NAV

Naproxen

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
Similar Structures
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 TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Symptomatic treatment ofAcute gouty arthritis••••••••••••••••••• •••••••• ••••••• ••••••• ••••••• •••• ••••••
Treatment ofAcute migraine••• •••••
Used in combination to treatAcute migraineCombination Product in combination with: Sumatriptan (DB00669)••••••••••••
Used in combination for symptomatic treatment ofAnkylosing spondylitisCombination Product in combination with: Esomeprazole (DB00736)•••••••••••••••••
Symptomatic treatment ofAnkylosing spondylitis••••••••••••••••••• ••••••• •••••••• ••••••• •••••••• ••••••• ••••••• ••••••• •••• ••••••
Contraindications & Blackbox Warnings
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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

TargetActionsOrganism
AProstaglandin G/H synthase 1
inhibitor
Humans
AProstaglandin G/H synthase 2
inhibitor
Humans
UPeptostreptococcal albumin-binding proteinNot AvailablePeptostreptococcus 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 AUC0-24hr 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 AUC0-12hrs of EC-Naprosyn were 4 hours and 845 mcgxhr/mL respectively, and Tmax and AUC0-12hrs 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

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
PathwayCategory
Naproxen Action PathwayDrug action
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

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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
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interactions in your software
AbacavirNaproxen may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbametapirThe serum concentration of Naproxen can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Naproxen can be increased when combined with Abatacept.
AbciximabThe risk or severity of bleeding and hemorrhage can be increased when Naproxen is combined with Abciximab.
AbirateroneThe 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
IngredientUNIICASInChI Key
Naproxen sodium9TN87S3A3C26159-34-2CDBRNDSHEYLDJV-FVGYRXGTSA-M
Product Images
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
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AnaproxTablet275 mg/1OralPhysicians Total Care, Inc.1980-09-042011-06-30US flag
AnaproxTablet275 mgOralAtnahs Pharma Uk Limited1995-12-31Not applicableCanada flag
AnaproxTablet275 mgOralSyntex Inc.1980-12-311996-09-30Canada flag
AnaproxTablet275 mg/1OralRoche Laboratories Inc.2006-05-172006-05-17US flag
Anaprox DSTablet550 mgOralAtnahs Pharma Uk Limited1995-12-31Not applicableCanada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
All Day ReliefTablet220 mg/1OralRemedy Repack2015-02-022017-03-10US flag
AnaproxTablet550 mg/1OralDirect Rx2016-07-11Not applicableUS flag
Apo Naproxen Tab 125mgTablet125 mgOralApotex Corporation1982-12-31Not applicableCanada flag
Apo-napro-NATablet275 mgOralApotex Corporation1989-12-31Not applicableCanada flag
Apo-napro-NA DSTablet550 mgOralApotex Corporation1993-12-31Not applicableCanada flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
7 Select Naproxen SodiumTablet, film coated220 mg/1Oral7-Eleven2014-08-112020-12-31US flag
7 Select Naproxen SodiumTablet, film coated220 mg/1Oral7 Eleven2014-08-052016-06-19US flag
AleveTablet220 mg/1OralLil' Drug Store Products, Inc2000-01-01Not applicableUS flag
AleveTablet200 mg/1OralLil' Drug Store Products, Inc.2017-08-252025-12-31US flag
AleveTablet200 mg/1OralLil' Drug Store Products, Inc.2002-04-302025-09-30US flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
AFLIXDOL® FORTE TABLETASNaproxen sodium (220 mg) + Acetaminophen (250 mg) + Caffeine (65 mg)TabletOralCOASPHARMA S.A.S. (PLANTA PALOQUEMAO)2023-10-09Not applicableColombia flag
AINEDAP® FORTENaproxen sodium (550 mg) + Caffeine (65 mg)Tablet, coatedOralQUIBI S.A. EN REESTRUCTURACION2023-03-22Not applicableColombia flag
Aleve NighttimeNaproxen sodium (220 mg) + Diphenhydramine hydrochloride (25 mg)TabletOralBayer2016-02-24Not applicableCanada flag
Aleve PMNaproxen sodium (220 mg/1) + Diphenhydramine hydrochloride (25 mg/1)Tablet, film coatedOralBayer Healthcare Llc.2014-09-09Not applicableUS flag
Aleve-D Sinus and ColdNaproxen sodium (220 mg/1) + Pseudoephedrine hydrochloride (120 mg/1)TabletOralBayer Healthcare Llc.2014-01-01Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Cold FAidNaproxen sodium (220 mg/1) + Chlorpheniramine maleate (4 mg/1) + Phenylephrine hydrochloride (10 mg/1)KitOralCold FAid2020-03-242022-03-31US flag
Cold FAidNaproxen sodium (220 mg/1) + Chlorpheniramine maleate (12 mg/1) + Phenylephrine hydrochloride (10 mg/1)KitOralCold FAid2019-05-062021-01-31US flag
Cold FAidNaproxen sodium (220 mg/1) + Chlorpheniramine maleate (4 mg/1) + Phenylephrine hydrochloride (10 mg/1)KitOralCold FAid2021-02-01Not applicableUS flag
Equipto - Naproxen External Cream Compounding KitNaproxen (1 g/1g)KitTopicalAlvix Laboratories2015-01-202018-03-08US flag
NaproPaxNaproxen (500 mg/1) + Capsaicin (0.0375 g/100g) + Menthol (5 1/100g)KitOral; TopicalBasiem2015-08-302016-03-04US flag

Categories

ATC Codes
G02CC02 — NaproxenM02AA12 — NaproxenM01AE56 — Naproxen and misoprostolM01AE52 — Naproxen and esomeprazoleM01AE02 — Naproxen
Drug Categories
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]
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
MSDS
Download (75.4 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
4CompletedNot AvailableDuodenal Ulcer1
4CompletedNot AvailableMigraine1
4CompletedBasic ScienceAcute Pain / Osseointegrated Dental Implantation1
4CompletedBasic SciencePoor Metabolizer Due to Cytochrome P450 CYP2C19 Variant / Poor Metabolizer Due to Cytochrome P450 CYP2C9 Variant1
4CompletedBasic ScienceRheumatoid Arthritis1

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
FormRouteStrength
TabletOral550 mg
TabletOral250 mg
Tablet, film coatedOral220 MG
GelCutaneous10.00000 g
GelCutaneous
TabletOral125 mg
TabletOral375 mg
Tablet, coatedOral
Tablet, film coatedOral100 mg
Capsule, liquid filledOral275 mg
Tablet, coatedOral275 mg
TabletOral275 mg
SuspensionOral
TabletOral250.00 mg
CapsuleOral220 mg/1
Tablet, film coatedOral242 mg
Kit; tabletOral500 mg/1
SuspensionOral2.500 g
SuppositoryRectal
TabletOral550.0000 mg
Tablet, coatedOral20 mg
Capsule, liquid filledOral250 mg
Capsule, liquid filledOral500 mg
Capsule, liquid filledOral50000000 mg
Capsule, liquid filledOral
TabletOral200 mg/1
KitTopical1 g/1g
Tablet, delayed releaseOral250 mg
GelTopical5.500 g
TabletOral275.000 mg
TabletOral660.000 mg
TabletOral250.000 mg
Capsule, liquid filledOral550 mg
Injection, powder, for solutionIntramuscular
Granule, for solutionOral
Tablet, film coatedOral220 mg/1
SolutionVaginal
GelTopical50 gr
TabletOral550.000 mg
Tablet, coatedOral100 mg
Powder, for suspensionOral2 g
TabletOral750 MG
TabletOral660 MG
Granule, for solutionOral220 MG
GelTopical1000000 g
GelTopical5 %
Injection, solutionIntramuscular275 mg
Tablet, coatedOral220 MG
Tablet, film coatedOral
GelTopical5 mg
Tablet, extended releaseOral375 mg
Tablet, extended releaseOral500 mg
Tablet, film coated, extended releaseOral375 mg/1
Tablet, film coated, extended releaseOral500 mg/1
Tablet, film coated, extended releaseOral750 mg/1
Injection, solutionIntramuscular
GelTopical10 g
Injection, powder, for suspensionParenteral2.5 g
SuspensionOral
KitOral; Topical
Granule, for suspensionOral500 MG
Tablet, delayed releaseOral
Tablet, extended releaseOral
CapsuleOral220 MG
Tablet, film coatedOral500 MG
Granule, for suspensionOral250 MG
Injection, powder, for solutionIntramuscular250 MG
Injection, powder, for solutionIntramuscular500 MG
SuspensionOral250 mg/10mL
SuspensionOral500 mg/20mL
TabletOral500 MG
TabletOral250 mg / tab
SuppositoryRectal500 mg / sup
SuspensionOral25 mg / mL
Tablet, extended releaseOral750 mg
Cream; kit; tabletOral; Topical
SuspensionOral2500 mg
SuspensionOral125 mg/5mL
SuspensionOral25 mg/1mL
TabletOral220 mg
TabletOral250 mg/1
TabletOral375 mg/1
TabletOral500 mg/1
TabletOral500 mg/500mg
Tablet, delayed releaseOral375 mg/1
Tablet, delayed releaseOral500 mg/1
CapsuleOral
TabletOral
SuspensionOral50 mg/ml
SolutionOral
Capsule, liquid filledOral220 mg/1
PowderNot applicable25 kg/25kg
TabletOral200 1/1
TabletOral220 mg/1
TabletOral275 mg/1
TabletOral550 mg/1
Tablet, coatedOral220 mg/1
Tablet, film coatedNot applicable220 mg/1
Tablet, film coatedOral200 mg/1
Tablet, film coatedOral275 mg/1
Tablet, film coatedOral550 mg/1
Tablet, film coated, extended releaseOral220 1/1
Tablet, film coated, extended releaseOral220 mg/1
TabletOral
Tablet, film coatedOral750 MG
GelTopical10 %
SuppositoryRectal250 mg
CapsuleOral550 MG
Injection, powder, for solutionIntramuscular275 mg
SolutionIntramuscular550 mg/5ml
SuppositoryRectal550 MG
Powder, for solutionOral2.5 g
SuspensionOral2.5 g
TabletOral25000000 mg
TabletOral273.864 mg
Powder, for suspensionOral3 g
TabletOral50000000 mg
Capsule, coatedOral250 mg
SolutionParenteral500 mg
Powder, for suspensionOral250000 g
Tablet, coatedOral550 mg
TabletOral100 mg
Tablet, coatedOral50000000 mg
Tablet, coatedOral547.729 mg
Tablet, film coated275 mg
Tablet, film coated550 mg
TabletOral500.00 mg
SuspensionOral3 g
SuppositoryRectal500 mg
KitOral
Granule
Tablet, coatedOral
GelTopical50 g
Tablet, film coatedOral275 mg
Tablet, film coatedOral550 mg
SuppositoryRectal50 mg
GelTopical0.1 g/50g
Tablet, coatedOral250 mg
Tablet, coatedOral500 mg
KitOral500 mg/1
Tablet, multilayer, extended releaseOral
Tablet, film coated, extended releaseOral
TabletOral680 MG
Granule, for suspensionOral550 MG
Injection, solutionIntramuscular550 MG
SuppositoryRectal275 MG
Tablet, delayed releaseOral375 mg
Tablet, delayed releaseOral500 mg
Tablet, film coatedOral200 MG
Tablet, film coatedOral
GelTopical
Tablet, delayed releaseOral
Tablet, extended releaseOral
Powder, for suspensionOral2.5 g
CapsuleOral
CreamTopical
GelTopical
Granule, for suspensionOral
SuppositoryRectal
CapsuleOral200 mg
TabletOral250 mg
Tablet, film coatedOral250 mg
CapsuleOral250 mg
CapsuleOral275 mg
Prices
Unit descriptionCostUnit
Naproxen 125 mg/5ml Suspension 500ml Bottle51.5USD bottle
Naprelan 750 mg 24 Hour tablet8.87USD tablet
Naprelan cr 500 mg tablet8.5USD tablet
Naprelan cr 750 mg tablet8.02USD tablet
Naprelan cr dosecrd 500-750 mg5.98USD each
Naprelan 375 mg 24 Hour tablet4.34USD tablet
Anaprox ds 550 mg tablet3.66USD tablet
Naprelan 500 mg 24 Hour tablet3.63USD tablet
Naprelan cr 375 mg tablet3.52USD tablet
Naproxen sodium powder2.63USD g
Anaprox 275 mg tablet2.52USD tablet
Naprosyn 500 mg tablet2.42USD tablet
Naproxen powder2.26USD g
Naprosyn 500 mg tablet ec2.19USD tablet
Naprosyn 375 mg tablet1.93USD tablet
Ec-naprosyn 375 mg tablet ec1.79USD tablet
Naprosyn 250 mg tablet1.47USD tablet
Naprosyn Sr 750 mg Sustained-Release Tablet1.43USD tablet
Anaprox Ds 550 mg Tablet1.33USD tablet
Naproxen 500 mg tablet1.32USD tablet
Naproxen sodium 550 mg tablet1.32USD tablet
Naproxen DR 500 mg Enteric Coated Tabs1.3USD tab
Naproxen DR 375 mg Enteric Coated Tabs1.11USD tab
Naprosyn E 500 mg Enteric-Coated Tablet1.09USD tablet
Naproxen 375 mg tablet1.08USD tablet
Apo-Naproxen Sr 750 mg Sustained-Release Tablet1.05USD tablet
Pms-Naproxen 500 mg Suppository0.87USD suppository
Naproxen sodium 275 mg tablet0.86USD tablet
Naproxen 250 mg tablet0.79USD tablet
Apo-Napro-Na Ds 550 mg Tablet0.7USD tablet
Novo-Naprox Sodium Ds 550 mg Tablet0.7USD tablet
Anaprox 275 mg Tablet0.69USD tablet
Apo-Naproxen Ec 500 mg Enteric-Coated Tablet0.61USD tablet
Mylan-Naproxen Ec 500 mg Enteric-Coated Tablet0.61USD tablet
Novo-Naprox Ec 500 mg Enteric-Coated Tablet0.61USD tablet
Pms-Naproxen Ec 500 mg Enteric-Coated Tablet0.61USD tablet
Naprosyn E 375 mg Enteric-Coated Tablet0.6USD tablet
Naprosyn E 250 mg Enteric-Coated Tablet0.46USD tablet
Apo-Napro-Na 275 mg Tablet0.36USD tablet
Novo-Naprox Sodium 275 mg Tablet0.36USD tablet
Apo-Naproxen Ec 375 mg Enteric-Coated Tablet0.34USD tablet
Mylan-Naproxen Ec 375 mg Enteric-Coated Tablet0.34USD tablet
Novo-Naprox Ec 375 mg Enteric-Coated Tablet0.34USD tablet
Pms-Naproxen Ec 375 mg Enteric-Coated Tablet0.34USD tablet
Apo-Naproxen Ec 250 mg Enteric-Coated Tablet0.26USD tablet
Novo-Naprox Ec 250 mg Enteric-Coated Tablet0.26USD tablet
Apo-Naproxen 500 mg Tablet0.22USD tablet
Novo-Naprox 500 mg Tablet0.22USD tablet
Nu-Naprox 500 mg Tablet0.22USD tablet
Aleve 220 mg gelcap0.19USD capsule
Naprosyn 125 mg/5ml Suspension0.18USD ml
Mediproxen tablet0.17USD tablet
Apo-Naproxen 375 mg Tablet0.15USD tablet
Naproxen sodium 220 mg tablet0.15USD tablet
Novo-Naprox 375 mg Tablet0.15USD tablet
Nu-Naprox 375 mg Tablet0.15USD tablet
CVS Pharmacy all day pain rlf 220 mg tb0.12USD tablet
Wal-proxen 220 mg tablet0.12USD tablet
Apo-Naproxen 250 mg Tablet0.11USD tablet
Novo-Naprox 250 mg Tablet0.11USD tablet
Nu-Naprox 250 mg Tablet0.11USD tablet
All day pain rlf 220 mg caplet0.1USD caplet
Aleve 220 mg caplet0.09USD caplet
Aleve 220 mg tablet0.09USD tablet
Wal-proxen 220 mg caplet0.09USD tablet
Apo-Naproxen 125 mg Tablet0.08USD tablet
All day pain relief 220 mg tablet0.07USD tablet
Naprosyn 25 mg/ml Suspension0.07USD ml
Naproxen sodium 220 mg caplet0.06USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5637320No1997-06-102014-06-10US flag
CA2034096No2002-03-262011-01-14Canada flag
US6060499Yes2000-05-092018-02-14US flag
US7332183Yes2008-02-192026-04-02US flag
US6586458Yes2003-07-012018-02-14US flag
US5872145Yes1999-02-162018-02-14US flag
US8022095Yes2011-09-202018-02-14US flag
US5900424Yes1999-05-042016-11-04US flag
US6369085Yes2002-04-092018-11-25US flag
US7411070Yes2008-08-122018-11-25US flag
US8852636No2014-10-072022-05-31US flag
US8858996No2014-10-142022-05-31US flag
US6926907No2005-08-092023-02-28US flag
US7745466No2010-06-292018-10-13US flag
US9161920No2015-10-202022-05-31US flag
US9198888No2015-12-012022-05-31US flag
US8945621No2015-02-032031-10-17US flag
US8557285No2013-10-152022-05-31US flag
US9220698No2015-12-292031-03-10US flag
US5714504Yes1998-02-032015-08-03US flag
US9345695No2016-05-242022-05-31US flag
US9393208No2016-07-192029-09-03US flag
US9707181No2017-07-182022-05-31US flag
US9693978No2017-07-042026-03-03US flag
US9693979No2017-07-042026-03-03US flag
US10028925No2018-07-242026-03-03US flag
US10022344No2018-07-172026-03-03US flag
US11090280No2021-08-172026-03-03US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)152°CMSDS Label
water solubility15.9 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP3.18HANSCH,C ET AL. (1995)
logS-4.16ADME Research, USCD
Caco2 permeability-4.83ADME Research, USCD
pKa4.15SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.0511 mg/mLALOGPS
logP3.29ALOGPS
logP2.99Chemaxon
logS-3.6ALOGPS
pKa (Strongest Acidic)4.19Chemaxon
pKa (Strongest Basic)-4.8Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area46.53 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity64.85 m3·mol-1Chemaxon
Polarizability24.81 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9948
Blood Brain Barrier+0.6881
Caco-2 permeable+0.9091
P-glycoprotein substrateNon-substrate0.586
P-glycoprotein inhibitor INon-inhibitor0.8747
P-glycoprotein inhibitor IINon-inhibitor0.8396
Renal organic cation transporterNon-inhibitor0.8615
CYP450 2C9 substrateNon-substrate0.7548
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.5715
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9521
CYP450 2C19 inhibitorNon-inhibitor0.9447
CYP450 3A4 inhibitorNon-inhibitor0.8905
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8598
Ames testAMES toxic0.5184
CarcinogenicityNon-carcinogens0.8685
BiodegradationNot ready biodegradable0.7809
Rat acute toxicity2.4579 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9588
hERG inhibition (predictor II)Non-inhibitor0.9144
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (7.95 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0540-1920000000-dfcdd431a9b1898cd2d2
MS/MS Spectrum - Quattro_QQQ 10V, N/ALC-MS/MSsplash10-001i-0190000000-64cc22cce1238357760e
MS/MS Spectrum - Quattro_QQQ 25V, N/ALC-MS/MSsplash10-0f79-0900000000-17f4e93fda31d93027a1
MS/MS Spectrum - Quattro_QQQ 40V, N/ALC-MS/MSsplash10-0fr6-0900000000-4dd08568cff27d62d867
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-000i-0910000000-149b16cac2d80de64d8a
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-00di-0900000000-e7dfead967f29853140d
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-01b9-0900000000-f5f45cee188a08ef62b1
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-014i-0900000000-6c076658da1c69f1b909
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-014i-0900000000-2e1269f26d5b927bca33
LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , PositiveLC-MS/MSsplash10-000i-0900000000-68cd0c5a3fcc15470c14
LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , PositiveLC-MS/MSsplash10-00di-0900000000-64e5ecb5632e32f89b2d
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-000i-0910000000-149b16cac2d80de64d8a
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00di-0900000000-e7dfead967f29853140d
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-01b9-0900000000-f5f45cee188a08ef62b1
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-014i-0900000000-6c076658da1c69f1b909
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-014i-0900000000-2e1269f26d5b927bca33
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-000i-0900000000-b913db958cba90673250
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0920000000-a5bd77ba01bc658df4bc
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0900000000-65e975d973899963d346
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0900000000-8c9b3567b262aa0d1274
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0uxr-0900000000-67b614b05eec76cfb0a3
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0zfr-0900000000-9bc41dda23e363868cf1
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0gb9-1900000000-bb719531e1c0794cfcbd
1H NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[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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insights and accelerate drug research.
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Details1. Prostaglandin G/H synthase 1
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. 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]
Details2. Prostaglandin G/H synthase 2
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. 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]
Details3. 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]

Enzymes

Details1. Cytochrome P450 2C8
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid 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 oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. 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]
  2. Jaja C, Bowman L, Wells L, Patel N, Xu H, Lyon M, Kutlar A: Preemptive Genotyping of CYP2C8 and CYP2C9 Allelic Variants Involved in NSAIDs Metabolism for Sickle Cell Disease Pain Management. Clin Transl Sci. 2015 Aug;8(4):272-80. doi: 10.1111/cts.12260. Epub 2015 Feb 2. [Article]
  3. Agundez JA, Garcia-Martin E, Martinez C: Genetically based impairment in CYP2C8- and CYP2C9-dependent NSAID metabolism as a risk factor for gastrointestinal bleeding: is a combination of pharmacogenomics and metabolomics required to improve personalized medicine? Expert Opin Drug Metab Toxicol. 2009 Jun;5(6):607-20. doi: 10.1517/17425250902970998 . [Article]
Details2. UDP-glucuronosyltransferase 2B7
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Glucuronosyltransferase activity
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.Its unique specificity for 3,4-catechol estrogens and estriol su...
Gene Name
UGT2B7
Uniprot ID
P16662
Uniprot Name
UDP-glucuronosyltransferase 2B7
Molecular Weight
60694.12 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
  2. 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]
Details3. UDP-glucuronosyltransferase 1-3
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. Isoform 2 lacks transferase activity but acts as a negative reg...
Gene Name
UGT1A3
Uniprot ID
P35503
Uniprot Name
UDP-glucuronosyltransferase 1-3
Molecular Weight
60337.835 Da
References
  1. 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]
Details4. UDP-glucuronosyltransferase 1-6
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. 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]
Details5. UDP-glucuronosyltransferase 1-7
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. Isoform 2 lacks transferase activity but acts as a negative reg...
Gene Name
UGT1A7
Uniprot ID
Q9HAW7
Uniprot Name
UDP-glucuronosyltransferase 1-7
Molecular Weight
59818.315 Da
References
  1. 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]
Details6. UDP-glucuronosyltransferase 1-8
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. Isoform 2 lacks transferase activity but acts as a negative reg...
Gene Name
UGT1A8
Uniprot ID
Q9HAW9
Uniprot Name
UDP-glucuronosyltransferase 1-8
Molecular Weight
59741.035 Da
References
  1. 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]
Details7. UDP-glucuronosyltransferase 1-9
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. 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]
Details8. UDP-glucuronosyltransferase 1-10
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Protein kinase c binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Isoform 2 lacks transferase activity but acts as a negative reg...
Gene Name
UGT1A10
Uniprot ID
Q9HAW8
Uniprot Name
UDP-glucuronosyltransferase 1-10
Molecular Weight
59809.075 Da
References
  1. 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]
Details9. Cytochrome P450 2C9
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid 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 oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
  2. 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]
  3. Rodrigues AD: Impact of CYP2C9 genotype on pharmacokinetics: are all cyclooxygenase inhibitors the same? Drug Metab Dispos. 2005 Nov;33(11):1567-75. Epub 2005 Aug 23. [Article]
  4. Flockhart Table of Drug Interactions [Link]
Details10. Cytochrome P450 1A2
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. 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]
  2. Miners JO, Coulter S, Tukey RH, Veronese ME, Birkett DJ: Cytochromes P450, 1A2, and 2C9 are responsible for the human hepatic O-demethylation of R- and S-naproxen. Biochem Pharmacol. 1996 Apr 26;51(8):1003-8. doi: 10.1016/0006-2952(96)85085-4. [Article]
  3. Frost C, Shenker A, Gandhi MD, Pursley J, Barrett YC, Wang J, Zhang D, Byon W, Boyd RA, LaCreta F: Evaluation of the effect of naproxen on the pharmacokinetics and pharmacodynamics of apixaban. Br J Clin Pharmacol. 2014 Oct;78(4):877-85. doi: 10.1111/bcp.12393. [Article]
  4. Flockhart Table of Drug Interactions [Link]

Carriers

Details1. Serum albumin
Kind
Protein
Organism
Humans
Pharmacological action
No
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. Banerjee T, Singh SK, Kishore N: Binding of naproxen and amitriptyline to bovine serum albumin: biophysical aspects. J Phys Chem B. 2006 Nov 30;110(47):24147-56. [Article]
  2. 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]
  3. 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]
  4. Davies NM, Anderson KE: Clinical pharmacokinetics of naproxen. Clin Pharmacokinet. 1997 Apr;32(4):268-93. doi: 10.2165/00003088-199732040-00002. [Article]

Transporters

Details1. Solute carrier organic anion transporter family member 1A2
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids (By similarity). Selectively inhibit...
Gene Name
SLCO1A2
Uniprot ID
P46721
Uniprot Name
Solute carrier organic anion transporter family member 1A2
Molecular Weight
74144.105 Da
References
  1. Shitara Y, Sugiyama D, Kusuhara H, Kato Y, Abe T, Meier PJ, Itoh T, Sugiyama Y: Comparative inhibitory effects of different compounds on rat oatpl (slc21a1)- and Oatp2 (Slc21a5)-mediated transport. Pharm Res. 2002 Feb;19(2):147-53. [Article]
Details2. Solute carrier family 22 member 6
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
Gene Name
SLC22A6
Uniprot ID
Q4U2R8
Uniprot Name
Solute carrier family 22 member 6
Molecular Weight
61815.78 Da
References
  1. Mulato AS, Ho ES, Cihlar T: Nonsteroidal anti-inflammatory drugs efficiently reduce the transport and cytotoxicity of adefovir mediated by the human renal organic anion transporter 1. J Pharmacol Exp Ther. 2000 Oct;295(1):10-5. [Article]
  2. Apiwattanakul N, Sekine T, Chairoungdua A, Kanai Y, Nakajima N, Sophasan S, Endou H: Transport properties of nonsteroidal anti-inflammatory drugs by organic anion transporter 1 expressed in Xenopus laevis oocytes. Mol Pharmacol. 1999 May;55(5):847-54. [Article]
Details3. Bile salt export pump
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Transporter activity
Specific Function
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes.
Gene Name
ABCB11
Uniprot ID
O95342
Uniprot Name
Bile salt export pump
Molecular Weight
146405.83 Da
References
  1. Pedersen JM, Matsson P, Bergstrom CA, Hoogstraate J, Noren A, LeCluyse EL, Artursson P: Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11). Toxicol Sci. 2013 Dec;136(2):328-43. doi: 10.1093/toxsci/kft197. Epub 2013 Sep 6. [Article]
Details4. P-glycoprotein 1
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
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. Frost C, Shenker A, Gandhi MD, Pursley J, Barrett YC, Wang J, Zhang D, Byon W, Boyd RA, LaCreta F: Evaluation of the effect of naproxen on the pharmacokinetics and pharmacodynamics of apixaban. Br J Clin Pharmacol. 2014 Oct;78(4):877-85. doi: 10.1111/bcp.12393. [Article]
Details5. Solute carrier family 22 member 8
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
Gene Name
SLC22A8
Uniprot ID
Q8TCC7
Uniprot Name
Solute carrier family 22 member 8
Molecular Weight
59855.585 Da
References
  1. Inhibition of Methotrexate Uptake via Organic Anion Transporters OAT1 and OAT3 by Glucuronides of Nonsteroidal Anti-inflammatory Drugs [Link]

Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55