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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

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 TargetPharmacologyConditionPotency
0.11 µM [IC50]
0.19 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
NAPROSYN
Primary
NAPROSYN
Primary
NAPROSYN
Primary
NAPROSYN
Primary
NAPROSYN

Cmax

ValueDoseCo-administeredAnalytePopulation
95 μg/L
500 mg 2 times / day steady-state, oral
NAPROXEN plasma
Homo sapiens
94 μg/mL
1000 mg 1 times / day steady-state, oral
NAPROXEN plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
1446 μg × h/mL
500 mg 2 times / day steady-state, oral
NAPROXEN plasma
Homo sapiens
1448 μg × h/mL
1000 mg 1 times / day steady-state, oral
NAPROXEN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
15 h
500 mg 2 times / day steady-state, oral
NAPROXEN plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
1%
500 mg 2 times / day steady-state, oral
NAPROXEN plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

Drug as perpetrator​

Drug as victim

PubMed

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.