U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C14H14O3
Molecular Weight 230.2592
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NAPROXEN

SMILES

COC1=CC2=CC=C(C=C2C=C1)[C@H](C)C(O)=O

InChI

InChIKey=CMWTZPSULFXXJA-VIFPVBQESA-N
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

HIDE SMILES / InChI
Molecular Formula C14H14O3
Molecular Weight 230.2592
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Naproxen (naproxen sodium, NAPROSYN®) is a propionic acid derivative related to the arylacetic acid group of nonsteroidal anti-inflammatory drugs (NSAIDs). It is an anti-inflammatory agent with analgesic and antipyretic properties. Both the acid and its sodium salt are used in the treatment of rheumatoid arthritis and other rheumatic or musculoskeletal disorders, dysmenorrhea, and acute gout. The mechanism of action of the naproxen (naproxen sodium, NAPROSYN®), like that of other NSAIDs, is not completely understood but involves inhibition of cyclooxygenase (COX-1 and COX-2).

CNS Activity

Originator

Approval Year

1976
72
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
7468
Ankylosing Spondylitis
 0.19 µM [IC50]
Inhibitor
7468
Ankylosing Spondylitis
 0.11 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Cyclooxygenase-1
Cyclooxygenase-2
Approved
7883
NAPROSYN
Primary
Cyclooxygenase-1
Cyclooxygenase-2
Approved
7883
NAPROSYN
Primary
Cyclooxygenase-1
Cyclooxygenase-2
Approved
7883
NAPROSYN
Primary
Cyclooxygenase-1
Cyclooxygenase-2
Approved
7883
NAPROSYN
Primary
Cyclooxygenase-1
Cyclooxygenase-2
Approved
7883
NAPROSYN
Approved (off-label)
8
PubMed

PubMed

TitleDatePubMed
Absence of pharmacokinetic interaction between orally co-administered naproxen sodium and diphenhydramine hydrochloride.
2000 Sep
Synthesis of some new 1-acylthiosemicarbazides, 1,3,4-oxadiazoles, 1,3,4-thiadiazoles and 1,2,4-triazole-3-thiones and their anti-inflammatory activities.
2001
[Two complex suicidal poisonings with drugs and their medicolegal aspects].
2001
Risk of upper gastrointestinal bleeding and perforation associated with low-dose aspirin as plain and enteric-coated formulations.
2001
Reduced incidence of gastroduodenal ulcers with celecoxib, a novel cyclooxygenase-2 inhibitor, compared to naproxen in patients with arthritis.
2001 Apr
Celecoxib and rofecoxib. The role of COX-2 inhibitors in dental practice.
2001 Apr
Risk of ulcer soars with combination of arthritis drugs.
2001 Apr
Pharmacokinetic/pharmacodynamic modeling of antipyretic and anti-inflammatory effects of naproxen in the rat.
2001 Apr
[Acupuncture contra antiphlogistics in acute lumbago].
2001 Apr 20
I'm taking over-the-counter ibuprofen every day for neck pain. Recently, my doctor gave me a prescription for naproxen for my arthritis. Should I be concerned about taking these two together?
2001 Aug
Localization of cyclooxygenase isozymes in cardiovascular tissues of dogs treated with naproxen.
2001 Aug 10
Directly coupled HPLC-NMR and HPLC-MS approaches for the rapid characterisation of drug metabolites in urine: application to the human metabolism of naproxen.
2001 Feb
[Chronic recurrent multifocal osteomyelitis].
2001 Feb
Analgesic and anti-inflammatory effects of Mangifera indica L. extract (Vimang).
2001 Feb
Determination of drug residues in water by the combination of liquid chromatography or capillary electrophoresis with electrospray mass spectrometry.
2001 Feb 23
Rhein, an active metabolite of diacerein, suppresses the interleukin-1alpha-induced proteoglycan degradation in cultured rabbit articular chondrocytes.
2001 Jan
Successful use of propranolol in migraine associated with electroconvulsive therapy.
2001 Jan
Prostaglandin H synthase-2 inhibitors interfere with prostaglandin H synthase-1 inhibition by nonsteroidal anti-inflammatory drugs.
2001 Jan 19
[Liver damage and nonsteroidal anti-inflammatory drugs: case non-case study in the French Pharmacovigilance Database].
2001 Jan-Feb
Allergic reactions due to ibuprofen in children.
2001 Jan-Feb
A possible mechanism of naproxen-induced lipid peroxidation in rat liver microsomes.
2001 Jul
Effects of non-steroidal antiinflammatory drugs and dexamethasone on the activity and expression of matrix metalloproteinase-1, matrix metalloproteinase-3 and tissue inhibitor of metalloproteinases-1 by bovine articular chondrocytes.
2001 Jul
Dapsone activation of CYP2C9-mediated metabolism: evidence for activation of multiple substrates and a two-site model.
2001 Jul
In vitro evaluation and intra-articular administration of biodegradable microspheres containing naproxen sodium.
2001 Jul-Aug
In vitro effects of NSAIDS and paracetamol on oxidative stress-related parameters of human erythrocytes.
2001 Jun
Determination of naproxen in pharmaceutical preparations by room-temperature phosphorescence. A comparative study of several organized media.
2001 Jun
By the way, doctor. Which drugs cause problems in the sun?
2001 Jun
[Treatment of pain due to unwanted lactation with a homeopathic preparation given in the immediate post-partum period].
2001 Jun
Treatment of de Quervain's disease:role of conservative management.
2001 Jun
Immune thrombocytopenia resulting from sensitivity to metabolites of naproxen and acetaminophen.
2001 Jun 15
Synthesis and cyclooxygenase inhibitory properties of novel (+) 2-(6-methoxy-2-naphthyl)propanoic acid (naproxene) derivatives.
2001 Mar
Peroxisomal proliferator-activated ligand therapy for HIV lipodystrophy.
2001 Mar
Acute postoperative swelling after hand surgery: an exploratory, double-blind, randomised study with paracetamol, naproxen, and placebo.
2001 Mar
Anti-lymphoma effect of naproxen and indomethacin in a patient with relapsed diffuse large B-cell lymphoma.
2001 Mar
High-performance liquid chromatographic method development and validation for the simultaneous quantitation of naproxen sodium and pseudoephedrine hydrochloride impurities.
2001 Mar
Neuroprotective effects of non-steroidal anti-inflammatory drugs by direct scavenging of nitric oxide radicals.
2001 Mar
Effect of lipophilicity on in vivo iontophoretic delivery. I. NSAIDs.
2001 Mar
Is rofecoxib safer than naproxen?
2001 Mar
Analysis of nonsteroidal antiinflammatory drugs in meconium and its relation to persistent pulmonary hypertension of the newborn.
2001 Mar
Effect of antipyretic drugs in children with malaria.
2001 Mar 1
Prostaglandin biosynthesis by fat body from true armyworms, Pseudaletia unipuncta.
2001 Mar 15
Simultaneous quantification of neutral and acidic pharmaceuticals and pesticides at the low-ng/l level in surface and waste water.
2001 Mar 16
Preventing recurrent upper gastrointestinal bleeding in patients with Helicobacter pylori infection who are taking low-dose aspirin or naproxen.
2001 Mar 29
Effect of cyclodextrin charge on complexation of neutral and charged substrates: comparison of (SBE)7M-beta-CD to HP-beta-CD.
2001 May
Severe reversible renal failure due to naproxen-associated acute interstitial nephritis.
2001 May
Effect of nonsteroidal anti-inflammatory drug use on the rate of gastrointestinal hospitalizations among people living in long-term care.
2001 May
Stereoselective synthesis of (S)-(+)-Naproxen catalyzed by carboxyl esterase in a multicompartment electrolyzer.
2001 May 28
Upper gastrointestinal toxicity of rofecoxib and naproxen.
2001 May 3
Upper gastrointestinal toxicity of rofecoxib and naproxen.
2001 May 3
Screening procedure for detection of non-steroidal anti-inflammatory drugs and their metabolites in urine as part of a systematic toxicological analysis procedure for acidic drugs and poisons by gas chromatography-mass spectrometry after extractive methylation.
2001 May-Jun
Patents

Patents

4675419
5
4962230
5
7238829
5
8222277
7
8409559
5
JP2000080034A
13
JP2002511777A
372
JP2002528495A
37
JP2002531515A
6
JP2002544210A
84
JP2003507415A
28
JP2007510681A
5
JP2009525778A
32
JP2009530408A
48
JP2010506837A
73
JP2011524416A
126
JP4264850B2
6
JP4657714B2
7
JP4660198B2
5
JP4756823B2
15
JP4774135B2
12
JP4787165B2
92
JPH03101618A
13
JPH03227948A
5
JPH04230329A
5
JPH10158210A
5
JPS5555135A
5
JPS6072813A
5
US5637320
5

Sample Use Guides

In Vivo Use Guide
Rheumatoid Arthritis, Osteoarthritis and Ankylosing Spondylitis: 1 tablet of NAPROSYN® (250 mg or 375 mg or 500 mg) twice daily. Acute Gout: The recommended starting dose is 750 mg of NAPROSYN® followed by 250 mg every 8 hours until the attack has subsided.
Route of Administration: Oral
In Vitro Use Guide
There are data on the N-(3-methylpyridin-2-yl)amide derivatives of flurbiprofen and naproxen (Flu-AM1 and Nap-AM1, respectively) with respect to their properties towards fatty acid amide hydrolase (FAAH). Flu-AM1 and Nap-AM1 inhibited FAAH-catalysed hydrolysis of [(3)H]anandamide by rat brain homogenates with IC50 values of 0.44 and 0.74 uM. The corresponding values for flurbiprofen and naproxen were 29 and >100 uM, respectively.
Substance Class Chemical
Created
by admin
on Mon Oct 21 22:21:57 UTC 2019
Edited
by admin
on Mon Oct 21 22:21:57 UTC 2019
Record UNII
57Y76R9ATQ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NAPROXEN
EP   GREEN BOOK   HSDB   INCI   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INN   USAN   INCI  
Official Name English
NAPROXEN [USP-RS]
Common Name English
NAPROXEN [GREEN BOOK]
Common Name English
NAPROXEN [EP]
Common Name English
PN400 COMPONENT NAPROXEN
Code English
NAPROXEN [MI]
Common Name English
NAPROXEN [HSDB]
Common Name English
NAPROXEN COMPONENT OF VIMOVO
Common Name English
(+)-(S)-6-METHOXY-.ALPHA.-METHYL-2-NAPHTHALENEACETIC ACID
Systematic Name English
NAPROXEN [USP]
Common Name English
NAPROXEN [INN]
Common Name English
NAPROXEN [USAN]
Common Name English
NAPROSYN
Brand Name English
2-NAPHTHALENEACETIC ACID, 6-METHOXY-.ALPHA.-METHYL-, (S)-
Common Name English
NAPROXEN [VANDF]
Common Name English
RS-3540
Code English
VIMOVO COMPONENT NAPROXEN
Common Name English
NAPROXEN [MART.]
Common Name English
NAPROXEN [WHO-DD]
Common Name English
NAPROXEN [INCI]
Common Name English
NAPROXEN [ORANGE BOOK]
Common Name English
NAPROXEN [JAN]
Common Name English
EC-NAPROSYN
Brand Name English
Classification Tree Code System Code
NDF-RT N0000175722
Created by admin on Mon Oct 21 22:21:57 UTC 2019 , Edited by admin on Mon Oct 21 22:21:57 UTC 2019
CFR 21 CFR 522.1468
Created by admin on Mon Oct 21 22:21:57 UTC 2019 , Edited by admin on Mon Oct 21 22:21:57 UTC 2019
NDF-RT N0000175721
Created by admin on Mon Oct 21 22:21:57 UTC 2019 , Edited by admin on Mon Oct 21 22:21:57 UTC 2019
WHO-ATC G02CC02
Created by admin on Mon Oct 21 22:21:57 UTC 2019 , Edited by admin on Mon Oct 21 22:21:57 UTC 2019
WHO-VATC QM01AE56
Created by admin on Mon Oct 21 22:21:57 UTC 2019 , Edited by admin on Mon Oct 21 22:21:57 UTC 2019
WHO-VATC QM02AA12
Created by admin on Mon Oct 21 22:21:57 UTC 2019 , Edited by admin on Mon Oct 21 22:21:57 UTC 2019
NCI_THESAURUS C1323
Created by admin on Mon Oct 21 22:21:57 UTC 2019 , Edited by admin on Mon Oct 21 22:21:57 UTC 2019
WHO-VATC QG02CC02
Created by admin on Mon Oct 21 22:21:57 UTC 2019 , Edited by admin on Mon Oct 21 22:21:57 UTC 2019
LIVERTOX 668
Created by admin on Mon Oct 21 22:21:57 UTC 2019 , Edited by admin on Mon Oct 21 22:21:57 UTC 2019
WHO-VATC QM01AE52
Created by admin on Mon Oct 21 22:21:57 UTC 2019 , Edited by admin on Mon Oct 21 22:21:57 UTC 2019
WHO-ATC M01AE52
Created by admin on Mon Oct 21 22:21:57 UTC 2019 , Edited by admin on Mon Oct 21 22:21:57 UTC 2019
WHO-ATC M02AA12
Created by admin on Mon Oct 21 22:21:57 UTC 2019 , Edited by admin on Mon Oct 21 22:21:57 UTC 2019
CFR 21 CFR 520.1468
Created by admin on Mon Oct 21 22:21:57 UTC 2019 , Edited by admin on Mon Oct 21 22:21:57 UTC 2019
WHO-VATC QM01AE02
Created by admin on Mon Oct 21 22:21:57 UTC 2019 , Edited by admin on Mon Oct 21 22:21:57 UTC 2019
WHO-ATC M01AE56
Created by admin on Mon Oct 21 22:21:57 UTC 2019 , Edited by admin on Mon Oct 21 22:21:57 UTC 2019
WHO-ATC M01AE02
Created by admin on Mon Oct 21 22:21:57 UTC 2019 , Edited by admin on Mon Oct 21 22:21:57 UTC 2019
NDF-RT N0000000160
Created by admin on Mon Oct 21 22:21:57 UTC 2019 , Edited by admin on Mon Oct 21 22:21:57 UTC 2019
Code System Code Type Description
DRUG BANK
DB00788
Created by admin on Mon Oct 21 22:21:57 UTC 2019 , Edited by admin on Mon Oct 21 22:21:57 UTC 2019
PRIMARY
INN
2979
Created by admin on Mon Oct 21 22:21:57 UTC 2019 , Edited by admin on Mon Oct 21 22:21:57 UTC 2019
PRIMARY
PUBCHEM
156391
Created by admin on Mon Oct 21 22:21:57 UTC 2019 , Edited by admin on Mon Oct 21 22:21:57 UTC 2019
PRIMARY
NCI_THESAURUS
C680
Created by admin on Mon Oct 21 22:21:57 UTC 2019 , Edited by admin on Mon Oct 21 22:21:57 UTC 2019
PRIMARY
HSDB
22204-53-1
Created by admin on Mon Oct 21 22:21:57 UTC 2019 , Edited by admin on Mon Oct 21 22:21:57 UTC 2019
PRIMARY
RXCUI
7258
Created by admin on Mon Oct 21 22:21:57 UTC 2019 , Edited by admin on Mon Oct 21 22:21:57 UTC 2019
PRIMARY RxNorm
LactMed
22204-53-1
Created by admin on Mon Oct 21 22:21:57 UTC 2019 , Edited by admin on Mon Oct 21 22:21:57 UTC 2019
PRIMARY
IUPHAR
5230
Created by admin on Mon Oct 21 22:21:57 UTC 2019 , Edited by admin on Mon Oct 21 22:21:57 UTC 2019
PRIMARY
MESH
D009288
Created by admin on Mon Oct 21 22:21:57 UTC 2019 , Edited by admin on Mon Oct 21 22:21:57 UTC 2019
PRIMARY
ChEMBL
CHEMBL154
Created by admin on Mon Oct 21 22:21:57 UTC 2019 , Edited by admin on Mon Oct 21 22:21:57 UTC 2019
PRIMARY
MERCK INDEX
M7769
Created by admin on Mon Oct 21 22:21:57 UTC 2019 , Edited by admin on Mon Oct 21 22:21:57 UTC 2019
PRIMARY Merck Index
CAS
22204-53-1
Created by admin on Mon Oct 21 22:21:57 UTC 2019 , Edited by admin on Mon Oct 21 22:21:57 UTC 2019
PRIMARY
EVMPD
SUB09159MIG
Created by admin on Mon Oct 21 22:21:57 UTC 2019 , Edited by admin on Mon Oct 21 22:21:57 UTC 2019
PRIMARY
EPA CompTox
22204-53-1
Created by admin on Mon Oct 21 22:21:57 UTC 2019 , Edited by admin on Mon Oct 21 22:21:57 UTC 2019
PRIMARY
WIKIPEDIA
NAPROXEN
Created by admin on Mon Oct 21 22:21:57 UTC 2019 , Edited by admin on Mon Oct 21 22:21:57 UTC 2019
PRIMARY
ECHA (EC/EINECS)
244-838-7
Created by admin on Mon Oct 21 22:21:57 UTC 2019 , Edited by admin on Mon Oct 21 22:21:57 UTC 2019
PRIMARY
Related Record Type Details
Structure of NAPROXEN LYSINE
SALT/SOLVATE -> PARENT
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
Structure of NAPROXEN
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
EP
URIDINE DIPHOSPHATE GLUCURONOSYLTRANSFERASE 1A3
METABOLIC ENZYME -> SUBSTRATE
Structure of NAPROXEN PIPERAZINE
SALT/SOLVATE -> PARENT
CYTOCHROME P450 1A2
METABOLIC ENZYME -> SUBSTRATE
Structure of NAPROXEN
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
USP
OAT-4
TRANSPORTER -> INHIBITOR
Structure of NAPROXEN AMINOBUTANOL
SALT/SOLVATE -> PARENT
CYTOCHROME P450 2C9
METABOLIC ENZYME -> SUBSTRATE
Structure of NAPROXEN SODIUM
SALT/SOLVATE -> PARENT
OAT-1
TRANSPORTER -> INHIBITOR
OAT-2
TRANSPORTER -> INHIBITOR
OAT-3
TRANSPORTER -> INHIBITOR
Related Record Type Details
Structure of 6-O-DEMETHYLNAPROXEN
METABOLITE INACTIVE -> PARENT
Naproxen is extensively metabolized to 6-0-desmethyl naproxen and both parent and metabolites do not induce metabolizing enzymes
Structure of 6-O-DEMETHYLNAPROXEN
METABOLITE INACTIVE -> PARENT
Structure of 6-O-DEMETHYLNAPROXEN
METABOLITE INACTIVE -> PARENT
Structure of 6-O-DEMETHYLNAPROXEN
METABOLITE INACTIVE -> PARENT
Related Record Type Details
Structure of NAPROXEN, (-)-
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 5-BROMONAPROXEN, (S)-
IMPURITY -> PARENT
UNSPECIFIED
EP
Structure of 5-CHLORONAPROXEN, (S)-
IMPURITY -> PARENT
UNSPECIFIED
EP
Structure of 6-METHOXY-2-NAPHTHOL
IMPURITY -> PARENT
UNSPECIFIED
EP
Structure of 2-BROMO-6-METHOXYNAPHTHALENE
IMPURITY -> PARENT
UNSPECIFIED
EP
Structure of .BETA.-NAPHTHYL METHYL ETHER
IMPURITY -> PARENT
UNSPECIFIED
EP
Structure of 2-ACETYL-6-METHOXYNAPHTHALENE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of NAPROXEN METHYL ESTER
IMPURITY -> PARENT
UNSPECIFIED
EP
Structure of 6-METHOXY-2-NAPHTHYLACETIC ACID
IMPURITY -> PARENT
UNSPECIFIED
EP
Structure of 6-O-DEMETHYLNAPROXEN
IMPURITY -> PARENT
UNSPECIFIED
EP
Structure of 2-ETHYL-6-METHOXYNAPHTHALENE
IMPURITY -> PARENT
UNSPECIFIED
EP
Structure of NAPROXEN ETHYL ESTER
IMPURITY -> PARENT
UNSPECIFIED
EP
Structure of 5-IODONAPROXEN, (S)-
IMPURITY -> PARENT
UNSPECIFIED
EP
Structure of 6-METHOXY-2-NAPHTHOIC ACID
IMPURITY -> PARENT
For the calculation of contents, multiply the peak areas by 2.0
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 1-(6-METHOXYNAPHTHALEN-2-YL)ETHANOL, (+/-)-
IMPURITY -> PARENT
UNSPECIFIED
EP
Related Record Type Details
Structure of NAPROXEN
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
EXCRETION PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC
ORAL BIOAVAILABILITY PHARMACOKINETIC
MAXIMUM TOLERATED DOSE TOXICITY
Tmax PHARMACOKINETIC FOOD EFFECT
PHARMACOKINETIC
Tmax PHARMACOKINETIC
Tmax PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966