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
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
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 |
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
PubMed
Title | Date | PubMed |
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Persistent pulmonary hypertension after maternal naproxen ingestion in a term newborn: a case report. | 2000 |
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Naproxen-induced leukocytoclastic vasculitis. | 2000 |
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Absence of pharmacokinetic interaction between orally co-administered naproxen sodium and diphenhydramine hydrochloride. | 2000 Sep |
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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 |
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[Two complex suicidal poisonings with drugs and their medicolegal aspects]. | 2001 |
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Differential regulation of interleukin-1 beta-induced cyclooxygenase-2 gene expression by nimesulide in human synovial fibroblasts. | 2001 |
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Nimesulide, a balanced drug for the treatment of osteoarthritis. | 2001 |
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Naproxen particle design using porous starch. | 2001 Apr |
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Naproxen-Eudragit microspheres: screening of process and formulation variables for the preparation of extended release tablets. | 2001 Apr |
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Reduced incidence of gastroduodenal ulcers with celecoxib, a novel cyclooxygenase-2 inhibitor, compared to naproxen in patients with arthritis. | 2001 Apr |
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Risk of ulcer soars with combination of arthritis drugs. | 2001 Apr |
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S-naproxen-beta-1-O-acyl glucuronide degradation kinetic studies by stopped-flow high-performance liquid chromatography-1H NMR and high-performance liquid chromatography-UV. | 2001 Apr |
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[Acupuncture contra antiphlogistics in acute lumbago]. | 2001 Apr 20 |
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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 |
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Localization of cyclooxygenase isozymes in cardiovascular tissues of dogs treated with naproxen. | 2001 Aug 10 |
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A look at the safety profile of over-the-counter naproxen sodium: a meta-analysis. | 2001 Feb |
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Efficacy of single-dose and multidose rofecoxib in the treatment of post-orthopedic surgery pain. | 2001 Jan |
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Successful use of propranolol in migraine associated with electroconvulsive therapy. | 2001 Jan |
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Prostaglandin H synthase-2 inhibitors interfere with prostaglandin H synthase-1 inhibition by nonsteroidal anti-inflammatory drugs. | 2001 Jan 19 |
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Alendronate and naproxen are synergistic for development of gastric ulcers. | 2001 Jan 8 |
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A possible mechanism of naproxen-induced lipid peroxidation in rat liver microsomes. | 2001 Jul |
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New issues about nitric oxide and its effects on the gastrointestinal tract. | 2001 Jul |
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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 |
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Addition of hydrogen bond donating excipients to oil solution: effect on in vitro drug release rate and viscosity. | 2001 Jul |
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Enantioselective inhibition of the binding of rac-profens to human serum albumin induced by lithocholate. | 2001 Jul |
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In vitro evaluation and intra-articular administration of biodegradable microspheres containing naproxen sodium. | 2001 Jul-Aug |
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In vitro effects of NSAIDS and paracetamol on oxidative stress-related parameters of human erythrocytes. | 2001 Jun |
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Determination of naproxen in pharmaceutical preparations by room-temperature phosphorescence. A comparative study of several organized media. | 2001 Jun |
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By the way, doctor. Which drugs cause problems in the sun? | 2001 Jun |
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Fixed drug eruption due to naproxen; lack of cross-reactivity with other propionic acid derivatives. | 2001 Jun |
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[The lack of awareness of the Israeli population regarding gastrointestinal complications from non-steroidal anti-inflammatory drugs]. | 2001 Jun |
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Treatment of de Quervain's disease:role of conservative management. | 2001 Jun |
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Inhibition of tendon cell proliferation and matrix glycosaminoglycan synthesis by non-steroidal anti-inflammatory drugs in vitro. | 2001 Jun |
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Immune thrombocytopenia resulting from sensitivity to metabolites of naproxen and acetaminophen. | 2001 Jun 15 |
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[Nitric oxide and gastroduodenal damage caused by NSAIDs. Recent findings and clinical implications]. | 2001 Mar |
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Synthesis and cyclooxygenase inhibitory properties of novel (+) 2-(6-methoxy-2-naphthyl)propanoic acid (naproxene) derivatives. | 2001 Mar |
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High-performance liquid chromatographic method development and validation for the simultaneous quantitation of naproxen sodium and pseudoephedrine hydrochloride impurities. | 2001 Mar |
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Neuroprotective effects of non-steroidal anti-inflammatory drugs by direct scavenging of nitric oxide radicals. | 2001 Mar |
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Rofecoxib, a COX-2 inhibitor, does not inhibit human gastric mucosal prostaglandin production. | 2001 Mar |
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Effect of antipyretic drugs in children with malaria. | 2001 Mar 1 |
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Effect of cyclodextrin charge on complexation of neutral and charged substrates: comparison of (SBE)7M-beta-CD to HP-beta-CD. | 2001 May |
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Synthesis, in vitro skin permeation studies, and PLS-analysis of new naproxen derivatives. | 2001 May |
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[The selective Cox-2 inhibition by rofecoxib reduces risk of severe gastrointestinal complications of anti-inflammatory therapy by more than 50%]. | 2001 May |
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Nimesulide reduces interleukin-1beta-induced cyclooxygenase-2 gene expression in human synovial fibroblasts. | 2001 May |
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Severe reversible renal failure due to naproxen-associated acute interstitial nephritis. | 2001 May |
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Effect of nonsteroidal anti-inflammatory drug use on the rate of gastrointestinal hospitalizations among people living in long-term care. | 2001 May |
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Stereoselective synthesis of (S)-(+)-Naproxen catalyzed by carboxyl esterase in a multicompartment electrolyzer. | 2001 May 28 |
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Upper gastrointestinal toxicity of rofecoxib and naproxen. | 2001 May 3 |
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Upper gastrointestinal toxicity of rofecoxib and naproxen. | 2001 May 3 |
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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
Sample Use Guides
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
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
Edited
Mon Oct 21 22:21:57 UTC 2019
by
admin
on
Mon Oct 21 22:21:57 UTC 2019
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Record UNII |
57Y76R9ATQ
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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Code System | Code | Type | Description | ||
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DB00788
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2979
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156391
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C680
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22204-53-1
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7258
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22204-53-1
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PRIMARY | |||
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5230
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D009288
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CHEMBL154
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PRIMARY | |||
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M7769
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PRIMARY | Merck Index | ||
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22204-53-1
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SUB09159MIG
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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
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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
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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
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PRIMARY |
Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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BINDER->LIGAND |
BINDING
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
EP
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METABOLIC ENZYME -> SUBSTRATE | |||
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SALT/SOLVATE -> PARENT | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
USP
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TRANSPORTER -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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SALT/SOLVATE -> PARENT | |||
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> INHIBITOR |
Related Record | Type | Details | ||
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METABOLITE INACTIVE -> PARENT |
Naproxen is extensively metabolized to 6-0-desmethyl naproxen and both parent and metabolites do not induce metabolizing enzymes
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METABOLITE INACTIVE -> PARENT | |||
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METABOLITE INACTIVE -> PARENT | |||
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METABOLITE INACTIVE -> PARENT |
Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
For the calculation of contents, multiply the peak areas by 2.0
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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EXCRETION | PHARMACOKINETIC |
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Volume of Distribution | PHARMACOKINETIC |
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ORAL BIOAVAILABILITY | PHARMACOKINETIC |
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MAXIMUM TOLERATED DOSE | TOXICITY |
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Tmax | PHARMACOKINETIC |
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FOOD EFFECT PHARMACOKINETIC |
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Tmax | PHARMACOKINETIC |
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Tmax | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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