U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of NAPROXEN SODIUM

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

HIDE SMILES / InChI
Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C14H13O3
Molecular Weight 229.2512
Charge -1
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
3913
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
91
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 0.11 µM [IC50]
Inhibitor
8297
 0.19 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
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
8429
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
8429
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
8429
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
8429
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
Page: 1102/129
healthy, 15
n = 1
Health Status: healthy
Age Group: 15
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/2552870
Page: 1102/129
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
Page: 1102/129
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/
Page: p.272
healthy, 20
n = 4
Health Status: healthy
Age Group: 20
Sex: M
Population Size: 4
Sources:
https://pubmed.ncbi.nlm.nih.gov/954349/
Page: p.272
Sources:
https://pubmed.ncbi.nlm.nih.gov/954349/
Page: p.272
70.4 g single, oral
Overdose
Dose: 70.4 g
Route: oral
Route: single
Dose: 70.4 g
Co-administed with::
alcohol, p.o
Sources:
https://pubmed.ncbi.nlm.nih.gov/24756481
Page: p.103
healthy, 28
n = 1
Health Status: healthy
Age Group: 28
Sex: M
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/24756481
Page: p.103
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
Page: p.103
26 g single, oral
Overdose
Dose: 26 g
Route: oral
Route: single
Dose: 26 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/31742906
Page: p.458
unhealthy, 58
n = 1
Health Status: unhealthy
Condition: Depressive syndrome|Anxiety
Age Group: 58
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/31742906
Page: p.458
Disc. AE: Thrombopenia...
AEs leading to
discontinuation/dose reduction:
Thrombopenia
Sources:
https://pubmed.ncbi.nlm.nih.gov/31742906
Page: p.458
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
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Pain|Primary Dysmenorrhea| Acute Tendonitis| Acute Bursitis
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017581s113,018164s063,020067s020lbl.pdf
Page: p.1
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
Page: p.1
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
Page: 1102/129
healthy, 15
n = 1
Health Status: healthy
Age Group: 15
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/2552870
Page: 1102/129
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
Page: 1102/129
healthy, 15
n = 1
Health Status: healthy
Age Group: 15
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/2552870
Page: 1102/129
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
Page: 1102/129
healthy, 15
n = 1
Health Status: healthy
Age Group: 15
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/2552870
Page: 1102/129
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
Page: 1102/129
healthy, 15
n = 1
Health Status: healthy
Age Group: 15
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/2552870
Page: 1102/129
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
Page: 1102/129
healthy, 15
n = 1
Health Status: healthy
Age Group: 15
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/2552870
Page: 1102/129
Drowsiness Disc. AE
70.4 g single, oral
Overdose
Dose: 70.4 g
Route: oral
Route: single
Dose: 70.4 g
Co-administed with::
alcohol, p.o
Sources:
https://pubmed.ncbi.nlm.nih.gov/24756481
Page: p.103
healthy, 28
n = 1
Health Status: healthy
Age Group: 28
Sex: M
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/24756481
Page: p.103
Metabolic acidosis Disc. AE
70.4 g single, oral
Overdose
Dose: 70.4 g
Route: oral
Route: single
Dose: 70.4 g
Co-administed with::
alcohol, p.o
Sources:
https://pubmed.ncbi.nlm.nih.gov/24756481
Page: p.103
healthy, 28
n = 1
Health Status: healthy
Age Group: 28
Sex: M
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/24756481
Page: p.103
Seizures Disc. AE
70.4 g single, oral
Overdose
Dose: 70.4 g
Route: oral
Route: single
Dose: 70.4 g
Co-administed with::
alcohol, p.o
Sources:
https://pubmed.ncbi.nlm.nih.gov/24756481
Page: p.103
healthy, 28
n = 1
Health Status: healthy
Age Group: 28
Sex: M
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/24756481
Page: p.103
Sinus tachycardia Disc. AE
70.4 g single, oral
Overdose
Dose: 70.4 g
Route: oral
Route: single
Dose: 70.4 g
Co-administed with::
alcohol, p.o
Sources:
https://pubmed.ncbi.nlm.nih.gov/24756481
Page: p.103
healthy, 28
n = 1
Health Status: healthy
Age Group: 28
Sex: M
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/24756481
Page: p.103
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
Page: p.458
unhealthy, 58
n = 1
Health Status: unhealthy
Condition: Depressive syndrome|Anxiety
Age Group: 58
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/31742906
Page: p.458
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
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Pain|Primary Dysmenorrhea| Acute Tendonitis| Acute Bursitis
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017581s113,018164s063,020067s020lbl.pdf
Page: p.1
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
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Pain|Primary Dysmenorrhea| Acute Tendonitis| Acute Bursitis
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017581s113,018164s063,020067s020lbl.pdf
Page: p.1
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
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Pain|Primary Dysmenorrhea| Acute Tendonitis| Acute Bursitis
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017581s113,018164s063,020067s020lbl.pdf
Page: p.1
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
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Pain|Primary Dysmenorrhea| Acute Tendonitis| Acute Bursitis
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017581s113,018164s063,020067s020lbl.pdf
Page: p.1
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
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Pain|Primary Dysmenorrhea| Acute Tendonitis| Acute Bursitis
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017581s113,018164s063,020067s020lbl.pdf
Page: p.1
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
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Pain|Primary Dysmenorrhea| Acute Tendonitis| Acute Bursitis
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017581s113,018164s063,020067s020lbl.pdf
Page: p.1
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
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Pain|Primary Dysmenorrhea| Acute Tendonitis| Acute Bursitis
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017581s113,018164s063,020067s020lbl.pdf
Page: p.1
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1037

OverviewOther

Other InhibitorOther SubstrateOther Inducer
OAT4
146

OAT3
642

OAT1
599

OAT2
145
CYP1A2
1054

CYP2C8
693

UGT1A1
418

UGT1A3
422

UGT1A6
307

UGT1A7
236

UGT1A8
283

UGT1A9
380

UGT1A10
291

UGT2B7
389
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
OAT3
644
 yes [IC50 4.67 uM]
OAT2
147
 yes [IC50 486 uM]
OAT1
603
 yes [IC50 5.67 uM]
OAT4
146
 yes [IC50 85.4 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP2C9
1037
 major
CYP1A2
1054
 minor
CYP2C8
693
 minor
UGT1A1
418
 yes
UGT1A10
291
 yes
UGT1A3
422
 yes
UGT1A6
307
 yes
UGT1A7
236
 yes
UGT1A8
283
 yes
UGT1A9
380
 yes
UGT2B7
389
 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
MolPort
MolPort-000-145-960
https://www.molport.com/shop/molecule-link/MolPort-000-145-960
ZINC
ZINC000000105216
http://zinc15.docking.org/substances/ZINC000000105216
eMolecules
494695
https://www.emolecules.com/cgi-bin/more?vid=494695
PubMed

PubMed

TitleDatePubMed
Effect of clopidogrel on naproxen-induced gastrointestinal blood loss in healthy volunteers.
1998
Naproxen availability from variable-dose and weight sustained-release tablets.
2001
Risk of ulcer soars with combination of arthritis drugs.
2001 Apr
[Acupuncture contra antiphlogistics in acute lumbago].
2001 Apr 20
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
Time and dose dependent augmentation of inhibitory effects of abciximab by aspirin.
2001 Feb
Analgesic and anti-inflammatory effects of Mangifera indica L. extract (Vimang).
2001 Feb
Determination of drug residues in water by the combination of liquid chromatography or capillary electrophoresis with electrospray mass spectrometry.
2001 Feb 23
Rhein, an active metabolite of diacerein, suppresses the interleukin-1alpha-induced proteoglycan degradation in cultured rabbit articular chondrocytes.
2001 Jan
Successful use of propranolol in migraine associated with electroconvulsive therapy.
2001 Jan
Randomized trial of low-dose misoprostol and naproxen vs. nabumetone to prevent recurrent upper gastrointestinal haemorrhage in users of non-steroidal anti-inflammatory drugs.
2001 Jan
Prostaglandin H synthase-2 inhibitors interfere with prostaglandin H synthase-1 inhibition by nonsteroidal anti-inflammatory drugs.
2001 Jan 19
Alendronate and naproxen are synergistic for development of gastric ulcers.
2001 Jan 8
A possible mechanism of naproxen-induced lipid peroxidation in rat liver microsomes.
2001 Jul
In vitro evaluation and intra-articular administration of biodegradable microspheres containing naproxen sodium.
2001 Jul-Aug
Interleukin-6 (IL-6) producing phaeochromocytoma: direct IL-6 suppression by non-steroidal anti-inflammatory drugs.
2001 Mar
Anti-lymphoma effect of naproxen and indomethacin in a patient with relapsed diffuse large B-cell lymphoma.
2001 Mar
High-performance liquid chromatographic method development and validation for the simultaneous quantitation of naproxen sodium and pseudoephedrine hydrochloride impurities.
2001 Mar
Pharmacokinetics, safety, and tolerability of BAY 12-9566 and nonsteroidal anti-inflammatory agents (naproxen, ibuprofen) during coadministration in patients with osteoarthritis.
2001 Mar
Neuroprotective effects of non-steroidal anti-inflammatory drugs by direct scavenging of nitric oxide radicals.
2001 Mar
Analysis of nonsteroidal antiinflammatory drugs in meconium and its relation to persistent pulmonary hypertension of the newborn.
2001 Mar
Synthesis, in vitro skin permeation studies, and PLS-analysis of new naproxen derivatives.
2001 May
Severe reversible renal failure due to naproxen-associated acute interstitial nephritis.
2001 May
Stereoselective synthesis of (S)-(+)-Naproxen catalyzed by carboxyl esterase in a multicompartment electrolyzer.
2001 May 28
Patents

Patents

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22
JP4774135B2
12
JP4787165B2
101
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 Fri Dec 15 15:20:18 GMT 2023
Edited
by admin
on Fri Dec 15 15:20:18 GMT 2023
Record UNII
9TN87S3A3C
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NAPROXEN SODIUM
USP  
Official Name English
NAPROXEN SODIUM COMPONENT OF TREXIMET
Common Name English
NAPRELAN
Brand Name English
NAPROXEN SODIUM [ORANGE BOOK]
Common Name English
NAPROXEN SODIUM [EP IMPURITY]
Common Name English
2-NAPHTHALENEACETIC ACID, 6-METHOXY-.ALPHA.-METHYL-, SODIUM SALT, (S)-
Common Name English
NAPROXEN SODIUM COMPONENT OF ALEVE-D
Common Name English
NAPROXEN SODIUM [USAN]
Common Name English
TREXIMET COMPONENT NAPROXEN SODIUM
Common Name English
NAPROXEN SODIUM ANHYDROUS
Common Name English
NAPROXEN SODIUM SALT
MI  
Common Name English
BAY117031
Code English
ANAPROX
Brand Name English
NAPROXEN SODIUM SALT [MI]
Common Name English
BAYH6689
Code English
NAPROXEN SODIUM [USP MONOGRAPH]
Common Name English
NAPROXEN SODIUM [USP IMPURITY]
Common Name English
NAPROXEN SODIUM [EP MONOGRAPH]
Common Name English
BAY-117031
Code English
NAPROXEN SODIUM [VANDF]
Common Name English
ALEVE
Brand Name English
NAPROXEN SODIUM [MART.]
Common Name English
Naproxen sodium [WHO-DD]
Common Name English
ALEVE-D COMPONENT NAPROXEN SODIUM
Common Name English
RS-3650
Code English
NAPROXEN SODIUM [USP-RS]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1323
Created by admin on Fri Dec 15 15:20:18 GMT 2023 , Edited by admin on Fri Dec 15 15:20:18 GMT 2023
Code System Code Type Description
RXCUI
142442
Created by admin on Fri Dec 15 15:20:18 GMT 2023 , Edited by admin on Fri Dec 15 15:20:18 GMT 2023
PRIMARY RxNorm
MERCK INDEX
m7769
Created by admin on Fri Dec 15 15:20:18 GMT 2023 , Edited by admin on Fri Dec 15 15:20:18 GMT 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
247-486-2
Created by admin on Fri Dec 15 15:20:18 GMT 2023 , Edited by admin on Fri Dec 15 15:20:18 GMT 2023
PRIMARY
EVMPD
SUB166156
Created by admin on Fri Dec 15 15:20:18 GMT 2023 , Edited by admin on Fri Dec 15 15:20:18 GMT 2023
PRIMARY
NCI_THESAURUS
C48006
Created by admin on Fri Dec 15 15:20:18 GMT 2023 , Edited by admin on Fri Dec 15 15:20:18 GMT 2023
PRIMARY
EVMPD
SUB03392MIG
Created by admin on Fri Dec 15 15:20:18 GMT 2023 , Edited by admin on Fri Dec 15 15:20:18 GMT 2023
PRIMARY
DRUG BANK
DBSALT000949
Created by admin on Fri Dec 15 15:20:18 GMT 2023 , Edited by admin on Fri Dec 15 15:20:18 GMT 2023
PRIMARY
RS_ITEM_NUM
1457403
Created by admin on Fri Dec 15 15:20:18 GMT 2023 , Edited by admin on Fri Dec 15 15:20:18 GMT 2023
PRIMARY
CAS
26159-34-2
Created by admin on Fri Dec 15 15:20:18 GMT 2023 , Edited by admin on Fri Dec 15 15:20:18 GMT 2023
PRIMARY
PUBCHEM
23681059
Created by admin on Fri Dec 15 15:20:18 GMT 2023 , Edited by admin on Fri Dec 15 15:20:18 GMT 2023
PRIMARY
ChEMBL
CHEMBL154
Created by admin on Fri Dec 15 15:20:18 GMT 2023 , Edited by admin on Fri Dec 15 15:20:18 GMT 2023
PRIMARY
SMS_ID
100000092256
Created by admin on Fri Dec 15 15:20:18 GMT 2023 , Edited by admin on Fri Dec 15 15:20:18 GMT 2023
PRIMARY
DAILYMED
9TN87S3A3C
Created by admin on Fri Dec 15 15:20:18 GMT 2023 , Edited by admin on Fri Dec 15 15:20:18 GMT 2023
PRIMARY
EPA CompTox
DTXSID7045576
Created by admin on Fri Dec 15 15:20:18 GMT 2023 , Edited by admin on Fri Dec 15 15:20:18 GMT 2023
PRIMARY
FDA UNII
9TN87S3A3C
Created by admin on Fri Dec 15 15:20:18 GMT 2023 , Edited by admin on Fri Dec 15 15:20:18 GMT 2023
PRIMARY
Related Record Type Details
Structure of NAPROXEN SODIUM
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
USP
Structure of NAPROXEN
PARENT -> SALT/SOLVATE
Structure of NAPROXEN SODIUM
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
EP
Related Record Type Details
Structure of 2-ETHYL-6-METHOXYNAPHTHALENE
IMPURITY -> PARENT
UNSPECIFIED
EP
Structure of 5-BROMONAPROXEN, (S)-
IMPURITY -> PARENT
UNSPECIFIED
EP
Structure of NAPROXEN METHYL ESTER
IMPURITY -> PARENT
UNSPECIFIED
EP
Structure of NAPROXEN ETHYL ESTER
IMPURITY -> PARENT
UNSPECIFIED
EP
Structure of 2-BROMO-6-METHOXYNAPHTHALENE
IMPURITY -> PARENT
UNSPECIFIED
EP
Structure of 6-METHOXY-2-NAPHTHOL
IMPURITY -> PARENT
UNSPECIFIED
EP
Structure of 5-IODONAPROXEN, (S)-
IMPURITY -> PARENT
UNSPECIFIED
EP
Structure of NAPROXEN, (-)-
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 2-ACETYL-6-METHOXYNAPHTHALENE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 6-O-DEMETHYLNAPROXEN
IMPURITY -> PARENT
UNSPECIFIED
EP
Structure of 2-METHOXYNAPHTHALENE
IMPURITY -> PARENT
UNSPECIFIED
EP
Structure of 1-(6-METHOXYNAPHTHALEN-2-YL)ETHANOL, (±)-
IMPURITY -> PARENT
UNSPECIFIED
EP
Structure of 6-METHOXY-2-NAPHTHYLACETIC ACID
IMPURITY -> PARENT
UNSPECIFIED
EP
Structure of 5-CHLORONAPROXEN, (S)-
IMPURITY -> PARENT
UNSPECIFIED
EP
Related Record Type Details
Structure of NAPROXEN
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