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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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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Risk of upper gastrointestinal bleeding and perforation associated with low-dose aspirin as plain and enteric-coated formulations. | 2001 |
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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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Celecoxib and rofecoxib. The role of COX-2 inhibitors in dental practice. | 2001 Apr |
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Risk of ulcer soars with combination of arthritis drugs. | 2001 Apr |
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Pharmacokinetic/pharmacodynamic modeling of antipyretic and anti-inflammatory effects of naproxen in the rat. | 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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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 |
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[Chronic recurrent multifocal osteomyelitis]. | 2001 Feb |
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Analgesic and anti-inflammatory effects of Mangifera indica L. extract (Vimang). | 2001 Feb |
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Determination of drug residues in water by the combination of liquid chromatography or capillary electrophoresis with electrospray mass spectrometry. | 2001 Feb 23 |
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Rhein, an active metabolite of diacerein, suppresses the interleukin-1alpha-induced proteoglycan degradation in cultured rabbit articular chondrocytes. | 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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[Liver damage and nonsteroidal anti-inflammatory drugs: case non-case study in the French Pharmacovigilance Database]. | 2001 Jan-Feb |
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Allergic reactions due to ibuprofen in children. | 2001 Jan-Feb |
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A possible mechanism of naproxen-induced lipid peroxidation in rat liver microsomes. | 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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Dapsone activation of CYP2C9-mediated metabolism: evidence for activation of multiple substrates and a two-site model. | 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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[Treatment of pain due to unwanted lactation with a homeopathic preparation given in the immediate post-partum period]. | 2001 Jun |
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Treatment of de Quervain's disease:role of conservative management. | 2001 Jun |
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Immune thrombocytopenia resulting from sensitivity to metabolites of naproxen and acetaminophen. | 2001 Jun 15 |
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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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Peroxisomal proliferator-activated ligand therapy for HIV lipodystrophy. | 2001 Mar |
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Acute postoperative swelling after hand surgery: an exploratory, double-blind, randomised study with paracetamol, naproxen, and placebo. | 2001 Mar |
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Anti-lymphoma effect of naproxen and indomethacin in a patient with relapsed diffuse large B-cell lymphoma. | 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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Effect of lipophilicity on in vivo iontophoretic delivery. I. NSAIDs. | 2001 Mar |
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Is rofecoxib safer than naproxen? | 2001 Mar |
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Analysis of nonsteroidal antiinflammatory drugs in meconium and its relation to persistent pulmonary hypertension of the newborn. | 2001 Mar |
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Effect of antipyretic drugs in children with malaria. | 2001 Mar 1 |
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Prostaglandin biosynthesis by fat body from true armyworms, Pseudaletia unipuncta. | 2001 Mar 15 |
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Simultaneous quantification of neutral and acidic pharmaceuticals and pesticides at the low-ng/l level in surface and waste water. | 2001 Mar 16 |
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Preventing recurrent upper gastrointestinal bleeding in patients with Helicobacter pylori infection who are taking low-dose aspirin or naproxen. | 2001 Mar 29 |
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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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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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PRIMARY | |||
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156391
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C680
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22204-53-1
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7258
Created by
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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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PRIMARY | |||
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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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