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Identification
NameNaproxen
Accession NumberDB00788  (APRD01135)
TypeSmall Molecule
GroupsApproved
Description

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. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
(+)-(S)-6-Methoxy-alpha-methyl-2-naphthaleneacetic acidNot AvailableNot Available
(+)-(S)-NaproxenNot AvailableNot Available
(+)-2-(6-Methoxy-2-naphthyl)propionic acidNot AvailableNot Available
(+)-2-(Methoxy-2-naphthyl)-propionic acidNot AvailableNot Available
(+)-2-(Methoxy-2-naphthyl)-propionsaeureNot AvailableNot Available
(+)-NaproxenNot AvailableNot Available
(S)-(+)-2-(6-Methoxy-2-naphthyl)propionic acidNot AvailableNot Available
(S)-(+)-NaproxenNot AvailableNot Available
(S)-2-(6-Methoxy-2-naphthyl)propanoic acidNot AvailableNot Available
(S)-2-(6-Methoxy-2-naphthyl)propionic acidNot AvailableNot Available
(S)-6-Methoxy-alpha-methyl-2-naphthaleneacetic acidNot AvailableNot Available
(S)-NaproxenNot AvailableNot Available
NaprolagNot AvailableIS
NaproxenGermanINN
NaproxèneFrenchINN
NaproxenoSpanishINN
NaproxenumLatinINN
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Naprosynsuspension125 mg/5mLoralGenentech, Inc.1987-03-23Not AvailableUs
Anaproxtablet275 mgoralGenentech, Inc.1980-09-04Not AvailableUs
Naprosyntablet250 mgoralGenentech, Inc.1976-03-11Not AvailableUs
Naprosyntablet375 mgoralGenentech, Inc.1976-03-11Not AvailableUs
Naprosyntablet500 mgoralGenentech, Inc.1976-03-11Not AvailableUs
Ec-naprosyntablet, delayed release375 mgoralGenentech, Inc.1994-10-14Not AvailableUs
Ec-naprosyntablet, delayed release500 mgoralGenentech, Inc.1994-10-14Not AvailableUs
Naprelantablet, film coated, extended release750 mgoralStat Rx USA2008-12-19Not AvailableUs
Naprelantablet, film coated, extended release375 mgoralRebel Distributors Corp1996-01-05Not AvailableUs
Naprelantablet, film coated, extended release500 mgoralRebel Distributors Corp1996-01-05Not AvailableUs
Naprelantablet, film coated, extended release500 mgoralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2011-11-29Not AvailableUs
Naprelantablet, film coated, extended release750 mgoralPd Rx Pharmaceuticals, Inc.2008-12-19Not AvailableUs
Naprelantablet, film coated, extended release375 mgoralALMATICA PHARMA INC.2014-01-17Not AvailableUs
Naprelantablet, film coated, extended release500 mgoralALMATICA PHARMA INC.2014-01-17Not AvailableUs
Naprelantablet, film coated, extended release750 mgoralALMATICA PHARMA INC.2014-01-17Not AvailableUs
Naprosyntablet500 mgoralA S Medication Solutions Llc1976-03-11Not AvailableUs
Naprelantablet, film coated, extended release375 mgoralPhysicians Total Care, Inc.2005-08-19Not AvailableUs
Naprelantablet, film coated, extended release375 mgoralShionogi Inc.1996-04-01Not AvailableUs
Naprelantablet, film coated, extended release750 mgoralShionogi Inc.1996-04-01Not AvailableUs
Naprelantablet, film coated, extended release500 mgoralShionogi Inc.1996-04-01Not AvailableUs
Naprelantablet, film coated, extended release375 mgoralbryant ranch prepack1996-01-05Not AvailableUs
Naprelantablet, film coated, extended release375 mgoralVictory Pharma, Inc.1996-01-05Not AvailableUs
Naprelantablet, film coated, extended release750 mgoralVictory Pharma, Inc.2008-12-19Not AvailableUs
Naprelantablet, film coated, extended release500 mgoralVictory Pharma, Inc.1996-01-05Not AvailableUs
NaprelankitoralVictory Pharma, Inc.2009-10-15Not AvailableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Naproxentablet250 mgoralTeva Pharmaceuticals USA Inc1993-12-22Not AvailableUs
Naproxentablet375 mgoralTeva Pharmaceuticals USA Inc1993-12-22Not AvailableUs
Naproxentablet500 mgoralTeva Pharmaceuticals USA Inc1993-12-22Not AvailableUs
Naproxen Sodiumtablet, film coated275 mgoralTeva Pharmaceuticals USA Inc1993-12-22Not AvailableUs
Naproxen Sodiumtablet, film coated550 mgoralTeva Pharmaceuticals USA Inc1993-12-22Not AvailableUs
Naproxentablet, delayed release375 mgoralTeva Pharmaceuticals USA Inc1998-07-31Not AvailableUs
Naproxentablet, delayed release500 mgoralTeva Pharmaceuticals USA Inc1998-07-29Not AvailableUs
Naproxentablet250 mgoralWest ward Pharmaceutical Corp2004-01-14Not AvailableUs
Naproxentablet375 mgoralWest ward Pharmaceutical Corp2004-01-14Not AvailableUs
Naproxentablet500 mgoralWest ward Pharmaceutical Corp2004-01-14Not AvailableUs
Naproxentablet, film coated550 mgoralWest ward Pharmaceutical Corp1996-05-14Not AvailableUs
Naproxentablet, film coated275 mgoralWest ward Pharmaceutical Corp1998-02-18Not AvailableUs
Naproxentablet500 mgoralKAISER FOUNDATION HOSPITALS2008-10-20Not AvailableUs
Naproxentablet500 mgoralLiberty Pharmaceuticals, Inc.2010-02-18Not AvailableUs
Naproxentablet500 mgoralLiberty Pharmaceuticals, Inc.2010-02-18Not AvailableUs
Naproxentablet375 mgoralNcs Health Care Of Ky, Inc Dba Vangard Labs2011-07-18Not AvailableUs
Naproxentablet250 mgoralNcs Health Care Of Ky, Inc Dba Vangard Labs2011-07-18Not AvailableUs
Naproxentablet500 mgoralNcs Health Care Of Ky, Inc Dba Vangard Labs2010-12-13Not AvailableUs
Naproxentablet500 mgoralNcs Health Care Of Ky, Inc Dba Vangard Labs2011-07-18Not AvailableUs
Naproxentablet, delayed release375 mgoralSandoz Inc1998-02-18Not AvailableUs
Naproxentablet, delayed release500 mgoralSandoz Inc1998-02-18Not AvailableUs
Naproxentablet250 mgoralMajor Pharmaceuticals2008-11-08Not AvailableUs
Naproxentablet375 mgoralMajor Pharmaceuticals2008-11-08Not AvailableUs
Naproxentablet500 mgoralMajor Pharmaceuticals2009-11-20Not AvailableUs
Naproxentablet375 mgoralMajor Pharmaceuticals2004-04-01Not AvailableUs
Naproxentablet500 mgoralMajor Pharmaceuticals2004-04-01Not AvailableUs
Naproxentablet250 mgoralMajor Pharmaceuticals2009-08-10Not AvailableUs
Naproxen Sodiumtablet275 mgoralMajor Pharmaceuticals2007-04-26Not AvailableUs
Naproxen Sodiumtablet550 mgoralMajor Pharmaceuticals2007-04-26Not AvailableUs
Naproxentablet250 mgoralMajor Pharmaceuticals2011-02-28Not AvailableUs
Naproxentablet375 mgoralMajor Pharmaceuticals2011-02-28Not AvailableUs
Naproxentablet500 mgoralMajor Pharmaceuticals2011-02-28Not AvailableUs
Naproxentablet500 mgoralBlenheim Pharmacal, Inc.2010-08-19Not AvailableUs
Naproxentablet500 mgoralBlenheim Pharmacal, Inc.2010-09-15Not AvailableUs
Naproxentablet375 mgoralBlenheim Pharmacal, Inc.2010-09-24Not AvailableUs
Naproxentablet500 mgoralBlenheim Pharmacal, Inc.2011-05-04Not AvailableUs
Naproxentablet500 mgoralBlenheim Pharmacal, Inc.2013-03-28Not AvailableUs
Naproxen Sodiumtablet275 mgoralBlenheim Pharmacal, Inc.2010-03-22Not AvailableUs
Naproxen Sodiumtablet550 mgoralBlenheim Pharmacal, Inc.2010-03-17Not AvailableUs
Naproxentablet375 mgoralBlenheim Pharmacal, Inc.2009-12-14Not AvailableUs
Naproxentablet500 mgoralBlenheim Pharmacal, Inc.2010-03-17Not AvailableUs
Naproxentablet375 mgoralSTAT Rx USA LLC2010-02-18Not AvailableUs
Naproxentablet500 mgoralSTAT Rx USA LLC2011-07-18Not AvailableUs
Naproxentablet, delayed release500 mgoralSTAT Rx USA LLC2010-09-23Not AvailableUs
Naproxen Sodiumtablet550 mgoralSTAT Rx USA LLC1998-02-18Not AvailableUs
Naproxen Sodiumtablet550 mgoralAtlantic Biologicals Corps2007-04-26Not AvailableUs
Naproxentablet250 mgoralRebel Distributors Corp.2010-02-18Not AvailableUs
Naproxentablet375 mgoralRebel Distributors Corp.2010-02-18Not AvailableUs
Naproxentablet500 mgoralRebel Distributors Corp.2010-02-18Not AvailableUs
Naproxen Sodiumtablet550 mgoralRebel Distributors Corp2007-04-26Not AvailableUs
Naproxentablet, delayed release500 mgoralRebel Distributors Corp2010-06-02Not AvailableUs
Naproxentablet500 mgoralREMEDYREPACK INC.2013-03-01Not AvailableUs
Naproxentablet375 mgoralREMEDYREPACK INC.2013-01-10Not AvailableUs
Naproxentablet500 mgoralREMEDYREPACK INC.2012-01-12Not AvailableUs
Naproxentablet500 mgoralREMEDYREPACK INC.2013-07-15Not AvailableUs
Naproxentablet500 mgoralREMEDYREPACK INC.2013-07-12Not AvailableUs
Naproxentablet500 mgoralREMEDYREPACK INC.2013-07-15Not AvailableUs
Naproxentablet500 mgoralREMEDYREPACK INC.2013-10-11Not AvailableUs
Naproxentablet500 mgoralREMEDYREPACK INC.2013-07-25Not AvailableUs
Naproxentablet250 mgoralMARKSANS PHARMA LIMITED2011-02-28Not AvailableUs
Naproxentablet375 mgoralMARKSANS PHARMA LIMITED2011-02-28Not AvailableUs
Naproxentablet500 mgoralMARKSANS PHARMA LIMITED2011-02-28Not AvailableUs
Naproxen delayed releasetablet375 mgoralCamber Pharmaceuticals2012-01-23Not AvailableUs
Naproxen delayed releasetablet500 mgoralCamber Pharmaceuticals2012-01-23Not AvailableUs
Naproxentablet250 mgoralCamber Pharmaceuticals2012-01-23Not AvailableUs
Naproxentablet375 mgoralCamber Pharmaceuticals2012-01-23Not AvailableUs
Naproxentablet500 mgoralCamber Pharmaceuticals2012-01-23Not AvailableUs
Naproxentablet375 mgoralAidarex Pharmaceuticals LLC2010-02-18Not AvailableUs
Naproxentablet500 mgoralAidarex Pharmaceuticals LLC2010-02-18Not AvailableUs
Naproxentablet, delayed release375 mgoralAidarex Pharmaceuticals LLC1998-07-31Not AvailableUs
Naproxentablet, delayed release500 mgoralAidarex Pharmaceuticals LLC1998-07-29Not AvailableUs
Naproxen Sodiumtablet275 mgoralAidarex Pharmaceuticals LLC2007-04-26Not AvailableUs
Naproxen Sodiumtablet550 mgoralAidarex Pharmaceuticals LLC2007-04-26Not AvailableUs
Naproxentablet250 mgoralAidarex Pharmaceuticals LLC2010-02-18Not AvailableUs
Naproxen Sodiumtablet550 mgoralRx Change Co.2014-11-11Not AvailableUs
Naproxentablet500 mgoralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2010-02-18Not AvailableUs
Naproxentablet500 mgoralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2007-07-01Not AvailableUs
Naproxen Sodiumtablet, film coated550 mgoralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2010-11-01Not AvailableUs
Naproxentablet250 mgoralRebel Distributors Corp2007-07-01Not AvailableUs
Naproxentablet375 mgoralRebel Distributors Corp2007-07-01Not AvailableUs
Naproxen Sodiumtablet275 mgoralAv Kare, Inc.2007-04-26Not AvailableUs
Naproxen Sodiumtablet550 mgoralAv Kare, Inc.2007-04-26Not AvailableUs
Naproxentablet500 mgoralAv Kare, Inc.2013-09-26Not AvailableUs
Naproxen delayed releasetablet375 mgoralAv Kare, Inc.2013-10-24Not AvailableUs
Naproxen delayed releasetablet500 mgoralAv Kare, Inc.2013-10-24Not AvailableUs
Naproxentablet375 mgoralSTAT Rx USA LLC2004-01-14Not AvailableUs
Naproxen Sodiumtablet550 mgoralSTAT Rx USA LLC2007-08-01Not AvailableUs
Naproxentablet500 mgoralSTAT Rx USA LLC2007-07-01Not AvailableUs
Naproxentablet250 mgoralPd Rx Pharmaceuticals, Inc.2004-01-14Not AvailableUs
Naproxentablet375 mgoralPd Rx Pharmaceuticals, Inc.2010-04-22Not AvailableUs
Naproxentablet500 mgoralPd Rx Pharmaceuticals, Inc.2010-02-18Not AvailableUs
Naproxentablet250 mgoralPd Rx Pharmaceuticals, Inc.2010-02-18Not AvailableUs
Naproxen Sodiumtablet, film coated275 mgoralPd Rx Pharmaceuticals, Inc.1993-12-22Not AvailableUs
Naproxentablet250 mgoralAphena Pharma Solutions Tennessee, Llc2009-08-10Not AvailableUs
Naproxentablet500 mgoralAphena Pharma Solutions Tennessee, Llc2004-04-01Not AvailableUs
Naproxentablet500 mgoralPharmaceutica North America, Inc.2013-08-07Not AvailableUs
Naproxen KitkitPharmaceutica North America, Inc2013-08-28Not AvailableUs
Naproxentablet375 mgoralREMEDYREPACK INC.2011-03-08Not AvailableUs
Naproxen Sodiumtablet550 mgoralREMEDYREPACK INC.2011-06-09Not AvailableUs
Naproxentablet500 mgoralREMEDYREPACK INC.2011-06-28Not AvailableUs
Naproxen Sodiumtablet550 mgoralREMEDYREPACK INC.2014-11-12Not AvailableUs
Naproxen Sodiumtablet550 mgoralREMEDYREPACK INC.2011-11-03Not AvailableUs
Naproxentablet250 mgoralREMEDYREPACK INC.2011-05-13Not AvailableUs
Naproxentablet500 mgoralREMEDYREPACK INC.2011-08-30Not AvailableUs
Naproxentablet500 mgoralREMEDYREPACK INC.2013-07-30Not AvailableUs
Naproxentablet500 mgoralREMEDYREPACK INC.2012-09-04Not AvailableUs
Naproxentablet500 mgoralLake Erie Medical DBA Quality Care Products LLC2010-09-28Not AvailableUs
Naproxentablet375 mgoralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2011-11-04Not AvailableUs
Naproxentablet, delayed release500 mgoralLake Erie Medical DBA Quality Care Products LLC2011-02-03Not AvailableUs
Naproxen Sodiumtablet275 mgoralAv Pak2012-10-11Not AvailableUs
Naproxen Sodiumtablet550 mgoralAv Pak2012-10-11Not AvailableUs
Naproxentablet250 mgoralAv Pak2015-02-05Not AvailableUs
Naproxentablet375 mgoralAv Pak2015-02-05Not AvailableUs
Naproxentablet500 mgoralAv Pak2015-02-05Not AvailableUs
Naproxentablet250 mgoralUnit Dose Services2010-02-18Not AvailableUs
Naproxentablet375 mgoralUnit Dose Services2007-07-01Not AvailableUs
Naproxentablet500 mgoralUnit Dose Services2010-02-18Not AvailableUs
Naproxen Sodiumtablet550 mgoralUnit Dose Services2007-04-26Not AvailableUs
Naproxen Sodiumtablet220 mgoralNorthwind Pharmaceuticals, LLC2014-07-14Not AvailableUs
Naproxentablet500 mgoralNorthwind Pharmaceuticals2014-05-28Not AvailableUs
Naproxen Sodiumtablet550 mgoralNorthwind Pharmaceuticals, LLC2014-08-07Not AvailableUs
Naproxen Sodiumtablet250 mgoralNorthwind Pharmaceuticals, LLC2014-08-26Not AvailableUs
Naproxentablet375 mgoralREMEDYREPACK INC.2013-07-25Not AvailableUs
Naproxentablet375 mgoralREMEDYREPACK INC.2012-12-28Not AvailableUs
Naproxentablet500 mgoralREMEDYREPACK INC.2013-06-04Not AvailableUs
Naproxentablet375 mgoralREMEDYREPACK INC.2013-05-15Not AvailableUs
Naproxentablet375 mgoralREMEDYREPACK INC.2013-05-15Not AvailableUs
Naproxentablet375 mgoralREMEDYREPACK INC.2013-05-15Not AvailableUs
Naproxentablet375 mgoralREMEDYREPACK INC.2013-05-15Not AvailableUs
Naproxentablet500 mgoralREMEDYREPACK INC.2013-12-05Not AvailableUs
Naproxentablet500 mgoralREMEDYREPACK INC.2013-07-08Not AvailableUs
Naproxentablet500 mgoralREMEDYREPACK INC.2013-07-01Not AvailableUs
Naproxentablet500 mgoralREMEDYREPACK INC.2013-07-08Not AvailableUs
Naproxentablet500 mgoralREMEDYREPACK INC.2014-02-20Not AvailableUs
Naproxentablet500 mgoralREMEDYREPACK INC.2013-06-24Not AvailableUs
Naproxentablet500 mgoralREMEDYREPACK INC.2013-07-08Not AvailableUs
Naproxentablet500 mgoralREMEDYREPACK INC.2014-04-16Not AvailableUs
Naproxen Sodiumtablet550 mgoralREMEDYREPACK INC.2013-08-23Not AvailableUs
Naproxen Sodiumtablet550 mgoralREMEDYREPACK INC.2014-07-10Not AvailableUs
Naproxentablet375 mgoralREMEDYREPACK INC.2013-07-09Not AvailableUs
Naproxentablet250 mgoralREMEDYREPACK INC.2013-08-27Not AvailableUs
Naproxentablet500 mgoralREMEDYREPACK INC.2013-12-05Not AvailableUs
Naproxentablet375 mgoralREMEDYREPACK INC.2014-03-03Not AvailableUs
Naproxentablet375 mgoralREMEDYREPACK INC.2014-05-01Not AvailableUs
Naproxentablet250 mgoralPolygen Pharmaceuticals LLC2012-02-01Not AvailableUs
Naproxentablet375 mgoralPolygen Pharmaceuticals LLC2012-02-01Not AvailableUs
Naproxentablet500 mgoralPolygen Pharmaceuticals LLC2012-02-01Not AvailableUs
Naproxentablet375 mgoralH.J. Harkins Company, Inc.2007-07-01Not AvailableUs
Naproxen Sodiumtablet550 mgoralH.J. Harkins Company, Inc.2007-07-01Not AvailableUs
Naproxentablet, delayed release500 mgoralH.J. Harkins Company, Inc.2010-09-23Not AvailableUs
Naproxentablet250 mgoralAmneal Pharmaceuticals of New York, LLC2010-02-18Not AvailableUs
Naproxentablet375 mgoralAmneal Pharmaceuticals of New York, LLC2010-02-18Not AvailableUs
Naproxentablet500 mgoralAmneal Pharmaceuticals of New York, LLC2010-02-18Not AvailableUs
Naproxen Sodiumtablet275 mgoralAmneal Pharmaceuticals2007-04-26Not AvailableUs
Naproxen Sodiumtablet550 mgoralAmneal Pharmaceuticals2007-04-26Not AvailableUs
Naproxentablet375 mgoralState of Florida DOH Central Pharmacy2009-07-01Not AvailableUs
Naproxentablet250 mgoralState of Florida DOH Central Pharmacy2009-07-01Not AvailableUs
Naproxentablet375 mgoralState of Florida DOH Central Pharmacy2009-07-01Not AvailableUs
Naproxentablet500 mgoralState of Florida DOH Central Pharmacy2009-07-01Not AvailableUs
Naproxen Sodiumtablet, film coated550 mgoralState of Florida DOH Central Pharmacy2009-07-01Not AvailableUs
Naproxen Sodiumtablet550 mgoralState of Florida DOH Central Pharmacy2013-01-01Not AvailableUs
Naproxentablet500 mgoralState of Florida DOH Central Pharmacy2014-01-01Not AvailableUs
Naproxen Sodiumtablet550 mgoralPhysicians Total Care, Inc.1994-01-14Not AvailableUs
Naproxentablet, delayed release500 mgoralPhysicians Total Care, Inc.2002-01-11Not AvailableUs
Naproxentablet500 mgoralCardinal Health2009-11-20Not AvailableUs
Naproxentablet250 mgoralCardinal Health2010-02-18Not AvailableUs
Naproxentablet250 mgoralCardinal Health2009-08-10Not AvailableUs
Naproxentablet500 mgoralCardinal Health2013-09-30Not AvailableUs
Naproxentablet500 mgoralCardinal Health2010-12-13Not AvailableUs
Naproxentablet375 mgoralPd Rx Pharmaceuticals, Inc.2010-02-18Not AvailableUs
Naproxentablet500 mgoralPd Rx Pharmaceuticals, Inc.2010-02-18Not AvailableUs
Naproxentablet, delayed release500 mgoralPd Rx Pharmaceuticals, Inc.2010-09-23Not AvailableUs
Naproxen Sodiumtablet550 mgoralPd Rx Pharmaceuticals, Inc.2007-04-26Not AvailableUs
Naproxentablet250 mgoralPd Rx Pharmaceuticals, Inc.2004-01-14Not AvailableUs
Naproxen Sodiumtablet275 mgoralPd Rx Pharmaceuticals, Inc.2007-08-01Not AvailableUs
Naproxentablet375 mgoralClinical Solutions Wholesale2010-02-18Not AvailableUs
Naproxentablet500 mgoralClinical Solutions Wholesale2010-02-18Not AvailableUs
Naproxentablet550 mgoralClinical Solutions Wholesale2010-02-18Not AvailableUs
Naproxen Sodiumtablet, film coated550 mgoralNew Horizon Rx Group, LLC2013-08-25Not AvailableUs
Naproxen Sodiumtablet275 mgoralHikma Pharmaceutical1998-02-18Not AvailableUs
Naproxentablet500 mgoralGolden State Medical Supply, Inc.2010-02-18Not AvailableUs
Naproxentablet375 mgoralREMEDYREPACK INC.2014-11-26Not AvailableUs
Naproxentablet250 mgoralREMEDYREPACK INC.2014-12-01Not AvailableUs
Naproxentablet500 mgoralDIRECT RX2014-01-01Not AvailableUs
Naproxen Sodiumcapsule550 mgoralDIRECT RX2014-01-01Not AvailableUs
Naproxentablet500 mgoralProficient Rx LP2007-07-01Not AvailableUs
Naproxen Sodiumtablet550 mgoralProficient Rx LP2007-04-26Not AvailableUs
Naproxen Sodiumtablet550 mgoralbryant ranch prepack2007-04-26Not AvailableUs
Naproxen Sodiumtablet550 mgoralbryant ranch prepack2009-07-30Not AvailableUs
Naproxentablet375 mgoralbryant ranch prepack2004-01-14Not AvailableUs
Naproxentablet500 mgoralbryant ranch prepack2010-02-18Not AvailableUs
Naprosyntablet250 mgoralbryant ranch prepack2009-09-01Not AvailableUs
Naproxen Sodiumtablet275 mgoralbryant ranch prepack2007-08-01Not AvailableUs
Naproxentablet, delayed release500 mgoralbryant ranch prepack2010-06-02Not AvailableUs
Naproxentablet250 mgoralAltura Pharmaceuticals, Inc.2010-01-01Not AvailableUs
Naproxentablet375 mgoralAltura Pharmaceuticals, Inc.2010-01-01Not AvailableUs
Naproxentablet500 mgoralAltura Pharmaceuticals, Inc.2010-01-01Not AvailableUs
Naproxen Sodiumtablet550 mgoralAltura Pharmaceuticals, Inc.2010-01-01Not AvailableUs
Naproxen Sodiumtablet275 mgoralAltura Pharmaceuticals, Inc.2010-01-01Not AvailableUs
Naproxentablet250 mgoralAmneal Pharmaceuticals of New York, LLC2010-02-18Not AvailableUs
Naproxentablet375 mgoralAmneal Pharmaceuticals of New York, LLC2010-02-18Not AvailableUs
Naproxentablet500 mgoralAmneal Pharmaceuticals of New York, LLC2010-02-18Not AvailableUs
Naproxen Sodiumtablet275 mgoralAmneal Pharmaceuticals of New York, LLC2007-04-26Not AvailableUs
Naproxen Sodiumtablet550 mgoralAmneal Pharmaceuticals of New York, LLC2007-04-26Not AvailableUs
Naproxen Sodiumtablet, film coated275 mgoralAurobindo Pharma Limited2011-10-31Not AvailableUs
Naproxen Sodiumtablet, film coated550 mgoralAurobindo Pharma Limited2011-10-31Not AvailableUs
Naproxentablet250 mgoralAurobindo Pharma Limited2011-11-08Not AvailableUs
Naproxentablet375 mgoralAurobindo Pharma Limited2011-11-08Not AvailableUs
Naproxentablet500 mgoralAurobindo Pharma Limited2011-11-08Not AvailableUs
Naproxentablet500 mgoralDispensing Solutions, Inc.2012-02-01Not AvailableUs
Naproxentablet375 mgoralDispensing Solutions, Inc.2010-02-18Not AvailableUs
Naproxentablet250 mgoralContract Pharmacy Services Pa2010-03-19Not AvailableUs
Naproxentablet375 mgoralContract Pharmacy Services Pa2010-03-19Not AvailableUs
Naproxentablet500 mgoralContract Pharmacy Services Pa2010-03-19Not AvailableUs
Naproxentablet375 mgoralAphena Pharma Solutions Tennessee, Llc2010-02-18Not AvailableUs
Naproxentablet500 mgoralAphena Pharma Solutions Tennessee, Llc2010-02-18Not AvailableUs
Naproxentablet250 mgoralAphena Pharma Solutions Tennessee, Llc2010-02-18Not AvailableUs
Naproxentablet500 mgoralAmerican Health Packaging2013-09-30Not AvailableUs
Naproxensuspension125 mg/5mLoralPalmetto Pharmaceuticals2013-06-25Not AvailableUs
Naproxentablet, delayed release500 mgoralCarilion Materials Management1998-07-29Not AvailableUs
Naproxentablet250 mgoralCarilion Materials Management2010-02-18Not AvailableUs
Naproxentablet375 mgoralCarilion Materials Management2007-07-01Not AvailableUs
Naproxen Sodiumtablet550 mgoralKeltman Pharmaceuticals Inc.2010-12-10Not AvailableUs
Naproxentablet500 mgoralKeltman Pharmaceuticals Inc.2009-04-27Not AvailableUs
Naproxentablet250 mgoralKeltman Pharmaceuticals Inc.2009-04-27Not AvailableUs
Naproxentablet375 mgoralKeltman Pharmaceuticals Inc.2010-10-04Not AvailableUs
Naproxen Sodiumtablet275 mgoralGlenmark Generics Inc., USA2007-08-01Not AvailableUs
Naproxen Sodiumtablet550 mgoralGlenmark Generics Inc., USA2007-08-01Not AvailableUs
Naproxentablet250 mgoralGlenmark Generics Inc., USA2007-07-01Not AvailableUs
Naproxentablet375 mgoralGlenmark Generics Inc., USA2007-07-01Not AvailableUs
Naproxentablet500 mgoralGlenmark Generics Inc., USA2007-07-01Not AvailableUs
Naproxen Sodiumtablet550 mgoralPreferred Pharmaceuticals, Inc2007-04-26Not AvailableUs
Naproxentablet500 mgoralPreferred Pharmaceuticals, Inc2007-07-01Not AvailableUs
Naproxentablet375 mgoralPreferred Pharmaceuticals, Inc2012-01-30Not AvailableUs
Naproxentablet500 mgoralPreferred Pharmaceuticals, Inc2012-01-30Not AvailableUs
Naproxentablet500 mgoralLife Line Home Care Services, Inc.2010-02-18Not AvailableUs
Naproxentablet500 mgoralMc Kesson Contract Packaging2012-01-25Not AvailableUs
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Alevetablet220 mgoralBayer Health Care Consumer Care2002-07-26Not AvailableUs
Alevecapsule, liquid filled220 mgoralBayer Health Care Llc, Consumer Care2007-02-20Not AvailableUs
Naproxen Sodiumcapsule, liquid filled220 mgoralWalgreen Company2014-08-04Not AvailableUs
Naproxen Sodiumcapsule, liquid filled220 mgoralWalgreens2014-10-31Not AvailableUs
Naproxen Sodiumcapsule, liquid filled220 mgoralWalgreen Company2010-11-30Not AvailableUs
Naproxen Sodiumcapsule, liquid filled220 mgoralTarget Corporation2014-12-30Not AvailableUs
Naproxen Sodiumcapsule, liquid filled220 mgoralRite Aid Corporation2010-12-15Not AvailableUs
Naproxen Sodiumcapsule, liquid filled220 mgoralSafeway2010-12-13Not AvailableUs
Naproxen Sodiumcapsule, liquid filled220 mgoralKroger Company2014-03-15Not AvailableUs
Naproxen Sodiumcapsule, liquid filled220 mgoralThe Kroger Co.2014-10-31Not AvailableUs
Naproxen Sodiumcapsule, liquid filled220 mgoralKroger Company2010-11-23Not AvailableUs
Naproxen Sodiumcapsule, liquid filled220 mgoralTOP CARE (Topco Associates LLC)2014-09-30Not AvailableUs
Naproxen Sodiumcapsule, liquid filled220 mgoralShopko Stores Operating Co., LLC.2014-12-31Not AvailableUs
Naproxen Sodiumcapsule, liquid filled220 mgoralShopko Stores Operating Co., LLC2013-07-30Not AvailableUs
Naproxen Sodiumcapsule, liquid filled220 mgoralH E B2011-01-04Not AvailableUs
Naproxen Sodiumcapsule, liquid filled220 mgoralEqualine (Super Valu)2014-09-30Not AvailableUs
Naproxen Sodiumcapsule, liquid filled220 mgoralMEIJER, INC.2014-09-30Not AvailableUs
Naproxen Sodiumcapsule, liquid filled220 mgoralMeijer Distribution Inc2011-01-14Not AvailableUs
Naproxen Sodiumcapsule, liquid filled220 mgoralCare One (American Sales Company)2014-10-31Not AvailableUs
Naproxen Sodiumcapsule, liquid filled220 mgoralHy Vee2014-09-30Not AvailableUs
Naproxen Sodiumcapsule, liquid filled220 mgoralHy Vee Inc2010-11-29Not AvailableUs
Naproxen Sodiumcapsule, liquid filled220 mgoralAmerisource Bergen (Good Neighbor Pharmacy) 461222014-11-30Not AvailableUs
Naproxen Sodiumcapsule, liquid filled220 mgoralEQUATE (Walmart Stores, Inc.)2014-09-30Not AvailableUs
Naproxen Sodiumcapsule, liquid filled220 mgoralSMART SENSE (Kmart)2014-12-31Not AvailableUs
Naproxentablet220 mgoralMedline Industries, Inc.2002-07-26Not AvailableUs
Alevetablet220 mgoralCardinal Health1994-01-11Not AvailableUs
Naproxen Sodiumcapsule, liquid filled220 mgoralWestern Family Foods, Inc.2014-12-31Not AvailableUs
Naproxen Sodiumcapsule, liquid filled220 mgoralWestern Family Foods Inc2011-01-18Not AvailableUs
Naproxen Sodiumcapsule, liquid filled220 mgoralHealthy Accents (DZA Brands, LLC)2014-09-30Not AvailableUs
Naproxen Sodiumcapsule, liquid filled220 mgoralDolgencorp, Inc. (DOLLAR GENERAL & REXALL)2014-11-30Not AvailableUs
Naproxen Sodiumcapsule, liquid filled220 mgoralCVS Pharmacy2014-11-30Not AvailableUs
Naproxen Sodiumcapsule, liquid filled220 mgoralCVS Pharmacy2010-11-23Not AvailableUs
Naproxen Sodiumcapsule, liquid filled220 mgoralMc Kesson (Health Mart)2014-10-31Not AvailableUs
Naproxen Sodiumcapsule, liquid filled220 mgoralQUALITY CHOICE (Chain Drug Marketing Association)2014-10-31Not AvailableUs
Alevetablet220 mgoralLil' Drug Store Products, Inc2000-01-01Not AvailableUs
Alevetablet220 mgoralBayer Inc Consumer CareNot AvailableNot AvailableCanada
Naproxen Sodiumtablet220 mgoralRugby Laboratories Inc2009-11-25Not AvailableUs
Naproxen Sodiumtablet220 mgoralRite Aid Corporation2001-05-16Not AvailableUs
Naproxen Sodiumtablet, film coated220 mgoralRite Aid Corporation2001-05-16Not AvailableUs
Naproxen Sodiumtablet220 mgoralMARKSANS PHARMA LIMITED2011-05-28Not AvailableUs
Naproxen Sodiumtablet220 mgoralMARKSANS PHARMA LIMITED2011-05-04Not AvailableUs
Naproxen Sodiumtablet220 mgoralThe Kroger Co.2014-11-09Not AvailableUs
Naproxen Sodiumtablet, film coated220 mgoralKroger Company2005-02-08Not AvailableUs
Naproxen Sodiumtablet220 mgoralKroger Company2014-03-06Not AvailableUs
Naproxen Sodiumtablet, film coated220 mgoralKroger Company1997-01-16Not AvailableUs
Naproxen Sodiumtablet220 mgoralTOP CARE (Topco Associates LLC)2014-06-30Not AvailableUs
Naproxen Sodiumtablet, film coated220 mgoralShopko Stores Operating Co., LLC2014-05-19Not AvailableUs
Naproxen Sodiumtablet, film coated220 mgoralMeijer Distribution Inc2004-05-28Not AvailableUs
Naproxen Sodiumtablet, film coated220 mgoralMeijer Distribution Inc2014-03-05Not AvailableUs
Naproxen Sodiumtablet220 mgoralMeijer Distribution Inc2014-03-05Not AvailableUs
Naproxen Sodiumtablet220 mgoralPerrigo New York Inc2014-04-11Not AvailableUs
Naproxen Sodiumtablet220 mgoralEQUATE (Walmart Stores, Inc.)2014-02-12Not AvailableUs
Naproxen Sodiumtablet220 mgoralEQUATE (Walmart Stores, Inc.)2014-04-30Not AvailableUs
Naproxen Sodiumtablet220 mgoralCardinal Health (Leader) 497812014-07-31Not AvailableUs
Naproxen Sodiumtablet, coated220 mgoralPolygen Pharmaceuticals LLC2012-06-11Not AvailableUs
Naproxen Sodiumtablet, coated220 mgoralPolygen Pharmaceuticals LLC2012-11-13Not AvailableUs
Naproxen Sodiumtablet220 mgoralMedline Industries2013-04-30Not AvailableUs
Naproxen Sodiumtablet220 mgoralPhysicians Total Care, Inc.2005-05-23Not AvailableUs
Naproxen Sodiumtablet, coated220 mgoralDr.Reddy's Laboratories Limited1998-07-29Not AvailableUs
Naproxen Sodiumtablet, coated220 mgoralDr.Reddy's Laboratories Limited1998-07-29Not AvailableUs
Naproxen Sodiumtablet, film coated220 mgoralHealthy Accents (DZA Brands, LLC)2013-12-30Not AvailableUs
Naproxen Sodiumtablet220 mgoralFamily Dollar (FAMILY WELLNESS)2012-08-15Not AvailableUs
Naproxen Sodiumtablet220 mgoralFamily Dollar (FAMILY WELLNESS)2013-11-01Not AvailableUs
Naproxen Sodiumtablet220 mgoralFamily Dollar (FAMILY WELLNESS)2014-04-30Not AvailableUs
Naproxen Sodiumtablet220 mgoralFamily Dollar (FAMILY WELLNESS)2014-04-30Not AvailableUs
Naproxentablet220 mgoralPharmadel LLC2013-03-25Not AvailableUs
Naproxen Sodiumtablet, coated220 mgoralAAA Pharmaceutical, Inc.2012-12-15Not AvailableUs
Naproxen Sodiumtablet, coated220 mgoralAAA Pharmaceutical, Inc.2012-12-15Not AvailableUs
Naproxen Sodiumtablet, film coated, extended release220 mgoralJ.P. BUSINESS ENTERPRISE2013-08-20Not AvailableUs
Naproxen Sodiumtablet220 mgoralKinray2009-11-25Not AvailableUs
Naproxen Sodiumtablet, coated220 mgoralKinray LLC2014-04-25Not AvailableUs
Naproxen Sodiumtablet, coated220 mgoralKinray LLC2014-04-25Not AvailableUs
Naproxen Sodiumtablet220 mgoralGranules India Limited2011-09-30Not AvailableUs
Naproxen Sodiumtablet220 mgoralGranules India Limited2011-09-30Not AvailableUs
Naproxen Sodiumtablet, coated220 mgoralChain Drug Marketing Association2009-09-03Not AvailableUs
Naproxen Sodiumtablet, coated220 mgoralChain Drug Marketing Association2009-06-19Not AvailableUs
Naproxen Sodiumtablet220 mgoralTYA Pharmaceuticals2014-04-11Not AvailableUs
Naproxen Sodiumtablet, coated220 mgoralWin Co Foods, Llc2014-12-15Not AvailableUs
Naproxen Sodiumtablet, coated220 mgoralWin Co Foods, Llc2014-12-15Not AvailableUs
Naproxencapsule220 mgoralChain Drug Consortium2014-10-27Not AvailableUs
Naproxentablet220 mgoralChain Drug Consortium2014-10-27Not AvailableUs
Naproxen Sodiumtablet, film coated, extended release220 mgoralSPIRIT PHARMACEUTICALS,LLC2011-08-01Not AvailableUs
Naproxen Sodiumtablet, film coated220 mgoralPreferred Pharmaceuticals, Inc2012-03-12Not AvailableUs
Naproxen Sodiumtablet, film coated220 mgoralMaximino Import2008-08-20Not AvailableUs
Naproxentablet220 mgoralPharmascience IncNot AvailableNot AvailableCanada
Naproxentablet220 mgoralPerrigo InternationalNot AvailableNot AvailableCanada
International Brands
NameCompany
AlidaseLaboratorios
AlpoxenActavis
AlpronAldril
ApainMarvic
ApranaxRoche
ApronaxBayer
BonylOrion
BruproxenBruluart
Bumaflex NNycomed
CongexBuxton
DebrilMonserrat
DeproxenDrug International
DysmenalgitKrewel Meuselbach
EmoxEmo-Farm
EmoxenEMO
EurogesicSaval
FabralginaFabra
Feminax UltraBayer
FlogotoneInterpharma
GerinapGerard
HonlowPanion & BF
ImprostanFarmacoop
InflamaxFarmaceutica
InzaAlphapharm
IraxenQuilab
JinkangpuliConba
LexinaxBrisafarma
MelgarHexa
MesselxenBiomep
MobilatSTADA
NaprometinRoche
Naprosyn CRAbdi Ibrahim
Naprosyn ECRoche
Naprosyn EnteroRoche
Naprosyn SRRoche
NaprosyneRoche
NaprovalLabinco
NapruxAndromaco
NeuralpronaLba
NoflamMylan
NopainMedicef
PrexanNew Research
PriaxenRemedica
PrincepsLaser
PronaxenOrion
ProxenGrünenthal
Proxen SRoche
Proxen SRRoche
ReleveGeneral Pharma
ReproDoctor's Chemical Works
ReuxenHelcor
RiproxenBioGenet
SanaproxPerumed
SeladinYSP
ServinaproxNovartis
TarproxenPolfa Tarchomin
TicoflexIncepta
TundraFrasca
XenarElder
Xenar-CRElder
Brand mixtures
Brand NameIngredients
ArthopanNaproxen and Pantoprazole
BrunadolNaproxen and Paracetamol
Lumbal LafrancolNaproxen and Caffeine
MomendolNaproxen and Sulodexide
NeuralgesicNaproxen and Paracetamol
Proxalin-PlusNaproxen and Paracetamol
SumigranNaproxen and Sumatriptan
VimovoNaproxen and Esomeprazole
Salts
Name/CASStructureProperties
Naproxen sodium
ThumbNot applicableDBSALT000949
CategoriesNot Available
CAS number22204-53-1
WeightAverage: 230.2592
Monoisotopic: 230.094294314
Chemical FormulaC14H14O3
InChI KeyCMWTZPSULFXXJA-VIFPVBQESA-N
InChI
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
IUPAC Name
(2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid
SMILES
COC1=CC2=C(C=C1)C=C(C=C2)[C@H](C)C(O)=O
Mass Specshow(7.95 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassPhenylpropanoids and Polyketides
ClassPhenylpropanoic Acids
SubclassNot Available
Direct parentPhenylpropanoic Acids
Alternative parentsNaphthalenes; Anisoles; Alkyl Aryl Ethers; Enolates; Carboxylic Acids; Polyamines
Substituentsanisole; phenol ether; alkyl aryl ether; benzene; ether; carboxylic acid; carboxylic acid derivative; polyamine; enolate
Classification descriptionThis compound belongs to the phenylpropanoic acids. These are compounds whose structure contain a benzene ring conjugated to a propanoic acid.
Pharmacology
IndicationFor the treatment of rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, tendinitis, bursitis, and acute gout. Also for the relief of mild to moderate pain and the treatment of primary dysmenorrhea.
PharmacodynamicsNaproxen is a member of the arylacetic acid group of nonsteroidal anti-inflammatory drugs (NSAIDs). Naproxen has analgesic and antipyretic properties. As with other NSAIDs, its mode of action is not fully understood; however, its ability to inhibit prostaglandin synthesis may be involved in the anti-inflammatory effect.
Mechanism of actionThe mechanism of action of naproxen, like that of other NSAIDs, is believed to be associated with the inhibition of cyclooxygenase activity. Two unique cyclooxygenases have been described in mammals. The constitutive cyclooxygenase, COX-1, synthesizes prostaglandins necessary for normal gastrointestinal and renal function. The inducible cyclooxygenase, COX-2, generates prostaglandins involved in inflammation. Inhibition of COX-1 is thought to be associated with gastrointestinal and renal toxicity while inhibition of COX-2 provides anti-inflammatory activity.
AbsorptionNaproxen itself is rapidly and completely absorbed from the GI tract with an in vivo bioavailability of 95%. Although naproxen itself is well absorbed, the sodium salt form is more rapidly absorbed resulting in higher peak plasma levels for a given dose. Food causes a slight decrease in the rate absorption.
Volume of distributionNot Available
Protein bindingAt therapeutic levels naproxen is greater than 99% albumin-bound.
Metabolism

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

SubstrateEnzymesProduct
Naproxen
O-DesmethylnaproxenDetails
Naproxen
Naproxen O-glucuronideDetails
O-Desmethylnaproxen
O-Desmethylnaproxen sulfateDetails
O-Desmethylnaproxen
O-Desmethylnaproxen acyl glucuronideDetails
O-Desmethylnaproxen
O-Desmethylnaproxen O-glucuronideDetails
Route of eliminationNot Available
Half lifeThe observed terminal elimination half-life is approximately 15 hours.
ClearanceNot Available
ToxicityORAL (LD50): Acute: 248 mg/kg [Rat]. 360 mg/kg [Mouse]. Symptoms of overdose include drowsiness, heartburn, indigestion, nausea, and vomiting.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9948
Blood Brain Barrier + 0.6881
Caco-2 permeable + 0.9091
P-glycoprotein substrate Non-substrate 0.586
P-glycoprotein inhibitor I Non-inhibitor 0.8747
P-glycoprotein inhibitor II Non-inhibitor 0.8396
Renal organic cation transporter Non-inhibitor 0.8615
CYP450 2C9 substrate Non-substrate 0.7548
CYP450 2D6 substrate Non-substrate 0.9116
CYP450 3A4 substrate Non-substrate 0.5715
CYP450 1A2 substrate Inhibitor 0.9107
CYP450 2C9 substrate Non-inhibitor 0.907
CYP450 2D6 substrate Non-inhibitor 0.9521
CYP450 2C19 substrate Non-inhibitor 0.9447
CYP450 3A4 substrate Non-inhibitor 0.8905
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8598
Ames test AMES toxic 0.5184
Carcinogenicity Non-carcinogens 0.8685
Biodegradation Not ready biodegradable 0.7809
Rat acute toxicity 2.4579 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9588
hERG inhibition (predictor II) Non-inhibitor 0.9144
Pharmacoeconomics
Manufacturers
  • Roche palo alto llc
  • Roxane laboratories inc
  • Actavis elizabeth llc
  • Alphapharm party ltd
  • Pliva inc
  • Sandoz inc
  • Teva pharmaceuticals usa inc
  • Amneal pharmaceuticals ny llc
  • Baxter healthcare corp anesthesia and critical care
  • Dava pharmaceuticals inc
  • Glenmark generics ltd
  • Hamilton pharmaceuticals ltd
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Mylan pharmaceuticals inc
  • Perrigo r and d co
  • Purepac pharmaceutical co
  • Teva pharmaceuticals usa
  • Watson laboratories inc
  • Westward pharmaceutical corp
  • Zydus pharmaceuticals usa inc
  • Banner pharmacaps inc
  • Stat trade inc
  • Watson laboratories inc florida
  • Bayer healthcare llc
  • Able laboratories inc
  • Contract pharmacal corp
  • Dr reddys laboratories inc
  • Dr reddys laboratories ltd
  • Hikma pharmaceuticals
  • L perrigo co
Packagers
Dosage forms
FormRouteStrength
Capsuleoral220 mg
Capsuleoral550 mg
Capsule, liquid filledoral220 mg
Kit
Kitoral
Suspensionoral125 mg/5mL
Tabletoral220 mg
Tabletoral250 mg
Tabletoral275 mg
Tabletoral375 mg
Tabletoral500 mg
Tabletoral550 mg
Tablet, coatedoral220 mg
Tablet, delayed releaseoral375 mg
Tablet, delayed releaseoral500 mg
Tablet, film coatedoral220 mg
Tablet, film coatedoral275 mg
Tablet, film coatedoral550 mg
Tablet, film coated, extended releaseoral220 mg
Tablet, film coated, extended releaseoral375 mg
Tablet, film coated, extended releaseoral500 mg
Tablet, film coated, extended releaseoral750 mg
Prices
Unit descriptionCostUnit
Naproxen 125 mg/5ml Suspension 500ml Bottle51.5USDbottle
Naprelan 750 mg 24 Hour tablet8.87USDtablet
Naprelan cr 500 mg tablet8.5USDtablet
Naprelan cr 750 mg tablet8.02USDtablet
Naprelan cr dosecrd 500-750 mg5.98USDeach
Naprelan 375 mg 24 Hour tablet4.34USDtablet
Anaprox ds 550 mg tablet3.66USDtablet
Naprelan 500 mg 24 Hour tablet3.63USDtablet
Naprelan cr 375 mg tablet3.52USDtablet
Naproxen sodium powder2.63USDg
Anaprox 275 mg tablet2.52USDtablet
Naprosyn 500 mg tablet2.42USDtablet
Naproxen powder2.26USDg
Naprosyn 500 mg tablet ec2.19USDtablet
Naprosyn 375 mg tablet1.93USDtablet
Ec-naprosyn 375 mg tablet ec1.79USDtablet
Naprosyn 250 mg tablet1.47USDtablet
Naprosyn Sr 750 mg Sustained-Release Tablet1.43USDtablet
Anaprox Ds 550 mg Tablet1.33USDtablet
Naproxen 500 mg tablet1.32USDtablet
Naproxen sodium 550 mg tablet1.32USDtablet
Naproxen DR 500 mg Enteric Coated Tabs1.3USDtab
Naproxen DR 375 mg Enteric Coated Tabs1.11USDtab
Naprosyn E 500 mg Enteric-Coated Tablet1.09USDtablet
Naproxen 375 mg tablet1.08USDtablet
Apo-Naproxen Sr 750 mg Sustained-Release Tablet1.05USDtablet
Pms-Naproxen 500 mg Suppository0.87USDsuppository
Naproxen sodium 275 mg tablet0.86USDtablet
Naproxen 250 mg tablet0.79USDtablet
Apo-Napro-Na Ds 550 mg Tablet0.7USDtablet
Novo-Naprox Sodium Ds 550 mg Tablet0.7USDtablet
Anaprox 275 mg Tablet0.69USDtablet
Apo-Naproxen Ec 500 mg Enteric-Coated Tablet0.61USDtablet
Mylan-Naproxen Ec 500 mg Enteric-Coated Tablet0.61USDtablet
Novo-Naprox Ec 500 mg Enteric-Coated Tablet0.61USDtablet
Pms-Naproxen Ec 500 mg Enteric-Coated Tablet0.61USDtablet
Naprosyn E 375 mg Enteric-Coated Tablet0.6USDtablet
Naprosyn E 250 mg Enteric-Coated Tablet0.46USDtablet
Apo-Napro-Na 275 mg Tablet0.36USDtablet
Novo-Naprox Sodium 275 mg Tablet0.36USDtablet
Apo-Naproxen Ec 375 mg Enteric-Coated Tablet0.34USDtablet
Mylan-Naproxen Ec 375 mg Enteric-Coated Tablet0.34USDtablet
Novo-Naprox Ec 375 mg Enteric-Coated Tablet0.34USDtablet
Pms-Naproxen Ec 375 mg Enteric-Coated Tablet0.34USDtablet
Apo-Naproxen Ec 250 mg Enteric-Coated Tablet0.26USDtablet
Novo-Naprox Ec 250 mg Enteric-Coated Tablet0.26USDtablet
Apo-Naproxen 500 mg Tablet0.22USDtablet
Novo-Naprox 500 mg Tablet0.22USDtablet
Nu-Naprox 500 mg Tablet0.22USDtablet
Aleve 220 mg gelcap0.19USDcapsule
Naprosyn 125 mg/5ml Suspension0.18USDml
Mediproxen tablet0.17USDtablet
Apo-Naproxen 375 mg Tablet0.15USDtablet
Naproxen sodium 220 mg tablet0.15USDtablet
Novo-Naprox 375 mg Tablet0.15USDtablet
Nu-Naprox 375 mg Tablet0.15USDtablet
CVS Pharmacy all day pain rlf 220 mg tb0.12USDtablet
Wal-proxen 220 mg tablet0.12USDtablet
Apo-Naproxen 250 mg Tablet0.11USDtablet
Novo-Naprox 250 mg Tablet0.11USDtablet
Nu-Naprox 250 mg Tablet0.11USDtablet
All day pain rlf 220 mg caplet0.1USDcaplet
Aleve 220 mg caplet0.09USDcaplet
Aleve 220 mg tablet0.09USDtablet
Wal-proxen 220 mg caplet0.09USDtablet
Apo-Naproxen 125 mg Tablet0.08USDtablet
All day pain relief 220 mg tablet0.07USDtablet
Naprosyn 25 mg/ml Suspension0.07USDml
Naproxen sodium 220 mg caplet0.06USDtablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
CountryPatent NumberApprovedExpires (estimated)
Canada20340962002-03-262011-01-14
United States56373201994-06-102014-06-10
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point153 °CPhysProp
water solubility15.9 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP3.18HANSCH,C ET AL. (1995)
logS-4.16ADME Research, USCD
Caco2 permeability-4.83ADME Research, USCD
pKa4.15SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.0511ALOGPS
logP3.29ALOGPS
logP2.99ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)4.19ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity64.85 m3·mol-1ChemAxon
Polarizability24.81 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
SpectraMS/MSLC-MS1D NMR2D NMR
References
Synthesis Reference

DrugSyn.org

US4009197
General Reference
  1. Kearney PM, Baigent C, Godwin J, Halls H, Emberson JR, Patrono C: Do selective cyclo-oxygenase-2 inhibitors and traditional non-steroidal anti-inflammatory drugs increase the risk of atherothrombosis? Meta-analysis of randomised trials. BMJ. 2006 Jun 3;332(7553):1302-8. Pubmed
  2. Zhang J, Ding EL, Song Y: Adverse effects of cyclooxygenase 2 inhibitors on renal and arrhythmia events: meta-analysis of randomized trials. JAMA. 2006 Oct 4;296(13):1619-32. Epub 2006 Sep 12. Pubmed
External Links
ResourceLink
KEGG DrugD00118
KEGG CompoundC01517
BindingDB50009860
ChEBI7476
ChEMBLCHEMBL154
Therapeutic Targets DatabaseDAP000968
PharmGKBPA450595
RxListhttp://www.rxlist.com/cgi/generic/naproxsod.htm
Drugs.comhttp://www.drugs.com/naproxen.html
PDRhealthhttp://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/ana1021.shtml
WikipediaNaproxen
ATC CodesG02CC02M01AE02M02AA12
AHFS Codes
  • 28:08.04.92
PDB EntriesNot Available
FDA labelshow(240 KB)
MSDSshow(75.4 KB)
Interactions
Drug Interactions
Drug
AcenocoumarolThe NSAID, naproxen, may increase the anticoagulant effect of acenocoumarol.
AlendronateIncreased risk of gastric toxicity
AnisindioneThe NSAID, naproxen, may increase the anticoagulant effect of anisindione.
ApixabanDue to pharmacodynamic interaction, a 50-60% increase in anti-Factor Xa activity may be observed with concomitant therapy.
Azilsartan medoxomilIncreases toxicity of each. May deteriorate renal function, particularly in volume depleted or elderly patients. Decreases effects of azilsartan by antagonism.
ColesevelamBile acid sequestrants may decrease the absorption of Nonsteroidal Anti-Inflammatory Agents. Monitor for decreased serum concentrations/therapeutic effects of nonsteroidal anti-inflammatory agents (NSAID) if coadministered with bile acid sequestrants. Separating the administration of doses by 2 or more hours may reduce (but not eliminate) the risk of interaction. The manufacturer of colesevelam recommends that drugs should be administered at least 1 hour before or 4 hours after colesevelam.
CyclosporineMonitor for nephrotoxicity
DicoumarolThe NSAID, naproxen, may increase the anticoagulant effect of dicumarol.
Ginkgo bilobaAdditive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
LithiumThe NSAID, naproxen, may decrease the renal excretion of lithium. Increased risk of lithium toxicity.
MethotrexateThe NSAID, naproxen, may decrease the renal excretion of methotrexate. Increased risk of methotrexate toxicity.
PralatrexateNSAIDs increase the risk of toxicity due to impairment of renal clearance of pralatrexate thus increasing exposure. Monitor for adverse effects or adjust dose of pralatrexate.
TapentadolIncreases the AUC of tapentadol by 17%. These changes are not considered clinically relevant and no change in dose is required.
TelmisartanConcomitant use of Telmisartan and Naproxen may increase the risk of acute renal failure and hyperkalemia. Monitor renal function at the beginning and during treatment.
TimololThe NSAID, Naproxen, may antagonize the antihypertensive effect of Timolol.
TrandolaprilThe NSAID, Naproxen, may reduce the antihypertensive effect of Trandolapril. Consider alternate therapy or monitor for changes in Trandolapril efficacy if Naproxen is initiated, discontinued or dose changed.
TreprostinilThe prostacyclin analogue, Treprostinil, may increase the risk of bleeding when combined with the NSAID, Naproxen. Monitor for increased bleeding during concomitant thearpy.
TriflusalThe metabolite of triflusal, 2-hydroxy-4-trifluoro-methyl-benzoic acid (HTB), impairs the serum protein binding of naproxen to the same extent as acetylsalisylic acid. Thus, the free fraction of glisentide may be increased. A dosage reduction may be required if used in combination.
VilazodoneIncreased risk of bleeding with concomitant use of NSAIDs with vilazodone.
WarfarinThe antiplatelet effects of naproxen may increase the bleed risk associated with warfarin. Consider alternate therapy or monitor for signs and symptoms of bleeding during concomitant therapy.
Food Interactions
  • Avoid alcohol.
  • Take with a full glass of water.
  • Take with food.

Targets

1. Prostaglandin G/H synthase 2

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Prostaglandin G/H synthase 2 P35354 Details

References:

  1. Albertini R, Aimbire F, Villaverde AB, Silva JA Jr, Costa MS: COX-2 mRNA expression decreases in the subplantar muscle of rat paw subjected to carrageenan-induced inflammation after low level laser therapy. Inflamm Res. 2007 Jun;56(6):228-9. Pubmed
  2. Dhir A, Naidu PS, Kulkarni SK: Neuroprotective effect of nimesulide, a preferential COX-2 inhibitor, against pentylenetetrazol (PTZ)-induced chemical kindling and associated biochemical parameters in mice. Seizure. 2007 Jun 29;. Pubmed
  3. Kumar P, Padi SS, Naidu PS, Kumar A: Cyclooxygenase inhibition attenuates 3-nitropropionic acid-induced neurotoxicity in rats: possible antioxidant mechanisms. Fundam Clin Pharmacol. 2007 Jun;21(3):297-306. Pubmed
  4. White WB: Cardiovascular effects of the selective cyclooxygenase-2 inhibitors. Subcell Biochem. 2007;42:145-58. Pubmed
  5. Hassan-Alin M, Naesdal J, Nilsson-Pieschl C, Langstrom G, Andersson T: Lack of Pharmacokinetic Interaction between Esomeprazole and the Nonsteroidal Anti-Inflammatory Drugs Naproxen and Rofecoxib in Healthy Subjects. Clin Drug Investig. 2005;25(11):731-40. Pubmed
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

2. Prostaglandin G/H synthase 1

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Prostaglandin G/H synthase 1 P23219 Details

References:

  1. James MJ, Cook-Johnson RJ, Cleland LG: Selective COX-2 Inhibitors, Eicosanoid Synthesis and Clinical Outcomes: A Case Study of System Failure. Lipids. 2007 Jun 2;. Pubmed

Enzymes

1. Cytochrome P450 2C9

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2C9 P11712 Details

References:

  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. Pubmed
  2. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  3. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

2. Cytochrome P450 1A2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 1A2 P05177 Details

References:

  1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  2. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. Pubmed
  3. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

3. Cytochrome P450 2C8

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2C8 P10632 Details

References:

  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. Pubmed
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

4. UDP-glucuronosyltransferase 1-1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
UDP-glucuronosyltransferase 1-1 P22309 Details

References:

  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. Pubmed

5. UDP-glucuronosyltransferase 2B7

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
UDP-glucuronosyltransferase 2B7 P16662 Details

References:

  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. Pubmed

Carriers

1. Serum albumin

Kind: protein

Organism: Human

Pharmacological action: no

Components

Name UniProt ID Details
Serum albumin P02768 Details

References:

  1. Banerjee T, Singh SK, Kishore N: Binding of naproxen and amitriptyline to bovine serum albumin: biophysical aspects. J Phys Chem B. 2006 Nov 30;110(47):24147-56. Pubmed

Transporters

1. Solute carrier organic anion transporter family member 1A2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier organic anion transporter family member 1A2 P46721 Details

References:

  1. Shitara Y, Sugiyama D, Kusuhara H, Kato Y, Abe T, Meier PJ, Itoh T, Sugiyama Y: Comparative inhibitory effects of different compounds on rat oatpl (slc21a1)- and Oatp2 (Slc21a5)-mediated transport. Pharm Res. 2002 Feb;19(2):147-53. Pubmed

2. Solute carrier family 22 member 6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 6 Q4U2R8 Details

References:

  1. Mulato AS, Ho ES, Cihlar T: Nonsteroidal anti-inflammatory drugs efficiently reduce the transport and cytotoxicity of adefovir mediated by the human renal organic anion transporter 1. J Pharmacol Exp Ther. 2000 Oct;295(1):10-5. Pubmed
  2. Apiwattanakul N, Sekine T, Chairoungdua A, Kanai Y, Nakajima N, Sophasan S, Endou H: Transport properties of nonsteroidal anti-inflammatory drugs by organic anion transporter 1 expressed in Xenopus laevis oocytes. Mol Pharmacol. 1999 May;55(5):847-54. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on October 08, 2013 14:24