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Identification
NameAlprazolam
Accession NumberDB00404  (APRD00280)
TypeSmall Molecule
GroupsApproved, Illicit, Investigational
Description

A triazolobenzodiazepine compound with antianxiety and sedative-hypnotic actions, that is efficacious in the treatment of panic disorders, with or without agoraphobia, and in generalized anxiety disorders. (From AMA Drug Evaluations Annual, 1994, p238)

Structure
Thumb
Synonyms
SynonymLanguageCode
8-Chloro-1-methyl-6-phenyl-4H-S-triazolo(4,3-a)(1,4)benzodiazepineNot AvailableNot Available
AlprazolamNot AvailableJP16/USP/INN
XanaxNot AvailableNot Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Xanaxtablet.25 mgoralPharmacia and Upjohn Company1981-10-16Not AvailableUs
Xanaxtablet.5 mgoralPharmacia and Upjohn Company1981-10-16Not AvailableUs
Xanax XRtablet, extended release.5 mgoralPharmacia and Upjohn Company2003-01-17Not AvailableUs
Xanax XRtablet, extended release1 mgoralPharmacia and Upjohn Company2003-01-17Not AvailableUs
Xanax XRtablet, extended release2 mgoralPharmacia and Upjohn Company2003-01-17Not AvailableUs
Xanax XRtablet, extended release3 mgoralPharmacia and Upjohn Company2003-01-17Not AvailableUs
Xanaxtablet1 mgoralPharmacia and Upjohn Company1981-10-16Not AvailableUs
Xanaxtablet2 mgoralPharmacia and Upjohn Company1981-10-16Not AvailableUs
Niravamtablet, orally disintegrating.25 mgoralSchwarz Pharma Inc.2005-01-20Not AvailableUs
Niravamtablet, orally disintegrating.5 mgoralSchwarz Pharma Inc.2005-01-20Not AvailableUs
Niravamtablet, orally disintegrating1 mgoralSchwarz Pharma Inc.2005-01-20Not AvailableUs
Niravamtablet, orally disintegrating2 mgoralSchwarz Pharma Inc.2005-01-20Not AvailableUs
Niravamtablet, orally disintegrating.5 mgoralSTAT Rx USA LLC2005-01-20Not AvailableUs
Niravamtablet, orally disintegrating.25 mgoralJazz Pharmaceuticals, Inc.2005-04-01Not AvailableUs
Niravamtablet, orally disintegrating.5 mgoralJazz Pharmaceuticals, Inc.2005-04-01Not AvailableUs
Niravamtablet, orally disintegrating1 mgoralJazz Pharmaceuticals, Inc.2005-04-01Not AvailableUs
Niravamtablet, orally disintegrating2 mgoralJazz Pharmaceuticals, Inc.2005-04-01Not AvailableUs
Alprazolam XRtablet, extended release1 mgoralLake Erie Medical DBA Quality Care Products LLC2003-01-17Not AvailableUs
Alprazolam XRtablet, extended release2 mgoralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2003-01-17Not AvailableUs
Alprazolamtablet1 mgoralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2011-11-30Not AvailableUs
Alprazolam XRtablet, extended release.5 mgoralGreenstone LLC2003-01-17Not AvailableUs
Alprazolam XRtablet, extended release1 mgoralGreenstone LLC2003-01-17Not AvailableUs
Alprazolam XRtablet, extended release2 mgoralGreenstone LLC2003-01-17Not AvailableUs
Alprazolam XRtablet, extended release3 mgoralGreenstone LLC2003-01-17Not AvailableUs
Alprazolamtablet.25 mgoralGreenstone LLC1981-10-16Not AvailableUs
Alprazolamtablet.5 mgoralGreenstone LLC1981-10-16Not AvailableUs
Alprazolamtablet1 mgoralGreenstone LLC1981-10-16Not AvailableUs
Alprazolamtablet2 mgoralGreenstone LLC1981-10-16Not AvailableUs
Alprazolamtablet.25 mgoralbryant ranch prepack1981-10-16Not AvailableUs
Alprazolamtablet2 mgoralbryant ranch prepack1981-10-16Not AvailableUs
Alprazolamtablet.25 mgoralContract Pharmacy Services Pa1981-10-16Not AvailableUs
Alprazolamtablet.5 mgoralContract Pharmacy Services Pa1981-10-16Not AvailableUs
Alprazolamtablet1 mgoralContract Pharmacy Services Pa1981-10-16Not AvailableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Alprazolamsolution, concentrate1 mg/mLoralRoxane Laboratories, Inc1993-10-31Not AvailableUs
Alprazolamtablet, extended release.5 mgoralGlobal Pharmaceuticals, Division of Impax Laboratories Inc.2007-05-24Not AvailableUs
Alprazolamtablet, extended release1 mgoralGlobal Pharmaceuticals, Division of Impax Laboratories Inc.2007-05-24Not AvailableUs
Alprazolamtablet, extended release2 mgoralGlobal Pharmaceuticals, Division of Impax Laboratories Inc.2007-05-24Not AvailableUs
Alprazolamtablet, extended release3 mgoralGlobal Pharmaceuticals, Division of Impax Laboratories Inc.2007-05-24Not AvailableUs
Alprazolamtablet.25 mgoralKAISER FOUNDATION HOSPITALS2011-06-08Not AvailableUs
Alprazolamtablet.5 mgoralKAISER FOUNDATION HOSPITALS2011-06-08Not AvailableUs
Alprazolamtablet.25 mgoralKAISER FOUNDATION HOSPITALS2008-07-14Not AvailableUs
Alprazolamtablet.5 mgoralKAISER FOUNDATION HOSPITALS2008-07-14Not AvailableUs
Alprazolamtablet.25 mgoralActavis Elizabeth LLC1995-01-03Not AvailableUs
Alprazolamtablet.5 mgoralActavis Elizabeth LLC1995-01-03Not AvailableUs
Alprazolamtablet1 mgoralActavis Elizabeth LLC1995-01-03Not AvailableUs
Alprazolamtablet2 mgoralActavis Elizabeth LLC1995-01-03Not AvailableUs
Alprazolam Extended Releasetablet, extended release.5 mgoralActavis Elizabeth LLC2007-02-13Not AvailableUs
Alprazolam Extended Releasetablet, extended release1 mgoralActavis Elizabeth LLC2007-02-13Not AvailableUs
Alprazolam Extended Releasetablet, extended release3 mgoralActavis Elizabeth LLC2007-02-13Not AvailableUs
Alprazolam Extended Releasetablet, extended release2 mgoralActavis Elizabeth LLC2007-02-13Not AvailableUs
Alprazolamtablet, orally disintegrating.25 mgoralActavis Elizabeth LLC2010-03-16Not AvailableUs
Alprazolamtablet, orally disintegrating.5 mgoralActavis Elizabeth LLC2010-03-16Not AvailableUs
Alprazolamtablet, orally disintegrating1 mgoralActavis Elizabeth LLC2010-03-16Not AvailableUs
Alprazolamtablet, orally disintegrating2 mgoralActavis Elizabeth LLC2010-03-16Not AvailableUs
Alprazolamtablet.25 mgoralMylan Pharmaceuticals Inc.2012-07-23Not AvailableUs
Alprazolamtablet.5 mgoralMylan Pharmaceuticals Inc.2010-02-25Not AvailableUs
Alprazolamtablet1 mgoralMylan Pharmaceuticals Inc.1994-01-28Not AvailableUs
Alprazolamtablet2 mgoralMylan Pharmaceuticals Inc.1994-01-28Not AvailableUs
Alprazolamtablet, extended release.5 mgoralMylan Pharmaceuticals Inc.2006-01-26Not AvailableUs
Alprazolamtablet, extended release1 mgoralMylan Pharmaceuticals Inc.2006-01-26Not AvailableUs
Alprazolamtablet.25 mgoralQualitest Pharmaceuticals2008-09-25Not AvailableUs
Alprazolamtablet.5 mgoralQualitest Pharmaceuticals2008-09-25Not AvailableUs
Alprazolamtablet1 mgoralQualitest Pharmaceuticals2008-09-25Not AvailableUs
Alprazolamtablet2 mgoralQualitest Pharmaceuticals2008-09-25Not AvailableUs
Alprazolamtablet.25 mgoralSandoz Inc1995-12-29Not AvailableUs
Alprazolamtablet.5 mgoralSandoz Inc1995-12-29Not AvailableUs
Alprazolamtablet1 mgoralSandoz Inc1995-12-29Not AvailableUs
Alprazolamtablet2 mgoralSandoz Inc1998-03-25Not AvailableUs
Alprazolamtablet.25 mgoralMajor Pharmaceuticals2008-04-02Not AvailableUs
Alprazolamtablet.5 mgoralMajor Pharmaceuticals2008-04-02Not AvailableUs
Alprazolamtablet1 mgoralMajor Pharmaceuticals2008-04-02Not AvailableUs
Alprazolamtablet2 mgoralMajor Pharmaceuticals2008-04-02Not AvailableUs
Alprazolamtablet.25 mgoralBlenheim Pharmacal, Inc.2010-12-10Not AvailableUs
Alprazolamtablet1 mgoralBlenheim Pharmacal, Inc.2010-04-13Not AvailableUs
Alprazolamtablet2 mgoralBlenheim Pharmacal, Inc.2010-04-23Not AvailableUs
Alprazolamtablet.5 mgoralApotheca, Inc2000-01-18Not AvailableUs
Alprazolamtablet1 mgoralApotheca, Inc2012-06-30Not AvailableUs
Alprazolamtablet.5 mgoralSTAT Rx USA LLC2011-03-25Not AvailableUs
Alprazolamtablet1 mgoralSTAT Rx USA LLC2011-03-25Not AvailableUs
Alprazolamtablet.25 mgoralSTAT Rx USA LLC1993-10-31Not AvailableUs
Alprazolam ERtablet, extended release2 mgoralSTAT Rx USA LLC2007-03-28Not AvailableUs
Alprazolamtablet.25 mgoralRebel Distributors Corp.1999-12-29Not AvailableUs
Alprazolamtablet.5 mgoralRebel Distributors Corp.1999-12-29Not AvailableUs
Alprazolamtablet1 mgoralRebel Distributors Corp.1999-12-29Not AvailableUs
Alprazolamtablet2 mgoralRebel Distributors Corp.1998-03-25Not AvailableUs
Alprazolamtablet, extended release.5 mgoralRebel Distributors Corp.2009-12-03Not AvailableUs
Alprazolamtablet, extended release1 mgoralRebel Distributors Corp.2009-12-03Not AvailableUs
Alprazolamtablet, extended release2 mgoralRebel Distributors Corp.2009-12-03Not AvailableUs
Alprazolamtablet, extended release2 mgoralRebel Distributors Corp.2009-12-03Not AvailableUs
Alprazolamtablet.5 mgoralAidarex Pharmaceuticals LLC2007-03-28Not AvailableUs
Alprazolamtablet1 mgoralAidarex Pharmaceuticals LLC2007-03-28Not AvailableUs
Alprazolamtablet2 mgoralAidarex Pharmaceuticals LLC2007-03-28Not AvailableUs
Alprazolamtablet.25 mgoralAidarex Pharmaceuticals LLC2007-03-28Not AvailableUs
Alprazolamtablet, extended release1 mgoralAidarex Pharmaceuticals LLC2009-12-03Not AvailableUs
Alprazolamtablet1 mgoralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC1995-12-29Not AvailableUs
Alprazolamtablet1 mgoralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2010-06-18Not AvailableUs
Alprazolamtablet.25 mgoralRebel Distributors Corp2010-06-18Not AvailableUs
Alprazolamtablet.25 mgoralRebel Distributors Corp2010-06-18Not AvailableUs
Alprazolamtablet1 mgoralRebel Distributors Corp2010-06-18Not AvailableUs
Alprazolamtablet, extended release.5 mgoralAv Kare, Inc.2013-05-21Not AvailableUs
Alprazolamtablet, extended release1 mgoralAv Kare, Inc.2013-05-21Not AvailableUs
Alprazolamtablet, extended release2 mgoralAv Kare, Inc.2013-05-21Not AvailableUs
Alprazolamtablet.5 mgoralPd Rx Pharmaceuticals, Inc.2009-12-31Not AvailableUs
Alprazolamtablet.25 mgoralPd Rx Pharmaceuticals, Inc.2011-09-07Not AvailableUs
Alprazolamtablet1 mgoralPd Rx Pharmaceuticals, Inc.2007-03-28Not AvailableUs
Alprazolamtablet.5 mgoralPd Rx Pharmaceuticals, Inc.2007-03-28Not AvailableUs
Alprazolamtablet.25 mgoralPd Rx Pharmaceuticals, Inc.2007-03-28Not AvailableUs
Alprazolamtablet1 mgoralPd Rx Pharmaceuticals, Inc.2008-09-25Not AvailableUs
Alprazolamtablet.25 mgoralSun Pharma Global FZE2010-06-18Not AvailableUs
Alprazolamtablet.5 mgoralSun Pharma Global FZE2010-06-18Not AvailableUs
Alprazolamtablet1 mgoralSun Pharma Global FZE2010-06-18Not AvailableUs
Alprazolamtablet2 mgoralSun Pharma Global FZE2010-06-18Not AvailableUs
Alprazolamtablet.5 mgoralREMEDYREPACK INC.2011-04-21Not AvailableUs
Alprazolamtablet, orally disintegrating.25 mgoralPar Pharmaceutical Inc.2009-01-09Not AvailableUs
Alprazolamtablet, orally disintegrating.5 mgoralPar Pharmaceutical Inc.2009-01-09Not AvailableUs
Alprazolamtablet, orally disintegrating1 mgoralPar Pharmaceutical Inc.2009-01-09Not AvailableUs
Alprazolamtablet, orally disintegrating2 mgoralPar Pharmaceutical Inc.2009-01-09Not AvailableUs
Alprazolamtablet.5 mgoralLake Erie Medical DBA Quality Care Products LLC2010-04-01Not AvailableUs
Alprazolamtablet.25 mgoralLake Erie Medical DBA Quality Care Products LLC2010-04-01Not AvailableUs
Alprazolamtablet2 mgoralLake Erie Medical DBA Quality Care Products LLC2010-04-01Not AvailableUs
Alprazolamtablet.25 mgoralA S Medication Solutions Llc2010-06-18Not AvailableUs
Alprazolamtablet.5 mgoralA S Medication Solutions Llc2010-06-18Not AvailableUs
Alprazolamtablet1 mgoralA S Medication Solutions Llc2010-06-18Not AvailableUs
Alprazolamtablet2 mgoralA S Medication Solutions Llc2010-10-15Not AvailableUs
Alprazolamtablet.25 mgoralA S Medication Solutions Llc2010-10-15Not AvailableUs
Alprazolamtablet2 mgoralUnit Dose Services1995-01-03Not AvailableUs
Alprazolamtablet.25 mgoralUnit Dose Services1995-12-29Not AvailableUs
Alprazolamtablet.5 mgoralUnit Dose Services1995-12-29Not AvailableUs
Alprazolamtablet1 mgoralUnit Dose Services1995-12-29Not AvailableUs
Alprazolamtablet.25 mgoralMylan Institutional Inc.2012-08-14Not AvailableUs
Alprazolamtablet.5 mgoralMylan Institutional Inc.2012-08-14Not AvailableUs
Alprazolamtablet1 mgoralMylan Institutional Inc.2012-08-14Not AvailableUs
Alprazolamtablet2 mgoralREMEDYREPACK INC.2014-05-12Not AvailableUs
Alprazolam EXTENDED-RELEASEtablet, extended release1 mgoralH.J. Harkins Company, Inc.2007-03-28Not AvailableUs
Alprazolamtablet.25 mgoralA S Medication Solutions Llc2008-09-25Not AvailableUs
Alprazolamtablet.5 mgoralA S Medication Solutions Llc2008-09-25Not AvailableUs
Alprazolamtablet1 mgoralA S Medication Solutions Llc2008-09-25Not AvailableUs
Alprazolamtablet2 mgoralA S Medication Solutions Llc2010-10-15Not AvailableUs
Alprazolamtablet, extended release1 mgoralA S Medication Solutions Llc2011-05-04Not AvailableUs
Alprazolamtablet.25 mgoralPhysicians Total Care, Inc.2005-03-17Not AvailableUs
Alprazolamtablet.5 mgoralPhysicians Total Care, Inc.2007-10-26Not AvailableUs
Alprazolamtablet1 mgoralPhysicians Total Care, Inc.2006-09-13Not AvailableUs
Alprazolamtablet2 mgoralPhysicians Total Care, Inc.2009-09-16Not AvailableUs
Alprazolamtablet.25 mgoralCardinal Health2007-12-03Not AvailableUs
Alprazolamtablet.5 mgoralCardinal Health2007-12-03Not AvailableUs
Alprazolamtablet.25 mgoralCardinal Health2008-04-02Not AvailableUs
Alprazolamtablet.25 mgoralCardinal Health2007-03-28Not AvailableUs
Alprazolamtablet.5 mgoralCardinal Health2007-03-28Not AvailableUs
Alprazolamtablet1 mgoralCardinal Health2007-03-28Not AvailableUs
Alprazolamtablet.25 mgoralCardinal Health2013-09-04Not AvailableUs
Alprazolamtablet.5 mgoralCardinal Health2009-12-31Not AvailableUs
Alprazolamtablet1 mgoralCardinal Health2009-12-31Not AvailableUs
Alprazolamtablet.25 mgoralCardinal Health2009-12-31Not AvailableUs
Alprazolamtablet1 mgoralCardinal Health2008-04-02Not AvailableUs
Alprazolamtablet.25 mgoralCardinal Health1993-10-31Not AvailableUs
Alprazolamtablet.5 mgoralCardinal Health1993-10-31Not AvailableUs
Alprazolamtablet1 mgoralCardinal Health1993-10-31Not AvailableUs
Alprazolamtablet.5 mgoralCardinal Health2008-04-02Not AvailableUs
Alprazolamtablet2 mgoralPd Rx Pharmaceuticals, Inc.2010-01-01Not AvailableUs
Alprazolamtablet1 mgoralPd Rx Pharmaceuticals, Inc.2009-12-31Not AvailableUs
Alprazolamtablet.5 mgoralPd Rx Pharmaceuticals, Inc.2008-09-25Not AvailableUs
Alprazolamtablet.25 mgoralPd Rx Pharmaceuticals, Inc.2008-09-25Not AvailableUs
Alprazolamtablet.25 mgoralGolden State Medical Supply, Inc.1993-10-19Not AvailableUs
Alprazolamtablet.5 mgoralGolden State Medical Supply, Inc.1993-10-19Not AvailableUs
Alprazolamtablet1 mgoralGolden State Medical Supply, Inc.1993-10-19Not AvailableUs
Alprazolamtablet2 mgoralGolden State Medical Supply, Inc.1993-10-19Not AvailableUs
Alprazolamtablet, extended release.5 mgoralApotex Corp2008-11-12Not AvailableUs
Alprazolamtablet, extended release1 mgoralApotex Corp2008-11-12Not AvailableUs
Alprazolamtablet, extended release2 mgoralApotex Corp2008-11-12Not AvailableUs
Alprazolamtablet, extended release3 mgoralApotex Corp2008-11-12Not AvailableUs
Alprazolamtablet.5 mgoralDIRECT RX2014-01-01Not AvailableUs
Alprazolamtablet1 mgoralDIRECT RX2014-01-01Not AvailableUs
Alprazolamtablet.25 mgoralDIRECT RX2014-01-01Not AvailableUs
Alprazolamtablet1 mgoralProficient Rx LP1994-01-28Not AvailableUs
Alprazolam EXTENDED-RELEASEtablet, extended release.5 mgoralbryant ranch prepack2007-03-28Not AvailableUs
Alprazolamtablet1 mgoralbryant ranch prepack2008-04-02Not AvailableUs
Alprazolam EXTENDED-RELEASEtablet, extended release.5 mgoralbryant ranch prepack2007-03-28Not AvailableUs
Alprazolam Extended Releasetablet, extended release.5 mgoralbryant ranch prepack2007-02-13Not AvailableUs
Alprazolamtablet.25 mgoralMc Kesson Packaging Services A Business Unit Of Mc Kesson Corporation2014-04-29Not AvailableUs
Alprazolamtablet.5 mgoralMc Kesson Packaging Services A Business Unit Of Mc Kesson Corporation2014-04-29Not AvailableUs
Alprazolamtablet1 mgoralMc Kesson Packaging Services A Business Unit Of Mc Kesson Corporation2014-04-29Not AvailableUs
Alprazolamtablet.25 mgoralBoca Pharmacal, LLC2010-10-15Not AvailableUs
Alprazolamtablet.5 mgoralBoca Pharmacal, LLC2010-10-15Not AvailableUs
Alprazolamtablet1 mgoralBoca Pharmacal, LLC2010-10-15Not AvailableUs
Alprazolamtablet2 mgoralBoca Pharmacal, LLC2010-10-15Not AvailableUs
Alprazolam extended releasetablet, extended release.5 mgoralCore Pharma, Llc2007-03-28Not AvailableUs
Alprazolam extended releasetablet, extended release1 mgoralCore Pharma, Llc2007-03-28Not AvailableUs
Alprazolam extended releasetablet, extended release2 mgoralCore Pharma, Llc2007-03-28Not AvailableUs
Alprazolam extended releasetablet, extended release3 mgoralCore Pharma, Llc2007-03-28Not AvailableUs
Alprazolamtablet.5 mgoralTYA Pharmaceuticals2010-06-18Not AvailableUs
Alprazolam Extended-releasetablet, extended release.5 mgoralRising Pharmaceuticals Inc2007-03-28Not AvailableUs
Alprazolam Extended-releasetablet, extended release1 mgoralRising Pharmaceuticals Inc2007-03-28Not AvailableUs
Alprazolam Extended-releasetablet, extended release2 mgoralRising Pharmaceuticals Inc2007-03-28Not AvailableUs
Alprazolam Extended-releasetablet, extended release3 mgoralRising Pharmaceuticals Inc2007-03-28Not AvailableUs
Alprazolamtablet, extended release.5 mgoralAmneal Pharmaceuticals, LLC2009-12-03Not AvailableUs
Alprazolamtablet, extended release1 mgoralAmneal Pharmaceuticals, LLC2009-12-03Not AvailableUs
Alprazolamtablet, extended release2 mgoralAmneal Pharmaceuticals, LLC2009-12-03Not AvailableUs
Alprazolamtablet, extended release3 mgoralAmneal Pharmaceuticals, LLC2009-12-03Not AvailableUs
Alprazolamtablet, extended release.5 mgoralAurobindo Pharma Limited2011-06-07Not AvailableUs
Alprazolamtablet, extended release1 mgoralAurobindo Pharma Limited2011-06-07Not AvailableUs
Alprazolamtablet, extended release2 mgoralAurobindo Pharma Limited2011-06-07Not AvailableUs
Alprazolamtablet, extended release3 mgoralAurobindo Pharma Limited2011-06-07Not AvailableUs
Alprazolamtablet1 mgoralDispensing Solutions, Inc.2008-09-25Not AvailableUs
Alprazolamtablet.25 mgoralContract Pharmacy Services Pa2011-03-25Not AvailableUs
Alprazolamtablet.5 mgoralContract Pharmacy Services Pa2011-03-25Not AvailableUs
Alprazolamtablet1 mgoralContract Pharmacy Services Pa2011-03-25Not AvailableUs
Alprazolamtablet.25 mgoralDAVA Pharmaceuticals, Inc.2007-03-28Not AvailableUs
Alprazolamtablet.5 mgoralDAVA Pharmaceuticals, Inc.2007-03-28Not AvailableUs
Alprazolamtablet1 mgoralDAVA Pharmaceuticals, Inc.2007-03-28Not AvailableUs
Alprazolamtablet2 mgoralDAVA Pharmaceuticals, Inc.2007-03-28Not AvailableUs
Alprazolamtablet.25 mgoralRed Pharm Drug Inc.2008-02-01Not AvailableUs
Alprazolamtablet.5 mgoralRed Pharm2008-06-01Not AvailableUs
Alprazolamtablet.25 mgoralAphena Pharma Solutions Tennessee, Llc1995-12-29Not AvailableUs
Alprazolamtablet1 mgoralAphena Pharma Solutions Tennessee, Llc1995-12-29Not AvailableUs
Alprazolamtablet.5 mgoralAphena Pharma Solutions Tennessee, Llc1995-12-29Not AvailableUs
Alprazolamtablet.25 mgoralAmerican Health Packaging2013-05-28Not AvailableUs
Alprazolamtablet.5 mgoralAmerican Health Packaging2013-05-28Not AvailableUs
Alprazolamtablet1 mgoralAmerican Health Packaging2013-05-28Not AvailableUs
Alprazolamtablet.25 mgoralAmerican Health Packaging2013-09-04Not AvailableUs
Alprazolamtablet.5 mgoralAmerican Health Packaging2013-09-04Not AvailableUs
Alprazolamtablet1 mgoralPreferred Pharmaceuticals, Inc.1999-12-29Not AvailableUs
Alprazolamtablet.25 mgoralPreferred Pharmaceuticals, Inc.1999-12-29Not AvailableUs
Alprazolamtablet.5 mgoralPreferred Pharmaceuticals, Inc.1999-12-29Not AvailableUs
Alprazolamtablet.25 mgoralPreferred Pharmaceuticals, Inc.2010-03-16Not AvailableUs
Alprazolamtablet.5 mgoralPreferred Pharmaceuticals, Inc.2010-03-16Not AvailableUs
Alprazolamtablet1 mgoralPreferred Pharmaceuticals, Inc.2010-03-16Not AvailableUs
Alprazolamtablet1 mgoralPreferred Pharmaceuticals, Inc.2014-10-20Not AvailableUs
Alprazolamtablet.5 mgoralPreferred Pharmaceuticals, Inc.2014-11-19Not AvailableUs
Alprazolamtablet.25 mgoralPreferred Pharmaceuticals, Inc.2014-10-22Not AvailableUs
Alprazolamtablet, extended release1 mgoralPreferred Pharmaceuticals, Inc.2013-04-22Not AvailableUs
Alprazolamtablet, extended release1 mgoralPreferred Pharmaceuticals, Inc.2012-11-15Not AvailableUs
Alprazolamtablet1 mgoralPreferred Pharmaceuticals, Inc.2012-01-12Not AvailableUs
Alprazolamtablet.5 mgoralPreferred Pharmaceuticals, Inc.2012-01-12Not AvailableUs
Alprazolamtablet.25 mgoralPreferred Pharmaceuticals, Inc.2012-01-12Not AvailableUs
Alprazolamtablet.5 mgoralLife Line Home Care Services, Inc.2012-01-26Not AvailableUs
Alprazolamtablet.25 mgoralMc Kesson Contract Packaging2011-10-24Not AvailableUs
Alprazolamtablet.5 mgoralMc Kesson Contract Packaging2011-10-17Not AvailableUs
Alprazolamtablet1 mgoralMc Kesson Contract Packaging2011-10-17Not AvailableUs
Over the Counter ProductsNot Available
International Brands
NameCompany
AlplaxNot Available
AlprazolanNot Available
AlpronaxNot Available
AlproxNot Available
AlvizNot Available
CassadanNot Available
EsparonNot Available
RalozamNot Available
RestylNot Available
SolanaxNot Available
TafilNot Available
TrankimazinNot Available
TranquinalNot Available
XanorNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
CAS number28981-97-7
WeightAverage: 308.765
Monoisotopic: 308.082874143
Chemical FormulaC17H13ClN4
InChI KeyVREFGVBLTWBCJP-UHFFFAOYSA-N
InChI
InChI=1S/C17H13ClN4/c1-11-20-21-16-10-19-17(12-5-3-2-4-6-12)14-9-13(18)7-8-15(14)22(11)16/h2-9H,10H2,1H3
IUPAC Name
12-chloro-3-methyl-9-phenyl-2,4,5,8-tetraazatricyclo[8.4.0.0^{2,6}]tetradeca-1(10),3,5,8,11,13-hexaene
SMILES
CC1=NN=C2CN=C(C3=CC=CC=C3)C3=C(C=CC(Cl)=C3)N12
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassBenzodiazepines
SubclassNot Available
Direct parentBenzodiazepines
Alternative parentsChlorobenzenes; Aryl Chlorides; Triazoles; Polyamines; Organochlorides
Substituentschlorobenzene; aryl halide; benzene; aryl chloride; 1,2,4-triazole; azole; polyamine; organochloride; organohalogen; organonitrogen compound
Classification descriptionThis compound belongs to the benzodiazepines. These are organic compounds containing a benzene ring fused to either isomers of diazepine(unsaturated seven-member heterocycle with two nitrogen atoms replacing two carbon atoms).
Pharmacology
IndicationFor the management of anxiety disorder or the short-term relief of symptoms of anxiety and for the treatment of panic disorder, with or without agoraphobia.
PharmacodynamicsAlprazolam, a benzodiazepine, is used to treat panic disorder and anxiety disorder. Unlike chlordiazepoxide, clorazepate, and prazepam, alprazolam has a shorter half-life and metabolites with minimal activity. Like other triazolo benzodiazepines such as triazolam, alprazolam may have significant drug interactions involving the hepatic cytochrome P-450 3A4 isoenzyme. Clinically, all benzodiazepines cause a dose-related central nervous system depressant activity varying from mild impairment of task performance to hypnosis. Unlike other benzodiazepines, alprazolam may also have some antidepressant activity, although clinical evidence of this is lacking.
Mechanism of actionBenzodiazepines bind nonspecifically to benzodiazepine receptors BNZ1, which mediates sleep, and BNZ2, which affects muscle relaxation, anticonvulsant activity, motor coordination, and memory. As benzodiazepine receptors are thought to be coupled to gamma-aminobutyric acid-A (GABAA) receptors, this enhances the effects of GABA by increasing GABA affinity for the GABA receptor. Binding of the inhibitory neurotransmitter GABA to the site opens the chloride channel, resulting in a hyperpolarized cell membrane that prevents further excitation of the cell.
AbsorptionReadily absorbed from the gastrointestinal tract. Bioavailability is 80-90%.
Volume of distributionNot Available
Protein binding80% (mainly to albumin)
Metabolism

Hepatic. Hydroxylated in the liver to α-hydroxyalprazolam, which is also active. This and other metabolites are later excreted in urine as glucuronides.

SubstrateEnzymesProduct
Alprazolam
alpha-HydroxyalprazolamDetails
Alprazolam
4-hydroxyalprazolamDetails
Route of eliminationAlprazolam and its metabolites are excreted primarily in the urine.
Half life6.3-26.9 hours
Clearance
  • 2.13 +/- 0.54 mL/min/kg [CYP3A inducers]
  • 0.90 +/- 0.21 mL/min/kg [without CYP3A inducers]
ToxicityOral, mouse: LD50=1020 mg/kg. Symptoms of overdose include confusion, coma, impaired coordination, sleepiness, and slowed reaction time.
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 + 1.0
Blood Brain Barrier + 0.9794
Caco-2 permeable + 0.8867
P-glycoprotein substrate Non-substrate 0.5099
P-glycoprotein inhibitor I Non-inhibitor 0.7301
P-glycoprotein inhibitor II Inhibitor 0.8354
Renal organic cation transporter Inhibitor 0.7688
CYP450 2C9 substrate Non-substrate 0.7907
CYP450 2D6 substrate Non-substrate 0.9164
CYP450 3A4 substrate Substrate 0.7353
CYP450 1A2 substrate Inhibitor 0.8758
CYP450 2C9 substrate Inhibitor 0.8076
CYP450 2D6 substrate Non-inhibitor 0.8137
CYP450 2C19 substrate Inhibitor 0.6519
CYP450 3A4 substrate Non-inhibitor 0.6308
CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.8913
Ames test Non AMES toxic 0.8957
Carcinogenicity Non-carcinogens 0.6779
Biodegradation Not ready biodegradable 1.0
Rat acute toxicity 2.3717 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.973
hERG inhibition (predictor II) Non-inhibitor 0.8733
Pharmacoeconomics
Manufacturers
  • Roxane laboratories inc
  • Actavis elizabeth llc
  • Amneal pharmaceuticals ny llc
  • Apotex inc
  • Barr laboratories inc
  • Corepharma llc
  • Impax laboratories inc
  • Mylan pharmaceuticals inc
  • Sandoz inc
  • Teva pharmaceuticals usa
  • Vintage pharmaceuticals llc
  • Watson laboratories inc florida
  • Zydus pharmaceuticals usa inc
  • Pharmacia and upjohn
  • Par pharmaceutical inc
  • Schwarz pharma inc
  • Alphapharm party ltd
  • Dava international inc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Sun pharma global inc
  • Teva pharmaceuticals usa inc
  • Watson laboratories inc
  • Pharmacia and upjohn co
Packagers
Dosage forms
FormRouteStrength
Solution, concentrateoral1 mg/mL
Tabletoral.25 mg
Tabletoral.5 mg
Tabletoral1 mg
Tabletoral2 mg
Tablet, extended releaseoral.5 mg
Tablet, extended releaseoral1 mg
Tablet, extended releaseoral2 mg
Tablet, extended releaseoral3 mg
Tablet, orally disintegratingoral.25 mg
Tablet, orally disintegratingoral.5 mg
Tablet, orally disintegratingoral1 mg
Tablet, orally disintegratingoral2 mg
Prices
Unit descriptionCostUnit
ALPRAZolam Intensol 1 mg/ml Concentrate 30ml Bottle67.03USDbottle
Niravam 2 mg Dispersible Tablet8.53USDdispersible tablet
Xanax xr 3 mg tablet7.25USDtablet
Xanax XR 3 mg 24 Hour tablet7.1USDtablet
Niravam 2 mg tablet6.86USDtablet
Niravam 1 mg Dispersible Tablet5.42USDdispersible tablet
Xanax xr 2 mg tablet4.84USDtablet
Xanax XR 2 mg 24 Hour tablet4.73USDtablet
Niravam 0.5 mg Dispersible Tablet4.2USDdispersible tablet
Niravam 1 mg tablet4.04USDtablet
Xanax 2 mg tablet3.82USDtablet
ALPRAZolam 3 mg 24 Hour tablet3.67USDtablet
Xanax XR 1 mg 24 Hour tablet3.64USDtablet
Xanax xr 1 mg tablet3.64USDtablet
Niravam 0.25 mg Dispersible Tablet3.45USDdispersible tablet
Niravam 0.5 mg tablet3.02USDtablet
Xanax XR 0.5 mg 24 Hour tablet3.01USDtablet
Xanax xr 0.5 mg tablet2.93USDtablet
ALPRAZolam 2 mg 24 Hour tablet2.53USDtablet
Niravam 0.25 mg tablet2.43USDtablet
ALPRAZolam 1 mg 24 Hour tablet2.33USDtablet
Xanax 1 mg tablet2.29USDtablet
Alprazolam 1 mg/ml oral conc2.23USDml
Xanax 0.5 mg tablet1.3USDtablet
Alprazolam 2 mg tablet1.22USDtablet
Xanax 0.25 mg tablet1.09USDtablet
ALPRAZolam 0.5 mg 24 Hour tablet1.07USDtablet
Alprazolam 1 mg tablet0.78USDtablet
Alprazolam 0.5 mg tablet0.67USDtablet
Alprazolam 0.25 mg tablet0.55USDtablet
Apo-Alpraz 0.5 mg Tablet0.1USDtablet
Mylan-Alprazolam 0.5 mg Tablet0.1USDtablet
Novo-Alprazol 0.5 mg Tablet0.1USDtablet
Apo-Alpraz 0.25 mg Tablet0.08USDtablet
Mylan-Alprazolam 0.25 mg Tablet0.08USDtablet
Novo-Alprazol 0.25 mg Tablet0.08USDtablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
CountryPatent NumberApprovedExpires (estimated)
United States60249811998-04-092018-04-09
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point228-229.5 °CHester, J.B., Jr.; US. Patent3,681,343; August 1,1972; assigned to The Upjohn Company. Hester, J.B., Jr.; US.Patent3,781,289; December 25,1973;assigned to The Upjohn Company. Hester, J.B., Jr.; U S . Patent 3,709898; January 9,1973; assigned t o The Upjohn Company.
water solubility40 mg/L at pH 7; 12 mg/mL at pH 1.2Not Available
logP2.12BIOBYTE (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.0324ALOGPS
logP2.23ALOGPS
logP2.37ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)18.3ChemAxon
pKa (Strongest Basic)5.08ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.07 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity98.88 m3·mol-1ChemAxon
Polarizability32.22 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
References
Synthesis Reference

Hester, J.B., Jr.; US. Patent 3,681,343; August 1,1972; assigned to The Upjohn Company. Hester, J.B., Jr.; US.Patent 3,781,289; December 25,1973;assigned to The Upjohn Company. Hester, J.B., Jr.; U S . Patent 3,709898; January 9,1973; assigned to The Upjohn Company.

General Reference
  1. Risse SC, Whitters A, Burke J, Chen S, Scurfield RM, Raskind MA: Severe withdrawal symptoms after discontinuation of alprazolam in eight patients with combat-induced posttraumatic stress disorder. J Clin Psychiatry. 1990 May;51(5):206-9. Pubmed
  2. Wolf B, Griffiths RR: Physical dependence on benzodiazepines: differences within the class. Drug Alcohol Depend. 1991 Dec 31;29(2):153-6. Pubmed
  3. Haque W, Watson DJ, Bryant SG: Death following suspected alprazolam withdrawal seizures: a case report. Tex Med. 1990 Jan;86(1):44-7. Pubmed
  4. Hori A: Pharmacotherapy for personality disorders. Psychiatry Clin Neurosci. 1998 Feb;52(1):13-9. Pubmed
  5. Garcia-Algar O, Lopez-Vilchez MA, Martin I, Mur A, Pellegrini M, Pacifici R, Rossi S, Pichini S: Confirmation of gestational exposure to alprazolam by analysis of biological matrices in a newborn with neonatal sepsis. Clin Toxicol (Phila). 2007;45(3):295-8. Pubmed
External Links
ResourceLink
KEGG DrugD00225
KEGG CompoundC06817
PubChem Compound2118
PubChem Substance46507078
ChemSpider2034
ChEBI2611
ChEMBLCHEMBL661
Therapeutic Targets DatabaseDAP000239
PharmGKBPA448333
RxListhttp://www.rxlist.com/cgi/generic/alpraz.htm
Drugs.comhttp://www.drugs.com/alprazolam.html
PDRhealthhttp://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/xan1491.shtml
WikipediaAlprazolam
ATC CodesN05BA12
AHFS Codes
  • 28:24.08
PDB EntriesNot Available
FDA labelshow(63.6 KB)
MSDSshow(47.3 KB)
Interactions
Drug Interactions
Drug
AmprenavirAmprenavir may increase the effect and toxicity of the benzodiazepine, alprazolam.
AprepitantAprepitant may increase the effect and toxicity of the benzodiazepine, alprazolam.
CarbamazepineCarbamazepine may decrease the effect of the benzodiazepine, alprazolam.
CimetidineCimetidine may increase the effect of the benzodiazepine, alprazolam.
ClarithromycinThe macrolide, clarithromycin, may increase the effect of the benzodiazepine, alprazolam.
ClozapineIncreased risk of toxicity
DelavirdineThe antiviral agent, delavirdine, may increase the effect and toxicity of the benzodiazepine, alprazolam.
DigoxinThe benzodiazepine, alprazolam, may increase the effect of digoxin.
EfavirenzThe antiviral agent, efavirenz, may increase the effect and toxicity of the benzodiazepine, alprazolam.
ErythromycinThe macrolide, erythromycin, may increase the effect of the benzodiazepine, alprazolam.
EthotoinEthotoin may increase the metabolism of alprazolam via CYP3A4.
FluconazoleFluconazole may increase the effect of the benzodiazepine, alprazolam.
FosamprenavirFosamprenavir may increase the effect and toxicity of the benzodiazepine, alprazolam.
FosphenytoinFosphenytoin may increase the metabolism of alprazolam via CYP3A4.
IndinavirThe protease inhibitor, indinavir, may increase the effect of the benzodiazepine, alprazolam.
ItraconazoleItraconazole may increase the effect of the benzodiazepine, alprazolam.
JosamycinThe macrolide, josamycin, may increase the effect of the benzodiazepine, alprazolam.
KavaKava may increase the effect of the benzodiazepine, alprazolam.
KetoconazoleKetoconazole may increase the effect of the benzodiazepine, alprazolam.
MephenytoinMephenytoin may increase the metabolism of alprazolam via CYP3A4.
NelfinavirThe protease inhibitor, nelfinavir, may increase the effect of the benzodiazepine, alprazolam.
OmeprazoleOmeprazole may increase the effect of the benzodiazepine, alprazolam.
PhenytoinPhenytoin may increase the metabolism of alprazolam via CYP3A4.
RitonavirThe protease inhibitor, ritonavir, may increase the effect of the benzodiazepine, alprazolam.
SaquinavirThe protease inhibitor, saquinavir, may increase the effect of the benzodiazepine, alprazolam.
St. John's WortSt. John's Wort may decrease the effect of the benzodiazepine, alprazolam.
TelaprevirTelaprevir inhibits systemic metabolism of alprazolam and dose adjustment may be necessary.
TelithromycinTelithromycin may increase the effect and toxicity of the benzodiazepine, alprazolam.
TipranavirTipranavir may decrease the metabolism and clearance of Alprazolam. Consider alternate therapy or monitor for Alprazolam toxic effects if Tipranavir is initiated or dose increased.
TriprolidineThe CNS depressants, Triprolidine and Alprazolam, may increase adverse/toxic effects due to additivity. Monitor for increased CNS depressant effects during concomitant therapy.
VoriconazoleVoriconazole may increase the serum concentration of alprazolam by decreasing its metabolism. Monitor for alprazolam toxicity if voriconazole is initiated or dose increased.
Food Interactions
  • Avoid alcohol.
  • Avoid excessive quantities of coffee or tea (Caffeine).
  • Avoid taking with grapefruit juice.
  • Take with food.

Targets

1. GABA-A receptor (anion channel)

Kind: protein group

Organism: Human

Pharmacological action: yes

Actions: positive allosteric modulator

Components

Name UniProt ID Details
Gamma-aminobutyric acid receptor subunit alpha-1 P14867 Details
Gamma-aminobutyric acid receptor subunit alpha-2 P47869 Details
Gamma-aminobutyric acid receptor subunit alpha-3 P34903 Details
Gamma-aminobutyric acid receptor subunit alpha-4 P48169 Details
Gamma-aminobutyric acid receptor subunit alpha-5 P31644 Details
Gamma-aminobutyric acid receptor subunit alpha-6 Q16445 Details
Gamma-aminobutyric acid receptor subunit beta-1 P18505 Details
Gamma-aminobutyric acid receptor subunit beta-2 P47870 Details
Gamma-aminobutyric acid receptor subunit beta-3 P28472 Details
Gamma-aminobutyric acid receptor subunit delta O14764 Details
Gamma-aminobutyric acid receptor subunit epsilon P78334 Details
Gamma-aminobutyric acid receptor subunit gamma-1 Q8N1C3 Details
Gamma-aminobutyric acid receptor subunit gamma-2 P18507 Details
Gamma-aminobutyric acid receptor subunit gamma-3 Q99928 Details
Gamma-aminobutyric acid receptor subunit pi O00591 Details
Gamma-aminobutyric acid receptor subunit theta Q9UN88 Details

References:

  1. Riss J, Cloyd J, Gates J, Collins S: Benzodiazepines in epilepsy: pharmacology and pharmacokinetics. Acta Neurol Scand. 2008 Aug;118(2):69-86. doi: 10.1111/j.1600-0404.2008.01004.×. Epub 2008 Mar 31. Pubmed
  2. Verster JC, Volkerts ER: Clinical pharmacology, clinical efficacy, and behavioral toxicity of alprazolam: a review of the literature. CNS Drug Rev. 2004 Spring;10(1):45-76. Pubmed

Enzymes

1. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 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
  4. Williams JA, Ring BJ, Cantrell VE, Jones DR, Eckstein J, Ruterbories K, Hamman MA, Hall SD, Wrighton SA: Comparative metabolic capabilities of CYP3A4, CYP3A5, and CYP3A7. Drug Metab Dispos. 2002 Aug;30(8):883-91. Pubmed

2. 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

3. Cytochrome P450 3A5

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 3A5 P20815 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

4. Cytochrome P450 3A7

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 3A7 P24462 Details

References:

  1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.

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Drug created on June 13, 2005 07:24 / Updated on March 27, 2014 13:23