NAPROXEN

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 Search

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

Targets

Primary Target	Pharmacology	Condition	Potency
Cyclooxygenase-2 184	Inhibitor 7464	Ankylosing Spondylitis	0.19 µM [IC50]
Cyclooxygenase-1 121	Inhibitor 7464	Ankylosing Spondylitis	0.11 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Osteoarthritis 148	Primary	Cyclooxygenase-1 Cyclooxygenase-2	Approved 7888	NAPROSYN
Rheumatoid Arthritis 152	Primary	Cyclooxygenase-1 Cyclooxygenase-2	Approved 7888	NAPROSYN
Bursitis 6	Primary	Cyclooxygenase-1 Cyclooxygenase-2	Approved 7888	NAPROSYN
Ankylosing Spondylitis 24	Primary	Cyclooxygenase-1 Cyclooxygenase-2	Approved 7888	NAPROSYN
Tendonitis 5	Primary	Cyclooxygenase-1 Cyclooxygenase-2	Approved 7888	NAPROSYN
Chronic fatigue syndrome 5			Approved (off-label) 8

PubMed

Title	Date	PubMed
Absence of pharmacokinetic interaction between orally co-administered naproxen sodium and diphenhydramine hydrochloride.	2000 Sep	11304721
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	11455679
[Two complex suicidal poisonings with drugs and their medicolegal aspects].	2001	11450365
Rofecoxib: a review of its use in the management of osteoarthritis, acute pain and rheumatoid arthritis.	2001	11398914
Differential regulation of interleukin-1 beta-induced cyclooxygenase-2 gene expression by nimesulide in human synovial fibroblasts.	2001	11296546
Nimesulide, a balanced drug for the treatment of osteoarthritis.	2001	11296545
Naproxen particle design using porous starch.	2001 Apr	11411896
Naproxen-Eudragit microspheres: screening of process and formulation variables for the preparation of extended release tablets.	2001 Apr	11338673
Reduced incidence of gastroduodenal ulcers with celecoxib, a novel cyclooxygenase-2 inhibitor, compared to naproxen in patients with arthritis.	2001 Apr	11316141
Endogenous prostaglandin E2 and insulin-like growth factor 1 can modulate the levels of parathyroid hormone receptor in human osteoarthritic osteoblasts.	2001 Apr	11315999
Celecoxib and rofecoxib. The role of COX-2 inhibitors in dental practice.	2001 Apr	11315375
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	11300749
Uniformly sized molecularly imprinted polymer for (S)-naproxen retention and molecular recognition properties in aqueous mobile phase.	2001 Apr 13	11355806
[Acupuncture contra antiphlogistics in acute lumbago].	2001 Apr 20	11402745
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	11475598
Localization of cyclooxygenase isozymes in cardiovascular tissues of dogs treated with naproxen.	2001 Aug 10	11457482
[Liver damage and nonsteroidal anti-inflammatory drugs: case non-case study in the French Pharmacovigilance Database].	2001 Jan-Feb	11322018
A possible mechanism of naproxen-induced lipid peroxidation in rat liver microsomes.	2001 Jul	11484909
New issues about nitric oxide and its effects on the gastrointestinal tract.	2001 Jul	11472246
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	11467888
Dapsone activation of CYP2C9-mediated metabolism: evidence for activation of multiple substrates and a two-site model.	2001 Jul	11408370
Addition of hydrogen bond donating excipients to oil solution: effect on in vitro drug release rate and viscosity.	2001 Jul	11408155
Enantioselective inhibition of the binding of rac-profens to human serum albumin induced by lithocholate.	2001 Jul	11400191
Determination of ibuprofen and naproxen in tablets.	2001 Jul	11377071
In vitro evaluation and intra-articular administration of biodegradable microspheres containing naproxen sodium.	2001 Jul-Aug	11428674
In vitro effects of NSAIDS and paracetamol on oxidative stress-related parameters of human erythrocytes.	2001 Jun	11484831
Determination of naproxen in pharmaceutical preparations by room-temperature phosphorescence. A comparative study of several organized media.	2001 Jun	11445962
By the way, doctor. Which drugs cause problems in the sun?	2001 Jun	11439284
[Treatment of pain due to unwanted lactation with a homeopathic preparation given in the immediate post-partum period].	2001 Jun	11431615
Fixed drug eruption due to naproxen; lack of cross-reactivity with other propionic acid derivatives.	2001 Jun	11422076
[The lack of awareness of the Israeli population regarding gastrointestinal complications from non-steroidal anti-inflammatory drugs].	2001 Jun	11420844
Treatment of de Quervain's disease:role of conservative management.	2001 Jun	11386780
Inhibition of tendon cell proliferation and matrix glycosaminoglycan synthesis by non-steroidal anti-inflammatory drugs in vitro.	2001 Jun	11386772
Immune thrombocytopenia resulting from sensitivity to metabolites of naproxen and acetaminophen.	2001 Jun 15	11389025
[Nitric oxide and gastroduodenal damage caused by NSAIDs. Recent findings and clinical implications].	2001 Mar	11320858
Synthesis and cyclooxygenase inhibitory properties of novel (+) 2-(6-methoxy-2-naphthyl)propanoic acid (naproxene) derivatives.	2001 Mar	11315336
Peroxisomal proliferator-activated ligand therapy for HIV lipodystrophy.	2001 Mar	11298105
Interleukin-6 (IL-6) producing phaeochromocytoma: direct IL-6 suppression by non-steroidal anti-inflammatory drugs.	2001 Mar	11298095
Effect of cyclodextrin charge on complexation of neutral and charged substrates: comparison of (SBE)7M-beta-CD to HP-beta-CD.	2001 May	11465424
Synthesis, in vitro skin permeation studies, and PLS-analysis of new naproxen derivatives.	2001 May	11465414
[The selective Cox-2 inhibition by rofecoxib reduces risk of severe gastrointestinal complications of anti-inflammatory therapy by more than 50%].	2001 May	11413920
Nimesulide reduces interleukin-1beta-induced cyclooxygenase-2 gene expression in human synovial fibroblasts.	2001 May	11399097
Severe reversible renal failure due to naproxen-associated acute interstitial nephritis.	2001 May	11388597
Effect of nonsteroidal anti-inflammatory drug use on the rate of gastrointestinal hospitalizations among people living in long-term care.	2001 May	11380750
The influence of polyvinylpyrrolidone on naproxen complexation with hydroxypropyl-beta-cyclodextrin.	2001 May	11297903
Stereoselective synthesis of (S)-(+)-Naproxen catalyzed by carboxyl esterase in a multicompartment electrolyzer.	2001 May 28	11384761
Upper gastrointestinal toxicity of rofecoxib and naproxen.	2001 May 3	11336057
Upper gastrointestinal toxicity of rofecoxib and naproxen.	2001 May 3	11336056
Isotachophoretic determination of naproxen in the presence of its metabolite in human serum.	2001 May 4	11382293
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	11386636

Patents

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

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Name

Type

Language

NAPROXEN

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