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

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	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
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-1 127	Inhibitor 8,297		0.11 µM [IC50]
Cyclooxygenase-2 196	Inhibitor 8,297		0.19 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Rheumatoid arthritis 316	Primary	Approved 8,429	NAPROSYN
Osteoarthritis 157	Primary	Approved 8,429	NAPROSYN
Ankylosing spondylitis 33	Primary	Approved 8,429	NAPROSYN
Tendonitis 6	Primary	Approved 8,429	NAPROSYN
Bursitis 6	Primary	Approved 8,429	NAPROSYN

C_max

Value	Dose	Co-administered	Analyte	Population
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

Value	Dose	Co-administered	Analyte	Population
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

T_1/2

Value	Dose	Co-administered	Analyte	Population
15 h	500 mg 2 times / day steady-state, oral		NAPROXEN plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
1%	500 mg 2 times / day steady-state, oral		NAPROXEN plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
12.5 g single, oral Overdose	healthy, 15 n = 1	Disc. AE: Abdominal pain, Nausea...
4 g single, oral Highest studied dose	healthy, 20 n = 4
70.4 g single, oral Overdose	healthy, 28 n = 1	Disc. AE: Sinus tachycardia, Drowsiness...
26 g single, oral Overdose	unhealthy, 58 n = 1	Disc. AE: Thrombopenia...
550 mg 2 times / day multiple, oral Recommended	unhealthy	Disc. AE: Cardiac thrombosis, Myocardial infarction...

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AEs

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AE	Significance	Dose	Population
Abdominal pain	Disc. AE	12.5 g single, oral Overdose	healthy, 15 n = 1
Dizziness	Disc. AE	12.5 g single, oral Overdose	healthy, 15 n = 1
Nausea	Disc. AE	12.5 g single, oral Overdose	healthy, 15 n = 1
Seizures	Disc. AE	12.5 g single, oral Overdose	healthy, 15 n = 1
Metabolic acidosis	severe Disc. AE	12.5 g single, oral Overdose	healthy, 15 n = 1

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
	substrate 1,037

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OAT4 146 OAT3 642 OAT1 599 OAT2 145	CYP1A2 1,054 CYP2C8 693 UGT1A1 418 UGT1A3 422 UGT1A6 307 UGT1A7 236 UGT1A8 283 UGT1A9 380 UGT1A10 291 UGT2B7 389

Drug as perpetrator

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Target	Modality	Activity
OAT3 644	inhibitor 3,277	yes [IC50 4.67 uM]
OAT2 147	inhibitor 3,277	yes [IC50 486 uM]
OAT1 603	inhibitor 3,277	yes [IC50 5.67 uM]
OAT4 146	inhibitor 3,277	yes [IC50 85.4 uM]

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Drug as victim

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Target	Modality	Activity
CYP2C9 1,037	substrate 3,367	major
CYP1A2 1,054	substrate 3,367	minor
CYP2C8 693	substrate 3,367	minor
UGT1A1 418	substrate 3,367	yes
UGT1A10 291	substrate 3,367	yes

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
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

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PubMed

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Title	Date	PubMed
Renal effects of selective cyclooxygenase-2 inhibition in normotensive salt-depleted subjects.	1999 Jul	10430112
Low-dose diclofenac, naproxen, and ibuprofen cohort study.	1999 Jul	10417034
Nimesulide, a balanced drug for the treatment of osteoarthritis.	2001	11296545
Risk of upper gastrointestinal bleeding and perforation associated with low-dose aspirin as plain and enteric-coated formulations.	2001	11228592
Endogenous prostaglandin E2 and insulin-like growth factor 1 can modulate the levels of parathyroid hormone receptor in human osteoarthritic osteoblasts.	2001 Apr	11315999

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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
Record UNII	57Y76R9ATQ
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

NAPROXEN

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

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Classification Tree

Code System

Code

Established Pharmacologic Class

NDF-RT

N0000175722

PART 522 IMPLANTATION OR INJECTABLE DOSAGE FORM NEW ANIMAL DRUGS

CFR

21 CFR 522.1468

Chemical Classes for Pharmacologic Classification

NDF-RT

N0000175721

Antiinflammatory products for vaginal administration

WHO-ATC

G02CC02

Propionic acid derivatives

WHO-VATC

QM01AE56

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Code System

Code

Type

Description

NSC

750183

PRIMARY

LACTMED

Naproxen

PRIMARY

DRUG BANK

DB00788

PRIMARY

INN

2979

PRIMARY

PUBCHEM

156391

PRIMARY

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Related Record

Type

Details


					4HZ67LW8L7

OAT-4

TRANSPORTER -> INHIBITOR


					15X32OGO88

NAPROXEN LYSINE

SALT/SOLVATE -> PARENT


					6D53G0FD0Z

PLASMA PROTEIN FRACTION (HUMAN)

BINDER->LIGAND

Interaction Type:

BINDING

Amount:

99 % (average)


					57Y76R9ATQ

NAPROXEN

BASIS OF STRENGTH->SUBSTANCE

Interaction Type:

ASSAY (TITRATION)

Qualification:

EP

Amount:

RELATIONSHIP_AMOUNT [99 to 101] WEIGHT PERCENT (limits)


					ZWJ2Y6JZWY

OAT-3

TRANSPORTER -> INHIBITOR

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Related Record

Type

Details


					XSN14HHQ8D

6-O-DEMETHYLNAPROXEN

METABOLITE INACTIVE -> PARENT

Comments:

Naproxen is extensively metabolized to 6-0-desmethyl naproxen and both parent and metabolites do not induce metabolizing enzymes


					XSN14HHQ8D

6-O-DEMETHYLNAPROXEN

METABOLITE INACTIVE -> PARENT


					XSN14HHQ8D

6-O-DEMETHYLNAPROXEN

METABOLITE INACTIVE -> PARENT


					XSN14HHQ8D

6-O-DEMETHYLNAPROXEN

METABOLITE INACTIVE -> PARENT


					V24GR4LI3I

NAPROXCINOD

PRODRUG -> METABOLITE ACTIVE

Amount:

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Related Record

Type

Details


					484XV9323P

NAPROXEN, (-)-

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:

RELATIONSHIP_AMOUNT [<2.5] PERCENT PEAK AREA (limits)


					QBW1M74OFY

5-BROMONAPROXEN, (S)-

IMPURITY -> PARENT

Comments:

UNSPECIFIED

Qualification:

EP


					R60QH2454J

5-CHLORONAPROXEN, (S)-

IMPURITY -> PARENT

Comments:

UNSPECIFIED

Qualification:

EP


					DL375UDR3E

6-METHOXY-2-NAPHTHOL

IMPURITY -> PARENT

Comments:

UNSPECIFIED

Qualification:

EP


					S19T080MRG

2-BROMO-6-METHOXYNAPHTHALENE

IMPURITY -> PARENT

Comments:

UNSPECIFIED

Qualification:

EP

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Related Record

Type

Details


					57Y76R9ATQ

NAPROXEN

ACTIVE MOIETY

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Name	Property Type	Amount	Parameters
EXCRETION	PHARMACOKINETIC	95 % (average) RENAL ROUTE

Volume of Distribution	PHARMACOKINETIC	0.16 Liters/Kilogram (average)

ORAL BIOAVAILABILITY	PHARMACOKINETIC	95 % (average)

MAXIMUM TOLERATED DOSE	TOXICITY	1250 mg/day (average) ORAL TABLET AND SUSPENSION
Tmax	PHARMACOKINETIC	[2 to 4] hours (average) ORAL TABLET	FOOD EFFECT PHARMACOKINETIC 12 hours [4 to 24] (average)

Tmax	PHARMACOKINETIC	[4 to 6] hours (average) [2 to 12] (limits) ORAL DELAYED RELEASE TABLET

Tmax	PHARMACOKINETIC	[1 to 4] hours (average) ORAL SUSPENSION

Biological Half-life	PHARMACOKINETIC	[12 to 17] hours (average)

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound

Drug as perpetrator