Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C14H13O3.Na |
| Molecular Weight | 252.241 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].COC1=CC2=CC=C(C=C2C=C1)[C@H](C)C([O-])=O
InChI
InChIKey=CDBRNDSHEYLDJV-FVGYRXGTSA-M
InChI=1S/C14H14O3.Na/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);/q;+1/p-1/t9-;/m0./s1
| Molecular Formula | C14H13O3 |
| Molecular Weight | 229.2512 |
| Charge | -1 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | Na |
| Molecular Weight | 22.98976928 |
| Charge | 1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 |
|---|---|---|
| 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 |
|
| Rofecoxib: a review of its use in the management of osteoarthritis, acute pain and rheumatoid arthritis. | 2001 |
|
| Differential regulation of interleukin-1 beta-induced cyclooxygenase-2 gene expression by nimesulide in human synovial fibroblasts. | 2001 |
|
| Nimesulide, a balanced drug for the treatment of osteoarthritis. | 2001 |
|
| Naproxen particle design using porous starch. | 2001 Apr |
|
| Naproxen-Eudragit microspheres: screening of process and formulation variables for the preparation of extended release tablets. | 2001 Apr |
|
| Reduced incidence of gastroduodenal ulcers with celecoxib, a novel cyclooxygenase-2 inhibitor, compared to naproxen in patients with arthritis. | 2001 Apr |
|
| Endogenous prostaglandin E2 and insulin-like growth factor 1 can modulate the levels of parathyroid hormone receptor in human osteoarthritic osteoblasts. | 2001 Apr |
|
| Celecoxib and rofecoxib. The role of COX-2 inhibitors in dental practice. | 2001 Apr |
|
| Rhein, an active metabolite of diacerein, down-regulates the production of pro-matrix metalloproteinases-1, -3, -9 and -13 and up-regulates the production of tissue inhibitor of metalloproteinase-1 in cultured rabbit articular chondrocytes. | 2001 Apr |
|
| Uniformly sized molecularly imprinted polymer for (S)-naproxen retention and molecular recognition properties in aqueous mobile phase. | 2001 Apr 13 |
|
| [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 |
|
| [Liver damage and nonsteroidal anti-inflammatory drugs: case non-case study in the French Pharmacovigilance Database]. | 2001 Jan-Feb |
|
| A possible mechanism of naproxen-induced lipid peroxidation in rat liver microsomes. | 2001 Jul |
|
| New issues about nitric oxide and its effects on the gastrointestinal tract. | 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 |
|
| Addition of hydrogen bond donating excipients to oil solution: effect on in vitro drug release rate and viscosity. | 2001 Jul |
|
| Enantioselective inhibition of the binding of rac-profens to human serum albumin induced by lithocholate. | 2001 Jul |
|
| Determination of ibuprofen and naproxen in tablets. | 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 |
|
| Fixed drug eruption due to naproxen; lack of cross-reactivity with other propionic acid derivatives. | 2001 Jun |
|
| [The lack of awareness of the Israeli population regarding gastrointestinal complications from non-steroidal anti-inflammatory drugs]. | 2001 Jun |
|
| Treatment of de Quervain's disease:role of conservative management. | 2001 Jun |
|
| Inhibition of tendon cell proliferation and matrix glycosaminoglycan synthesis by non-steroidal anti-inflammatory drugs in vitro. | 2001 Jun |
|
| Immune thrombocytopenia resulting from sensitivity to metabolites of naproxen and acetaminophen. | 2001 Jun 15 |
|
| [Nitric oxide and gastroduodenal damage caused by NSAIDs. Recent findings and clinical implications]. | 2001 Mar |
|
| 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 |
|
| Interleukin-6 (IL-6) producing phaeochromocytoma: direct IL-6 suppression by non-steroidal anti-inflammatory drugs. | 2001 Mar |
|
| Effect of cyclodextrin charge on complexation of neutral and charged substrates: comparison of (SBE)7M-beta-CD to HP-beta-CD. | 2001 May |
|
| Synthesis, in vitro skin permeation studies, and PLS-analysis of new naproxen derivatives. | 2001 May |
|
| [The selective Cox-2 inhibition by rofecoxib reduces risk of severe gastrointestinal complications of anti-inflammatory therapy by more than 50%]. | 2001 May |
|
| Nimesulide reduces interleukin-1beta-induced cyclooxygenase-2 gene expression in human synovial fibroblasts. | 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 |
|
| The influence of polyvinylpyrrolidone on naproxen complexation with hydroxypropyl-beta-cyclodextrin. | 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 |
|
| Isotachophoretic determination of naproxen in the presence of its metabolite in human serum. | 2001 May 4 |
|
| 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
Tue Oct 22 00:35:26 UTC 2019
by
admin
on
Tue Oct 22 00:35:26 UTC 2019
|
| Record UNII |
9TN87S3A3C
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
NCI_THESAURUS |
C1323
Created by
admin on Tue Oct 22 00:35:27 UTC 2019 , Edited by admin on Tue Oct 22 00:35:27 UTC 2019
|
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
142442
Created by
admin on Tue Oct 22 00:35:27 UTC 2019 , Edited by admin on Tue Oct 22 00:35:27 UTC 2019
|
PRIMARY | RxNorm | ||
|
M7769
Created by
admin on Tue Oct 22 00:35:27 UTC 2019 , Edited by admin on Tue Oct 22 00:35:27 UTC 2019
|
PRIMARY | Merck Index | ||
|
247-486-2
Created by
admin on Tue Oct 22 00:35:27 UTC 2019 , Edited by admin on Tue Oct 22 00:35:27 UTC 2019
|
PRIMARY | |||
|
SUB166156
Created by
admin on Tue Oct 22 00:35:27 UTC 2019 , Edited by admin on Tue Oct 22 00:35:27 UTC 2019
|
PRIMARY | |||
|
C48006
Created by
admin on Tue Oct 22 00:35:27 UTC 2019 , Edited by admin on Tue Oct 22 00:35:27 UTC 2019
|
PRIMARY | |||
|
SUB03392MIG
Created by
admin on Tue Oct 22 00:35:27 UTC 2019 , Edited by admin on Tue Oct 22 00:35:27 UTC 2019
|
PRIMARY | |||
|
26159-34-2
Created by
admin on Tue Oct 22 00:35:27 UTC 2019 , Edited by admin on Tue Oct 22 00:35:27 UTC 2019
|
PRIMARY | |||
|
23681059
Created by
admin on Tue Oct 22 00:35:27 UTC 2019 , Edited by admin on Tue Oct 22 00:35:27 UTC 2019
|
PRIMARY | |||
|
CHEMBL154
Created by
admin on Tue Oct 22 00:35:27 UTC 2019 , Edited by admin on Tue Oct 22 00:35:27 UTC 2019
|
PRIMARY | |||
|
26159-34-2
Created by
admin on Tue Oct 22 00:35:27 UTC 2019 , Edited by admin on Tue Oct 22 00:35:27 UTC 2019
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
USP
|
||
|
|
PARENT -> SALT/SOLVATE | |||
|
BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
EP
|
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
IMPURITY -> PARENT |
UNSPECIFIED
EP
|
||
|
IMPURITY -> PARENT |
UNSPECIFIED
EP
|
||
|
IMPURITY -> PARENT |
UNSPECIFIED
EP
|
||
|
IMPURITY -> PARENT |
UNSPECIFIED
EP
|
||
|
IMPURITY -> PARENT |
UNSPECIFIED
EP
|
||
|
IMPURITY -> PARENT |
UNSPECIFIED
EP
|
||
|
IMPURITY -> PARENT |
UNSPECIFIED
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
UNSPECIFIED
EP
|
||
|
IMPURITY -> PARENT |
UNSPECIFIED
EP
|
||
|
IMPURITY -> PARENT |
UNSPECIFIED
EP
|
||
|
IMPURITY -> PARENT |
UNSPECIFIED
EP
|
||
|
IMPURITY -> PARENT |
UNSPECIFIED
EP
|
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
ACTIVE MOIETY |