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
- 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
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
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- 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 •••••••••••• ••••••• ••••••• •••••••• ••••••• •••••••• ••••••• ••••••• ••••••• •••• •••••• - Contraindications & Blackbox Warnings
- Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API
- 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 AProstaglandin G/H synthase 1 inhibitorHumans AProstaglandin G/H synthase 2 inhibitorHumans 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 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
- 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
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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 Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir 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
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Naproxen sodium 9TN87S3A3C 26159-34-2 CDBRNDSHEYLDJV-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
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Anaprox Tablet 275 mg/1 Oral Physicians Total Care, Inc. 1980-09-04 2011-06-30 US Anaprox Tablet 275 mg Oral Atnahs Pharma Uk Limited 1995-12-31 Not applicable Canada Anaprox Tablet 275 mg Oral Syntex Inc. 1980-12-31 1996-09-30 Canada Anaprox Tablet 275 mg/1 Oral Roche Laboratories Inc. 2006-05-17 2006-05-17 US Anaprox DS Tablet 550 mg Oral Atnahs Pharma Uk Limited 1995-12-31 Not applicable Canada - 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 US Anaprox Tablet 550 mg/1 Oral Direct Rx 2016-07-11 Not applicable US Apo Naproxen Tab 125mg Tablet 125 mg Oral Apotex Corporation 1982-12-31 Not applicable Canada Apo-napro-NA Tablet 275 mg Oral Apotex Corporation 1989-12-31 Not applicable Canada Apo-napro-NA DS Tablet 550 mg Oral Apotex Corporation 1993-12-31 Not applicable Canada - 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 2014-08-11 2020-12-31 US 7 Select Naproxen Sodium Tablet, film coated 220 mg/1 Oral 7 Eleven 2014-08-05 2016-06-19 US Aleve Tablet 220 mg/1 Oral Lil' Drug Store Products, Inc 2000-01-01 Not applicable US Aleve Tablet 200 mg/1 Oral Lil' Drug Store Products, Inc. 2017-08-25 2025-12-31 US Aleve Tablet 200 mg/1 Oral Lil' Drug Store Products, Inc. 2002-04-30 2025-09-30 US - 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 Colombia AINEDAP® FORTE Naproxen sodium (550 mg) + Caffeine (65 mg) Tablet, coated Oral QUIBI S.A. EN REESTRUCTURACION 2023-03-22 Not applicable Colombia Aleve Nighttime Naproxen sodium (220 mg) + Diphenhydramine hydrochloride (25 mg) Tablet Oral Bayer 2016-02-24 Not applicable Canada Aleve PM Naproxen sodium (220 mg/1) + Diphenhydramine hydrochloride (25 mg/1) Tablet, film coated Oral Bayer Healthcare Llc. 2014-09-09 Not applicable US 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 US - 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 US 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 US 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 US Equipto - Naproxen External Cream Compounding Kit Naproxen (1 g/1g) Kit Topical Alvix Laboratories 2015-01-20 2018-03-08 US NaproPax Naproxen (500 mg/1) + Capsaicin (0.0375 g/100g) + Menthol (5 1/100g) Kit Oral; Topical Basiem 2015-08-30 2016-03-04 US
Categories
- ATC Codes
- G02CC02 — Naproxen
- G02CC — Antiinflammatory products for vaginal administration
- G02C — OTHER GYNECOLOGICALS
- G02 — OTHER GYNECOLOGICALS
- G — GENITO URINARY SYSTEM AND SEX HORMONES
- 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
- M01AE — Propionic acid derivatives
- M01A — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS
- M01 — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
- M — MUSCULO-SKELETAL SYSTEM
- M01AE — Propionic acid derivatives
- M01A — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS
- M01 — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
- M — MUSCULO-SKELETAL 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
- Antirheumatic Agents
- 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
- 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
- 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]
- 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]
- Brutzkus JC, Varacallo M: Naproxen . [Article]
- 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]
- 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]
- Davies NM, Anderson KE: Clinical pharmacokinetics of naproxen. Clin Pharmacokinet. 1997 Apr;32(4):268-93. doi: 10.2165/00003088-199732040-00002. [Article]
- 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]
- 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]
- 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]
- 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]
- 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]
- Naprelan FDA Label [Link]
- Naprosyn FDA Label [Link]
- Over-the-counter Medications in Pregnancy [Link]
- Treximet FDA Label [Link]
- 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
- 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);">
Phase Status Purpose Conditions Count 4 Completed Not Available Duodenal Ulcer 1 4 Completed Not Available Migraine 1 4 Completed Basic Science Acute Pain / Osseointegrated Dental Implantation 1 4 Completed Basic Science Poor Metabolizer Due to Cytochrome P450 CYP2C19 Variant / Poor Metabolizer Due to Cytochrome P450 CYP2C9 Variant 1 4 Completed Basic Science Rheumatoid Arthritis 1
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 Oral 250 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 Suppository Rectal 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 275.000 mg Tablet Oral 660.000 mg Tablet Oral 250.000 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 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 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 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 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 Gel Topical Tablet, delayed release Oral Tablet, extended 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 US CA2034096 No 2002-03-26 2011-01-14 Canada US6060499 Yes 2000-05-09 2018-02-14 US US7332183 Yes 2008-02-19 2026-04-02 US US6586458 Yes 2003-07-01 2018-02-14 US US5872145 Yes 1999-02-16 2018-02-14 US US8022095 Yes 2011-09-20 2018-02-14 US US5900424 Yes 1999-05-04 2016-11-04 US US6369085 Yes 2002-04-09 2018-11-25 US US7411070 Yes 2008-08-12 2018-11-25 US US8852636 No 2014-10-07 2022-05-31 US US8858996 No 2014-10-14 2022-05-31 US US6926907 No 2005-08-09 2023-02-28 US US7745466 No 2010-06-29 2018-10-13 US US9161920 No 2015-10-20 2022-05-31 US US9198888 No 2015-12-01 2022-05-31 US US8945621 No 2015-02-03 2031-10-17 US US8557285 No 2013-10-15 2022-05-31 US US9220698 No 2015-12-29 2031-03-10 US US5714504 Yes 1998-02-03 2015-08-03 US US9345695 No 2016-05-24 2022-05-31 US US9393208 No 2016-07-19 2029-09-03 US US9707181 No 2017-07-18 2022-05-31 US US9693978 No 2017-07-04 2026-03-03 US US9693979 No 2017-07-04 2026-03-03 US US10028925 No 2018-07-24 2026-03-03 US US10022344 No 2018-07-17 2026-03-03 US US11090280 No 2021-08-17 2026-03-03 US
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
Spectra
- Mass Spec (NIST)
- Download (7.95 KB)
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 165.2428984 predictedDarkChem Lite v0.1.0 [M-H]- 165.6894984 predictedDarkChem Lite v0.1.0 [M-H]- 165.2465984 predictedDarkChem Lite v0.1.0 [M-H]- 164.9187984 predictedDarkChem Lite v0.1.0 [M-H]- 165.3348984 predictedDarkChem Lite v0.1.0 [M-H]- 155.95302 predictedDeepCCS 1.0 (2019) [M+H]+ 165.3139984 predictedDarkChem Lite v0.1.0 [M+H]+ 167.3790984 predictedDarkChem Lite v0.1.0 [M+H]+ 166.0776984 predictedDarkChem Lite v0.1.0 [M+H]+ 165.7917984 predictedDarkChem Lite v0.1.0 [M+H]+ 166.0621984 predictedDarkChem Lite v0.1.0 [M+H]+ 158.31102 predictedDeepCCS 1.0 (2019) [M+Na]+ 165.6027984 predictedDarkChem Lite v0.1.0 [M+Na]+ 165.6981984 predictedDarkChem Lite v0.1.0 [M+Na]+ 165.2845984 predictedDarkChem Lite v0.1.0 [M+Na]+ 165.0297984 predictedDarkChem Lite v0.1.0 [M+Na]+ 165.4392984 predictedDarkChem Lite v0.1.0 [M+Na]+ 164.40416 predictedDeepCCS 1.0 (2019)
Targets
![](https://go.drugbank.com/assets/locked/DrugTargets2-682eb846d210ae4bf33ca03febccfb57bb1c61318e699b729e5df4dfab2c5b67.png)
- 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
- 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
- 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]
- 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]
- Brutzkus JC, Varacallo M: Naproxen . [Article]
- 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
- 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]
- 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
- 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
- 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]
- 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]
- 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]
- 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
- 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]
- 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]
- 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
- 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]
- 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
- 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]
- 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
- 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]
- 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
- 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]
- 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
- 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]
- 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
- 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]
- 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
- 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]
- 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]
- 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]
- Flockhart Table of Drug Interactions [Link]
- 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
- 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]
- 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]
- 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]
- Flockhart Table of Drug Interactions [Link]
Carriers
- 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
- 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]
- 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]
- 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]
- Davies NM, Anderson KE: Clinical pharmacokinetics of naproxen. Clin Pharmacokinet. 1997 Apr;32(4):268-93. doi: 10.2165/00003088-199732040-00002. [Article]
Transporters
- 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
- 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]
- 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
- 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]
- 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]
- 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
- 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]
- 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
- 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]
- 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
- 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