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 ( + )
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 No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/mesh/68009288

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

CNS Active
4002
Curator's Comment: Naproxen is a potent inhibitor of prostaglandin synthesis in vitro. Naproxen concentrations reached during therapy have produced in vivo effects. Prostaglandins sensitize afferent nerves and potentiate the action of bradykinin in inducing pain in animal models.

Originator

Syntex
47
Curator's Comment: Syntex was integrated into the Roche group in 1994.

Approval Year

1976
92
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
 0.11 µM [IC50]
Inhibitor
8504
 0.19 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
NAPROSYN

Approved Use

NAPROSYN is indicated: For the relief of the signs and symptoms of rheumatoid arthritis. For the relief of the signs and symptoms of osteoarthritis. For the relief of the signs and symptoms of ankylosing spondylitis. For the relief of the signs and symptoms of juvenile arthritis. NAPROSYN is also indicated: For relief of the signs and symptoms of tendonitis. For relief of the signs and symptoms of bursitis. For relief of the signs and symptoms of acute gout. For the management of pain. For the management of primary dysmenorrhea.

Launch Date

1976
Primary
Approved
8583
NAPROSYN

Approved Use

NAPROSYN is indicated: For the relief of the signs and symptoms of rheumatoid arthritis. For the relief of the signs and symptoms of osteoarthritis. For the relief of the signs and symptoms of ankylosing spondylitis. For the relief of the signs and symptoms of juvenile arthritis. NAPROSYN is also indicated: For relief of the signs and symptoms of tendonitis. For relief of the signs and symptoms of bursitis. For relief of the signs and symptoms of acute gout. For the management of pain. For the management of primary dysmenorrhea.

Launch Date

1976
Primary
Approved
8583
NAPROSYN

Approved Use

NAPROSYN is indicated: For the relief of the signs and symptoms of rheumatoid arthritis. For the relief of the signs and symptoms of osteoarthritis. For the relief of the signs and symptoms of ankylosing spondylitis. For the relief of the signs and symptoms of juvenile arthritis. NAPROSYN is also indicated: For relief of the signs and symptoms of tendonitis. For relief of the signs and symptoms of bursitis. For relief of the signs and symptoms of acute gout. For the management of pain. For the management of primary dysmenorrhea.

Launch Date

1976
Primary
Approved
8583
NAPROSYN

Approved Use

NAPROSYN is indicated: For the relief of the signs and symptoms of rheumatoid arthritis. For the relief of the signs and symptoms of osteoarthritis. For the relief of the signs and symptoms of ankylosing spondylitis. For the relief of the signs and symptoms of juvenile arthritis. NAPROSYN is also indicated: For relief of the signs and symptoms of tendonitis. For relief of the signs and symptoms of bursitis. For relief of the signs and symptoms of acute gout. For the management of pain. For the management of primary dysmenorrhea.

Launch Date

1976
Primary
Approved
8583
NAPROSYN

Approved Use

NAPROSYN is indicated: For the relief of the signs and symptoms of rheumatoid arthritis. For the relief of the signs and symptoms of osteoarthritis. For the relief of the signs and symptoms of ankylosing spondylitis. For the relief of the signs and symptoms of juvenile arthritis. NAPROSYN is also indicated: For relief of the signs and symptoms of tendonitis. For relief of the signs and symptoms of bursitis. For relief of the signs and symptoms of acute gout. For the management of pain. For the management of primary dysmenorrhea.

Launch Date

1976
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
95 μg/L
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020353s034lbl.pdf
500 mg 2 times / day steady-state, oral
dose: 500 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
NAPROXEN plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
94 μg/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020353s034lbl.pdf
1000 mg 1 times / day steady-state, oral
dose: 1000 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
NAPROXEN plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1446 μg × h/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020353s034lbl.pdf
500 mg 2 times / day steady-state, oral
dose: 500 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
NAPROXEN plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
1448 μg × h/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020353s034lbl.pdf
1000 mg 1 times / day steady-state, oral
dose: 1000 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
NAPROXEN plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
15 h
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020353s034lbl.pdf
500 mg 2 times / day steady-state, oral
dose: 500 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
NAPROXEN plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
1%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020353s034lbl.pdf
500 mg 2 times / day steady-state, oral
dose: 500 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
NAPROXEN plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
12.5 g single, oral
Overdose
Dose: 12.5 g
Route: oral
Route: single
Dose: 12.5 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/2552870
healthy, 15
Health Status: healthy
Age Group: 15
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/2552870
Disc. AE: Abdominal pain, Nausea...
AEs leading to
discontinuation/dose reduction:
Abdominal pain
Nausea
Dizziness
Seizures
Metabolic acidosis (severe)
Sources:
https://pubmed.ncbi.nlm.nih.gov/2552870
4 g single, oral
Highest studied dose
Dose: 4 g
Route: oral
Route: single
Dose: 4 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/954349/
healthy, 20
Health Status: healthy
Age Group: 20
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/954349/
Sources:
https://pubmed.ncbi.nlm.nih.gov/954349/
70.4 g single, oral
Overdose
Dose: 70.4 g
Route: oral
Route: single
Dose: 70.4 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/24756481
healthy, 28
Health Status: healthy
Age Group: 28
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/24756481
Disc. AE: Sinus tachycardia, Drowsiness...
AEs leading to
discontinuation/dose reduction:
Sinus tachycardia
Drowsiness
Metabolic acidosis
Seizures
Sources:
https://pubmed.ncbi.nlm.nih.gov/24756481
26 g single, oral
Overdose
Dose: 26 g
Route: oral
Route: single
Dose: 26 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/31742906
unhealthy, 58
Health Status: unhealthy
Age Group: 58
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/31742906
Disc. AE: Thrombopenia...
AEs leading to
discontinuation/dose reduction:
Thrombopenia
Sources:
https://pubmed.ncbi.nlm.nih.gov/31742906
550 mg 2 times / day multiple, oral
Recommended
Dose: 550 mg, 2 times / day
Route: oral
Route: multiple
Dose: 550 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017581s113,018164s063,020067s020lbl.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017581s113,018164s063,020067s020lbl.pdf
Disc. AE: Cardiac thrombosis, Myocardial infarction...
AEs leading to
discontinuation/dose reduction:
Cardiac thrombosis (grade 3-5)
Myocardial infarction (grade 3-5)
Stroke (grade 3-5)
Gastrointestinal disorder NOS (grade 3-5)
Gastrointestinal bleeding (grade 3-5)
Gastrointestinal ulcer (grade 3-5)
Perforation stomach (grade 3-5)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017581s113,018164s063,020067s020lbl.pdf
AEs

AEs

AESignificanceDosePopulation
Abdominal pain Disc. AE
12.5 g single, oral
Overdose
Dose: 12.5 g
Route: oral
Route: single
Dose: 12.5 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/2552870
healthy, 15
Health Status: healthy
Age Group: 15
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/2552870
Dizziness Disc. AE
12.5 g single, oral
Overdose
Dose: 12.5 g
Route: oral
Route: single
Dose: 12.5 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/2552870
healthy, 15
Health Status: healthy
Age Group: 15
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/2552870
Nausea Disc. AE
12.5 g single, oral
Overdose
Dose: 12.5 g
Route: oral
Route: single
Dose: 12.5 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/2552870
healthy, 15
Health Status: healthy
Age Group: 15
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/2552870
Seizures Disc. AE
12.5 g single, oral
Overdose
Dose: 12.5 g
Route: oral
Route: single
Dose: 12.5 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/2552870
healthy, 15
Health Status: healthy
Age Group: 15
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/2552870
Metabolic acidosis severe
Disc. AE
12.5 g single, oral
Overdose
Dose: 12.5 g
Route: oral
Route: single
Dose: 12.5 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/2552870
healthy, 15
Health Status: healthy
Age Group: 15
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/2552870
Drowsiness Disc. AE
70.4 g single, oral
Overdose
Dose: 70.4 g
Route: oral
Route: single
Dose: 70.4 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/24756481
healthy, 28
Health Status: healthy
Age Group: 28
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/24756481
Metabolic acidosis Disc. AE
70.4 g single, oral
Overdose
Dose: 70.4 g
Route: oral
Route: single
Dose: 70.4 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/24756481
healthy, 28
Health Status: healthy
Age Group: 28
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/24756481
Seizures Disc. AE
70.4 g single, oral
Overdose
Dose: 70.4 g
Route: oral
Route: single
Dose: 70.4 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/24756481
healthy, 28
Health Status: healthy
Age Group: 28
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/24756481
Sinus tachycardia Disc. AE
70.4 g single, oral
Overdose
Dose: 70.4 g
Route: oral
Route: single
Dose: 70.4 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/24756481
healthy, 28
Health Status: healthy
Age Group: 28
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/24756481
Thrombopenia Disc. AE
26 g single, oral
Overdose
Dose: 26 g
Route: oral
Route: single
Dose: 26 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/31742906
unhealthy, 58
Health Status: unhealthy
Age Group: 58
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/31742906
Cardiac thrombosis grade 3-5
Disc. AE
550 mg 2 times / day multiple, oral
Recommended
Dose: 550 mg, 2 times / day
Route: oral
Route: multiple
Dose: 550 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017581s113,018164s063,020067s020lbl.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017581s113,018164s063,020067s020lbl.pdf
Gastrointestinal bleeding grade 3-5
Disc. AE
550 mg 2 times / day multiple, oral
Recommended
Dose: 550 mg, 2 times / day
Route: oral
Route: multiple
Dose: 550 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017581s113,018164s063,020067s020lbl.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017581s113,018164s063,020067s020lbl.pdf
Gastrointestinal disorder NOS grade 3-5
Disc. AE
550 mg 2 times / day multiple, oral
Recommended
Dose: 550 mg, 2 times / day
Route: oral
Route: multiple
Dose: 550 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017581s113,018164s063,020067s020lbl.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017581s113,018164s063,020067s020lbl.pdf
Gastrointestinal ulcer grade 3-5
Disc. AE
550 mg 2 times / day multiple, oral
Recommended
Dose: 550 mg, 2 times / day
Route: oral
Route: multiple
Dose: 550 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017581s113,018164s063,020067s020lbl.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017581s113,018164s063,020067s020lbl.pdf
Myocardial infarction grade 3-5
Disc. AE
550 mg 2 times / day multiple, oral
Recommended
Dose: 550 mg, 2 times / day
Route: oral
Route: multiple
Dose: 550 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017581s113,018164s063,020067s020lbl.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017581s113,018164s063,020067s020lbl.pdf
Perforation stomach grade 3-5
Disc. AE
550 mg 2 times / day multiple, oral
Recommended
Dose: 550 mg, 2 times / day
Route: oral
Route: multiple
Dose: 550 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017581s113,018164s063,020067s020lbl.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017581s113,018164s063,020067s020lbl.pdf
Stroke grade 3-5
Disc. AE
550 mg 2 times / day multiple, oral
Recommended
Dose: 550 mg, 2 times / day
Route: oral
Route: multiple
Dose: 550 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017581s113,018164s063,020067s020lbl.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017581s113,018164s063,020067s020lbl.pdf
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1193

OverviewOther

Other InhibitorOther SubstrateOther Inducer
OAT4
150

OAT3
747

OAT1
725

OAT2
153
CYP1A2
1197

CYP2C8
810

UGT1A1
479

UGT1A3
470

UGT1A6
343

UGT1A7
249

UGT1A8
323

UGT1A9
423

UGT1A10
331

UGT2B7
456
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
OAT3
749
 yes [IC50 4.67 uM]
OAT2
155
 yes [IC50 486 uM]
OAT1
730
 yes [IC50 5.67 uM]
OAT4
150
 yes [IC50 85.4 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP2C9
1193
 major
CYP1A2
1197
 minor
CYP2C8
810
 minor
UGT1A1
479
 yes
UGT1A10
331
 yes
UGT1A3
470
 yes
UGT1A6
343
 yes
UGT1A7
249
 yes
UGT1A8
323
 yes
UGT1A9
423
 yes
UGT2B7
456
 yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:7476
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:7476
ChemicalBook
CB8274937
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB8274937
ChemicalBook
CB8422325
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB8422325
eMolecules
494695
https://www.emolecules.com/cgi-bin/more?vid=494695
MolPort
MolPort-000-145-960
https://www.molport.com/shop/molecule-link/MolPort-000-145-960
ZINC
ZINC000000105216
http://zinc15.docking.org/substances/ZINC000000105216
PubMed

PubMed

TitleDatePubMed
Localization of cyclooxygenase isozymes in cardiovascular tissues of dogs treated with naproxen.
2001-08-10
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?
2001-08
A possible mechanism of naproxen-induced lipid peroxidation in rat liver microsomes.
2001-07
New issues about nitric oxide and its effects on the gastrointestinal tract.
2001-07
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.
2001-07
Dapsone activation of CYP2C9-mediated metabolism: evidence for activation of multiple substrates and a two-site model.
2001-07
Addition of hydrogen bond donating excipients to oil solution: effect on in vitro drug release rate and viscosity.
2001-07
Enantioselective inhibition of the binding of rac-profens to human serum albumin induced by lithocholate.
2001-07
Determination of ibuprofen and naproxen in tablets.
2001-07
In vitro evaluation and intra-articular administration of biodegradable microspheres containing naproxen sodium.
2001-06-29
Immune thrombocytopenia resulting from sensitivity to metabolites of naproxen and acetaminophen.
2001-06-15
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.
2001-06-02
In vitro effects of NSAIDS and paracetamol on oxidative stress-related parameters of human erythrocytes.
2001-06
Determination of naproxen in pharmaceutical preparations by room-temperature phosphorescence. A comparative study of several organized media.
2001-06
By the way, doctor. Which drugs cause problems in the sun?
2001-06
[Treatment of pain due to unwanted lactation with a homeopathic preparation given in the immediate post-partum period].
2001-06
Fixed drug eruption due to naproxen; lack of cross-reactivity with other propionic acid derivatives.
2001-06
[The lack of awareness of the Israeli population regarding gastrointestinal complications from non-steroidal anti-inflammatory drugs].
2001-06
Treatment of de Quervain's disease:role of conservative management.
2001-06
Inhibition of tendon cell proliferation and matrix glycosaminoglycan synthesis by non-steroidal anti-inflammatory drugs in vitro.
2001-06
Stereoselective synthesis of (S)-(+)-Naproxen catalyzed by carboxyl esterase in a multicompartment electrolyzer.
2001-05-28
Isotachophoretic determination of naproxen in the presence of its metabolite in human serum.
2001-05-04
Upper gastrointestinal toxicity of rofecoxib and naproxen.
2001-05-03
Upper gastrointestinal toxicity of rofecoxib and naproxen.
2001-05-03
Effect of cyclodextrin charge on complexation of neutral and charged substrates: comparison of (SBE)7M-beta-CD to HP-beta-CD.
2001-05
Synthesis, in vitro skin permeation studies, and PLS-analysis of new naproxen derivatives.
2001-05
[The selective Cox-2 inhibition by rofecoxib reduces risk of severe gastrointestinal complications of anti-inflammatory therapy by more than 50%].
2001-05
Nimesulide reduces interleukin-1beta-induced cyclooxygenase-2 gene expression in human synovial fibroblasts.
2001-05
Severe reversible renal failure due to naproxen-associated acute interstitial nephritis.
2001-05
Effect of nonsteroidal anti-inflammatory drug use on the rate of gastrointestinal hospitalizations among people living in long-term care.
2001-05
The influence of polyvinylpyrrolidone on naproxen complexation with hydroxypropyl-beta-cyclodextrin.
2001-05
[Liver damage and nonsteroidal anti-inflammatory drugs: case non-case study in the French Pharmacovigilance Database].
2001-04-27
[Acupuncture contra antiphlogistics in acute lumbago].
2001-04-20
Uniformly sized molecularly imprinted polymer for (S)-naproxen retention and molecular recognition properties in aqueous mobile phase.
2001-04-13
Naproxen particle design using porous starch.
2001-04
Naproxen-Eudragit microspheres: screening of process and formulation variables for the preparation of extended release tablets.
2001-04
Reduced incidence of gastroduodenal ulcers with celecoxib, a novel cyclooxygenase-2 inhibitor, compared to naproxen in patients with arthritis.
2001-04
Endogenous prostaglandin E2 and insulin-like growth factor 1 can modulate the levels of parathyroid hormone receptor in human osteoarthritic osteoblasts.
2001-04
Celecoxib and rofecoxib. The role of COX-2 inhibitors in dental practice.
2001-04
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.
2001-04
[Nitric oxide and gastroduodenal damage caused by NSAIDs. Recent findings and clinical implications].
2001-03
Synthesis and cyclooxygenase inhibitory properties of novel (+) 2-(6-methoxy-2-naphthyl)propanoic acid (naproxene) derivatives.
2001-03
Peroxisomal proliferator-activated ligand therapy for HIV lipodystrophy.
2001-03
Interleukin-6 (IL-6) producing phaeochromocytoma: direct IL-6 suppression by non-steroidal anti-inflammatory drugs.
2001-03
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
Absence of pharmacokinetic interaction between orally co-administered naproxen sodium and diphenhydramine hydrochloride.
2000-09
Patents

Patents

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JP4264850B2
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5
JP4756823B2
22
JP4774135B2
12
JP4787165B2
104
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 Mar 31 17:49:41 GMT 2025
Edited
by admin
on Mon Mar 31 17:49:41 GMT 2025
Record UNII
57Y76R9ATQ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
VIMOVO COMPONENT NAPROXEN
Preferred Name English
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
PN400 COMPONENT NAPROXEN
Code English
NAPROXEN [MI]
Common Name English
NAPROXEN [HSDB]
Common Name English
(+)-(S)-6-METHOXY-.ALPHA.-METHYL-2-NAPHTHALENEACETIC ACID
Systematic Name English
naproxen [INN]
Common Name English
NAPROXEN [USAN]
Common Name English
NAPROSYN
Brand Name English
Naproxen [WHO-DD]
Common Name English
2-NAPHTHALENEACETIC ACID, 6-METHOXY-.ALPHA.-METHYL-, (S)-
Common Name English
NAPROXEN [VANDF]
Common Name English
NAPROXEN [EP MONOGRAPH]
Common Name English
RS-3540
Code English
NAPROXEN [MART.]
Common Name English
NSC-757239
Code English
NAPROXEN [USP MONOGRAPH]
Common Name English
NSC-750183
Code 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 Mar 31 17:49:41 GMT 2025 , Edited by admin on Mon Mar 31 17:49:41 GMT 2025
CFR 21 CFR 522.1468
Created by admin on Mon Mar 31 17:49:41 GMT 2025 , Edited by admin on Mon Mar 31 17:49:41 GMT 2025
NDF-RT N0000175721
Created by admin on Mon Mar 31 17:49:41 GMT 2025 , Edited by admin on Mon Mar 31 17:49:41 GMT 2025
WHO-ATC G02CC02
Created by admin on Mon Mar 31 17:49:41 GMT 2025 , Edited by admin on Mon Mar 31 17:49:41 GMT 2025
WHO-VATC QM01AE56
Created by admin on Mon Mar 31 17:49:41 GMT 2025 , Edited by admin on Mon Mar 31 17:49:41 GMT 2025
WHO-VATC QM02AA12
Created by admin on Mon Mar 31 17:49:41 GMT 2025 , Edited by admin on Mon Mar 31 17:49:41 GMT 2025
NCI_THESAURUS C1323
Created by admin on Mon Mar 31 17:49:41 GMT 2025 , Edited by admin on Mon Mar 31 17:49:41 GMT 2025
WHO-VATC QG02CC02
Created by admin on Mon Mar 31 17:49:41 GMT 2025 , Edited by admin on Mon Mar 31 17:49:41 GMT 2025
LIVERTOX NBK548159
Created by admin on Mon Mar 31 17:49:41 GMT 2025 , Edited by admin on Mon Mar 31 17:49:41 GMT 2025
WHO-VATC QM01AE52
Created by admin on Mon Mar 31 17:49:41 GMT 2025 , Edited by admin on Mon Mar 31 17:49:41 GMT 2025
WHO-ATC M01AE52
Created by admin on Mon Mar 31 17:49:41 GMT 2025 , Edited by admin on Mon Mar 31 17:49:41 GMT 2025
WHO-ATC M02AA12
Created by admin on Mon Mar 31 17:49:41 GMT 2025 , Edited by admin on Mon Mar 31 17:49:41 GMT 2025
CFR 21 CFR 520.1468
Created by admin on Mon Mar 31 17:49:41 GMT 2025 , Edited by admin on Mon Mar 31 17:49:41 GMT 2025
WHO-VATC QM01AE02
Created by admin on Mon Mar 31 17:49:41 GMT 2025 , Edited by admin on Mon Mar 31 17:49:41 GMT 2025
WHO-ATC M01AE56
Created by admin on Mon Mar 31 17:49:41 GMT 2025 , Edited by admin on Mon Mar 31 17:49:41 GMT 2025
WHO-ATC M01AE02
Created by admin on Mon Mar 31 17:49:41 GMT 2025 , Edited by admin on Mon Mar 31 17:49:41 GMT 2025
NDF-RT N0000000160
Created by admin on Mon Mar 31 17:49:41 GMT 2025 , Edited by admin on Mon Mar 31 17:49:41 GMT 2025
Code System Code Type Description
NSC
750183
Created by admin on Mon Mar 31 17:49:41 GMT 2025 , Edited by admin on Mon Mar 31 17:49:41 GMT 2025
PRIMARY
LACTMED
Naproxen
Created by admin on Mon Mar 31 17:49:41 GMT 2025 , Edited by admin on Mon Mar 31 17:49:41 GMT 2025
PRIMARY
DRUG BANK
DB00788
Created by admin on Mon Mar 31 17:49:41 GMT 2025 , Edited by admin on Mon Mar 31 17:49:41 GMT 2025
PRIMARY
INN
2979
Created by admin on Mon Mar 31 17:49:41 GMT 2025 , Edited by admin on Mon Mar 31 17:49:41 GMT 2025
PRIMARY
PUBCHEM
156391
Created by admin on Mon Mar 31 17:49:41 GMT 2025 , Edited by admin on Mon Mar 31 17:49:41 GMT 2025
PRIMARY
NCI_THESAURUS
C680
Created by admin on Mon Mar 31 17:49:41 GMT 2025 , Edited by admin on Mon Mar 31 17:49:41 GMT 2025
PRIMARY
HSDB
3369
Created by admin on Mon Mar 31 17:49:41 GMT 2025 , Edited by admin on Mon Mar 31 17:49:41 GMT 2025
PRIMARY
RXCUI
7258
Created by admin on Mon Mar 31 17:49:41 GMT 2025 , Edited by admin on Mon Mar 31 17:49:41 GMT 2025
PRIMARY RxNorm
CHEBI
59527
Created by admin on Mon Mar 31 17:49:41 GMT 2025 , Edited by admin on Mon Mar 31 17:49:41 GMT 2025
PRIMARY
RS_ITEM_NUM
1457301
Created by admin on Mon Mar 31 17:49:41 GMT 2025 , Edited by admin on Mon Mar 31 17:49:41 GMT 2025
PRIMARY
IUPHAR
5230
Created by admin on Mon Mar 31 17:49:41 GMT 2025 , Edited by admin on Mon Mar 31 17:49:41 GMT 2025
PRIMARY
MESH
D009288
Created by admin on Mon Mar 31 17:49:41 GMT 2025 , Edited by admin on Mon Mar 31 17:49:41 GMT 2025
PRIMARY
SMS_ID
100000090383
Created by admin on Mon Mar 31 17:49:41 GMT 2025 , Edited by admin on Mon Mar 31 17:49:41 GMT 2025
PRIMARY
DAILYMED
57Y76R9ATQ
Created by admin on Mon Mar 31 17:49:41 GMT 2025 , Edited by admin on Mon Mar 31 17:49:41 GMT 2025
PRIMARY
ChEMBL
CHEMBL154
Created by admin on Mon Mar 31 17:49:41 GMT 2025 , Edited by admin on Mon Mar 31 17:49:41 GMT 2025
PRIMARY
DRUG CENTRAL
1883
Created by admin on Mon Mar 31 17:49:41 GMT 2025 , Edited by admin on Mon Mar 31 17:49:41 GMT 2025
PRIMARY
MERCK INDEX
m7769
Created by admin on Mon Mar 31 17:49:41 GMT 2025 , Edited by admin on Mon Mar 31 17:49:41 GMT 2025
PRIMARY Merck Index
NSC
757239
Created by admin on Mon Mar 31 17:49:41 GMT 2025 , Edited by admin on Mon Mar 31 17:49:41 GMT 2025
PRIMARY
FDA UNII
57Y76R9ATQ
Created by admin on Mon Mar 31 17:49:41 GMT 2025 , Edited by admin on Mon Mar 31 17:49:41 GMT 2025
PRIMARY
CAS
22204-53-1
Created by admin on Mon Mar 31 17:49:41 GMT 2025 , Edited by admin on Mon Mar 31 17:49:41 GMT 2025
PRIMARY
EVMPD
SUB09159MIG
Created by admin on Mon Mar 31 17:49:41 GMT 2025 , Edited by admin on Mon Mar 31 17:49:41 GMT 2025
PRIMARY
EPA CompTox
DTXSID4040686
Created by admin on Mon Mar 31 17:49:41 GMT 2025 , Edited by admin on Mon Mar 31 17:49:41 GMT 2025
PRIMARY
CHEBI
7476
Created by admin on Mon Mar 31 17:49:41 GMT 2025 , Edited by admin on Mon Mar 31 17:49:41 GMT 2025
PRIMARY
WIKIPEDIA
NAPROXEN
Created by admin on Mon Mar 31 17:49:41 GMT 2025 , Edited by admin on Mon Mar 31 17:49:41 GMT 2025
PRIMARY
ECHA (EC/EINECS)
244-838-7
Created by admin on Mon Mar 31 17:49:41 GMT 2025 , Edited by admin on Mon Mar 31 17:49:41 GMT 2025
PRIMARY
Related Record Type Details
Structure of Naproxen, (±)-
RACEMATE -> ENANTIOMER
Structure of NAPROXEN LYSINE
SALT/SOLVATE -> PARENT
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
Structure of NAPROXEN
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
EP
Structure of Calcium naproxen
SALT/SOLVATE -> PARENT
Structure of NAPROXEN PIPERAZINE
SALT/SOLVATE -> PARENT
Structure of CETYLTRIMETHYLAMMONIUM NAPROXENATE
SALT/SOLVATE -> PARENT
CYTOCHROME P450 1A2
METABOLIC ENZYME -> SUBSTRATE
Structure of NAPROXEN
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
USP
Structure of NAPROXEN AMINOBUTANOL
SALT/SOLVATE -> PARENT
CYTOCHROME P450 2C9
METABOLIC ENZYME -> SUBSTRATE
URIDINE DIPHOSPHATE GLUCURONOSYLTRANSFERASE 1A3
METABOLIC ENZYME -> SUBSTRATE
OAT-3
TRANSPORTER -> INHIBITOR
Structure of OTENAPROXESUL
DERIVATIVE -> PARENT
Structure of Naproxen sodium
SALT/SOLVATE -> PARENT
OAT-4
TRANSPORTER -> INHIBITOR
OAT-1
TRANSPORTER -> INHIBITOR
OAT-2
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
Structure of NAPROXCINOD
PRODRUG -> METABOLITE ACTIVE
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 2-METHOXYNAPHTHALENE
IMPURITY -> PARENT
UNSPECIFIED
EP
Structure of RAC-NAPROXEN 2-PROPYL ESTER
IMPURITY -> PARENT
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 NOTICE
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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