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naproxen 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
	1883	22204-53-1

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: methoxypropiocin naproxen naprosyn aproxen naproxen sodium aleve	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. Molecular weight: 230.26 Formula: C14H14O3 CLOGP: 2.82 LIPINSKI: 0 HAC: 3 HDO: 1 TPSA: 46.53 ALOGS: -3.65 ROTB: 3 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

methoxypropiocin
naproxen
naprosyn
aproxen
naproxen sodium
aleve

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.

Molecular weight: 230.26
Formula: C14H14O3
CLOGP: 2.82
LIPINSKI: 0
HAC: 3
HDO: 1
TPSA: 46.53
ALOGS: -3.65
ROTB: 3

Status: OFP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

Dose	Unit	Route
0.50	g	O
0.50	g	R
0.50	g	O

ADMET properties:

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Property	Value	Reference
BA (Bioavailability)	99 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
BDDCS (Biopharmaceutical Drug Disposition Classification System)	2	Benet LZ, Broccatelli F, Oprea TI
t_half (Half-life)	16.63 hours	Lombardo F, Berellini G, Obach RS
MRTD (Maximum Recommended Therapeutic Daily Dose)	108.57 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
EoM (Fraction excreted unchanged in urine)	0.50 %	Benet LZ, Broccatelli F, Oprea TI
S (Water solubility)	0.12 mg/mL	Benet LZ, Broccatelli F, Oprea TI
Vd (Volume of distribution)	0.09 L/kg	Lombardo F, Berellini G, Obach RS
CL (Clearance)	0.07 mL/min/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.00 %	Lombardo F, Berellini G, Obach RS

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Approvals:

Date	Agency	Company	Orphan
March 11, 1976	FDA	ROCHE PALO

FDA Adverse Event Reporting System (Female)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
C-reactive protein abnormal	405.87	10.10	659	232788	45437	63210138
Death	400.05	10.10	473	232974	373908	62881667
Pharyngitis	371.05	10.10	413	233034	19730	63235845
Red blood cell sedimentation rate abnormal	366.81	10.10	407	233040	19375	63236200
Ankylosing spondylitis	312.12	10.10	279	233168	10195	63245380
Rheumatoid arthritis	270.49	10.10	1727	231720	252092	63003483
Drug hypersensitivity	260.09	10.10	1993	231454	308694	62946881
Musculoskeletal stiffness	258.60	10.10	1351	232096	183267	63072308
Psoriatic arthropathy	258.16	10.10	832	232615	90688	63164887
Deafness transitory	249.76	10.10	129	233318	1841	63253734

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FDA Adverse Event Reporting System (Male)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Ankylosing spondylitis	379.06	10.85	206	79775	5398	34871552
Gastric haemorrhage	249.99	10.85	199	79782	10062	34866888
Arthralgia	242.98	10.85	897	79084	169144	34707806
Psoriatic arthropathy	231.22	10.85	255	79726	19543	34857407
Joint swelling	208.57	10.85	438	79543	59452	34817498
Musculoskeletal stiffness	203.23	10.85	375	79606	46305	34830645
Duodenal ulcer	199.11	10.85	175	79806	10157	34866793
Pain	182.57	10.85	937	79044	203738	34673212
Psoriasis	143.45	10.85	291	79690	38521	34838429
Lip swelling	131.72	10.85	173	79808	15907	34861043

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FDA Adverse Event Reporting System (Geriatric)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Psoriatic arthropathy	513.67	10.08	926	263846	77073	79402543
Ankylosing spondylitis	475.80	10.08	364	264408	11841	79467775
C-reactive protein abnormal	452.42	10.08	673	264099	47694	79431922
Musculoskeletal stiffness	441.14	10.08	1431	263341	173577	79306039
Death	440.11	10.08	754	264018	565760	78913856
Rheumatoid arthritis	436.09	10.08	1602	263170	206868	79272748
Arthralgia	392.64	10.08	3238	261534	568565	78911051
Synovitis	373.91	10.08	1226	263546	149508	79330108
Pain	365.22	10.08	3752	261020	700050	78779566
Joint swelling	352.82	10.08	1889	262883	286757	79192859

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	G02CC02	GENITO URINARY SYSTEM AND SEX HORMONES OTHER GYNECOLOGICALS OTHER GYNECOLOGICALS Antiinflammatory products for vaginal administration
ATC	M01AE02	MUSCULO-SKELETAL SYSTEM ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS Propionic acid derivatives
ATC	M01AE52	MUSCULO-SKELETAL SYSTEM ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS Propionic acid derivatives
ATC	M01AE56	MUSCULO-SKELETAL SYSTEM ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS Propionic acid derivatives
ATC	M02AA12	MUSCULO-SKELETAL SYSTEM TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN Antiinflammatory preparations, non-steroids for topical use
CHEBI has role	CHEBI:35475	non-steroidal anti-inflammatory agent
CHEBI has role	CHEBI:35493	anti-pyretic
CHEBI has role	CHEBI:35703	Xenobiotic
CHEBI has role	CHEBI:35845	gout suppressants
CHEBI has role	CHEBI:50629	COX-2 inhibitor

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Drug Use | Suggest Off label Use Form| |View source of the data|

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Disease	Relation	SNOMED_ID	DOID
Sinus headache	indication	4969004
Ankylosing spondylitis	indication	9631008	DOID:7147
Pain	indication	22253000
Toothache	indication	27355003
Tendinitis	indication	34840004	DOID:971
Migraine	indication	37796009	DOID:6364
Joint pain	indication	57676002
Nasal discharge	indication	64531003
Muscle pain	indication	68962001
Rheumatoid arthritis	indication	69896004	DOID:7148

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🐶 Veterinary Drug Use

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Species	Use	Relation
Horses	Myositis	Indication
Horses	Pain and inflammation associated with arthritis	Indication
Horses	Soft tissue diseases of the musculoskeletal system	Indication

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🐶 Veterinary products

Product	Applicant	Ingredients
Equiproxen 10% Solution	Zoetis Inc.	1
Equiproxen Granules	Zoetis Inc.	1

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	4.36	acidic

Orange Book patent data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Patent number	Patent expiration date	Patent use
500MG;EQ 85MG BASE	TREXIMET	CURRAX	N021926	April 15, 2008	RX	TABLET	ORAL	7332183	Oct. 2, 2025	TREATMENT OF MIGRAINE
60MG;EQ 10MG BASE	TREXIMET	CURRAX	N021926	May 14, 2015	DISCN	TABLET	ORAL	7332183	Oct. 2, 2025	ACUTE TREATMENT OF MIGRAINE
EQ 200MG BASE	NAPROXEN SODIUM	BIONPHARMA	N021920	Feb. 17, 2006	OTC	CAPSULE	ORAL	10022344	March 3, 2026	TEMPORARY REDUCTION OF FEVER
EQ 200MG BASE	NAPROXEN SODIUM	BIONPHARMA	N021920	Feb. 17, 2006	OTC	CAPSULE	ORAL	10022344	March 3, 2026	TEMPORARY RELIEF OF MINOR ACHES AND PAINS
EQ 200MG BASE	NAPROXEN SODIUM	BIONPHARMA	N021920	Feb. 17, 2006	OTC	CAPSULE	ORAL	10028925	March 3, 2026	TEMPORARY REDUCTION OF FEVER
EQ 200MG BASE	NAPROXEN SODIUM	BIONPHARMA	N021920	Feb. 17, 2006	OTC	CAPSULE	ORAL	10028925	March 3, 2026	TEMPORARY RELIEF OF MINOR ACHES AND PAINS
EQ 200MG BASE	NAPROXEN SODIUM	BIONPHARMA	N021920	Feb. 17, 2006	OTC	CAPSULE	ORAL	11090280	March 3, 2026	TEMPORARY REDUCTION OF FEVER
EQ 200MG BASE	NAPROXEN SODIUM	BIONPHARMA	N021920	Feb. 17, 2006	OTC	CAPSULE	ORAL	11090280	March 3, 2026	TEMPORARY RELIEF OF MINOR ACHES AND PAINS
EQ 20MG BASE;375MG	VIMOVO	HORIZON	N022511	April 30, 2010	RX	TABLET, DELAYED RELEASE	ORAL	9393208	Sept. 3, 2029	RISK-REDUCTION OF NSAID-ASSOCIATED GASTRIC ULCER IN PATIENTS REQUIRING NSAID TREATMENT
EQ 20MG BASE;375MG	VIMOVO	HORIZON	N022511	April 30, 2010	RX	TABLET, DELAYED RELEASE	ORAL	8945621	Oct. 17, 2031	RISK-REDUCTION OF NSAID-ASSOCIATED GASTRIC ULCERS IN PATIENTS ALSO TAKING LOW DOSE ASPIRIN

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Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Prostaglandin G/H synthase 2	Enzyme	P35354	PGH2_HUMAN	INHIBITOR	IC50	5.60	CHEMBL	CHEMBL
Prostaglandin G/H synthase 1	Enzyme	P23219	PGH1_HUMAN	INHIBITOR	IC50	5.16	WOMBAT-PK	CHEMBL
Aldo-keto reductase family 1 member C2	Enzyme	P52895	AK1C2_HUMAN		IC50	4.50	CHEMBL
Aldo-keto reductase family 1 member C3	Enzyme	P42330	AK1C3_HUMAN		IC50	6.32	CHEMBL
Prostaglandin G/H synthase 1	Enzyme		PGH1_SHEEP		IC50	6.74	CHEMBL
Prostaglandin-H2 D-isomerase	Enzyme		PTGDS_MOUSE		IC50	4.89	CHEMBL
Prostaglandin G/H synthase 2	Enzyme		PGH2_SHEEP		IC50	5.47	CHEMBL
Prostaglandin G/H synthase 1	Enzyme		PGH1_BOVIN		IC50	4.96	CHEMBL
Hormone-sensitive lipase	Enzyme		LIPS_RAT		IC50	5.92	CHEMBL
Cyclooxygenase	Enzyme		PGH2_RAT PGH1_RAT		IC50	7.22	CHEMBL

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External reference:

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ID	Source
NPS	PDB_CHEM_ID
002380	NDDF
002381	NDDF
11847009	SNOMEDCT_US
142442	RXNORM
156391	PUBCHEM_CID
2108	MMSL
2111	MMSL
26159-34-2	SECONDARY_CAS_RN
27852	MMSL

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Aleve	HUMAN OTC DRUG LABEL	1	0280-6010	TABLET	220 mg	ORAL	NDA	17 sections
Aleve	HUMAN OTC DRUG LABEL	1	0280-6010	TABLET	220 mg	ORAL	NDA	17 sections
Aleve	HUMAN OTC DRUG LABEL	1	0280-6010	TABLET	220 mg	ORAL	NDA	17 sections
Aleve Headache Pain	HUMAN OTC DRUG LABEL	1	0280-0041	TABLET	220 mg	ORAL	NDA	17 sections
Aleve Headache Pain	HUMAN OTC DRUG LABEL	1	0280-0041	TABLET	220 mg	ORAL	NDA	17 sections
Aleve PM	HUMAN OTC DRUG LABEL	2	0280-1200	TABLET, FILM COATED	220 mg	ORAL	NDA	17 sections
Aleve PM	HUMAN OTC DRUG LABEL	2	0280-1200	TABLET, FILM COATED	220 mg	ORAL	NDA	17 sections
Aleve PM	HUMAN OTC DRUG LABEL	2	0280-1200	TABLET, FILM COATED	220 mg	ORAL	NDA	17 sections
AleveCaplets	HUMAN OTC DRUG LABEL	1	0280-6000	TABLET	220 mg	ORAL	NDA	17 sections
AleveCaplets	HUMAN OTC DRUG LABEL	1	0280-6000	TABLET	220 mg	ORAL	NDA	17 sections

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