tablet	3.52USD	tablet
Naproxen sodium powder	2.63USD	g
Anaprox 275 mg tablet	2.52USD	tablet
Naprosyn 500 mg tablet	2.42USD	tablet
Naproxen powder	2.26USD	g
Naprosyn 500 mg tablet ec	2.19USD	tablet
Naprosyn 375 mg tablet	1.93USD	tablet
Ec-naprosyn 375 mg tablet ec	1.79USD	tablet
Naprosyn 250 mg tablet	1.47USD	tablet
Naprosyn Sr 750 mg Sustained-Release Tablet	1.43USD	tablet
Anaprox Ds 550 mg Tablet	1.33USD	tablet
Naproxen 500 mg tablet	1.32USD	tablet
Naproxen sodium 550 mg tablet	1.32USD	tablet
Naproxen DR 500 mg Enteric Coated Tabs	1.3USD	tab
Naproxen DR 375 mg Enteric Coated Tabs	1.11USD	tab
Naprosyn E 500 mg Enteric-Coated Tablet	1.09USD	tablet
Naproxen 375 mg tablet	1.08USD	tablet
Apo-Naproxen Sr 750 mg Sustained-Release Tablet	1.05USD	tablet
Pms-Naproxen 500 mg Suppository	0.87USD	suppository
Naproxen sodium 275 mg tablet	0.86USD	tablet
Naproxen 250 mg tablet	0.79USD	tablet
Apo-Napro-Na Ds 550 mg Tablet	0.7USD	tablet
Novo-Naprox Sodium Ds 550 mg Tablet	0.7USD	tablet
Anaprox 275 mg Tablet	0.69USD	tablet
Apo-Naproxen Ec 500 mg Enteric-Coated Tablet	0.61USD	tablet
Mylan-Naproxen Ec 500 mg Enteric-Coated Tablet	0.61USD	tablet
Novo-Naprox Ec 500 mg Enteric-Coated Tablet	0.61USD	tablet
Pms-Naproxen Ec 500 mg Enteric-Coated Tablet	0.61USD	tablet
Naprosyn E 375 mg Enteric-Coated Tablet	0.6USD	tablet
Naprosyn E 250 mg Enteric-Coated Tablet	0.46USD	tablet
Apo-Napro-Na 275 mg Tablet	0.36USD	tablet
Novo-Naprox Sodium 275 mg Tablet	0.36USD	tablet
Apo-Naproxen Ec 375 mg Enteric-Coated Tablet	0.34USD	tablet
Mylan-Naproxen Ec 375 mg Enteric-Coated Tablet	0.34USD	tablet
Novo-Naprox Ec 375 mg Enteric-Coated Tablet	0.34USD	tablet
Pms-Naproxen Ec 375 mg Enteric-Coated Tablet	0.34USD	tablet
Apo-Naproxen Ec 250 mg Enteric-Coated Tablet	0.26USD	tablet
Novo-Naprox Ec 250 mg Enteric-Coated Tablet	0.26USD	tablet
Apo-Naproxen 500 mg Tablet	0.22USD	tablet
Novo-Naprox 500 mg Tablet	0.22USD	tablet
Nu-Naprox 500 mg Tablet	0.22USD	tablet
Aleve 220 mg gelcap	0.19USD	capsule
Naprosyn 125 mg/5ml Suspension	0.18USD	ml
Mediproxen tablet	0.17USD	tablet
Apo-Naproxen 375 mg Tablet	0.15USD	tablet
Naproxen sodium 220 mg tablet	0.15USD	tablet
Novo-Naprox 375 mg Tablet	0.15USD	tablet
Nu-Naprox 375 mg Tablet	0.15USD	tablet
CVS Pharmacy all day pain rlf 220 mg tb	0.12USD	tablet
Wal-proxen 220 mg tablet	0.12USD	tablet
Apo-Naproxen 250 mg Tablet	0.11USD	tablet
Novo-Naprox 250 mg Tablet	0.11USD	tablet
Nu-Naprox 250 mg Tablet	0.11USD	tablet
All day pain rlf 220 mg caplet	0.1USD	caplet
Aleve 220 mg caplet	0.09USD	caplet
Aleve 220 mg tablet	0.09USD	tablet
Wal-proxen 220 mg caplet	0.09USD	tablet
Apo-Naproxen 125 mg Tablet	0.08USD	tablet
All day pain relief 220 mg tablet	0.07USD	tablet
Naprosyn 25 mg/ml Suspension	0.07USD	ml
Naproxen sodium 220 mg caplet	0.06USD	tablet

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
US5637320	No	1997-06-10	2014-06-10
CA2034096	No	2002-03-26	2011-01-14
US6060499	Yes	2000-05-09	2018-02-14
US7332183	Yes	2008-02-19	2026-04-02
US6586458	Yes	2003-07-01	2018-02-14
US5872145	Yes	1999-02-16	2018-02-14
US8022095	Yes	2011-09-20	2018-02-14
US5900424	Yes	1999-05-04	2016-11-04
US6369085	Yes	2002-04-09	2018-11-25
US7411070	Yes	2008-08-12	2018-11-25
US8852636	No	2014-10-07	2022-05-31
US8858996	No	2014-10-14	2022-05-31
US6926907	No	2005-08-09	2023-02-28
US7745466	No	2010-06-29	2018-10-13
US9161920	No	2015-10-20	2022-05-31
US9198888	No	2015-12-01	2022-05-31
US8945621	No	2015-02-03	2031-10-17
US8557285	No	2013-10-15	2022-05-31
US9220698	No	2015-12-29	2031-03-10
US5714504	Yes	1998-02-03	2015-08-03
US9345695	No	2016-05-24	2022-05-31
US9393208	No	2016-07-19	2029-09-03
US9707181	No	2017-07-18	2022-05-31
US9693978	No	2017-07-04	2026-03-03
US9693979	No	2017-07-04	2026-03-03
US10028925	No	2018-07-24	2026-03-03
US10022344	No	2018-07-17	2026-03-03
US11090280	No	2021-08-17	2026-03-03

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	152°C	MSDS Label
water solubility	15.9 mg/L (at 25 °C)	YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP	3.18	HANSCH,C ET AL. (1995)
logS	-4.16	ADME Research, USCD
Caco2 permeability	-4.83	ADME Research, USCD
pKa	4.15	SANGSTER (1994)

Predicted Properties

Property	Value	Source
Water Solubility	0.0511 mg/mL	ALOGPS
logP	3.29	ALOGPS
logP	2.99	Chemaxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	4.19	Chemaxon
pKa (Strongest Basic)	-4.8	Chemaxon
Physiological Charge	-1	Chemaxon
Hydrogen Acceptor Count	3	Chemaxon
Hydrogen Donor Count	1	Chemaxon
Polar Surface Area	46.53 Å2	Chemaxon
Rotatable Bond Count	3	Chemaxon
Refractivity	64.85 m3·mol-1	Chemaxon
Polarizability	24.81 Å3	Chemaxon
Number of Rings	2	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.9948
Blood Brain Barrier	+	0.6881
Caco-2 permeable	+	0.9091
P-glycoprotein substrate	Non-substrate	0.586
P-glycoprotein inhibitor I	Non-inhibitor	0.8747
P-glycoprotein inhibitor II	Non-inhibitor	0.8396
Renal organic cation transporter	Non-inhibitor	0.8615
CYP450 2C9 substrate	Non-substrate	0.7548
CYP450 2D6 substrate	Non-substrate	0.9116
CYP450 3A4 substrate	Non-substrate	0.5715
CYP450 1A2 substrate	Inhibitor	0.9107
CYP450 2C9 inhibitor	Non-inhibitor	0.907
CYP450 2D6 inhibitor	Non-inhibitor	0.9521
CYP450 2C19 inhibitor	Non-inhibitor	0.9447
CYP450 3A4 inhibitor	Non-inhibitor	0.8905
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.8598
Ames test	AMES toxic	0.5184
Carcinogenicity	Non-carcinogens	0.8685
Biodegradation	Not ready biodegradable	0.7809
Rat acute toxicity	2.4579 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9588
hERG inhibition (predictor II)	Non-inhibitor	0.9144

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

Spectra

Mass Spec (NIST)

Download (7.95 KB)

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-0540-1920000000-dfcdd431a9b1898cd2d2
MS/MS Spectrum - Quattro_QQQ 10V, N/A	LC-MS/MS	splash10-001i-0190000000-64cc22cce1238357760e
MS/MS Spectrum - Quattro_QQQ 25V, N/A	LC-MS/MS	splash10-0f79-0900000000-17f4e93fda31d93027a1
MS/MS Spectrum - Quattro_QQQ 40V, N/A	LC-MS/MS	splash10-0fr6-0900000000-4dd08568cff27d62d867
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	LC-MS/MS	splash10-000i-0910000000-149b16cac2d80de64d8a
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	LC-MS/MS	splash10-00di-0900000000-e7dfead967f29853140d
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	LC-MS/MS	splash10-01b9-0900000000-f5f45cee188a08ef62b1
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	LC-MS/MS	splash10-014i-0900000000-6c076658da1c69f1b909
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	LC-MS/MS	splash10-014i-0900000000-2e1269f26d5b927bca33
LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	LC-MS/MS	splash10-000i-0900000000-68cd0c5a3fcc15470c14
LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	LC-MS/MS	splash10-00di-0900000000-64e5ecb5632e32f89b2d
LC-MS/MS Spectrum - LC-ESI-QQ , negative	LC-MS/MS	splash10-000i-0910000000-149b16cac2d80de64d8a
LC-MS/MS Spectrum - LC-ESI-QQ , negative	LC-MS/MS	splash10-00di-0900000000-e7dfead967f29853140d
LC-MS/MS Spectrum - LC-ESI-QQ , negative	LC-MS/MS	splash10-01b9-0900000000-f5f45cee188a08ef62b1
LC-MS/MS Spectrum - LC-ESI-QQ , negative	LC-MS/MS	splash10-014i-0900000000-6c076658da1c69f1b909
LC-MS/MS Spectrum - LC-ESI-QQ , negative	LC-MS/MS	splash10-014i-0900000000-2e1269f26d5b927bca33
LC-MS/MS Spectrum - LC-ESI-IT , positive	LC-MS/MS	splash10-000i-0900000000-b913db958cba90673250
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-000i-0920000000-a5bd77ba01bc658df4bc
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0udi-0900000000-65e975d973899963d346
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-000i-0900000000-8c9b3567b262aa0d1274
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0uxr-0900000000-67b614b05eec76cfb0a3
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0zfr-0900000000-9bc41dda23e363868cf1
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0gb9-1900000000-bb719531e1c0794cfcbd
1H 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]-	165.2428984	predicted	DarkChem Lite v0.1.0
[M-H]-	165.6894984	predicted	DarkChem Lite v0.1.0
[M-H]-	165.2465984	predicted	DarkChem Lite v0.1.0
[M-H]-	164.9187984	predicted	DarkChem Lite v0.1.0
[M-H]-	165.3348984	predicted	DarkChem Lite v0.1.0
[M-H]-	155.95302	predicted	DeepCCS 1.0 (2019)
[M+H]+	165.3139984	predicted	DarkChem Lite v0.1.0
[M+H]+	167.3790984	predicted	DarkChem Lite v0.1.0
[M+H]+	166.0776984	predicted	DarkChem Lite v0.1.0
[M+H]+	165.7917984	predicted	DarkChem Lite v0.1.0
[M+H]+	166.0621984	predicted	DarkChem Lite v0.1.0
[M+H]+	158.31102	predicted	DeepCCS 1.0 (2019)
[M+Na]+	165.6027984	predicted	DarkChem Lite v0.1.0
[M+Na]+	165.6981984	predicted	DarkChem Lite v0.1.0
[M+Na]+	165.2845984	predicted	DarkChem Lite v0.1.0
[M+Na]+	165.0297984	predicted	DarkChem Lite v0.1.0
[M+Na]+	165.4392984	predicted	DarkChem Lite v0.1.0
[M+Na]+	164.40416	predicted	DeepCCS 1.0 (2019)

Targets

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Details1. Pancreatic triacylglycerol lipase

Kind

Protein

Organism

Humans

Pharmacological action

Yes

Actions

Inhibitor

General Function

Plays an important role in fat metabolism. It preferentially splits the esters of long-chain fatty acids at positions 1 and 3, producing mainly 2-monoacylglycerol and free fatty acids, and shows considerably higher activity against insoluble emulsified substrates than against soluble ones

Specific Function

All-trans-retinyl-palmitate hydrolase, all-trans-retinol forming activity

Gene Name

PNLIP

Uniprot ID

P16233

Uniprot Name

Pancreatic triacylglycerol lipase

Molecular Weight

51156.48 Da

References

1. 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]

Binding Properties

×

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	21000	N/A	N/A	A31046
IC 50 (nM)	11000	N/A	N/A	A27759 / A27761

Details

Binding Properties2. 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

1. James MJ, Cook-Johnson RJ, Cleland LG: Selective COX-2 inhibitors, eicosanoid synthesis and clinical outcomes: a case study of system failure. Lipids. 2007 Sep;42(9):779-85. Epub 2007 Jun 2. [Article]
2. Brutzkus JC, Varacallo M: Naproxen . [Article]
3. 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]

Binding Properties

×

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	2500	N/A	N/A	A27777
IC 50 (nM)	9700	N/A	N/A	A27774
IC 50 (nM)	1010000	N/A	N/A	A27759
IC 50 (nM)	18900	N/A	N/A	A27761
IC 50 (nM)	12400	N/A	N/A	A27808 / A28423
Ki (nM)	>10000	N/A	N/A	A5629 / A27471

Details

Binding Properties3. 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

1. Dhir A, Naidu PS, Kulkarni SK: Neuroprotective effect of nimesulide, a preferential COX-2 inhibitor, against pentylenetetrazol (PTZ)-induced chemical kindling and associated biochemical parameters in mice. Seizure. 2007 Dec;16(8):691-7. Epub 2007 Jul 2. [Article]
2. Hassan-Alin M, Naesdal J, Nilsson-Pieschl C, Langstrom G, Andersson T: Lack of Pharmacokinetic Interaction between Esomeprazole and the Nonsteroidal Anti-Inflammatory Drugs Naproxen and Rofecoxib in Healthy Subjects. Clin Drug Investig. 2005;25(11):731-40. [Article]
3. Brutzkus JC, Varacallo M: Naproxen . [Article]
4. 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. Peptostreptococcal albumin-binding protein

Kind

Protein

Organism

Peptostreptococcus magnus

Pharmacological action

Unknown

General Function

Not Available

Specific Function

Binds serum albumin.

Gene Name

pab

Uniprot ID

Q51911

Uniprot Name

Peptostreptococcal albumin-binding protein

Molecular Weight

43057.45 Da

References

1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
2. Lejon S, Cramer JF, Nordberg P: Structural basis for the binding of naproxen to human serum albumin in the presence of fatty acids and the GA module. Acta Crystallogr Sect F Struct Biol Cryst Commun. 2008 Feb 1;64(Pt 2):64-9. doi: 10.1107/S174430910706770X. Epub 2008 Jan 18. [Article]

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Drug created at June 13, 2005 13:24 / Updated at September 15, 2024 21:55