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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
8-Chloro-1-methyl-6-phenyl-4H-S-triazolo(4,3-a)(1,4)benzodiazepine
Alprazolam
Xanax
External Identifiers
  • TUS-1
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Alprazolamtablet.25 mg/1oralbryant ranch prepack1981-10-16Not applicableUs
Alprazolamtablet2 mgoralJamp Pharma CorporationNot applicableNot applicableCanada
Alprazolamtablet2 mg/1oralGreenstone LLC1981-10-16Not applicableUs
Alprazolamtablet1 mgoralJamp Pharma CorporationNot applicableNot applicableCanada
Alprazolamtablet1 mg/1oralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2011-11-30Not applicableUs
Alprazolamtablet1 mg/1oralGreenstone LLC1981-10-16Not applicableUs
Alprazolamtablet0.50 mgoralSanis Health Inc2010-04-30Not applicableCanada
Alprazolamtablet0.5 mgoralJamp Pharma CorporationNot applicableNot applicableCanada
Alprazolamtablet1 mg/1oralContract Pharmacy Services Pa1981-10-16Not applicableUs
Alprazolamtablet.5 mg/1oralGreenstone LLC1981-10-16Not applicableUs
Alprazolamtablet.5 mg/1oralContract Pharmacy Services Pa1981-10-16Not applicableUs
Alprazolamtablet0.25 mgoralSanis Health Inc2010-04-30Not applicableCanada
Alprazolamtablet0.25 mgoralJamp Pharma CorporationNot applicableNot applicableCanada
Alprazolamtablet.25 mg/1oralGreenstone LLC1981-10-16Not applicableUs
Alprazolamtablet.25 mg/1oralContract Pharmacy Services Pa1981-10-16Not applicableUs
Alprazolamtablet2 mg/1oralbryant ranch prepack1981-10-16Not applicableUs
Alprazolam Tablets 0.25tablet0.25 mgoralPrempharm Inc1996-12-302005-08-05Canada
Alprazolam Tablets 0.5mgtablet0.5 mgoralPrempharm Inc1996-12-302005-08-05Canada
Alprazolam Tstablet2 mgoralPro Doc LimiteeNot applicableNot applicableCanada
Alprazolam XRtablet, extended release.5 mg/1oralGreenstone LLC2003-01-17Not applicableUs
Alprazolam XRtablet, extended release2 mg/1oralGreenstone LLC2003-01-17Not applicableUs
Alprazolam XRtablet, extended release.5 mg/1oralLake Erie Medical DBA Quality Care Products LLC2003-01-17Not applicableUs
Alprazolam XRtablet, extended release2 mg/1oralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2003-01-17Not applicableUs
Alprazolam XRtablet, extended release1 mg/1oralLake Erie Medical DBA Quality Care Products LLC2003-01-17Not applicableUs
Alprazolam XRtablet, extended release1 mg/1oralGreenstone LLC2003-01-17Not applicableUs
Alprazolam XRtablet, extended release3 mg/1oralGreenstone LLC2003-01-17Not applicableUs
Alprazolam-0.25 Tab 0.25mgtablet.25 mgoralPro Doc Limitee1991-12-31Not applicableCanada
Alprazolam-0.5 Tab 0.5mgtablet.5 mgoralPro Doc Limitee1991-12-31Not applicableCanada
Alprazolam-1tablet1 mgoralPro Doc Limitee2004-04-01Not applicableCanada
Ipg-alprazolamtablet0.5 mgoralInternational Pharmaceutical Generics LtdNot applicableNot applicableCanada
Ipg-alprazolamtablet0.25 mgoralInternational Pharmaceutical Generics LtdNot applicableNot applicableCanada
Ipg-alprazolamtablet2 mgoralInternational Pharmaceutical Generics LtdNot applicableNot applicableCanada
Ipg-alprazolamtablet1 mgoralInternational Pharmaceutical Generics LtdNot applicableNot applicableCanada
Jamp-alprazolamtablet2 mgoralJamp Pharma Corporation2015-10-25Not applicableCanada
Jamp-alprazolamtablet1 mgoralJamp Pharma Corporation2014-05-15Not applicableCanada
Jamp-alprazolamtablet0.5 mgoralJamp Pharma Corporation2014-05-15Not applicableCanada
Jamp-alprazolamtablet0.25 mgoralJamp Pharma Corporation2014-05-15Not applicableCanada
Mylan-alprazolamtablet1 mgoralMylan Pharmaceuticals Ulc1997-01-09Not applicableCanada
Mylan-alprazolamtablet0.5 mgoralMylan Pharmaceuticals Ulc1994-12-31Not applicableCanada
Mylan-alprazolamtablet0.25 mgoralMylan Pharmaceuticals Ulc1994-12-31Not applicableCanada
Mylan-alprazolamtablet2 mgoralMylan Pharmaceuticals Ulc1997-01-09Not applicableCanada
Nat-alprazolamtablet0.5 mgoralNatco Pharma (Canada) Inc2015-07-22Not applicableCanada
Nat-alprazolamtablet2 mgoralNatco Pharma (Canada) Inc2016-05-05Not applicableCanada
Nat-alprazolamtablet0.25 mgoralNatco Pharma (Canada) Inc2015-07-22Not applicableCanada
Nat-alprazolamtablet1 mgoralNatco Pharma (Canada) Inc2015-07-22Not applicableCanada
Niravamtablet, orally disintegrating.5 mg/1oralJazz Pharmaceuticals, Inc.2005-04-01Not applicableUs
Niravamtablet, orally disintegrating.25 mg/1oralJazz Pharmaceuticals, Inc.2005-04-01Not applicableUs
Niravamtablet, orally disintegrating.5 mg/1oralSTAT Rx USA LLC2005-01-20Not applicableUs
Niravamtablet, orally disintegrating2 mg/1oralJazz Pharmaceuticals, Inc.2005-04-01Not applicableUs
Niravamtablet, orally disintegrating1 mg/1oralJazz Pharmaceuticals, Inc.2005-04-01Not applicableUs
Ntp-alprazolamtablet0.5 mgoralTeva Canada LimitedNot applicableNot applicableCanada
Ntp-alprazolamtablet0.25 mgoralTeva Canada LimitedNot applicableNot applicableCanada
Nu-alpraz Tab 0.25mgtablet.25 mgoralNu Pharm Inc1991-12-312012-09-04Canada
Nu-alpraz Tab 0.5mgtablet.5 mgoralNu Pharm Inc1991-12-312012-09-04Canada
Ratio-alprazolamtablet0.5 mgoralRatiopharm Inc Division Of Teva Canada Limited1998-03-022006-08-04Canada
Ratio-alprazolamtablet0.25 mgoralRatiopharm Inc Division Of Teva Canada Limited1989-12-312006-08-04Canada
Riva-alprazolamtablet2 mgoralLaboratoire Riva Inc2015-06-05Not applicableCanada
Riva-alprazolamtablet1 mgoralLaboratoire Riva Inc2014-11-20Not applicableCanada
Riva-alprazolamtablet0.5 mgoralLaboratoire Riva Inc2014-11-20Not applicableCanada
Riva-alprazolamtablet0.25 mgoralLaboratoire Riva Inc2014-11-20Not applicableCanada
Riva-alprazolam 0.25 mgtablet0.25 mgoralLaboratoire Riva IncNot applicableNot applicableCanada
Riva-alprazolam 0.5 mgtablet0.5 mgoralLaboratoire Riva IncNot applicableNot applicableCanada
Teva-alprazolamtablet0.25 mgoralTeva Canada Limited1991-12-31Not applicableCanada
Teva-alprazolamtablet0.5 mgoralTeva Canada Limited1993-09-23Not applicableCanada
Xanaxtablet.25 mg/1oralPharmacia and Upjohn Company1981-10-16Not applicableUs
Xanaxtablet2 mg/1oralPharmacia and Upjohn Company1981-10-16Not applicableUs
Xanaxtablet1 mg/1oralPharmacia and Upjohn Company1981-10-16Not applicableUs
Xanaxtablet.5 mg/1oralPharmacia and Upjohn Company1981-10-16Not applicableUs
Xanax Tab 0.25mgtablet0.25 mgoralPfizer Canada Inc1981-12-31Not applicableCanada
Xanax Tab 0.5mgtablet0.5 mgoralPfizer Canada Inc1981-12-31Not applicableCanada
Xanax Tab 1mgtablet1 mgoralPfizer Canada Inc1993-12-31Not applicableCanada
Xanax Ts Tab 2mgtablet2 mgoralPfizer Canada Inc1993-12-31Not applicableCanada
Xanax XRtablet, extended release3 mg/1oralPharmacia And Upjohn Company Llc2003-01-17Not applicableUs
Xanax XRtablet, extended release2 mg/1oralPharmacia And Upjohn Company Llc2003-01-17Not applicableUs
Xanax XRtablet, extended release1 mg/1oralPharmacia And Upjohn Company Llc2003-01-17Not applicableUs
Xanax XRtablet, extended release.5 mg/1oralPharmacia And Upjohn Company Llc2003-01-17Not applicableUs
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Alprazolamtablet.5 mg/1oralQualitest Pharmaceuticals2008-09-25Not applicableUs
Alprazolamtablet.25 mg/1oralBlenheim Pharmacal, Inc.2011-09-14Not applicableUs
Alprazolamtablet2 mg/1oralRebel Distributors Corp.1998-03-25Not applicableUs
Alprazolamtablet.5 mg/1oralPd Rx Pharmaceuticals, Inc.2009-12-31Not applicableUs
Alprazolamtablet.5 mg/1oralREMEDYREPACK INC.2011-04-21Not applicableUs
Alprazolamtablet.5 mg/1oralUnit Dose Services1995-12-29Not applicableUs
Alprazolamtablet2 mg/1oralPhysicians Total Care, Inc.2009-09-16Not applicableUs
Alprazolamtablet.25 mg/1oralPd Rx Pharmaceuticals, Inc.2008-09-25Not applicableUs
Alprazolamtablet1 mg/1oralDIRECT RX2014-01-01Not applicableUs
Alprazolamtablet.25 mg/1oralMc Kesson Packaging Services A Business Unit Of Mc Kesson Corporation2014-04-29Not applicableUs
Alprazolamtablet, extended release3 mg/1oralAmneal Pharmaceuticals, LLC2009-12-03Not applicableUs
Alprazolamtablet1 mg/1oralDAVA Pharmaceuticals, Inc.2007-03-28Not applicableUs
Alprazolamtablet1 mg/1oralPreferred Pharmaceuticals, Inc.2014-10-20Not applicableUs
Alprazolamtablet.25 mg/1oralMc Kesson Contract Packaging2011-10-24Not applicableUs
Alprazolamtablet.25 mg/1oralMylan Institutional Inc.1998-10-26Not applicableUs
Alprazolamtablet.5 mg/1oralCardinal Health2007-12-03Not applicableUs
Alprazolamtablet.5 mg/1oralGolden State Medical Supply, Inc.1993-10-19Not applicableUs
Alprazolamtablet25 mg/1oralDIRECT RX2014-01-01Not applicableUs
Alprazolamtablet1 mg/1oralMc Kesson Packaging Services A Business Unit Of Mc Kesson Corporation2014-04-29Not applicableUs
Alprazolamtablet, extended release1 mg/1oralAurobindo Pharma Limited2011-06-07Not applicableUs
Alprazolamtablet.25 mg/1oralRed Pharm Drug Inc.2008-02-01Not applicableUs
Alprazolamtablet.25 mg/1oralPreferred Pharmaceuticals, Inc.2010-06-18Not applicableUs
Alprazolamtablet1 mg/1oralMc Kesson Contract Packaging2011-10-17Not applicableUs
Alprazolamsolution, concentrate1 mg/mLoralRoxane Laboratories, Inc1993-10-31Not applicableUs
Alprazolamtablet2 mg/1oralQualitest Pharmaceuticals2008-09-25Not applicableUs
Alprazolamtablet1 mg/1oralBlenheim Pharmacal, Inc.2010-04-13Not applicableUs
Alprazolamtablet, extended release1 mg/1oralRebel Distributors Corp.2009-12-03Not applicableUs
Alprazolamtablet1 mg/1oralPd Rx Pharmaceuticals, Inc.2007-03-28Not applicableUs
Alprazolamtablet, orally disintegrating.5 mg/1oralPar Pharmaceutical Inc.2009-01-09Not applicableUs
Alprazolamtablet.25 mg/1oralMylan Pharmaceuticals Inc.2012-07-23Not applicableUs
Alprazolamtablet.5 mg/1oralKAISER FOUNDATION HOSPITALS2011-06-08Not applicableUs
Alprazolamtablet1 mg/1oralSandoz Inc1995-12-29Not applicableUs
Alprazolamtablet.5 mg/1oralSTAT Rx USA LLC2011-03-25Not applicableUs
Alprazolamtablet.25 mg/1oralAidarex Pharmaceuticals LLC2007-03-28Not applicableUs
Alprazolamtablet1 mg/1oralMedsource Pharmaceuticals1995-12-29Not applicableUs
Alprazolamtablet.25 mg/1oralA S Medication Solutions Llc2010-06-18Not applicableUs
Alprazolamtablet.5 mg/1oralA S Medication Solutions Llc2008-09-25Not applicableUs
Alprazolamtablet1 mg/1oralCardinal Health2009-12-31Not applicableUs
Alprazolamtablet2 mg/1oralApotex Corp.2007-01-19Not applicableUs
Alprazolamtablet2 mg/1oralProficient Rx LP1998-03-25Not applicableUs
Alprazolamtablet2 mg/1oralAurobindo Pharma Limited2015-07-31Not applicableUs
Alprazolamtablet.5 mg/1oralAmerican Health Packaging2013-09-04Not applicableUs
Alprazolamtablet.25 mg/1oralPreferred Pharmaceuticals, Inc.2012-01-12Not applicableUs
Alprazolamtablet.25 mg/1oralQualitest Pharmaceuticals2008-09-25Not applicableUs
Alprazolamtablet2 mg/1oralActavis Pharma, Inc.1995-01-03Not applicableUs
Alprazolamtablet.25 mg/1oralBlenheim Pharmacal, Inc.2010-12-10Not applicableUs
Alprazolamtablet1 mg/1oralRebel Distributors Corp.1999-12-29Not applicableUs
Alprazolamtablet1 mg/1oralRebel Distributors Corp2010-06-18Not applicableUs
Alprazolamtablet2 mg/1oralSun Pharma Global FZE2010-06-18Not applicableUs
Alprazolamtablet.25 mg/1oralUnit Dose Services1995-12-29Not applicableUs
Alprazolamtablet1 mg/1oralPhysicians Total Care, Inc.2006-09-13Not applicableUs
Alprazolamtablet.5 mg/1oralPd Rx Pharmaceuticals, Inc.2008-09-25Not applicableUs
Alprazolamtablet.5 mg/1oralDIRECT RX2014-01-01Not applicableUs
Alprazolamtablet, extended release2 mg/1oralAmneal Pharmaceuticals, LLC2009-12-03Not applicableUs
Alprazolamtablet.5 mg/1oralDAVA Pharmaceuticals, Inc.2007-03-28Not applicableUs
Alprazolamtablet1 mg/1oralPreferred Pharmaceuticals, Inc.2010-03-16Not applicableUs
Alprazolamtablet.5 mg/1oralLife Line Home Care Services, Inc.2012-01-26Not applicableUs
Alprazolamtablet.5 mg/1oralCardinal Health2008-04-02Not applicableUs
Alprazolamtablet, orally disintegrating2 mg/1oralActavis Elizabeth LLC2010-03-16Not applicableUs
Alprazolamtablet.25 mg/1oralKAISER FOUNDATION HOSPITALS2011-06-08Not applicableUs
Alprazolamtablet.5 mg/1oralSandoz Inc1995-12-29Not applicableUs
Alprazolamtablet1 mg/1oralApotheca, Inc2012-06-30Not applicableUs
Alprazolamtablet2 mg/1oralAidarex Pharmaceuticals LLC2007-03-28Not applicableUs
Alprazolamtablet.5 mg/1oralMedsource Pharmaceuticals2008-09-25Not applicableUs
Alprazolamtablet2 mg/1oralLake Erie Medical DBA Quality Care Products LLC2010-04-01Not applicableUs
Alprazolamtablet.25 mg/1oralA S Medication Solutions Llc2008-09-25Not applicableUs
Alprazolamtablet.5 mg/1oralCardinal Health2009-12-31Not applicableUs
Alprazolamtablet1 mg/1oralApotex Corp.2007-01-19Not applicableUs
Alprazolamtablet1 mg/1oralProficient Rx LP1995-12-29Not applicableUs
Alprazolamtablet1 mg/1oralAurobindo Pharma Limited2015-07-31Not applicableUs
Alprazolamtablet.25 mg/1oralAmerican Health Packaging2013-09-04Not applicableUs
Alprazolamtablet.5 mg/1oralPreferred Pharmaceuticals, Inc.2012-01-12Not applicableUs
Alprazolamtablet1 mg/1oralActavis Pharma, Inc.1995-01-03Not applicableUs
Alprazolamtablet2 mg/1oralMajor Pharmaceuticals2008-04-02Not applicableUs
Alprazolamtablet.5 mg/1oralRebel Distributors Corp.1999-12-29Not applicableUs
Alprazolamtablet.25 mg/1oralRebel Distributors Corp2010-06-18Not applicableUs
Alprazolamtablet1 mg/1oralSun Pharma Global FZE2010-06-18Not applicableUs
Alprazolamtablet2 mg/1oralUnit Dose Services1995-01-03Not applicableUs
Alprazolamtablet.5 mg/1oralPhysicians Total Care, Inc.2007-10-26Not applicableUs
Alprazolamtablet1 mg/1oralPd Rx Pharmaceuticals, Inc.2009-12-31Not applicableUs
Alprazolamtablet.25 mg/1oralREMEDYREPACK INC.2015-03-17Not applicableUs
Alprazolamtablet, extended release1 mg/1oralAmneal Pharmaceuticals, LLC2009-12-03Not applicableUs
Alprazolamtablet.25 mg/1oralDAVA Pharmaceuticals, Inc.2007-03-28Not applicableUs
Alprazolamtablet.5 mg/1oralPreferred Pharmaceuticals, Inc.2010-03-16Not applicableUs
Alprazolamtablet2 mg/1oralBionpharma Inc.2015-10-01Not applicableUs
Alprazolamtablet1 mg/1oralCardinal Health2008-04-02Not applicableUs
Alprazolamtablet, extended release1 mg/1oralMylan Pharmaceuticals Inc.2006-01-26Not applicableUs
Alprazolamtablet, extended release3 mg/1oralGlobal Pharmaceuticals, Division of Impax Laboratories Inc.2007-05-24Not applicableUs
Alprazolamtablet.25 mg/1oralSandoz Inc1995-12-29Not applicableUs
Alprazolamtablet.5 mg/1oralApotheca, Inc2000-01-18Not applicableUs
Alprazolamtablet1 mg/1oralAidarex Pharmaceuticals LLC2007-03-28Not applicableUs
Alprazolamtablet1 mg/1oralPd Rx Pharmaceuticals, Inc.1995-12-29Not applicableUs
Alprazolamtablet.25 mg/1oralLake Erie Medical DBA Quality Care Products LLC2010-04-01Not applicableUs
Alprazolamtablet.25 mg/1oralCardinal Health2013-09-04Not applicableUs
Alprazolamtablet.5 mg/1oralApotex Corp.2007-01-19Not applicableUs
Alprazolamtablet, extended release.5 mg/1oralProficient Rx LP2006-01-26Not applicableUs
Alprazolamtablet2 mg/1oralBoca Pharmacal, LLC2010-10-15Not applicableUs
Alprazolamtablet.5 mg/1oralAurobindo Pharma Limited2015-07-31Not applicableUs
Alprazolamtablet.5 mg/1oralAphena Pharma Solutions Tennessee, Llc1995-12-29Not applicableUs
Alprazolamtablet1 mg/1oralPreferred Pharmaceuticals, Inc.2012-01-12Not applicableUs
Alprazolamtablet, orally disintegrating1 mg/1oralActavis Elizabeth LLC2010-03-16Not applicableUs
Alprazolamtablet1 mg/1oralMajor Pharmaceuticals2008-04-02Not applicableUs
Alprazolamtablet.25 mg/1oralRebel Distributors Corp.1999-12-29Not applicableUs
Alprazolamtablet.25 mg/1oralRebel Distributors Corp2010-06-18Not applicableUs
Alprazolamtablet.5 mg/1oralSun Pharma Global FZE2010-06-18Not applicableUs
Alprazolamtablet.25 mg/1oralA S Medication Solutions Llc2010-10-15Not applicableUs
Alprazolamtablet.25 mg/1oralPhysicians Total Care, Inc.2005-03-17Not applicableUs
Alprazolamtablet1 mg/1oralCardinal Health1993-10-31Not applicableUs
Alprazolamtablet, extended release3 mg/1oralApotex Corp2008-11-12Not applicableUs
Alprazolamtablet1 mg/1oralbryant ranch prepack2008-04-02Not applicableUs
Alprazolamtablet, extended release.5 mg/1oralAmneal Pharmaceuticals, LLC2009-12-03Not applicableUs
Alprazolamtablet1 mg/1oralContract Pharmacy Services Pa2011-03-25Not applicableUs
Alprazolamtablet.25 mg/1oralPreferred Pharmaceuticals, Inc.2010-03-16Not applicableUs
Alprazolamtablet1 mg/1oralBionpharma Inc.2015-10-01Not applicableUs
Alprazolamtablet.25 mg/1oralCardinal Health2008-04-02Not applicableUs
Alprazolamtablet, extended release.5 mg/1oralMylan Pharmaceuticals Inc.2006-01-26Not applicableUs
Alprazolamtablet.5 mg/1oralActavis Pharma, Inc.1995-01-03Not applicableUs
Alprazolamtablet, extended release2 mg/1oralGlobal Pharmaceuticals, Division of Impax Laboratories Inc.2007-05-24Not applicableUs
Alprazolamtablet1 mg/1oralNcs Health Care Of Ky, Inc Dba Vangard Labs1995-01-03Not applicableUs
Alprazolamtablet.25 mg/1oralBlenheim Pharmacal, Inc.2013-11-15Not applicableUs
Alprazolamtablet.5 mg/1oralAidarex Pharmaceuticals LLC2007-03-28Not applicableUs
Alprazolamtablet1 mg/1oralPd Rx Pharmaceuticals, Inc.2008-09-25Not applicableUs
Alprazolamtablet.5 mg/1oralLake Erie Medical DBA Quality Care Products LLC2010-04-01Not applicableUs
Alprazolamtablet2 mg/1oralREMEDYREPACK INC.2014-05-12Not applicableUs
Alprazolamtablet1 mg/1oralCardinal Health2007-03-28Not applicableUs
Alprazolamtablet.25 mg/1oralApotex Corp.2007-01-19Not applicableUs
Alprazolamtablet1 mg/1oralProficient Rx LP1994-01-28Not applicableUs
Alprazolamtablet1 mg/1oralBoca Pharmacal, LLC2010-10-15Not applicableUs
Alprazolamtablet.25 mg/1oralAurobindo Pharma Limited2015-07-31Not applicableUs
Alprazolamtablet1 mg/1oralAphena Pharma Solutions Tennessee, Llc1995-12-29Not applicableUs
Alprazolamtablet, extended release1 mg/1oralPreferred Pharmaceuticals, Inc.2012-11-15Not applicableUs
Alprazolamtablet1 mg/1oralAmerican Health Packaging2013-05-282015-12-29Us
Alprazolamtablet, orally disintegrating.5 mg/1oralActavis Elizabeth LLC2010-03-16Not applicableUs
Alprazolamtablet, extended release1 mg/1oralA S Medication Solutions Llc2011-05-04Not applicableUs
Alprazolamtablet.5 mg/1oralCardinal Health1993-10-31Not applicableUs
Alprazolamtablet, extended release2 mg/1oralApotex Corp2008-11-12Not applicableUs
Alprazolamtablet.5 mg/1oralTYA Pharmaceuticals2010-06-18Not applicableUs
Alprazolamtablet.5 mg/1oralContract Pharmacy Services Pa2011-03-25Not applicableUs
Alprazolamtablet.5 mg/1oralPreferred Pharmaceuticals, Inc.1999-12-29Not applicableUs
Alprazolamtablet.5 mg/1oralBionpharma Inc.2015-10-01Not applicableUs
Alprazolamtablet2 mg/1oralPd Rx Pharmaceuticals, Inc.1998-03-25Not applicableUs
Alprazolamtablet2 mg/1oralMylan Pharmaceuticals Inc.1994-01-28Not applicableUs
Alprazolamtablet.25 mg/1oralActavis Pharma, Inc.1995-01-03Not applicableUs
Alprazolamtablet.5 mg/1oralMajor Pharmaceuticals2008-04-02Not applicableUs
Alprazolamtablet1 mg/1oralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2010-06-18Not applicableUs
Alprazolamtablet.25 mg/1oralSun Pharma Global FZE2010-06-18Not applicableUs
Alprazolamtablet2 mg/1oralA S Medication Solutions Llc2010-10-15Not applicableUs
Alprazolamtablet1 mg/1oralMylan Institutional Inc.1998-10-23Not applicableUs
Alprazolamtablet.5 mg/1oralCardinal Health2007-03-28Not applicableUs
Alprazolamtablet2 mg/1oralGolden State Medical Supply, Inc.1993-10-19Not applicableUs
Alprazolamtablet.5 mg/1oralProficient Rx LP1995-12-29Not applicableUs
Alprazolamtablet.5 mg/1oralBoca Pharmacal, LLC2010-10-15Not applicableUs
Alprazolamtablet, extended release3 mg/1oralAurobindo Pharma Limited2011-06-07Not applicableUs
Alprazolamtablet.25 mg/1oralAphena Pharma Solutions Tennessee, Llc1995-12-29Not applicableUs
Alprazolamtablet, extended release1 mg/1oralPreferred Pharmaceuticals, Inc.2013-04-22Not applicableUs
Alprazolamtablet.5 mg/1oralAmerican Health Packaging2013-05-282015-12-29Us
Alprazolamtablet, orally disintegrating.25 mg/1oralActavis Elizabeth LLC2010-03-16Not applicableUs
Alprazolamtablet, extended release1 mg/1oralGlobal Pharmaceuticals, Division of Impax Laboratories Inc.2007-05-24Not applicableUs
Alprazolamtablet.5 mg/1oralNcs Health Care Of Ky, Inc Dba Vangard Labs1995-01-03Not applicableUs
Alprazolamtablet.25 mg/1oralBlenheim Pharmacal, Inc.2013-05-22Not applicableUs
Alprazolamtablet, extended release2 mg/1oralRebel Distributors Corp.2009-12-03Not applicableUs
Alprazolamtablet.25 mg/1oralPd Rx Pharmaceuticals, Inc.2007-03-28Not applicableUs
Alprazolamtablet, orally disintegrating2 mg/1oralPar Pharmaceutical Inc.2009-01-09Not applicableUs
Alprazolamtablet2 mg/1oralA S Medication Solutions Llc2010-10-15Not applicableUs
Alprazolamtablet.25 mg/1oralCardinal Health1993-10-31Not applicableUs
Alprazolamtablet, extended release1 mg/1oralApotex Corp2008-11-12Not applicableUs
Alprazolamtablet, extended release.5 mg/1oralProficient Rx LP2011-06-07Not applicableUs
Alprazolamtablet.25 mg/1oralContract Pharmacy Services Pa2011-03-25Not applicableUs
Alprazolamtablet.25 mg/1oralPreferred Pharmaceuticals, Inc.1999-12-29Not applicableUs
Alprazolamtablet.25 mg/1oralBionpharma Inc.2015-10-01Not applicableUs
Alprazolamtablet.25 mg/1oralPreferred Pharmaceuticals, Inc.2016-03-01Not applicableUs
Alprazolamtablet1 mg/1oralMylan Pharmaceuticals Inc.1994-01-28Not applicableUs
Alprazolamtablet.5 mg/1oralKAISER FOUNDATION HOSPITALS2008-07-14Not applicableUs
Alprazolamtablet.25 mg/1oralMajor Pharmaceuticals2008-04-02Not applicableUs
Alprazolamtablet.25 mg/1oralSTAT Rx USA LLC1993-10-31Not applicableUs
Alprazolamtablet1 mg/1oralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC1995-12-29Not applicableUs
Alprazolamtablet2 mg/1oralMedsource Pharmaceuticals1995-01-03Not applicableUs
Alprazolamtablet1 mg/1oralA S Medication Solutions Llc2010-06-18Not applicableUs
Alprazolamtablet.25 mg/1oralCardinal Health2007-12-03Not applicableUs
Alprazolamtablet.25 mg/1oralGolden State Medical Supply, Inc.1993-10-19Not applicableUs
Alprazolamtablet.25 mg/1oralDIRECT RX2014-01-01Not applicableUs
Alprazolamtablet.5 mg/1oralMc Kesson Packaging Services A Business Unit Of Mc Kesson Corporation2014-04-29Not applicableUs
Alprazolamtablet, extended release.5 mg/1oralAurobindo Pharma Limited2011-06-07Not applicableUs
Alprazolamtablet2 mg/1oralDAVA Pharmaceuticals, Inc.2007-03-28Not applicableUs
Alprazolamtablet.5 mg/1oralPreferred Pharmaceuticals, Inc.2010-06-18Not applicableUs
Alprazolamtablet.5 mg/1oralMc Kesson Contract Packaging2011-10-17Not applicableUs
Alprazolamtablet1 mg/1oralQualitest Pharmaceuticals2008-09-25Not applicableUs
Alprazolamtablet.25 mg/1oralBlenheim Pharmacal, Inc.2009-12-16Not applicableUs
Alprazolamtablet, extended release.5 mg/1oralRebel Distributors Corp.2009-12-03Not applicableUs
Alprazolamtablet.25 mg/1oralPd Rx Pharmaceuticals, Inc.2011-09-07Not applicableUs
Alprazolamtablet, orally disintegrating.25 mg/1oralPar Pharmaceutical Inc.2009-01-09Not applicableUs
Alprazolamtablet1 mg/1oralUnit Dose Services1995-12-29Not applicableUs
Alprazolamtablet.5 mg/1oralMylan Institutional Inc.1998-10-23Not applicableUs
Alprazolamtablet.25 mg/1oralCardinal Health2007-03-28Not applicableUs
Alprazolamtablet1 mg/1oralGolden State Medical Supply, Inc.1993-10-19Not applicableUs
Alprazolamtablet1 mg/1oralDIRECT RX2015-01-01Not applicableUs
Alprazolamtablet.25 mg/1oralBoca Pharmacal, LLC2010-10-15Not applicableUs
Alprazolamtablet, extended release2 mg/1oralAurobindo Pharma Limited2011-06-07Not applicableUs
Alprazolamtablet.5 mg/1oralRed Pharm2008-06-01Not applicableUs
Alprazolamtablet2 mg/1oralPreferred Pharmaceuticals Inc.2015-10-19Not applicableUs
Alprazolamtablet.25 mg/1oralAmerican Health Packaging2013-05-282015-12-29Us
Alprazolamtablet, extended release.5 mg/1oralGlobal Pharmaceuticals, Division of Impax Laboratories Inc.2007-05-24Not applicableUs
Alprazolamtablet.25 mg/1oralNcs Health Care Of Ky, Inc Dba Vangard Labs1995-01-03Not applicableUs
Alprazolamtablet2 mg/1oralBlenheim Pharmacal, Inc.2010-04-23Not applicableUs
Alprazolamtablet, extended release2 mg/1oralRebel Distributors Corp.2009-12-03Not applicableUs
Alprazolamtablet.5 mg/1oralPd Rx Pharmaceuticals, Inc.2007-03-28Not applicableUs
Alprazolamtablet, orally disintegrating1 mg/1oralPar Pharmaceutical Inc.2009-01-09Not applicableUs
Alprazolamtablet1 mg/1oralA S Medication Solutions Llc2008-09-25Not applicableUs
Alprazolamtablet.25 mg/1oralCardinal Health2009-12-31Not applicableUs
Alprazolamtablet, extended release.5 mg/1oralApotex Corp2008-11-12Not applicableUs
Alprazolamtablet, extended release1 mg/1oralProficient Rx LP2011-06-07Not applicableUs
Alprazolamtablet1 mg/1oralDispensing Solutions, Inc.2008-09-25Not applicableUs
Alprazolamtablet1 mg/1oralPreferred Pharmaceuticals, Inc.1999-12-29Not applicableUs
Alprazolamtablet1 mg/1oralPreferred Pharmaceuticals, Inc.2015-04-16Not applicableUs
Alprazolamtablet.5 mg/1oralMylan Pharmaceuticals Inc.2010-02-25Not applicableUs
Alprazolamtablet.25 mg/1oralKAISER FOUNDATION HOSPITALS2008-07-14Not applicableUs
Alprazolamtablet2 mg/1oralSandoz Inc1998-03-25Not applicableUs
Alprazolamtablet1 mg/1oralSTAT Rx USA LLC2011-03-25Not applicableUs
Alprazolamtablet, extended release1 mg/1oralAidarex Pharmaceuticals LLC2009-12-03Not applicableUs
Alprazolamtablet, extended release1 mg/1oralMedsource Pharmaceuticals2011-06-07Not applicableUs
Alprazolamtablet.5 mg/1oralA S Medication Solutions Llc2010-06-18Not applicableUs
Alprazolam ERtablet, extended release2 mg/1oralSTAT Rx USA LLC2007-03-28Not applicableUs
Alprazolam Extended Releasetablet, extended release.5 mg/1oralActavis Elizabeth LLC2007-02-13Not applicableUs
Alprazolam Extended Releasetablet, extended release3 mg/1oralActavis Elizabeth LLC2007-02-13Not applicableUs
Alprazolam Extended Releasetablet, extended release1 mg/1oralCore Pharma, Llc2007-03-282016-03-16Us
Alprazolam Extended Releasetablet, extended release.5 mg/1oralbryant ranch prepack2007-02-13Not applicableUs
Alprazolam Extended Releasetablet, extended release.5 mg/1oralCore Pharma, Llc2007-03-282016-03-16Us
Alprazolam Extended Releasetablet, extended release3 mg/1oralCore Pharma, Llc2007-03-282016-03-16Us
Alprazolam Extended Releasetablet, extended release1 mg/1oralActavis Elizabeth LLC2007-02-13Not applicableUs
Alprazolam Extended Releasetablet, extended release2 mg/1oralActavis Elizabeth LLC2007-02-13Not applicableUs
Alprazolam Extended Releasetablet, extended release2 mg/1oralCore Pharma, Llc2007-03-282016-03-16Us
Alprazolam Extended-releasetablet, extended release.5 mg/1oralbryant ranch prepack2007-03-28Not applicableUs
Alprazolam Extended-releasetablet, extended release1 mg/1oralH.J. Harkins Company, Inc.2007-03-28Not applicableUs
Alprazolam Extended-releasetablet, extended release.5 mg/1oralbryant ranch prepack2007-03-28Not applicableUs
Apo-alpraztablet1 mgoralApotex Inc2001-04-16Not applicableCanada
Apo-alpraz Tab 0.25mgtablet0.25 mgoralApotex Inc1990-12-31Not applicableCanada
Apo-alpraz Tab 0.5mgtablet.5 mgoralApotex Inc1990-12-31Not applicableCanada
Apo-alpraz Tstablet2 mgoralApotex Inc2001-04-16Not applicableCanada
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not 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 mixtures
NameLabellerIngredients
GabazolaminePhysician Therapeutics Llc
Gabazolamine-0.5Physician Therapeutics Llc
Sentrazolam AmPhysician Therapeutics Llc
SaltsNot Available
Categories
UNIIYU55MQ3IZY
CAS number28981-97-7
WeightAverage: 308.765
Monoisotopic: 308.082874143
Chemical FormulaC17H13ClN4
InChI KeyInChIKey=VREFGVBLTWBCJP-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[8.4.0.0²,⁶]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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 1,4-benzodiazepines. These are organic compounds containing a benzene ring fused to a 1,4-azepine.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzodiazepines
Sub Class1,4-benzodiazepines
Direct Parent1,4-benzodiazepines
Alternative Parents
Substituents
  • 1,4-benzodiazepine
  • Phenyl-1,3,4-triazole
  • Phenyl-1,2,4-triazole
  • Phenyltriazole
  • Chlorobenzene
  • Benzenoid
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl chloride
  • Heteroaromatic compound
  • 1,2,4-triazole
  • Triazole
  • Azole
  • Ketimine
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Imine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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.
Related Articles
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
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9794
Caco-2 permeable+0.8867
P-glycoprotein substrateNon-substrate0.5099
P-glycoprotein inhibitor INon-inhibitor0.7301
P-glycoprotein inhibitor IIInhibitor0.8354
Renal organic cation transporterInhibitor0.7688
CYP450 2C9 substrateNon-substrate0.7907
CYP450 2D6 substrateNon-substrate0.9164
CYP450 3A4 substrateSubstrate0.7353
CYP450 1A2 substrateInhibitor0.8758
CYP450 2C9 inhibitorInhibitor0.8076
CYP450 2D6 inhibitorNon-inhibitor0.8137
CYP450 2C19 inhibitorInhibitor0.6519
CYP450 3A4 inhibitorNon-inhibitor0.6308
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8913
Ames testNon AMES toxic0.8957
CarcinogenicityNon-carcinogens0.6779
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.3717 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.973
hERG inhibition (predictor II)Non-inhibitor0.8733
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
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
Tabletoral0.50 mg
Tabletoral25 mg/1
Tablet, extended releaseoral.5 mg/1
Tablet, extended releaseoral1 mg/1
Tablet, extended releaseoral2 mg/1
Tablet, extended releaseoral3 mg/1
Tablet, orally disintegratingoral.25 mg/1
Tablet, orally disintegratingoral.5 mg/1
Tablet, orally disintegratingoral1 mg/1
Tablet, orally disintegratingoral2 mg/1
Tabletoral.25 mg
Tabletoral0.25 mg
Tabletoral.5 mg
Kit
Tabletoral0.5 mg
Tabletoral.25 mg/1
Tabletoral.5 mg/1
Tabletoral1 mg/1
Tabletoral2 mg/1
Tabletoral1 mg
Tabletoral2 mg
Prices
Unit descriptionCostUnit
ALPRAZolam Intensol 1 mg/ml Concentrate 30ml Bottle67.03USD bottle
Niravam 2 mg Dispersible Tablet8.53USD dispersible tablet
Xanax xr 3 mg tablet7.25USD tablet
Xanax XR 3 mg 24 Hour tablet7.1USD tablet
Niravam 2 mg tablet6.86USD tablet
Niravam 1 mg Dispersible Tablet5.42USD dispersible tablet
Xanax xr 2 mg tablet4.84USD tablet
Xanax XR 2 mg 24 Hour tablet4.73USD tablet
Niravam 0.5 mg Dispersible Tablet4.2USD dispersible tablet
Niravam 1 mg tablet4.04USD tablet
Xanax 2 mg tablet3.82USD tablet
ALPRAZolam 3 mg 24 Hour tablet3.67USD tablet
Xanax XR 1 mg 24 Hour tablet3.64USD tablet
Xanax xr 1 mg tablet3.64USD tablet
Niravam 0.25 mg Dispersible Tablet3.45USD dispersible tablet
Niravam 0.5 mg tablet3.02USD tablet
Xanax XR 0.5 mg 24 Hour tablet3.01USD tablet
Xanax xr 0.5 mg tablet2.93USD tablet
ALPRAZolam 2 mg 24 Hour tablet2.53USD tablet
Niravam 0.25 mg tablet2.43USD tablet
ALPRAZolam 1 mg 24 Hour tablet2.33USD tablet
Xanax 1 mg tablet2.29USD tablet
Alprazolam 1 mg/ml oral conc2.23USD ml
Xanax 0.5 mg tablet1.3USD tablet
Alprazolam 2 mg tablet1.22USD tablet
Xanax 0.25 mg tablet1.09USD tablet
ALPRAZolam 0.5 mg 24 Hour tablet1.07USD tablet
Alprazolam 1 mg tablet0.78USD tablet
Alprazolam 0.5 mg tablet0.67USD tablet
Alprazolam 0.25 mg tablet0.55USD tablet
Apo-Alpraz 0.5 mg Tablet0.1USD tablet
Mylan-Alprazolam 0.5 mg Tablet0.1USD tablet
Novo-Alprazol 0.5 mg Tablet0.1USD tablet
Apo-Alpraz 0.25 mg Tablet0.08USD tablet
Mylan-Alprazolam 0.25 mg Tablet0.08USD tablet
Novo-Alprazol 0.25 mg Tablet0.08USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6024981 No1998-04-092018-04-09Us
US6221392 No1998-04-092018-04-09Us
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 Solubility0.0324 mg/mLALOGPS
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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
MSMass Spectrum (Electron Ionization)splash10-0kdi-4792000000-9f1cdda14e36000955d3View in MoNA
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 References
  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:2335496 ]
  2. Wolf B, Griffiths RR: Physical dependence on benzodiazepines: differences within the class. Drug Alcohol Depend. 1991 Dec 31;29(2):153-6. [PubMed:1686752 ]
  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:2300914 ]
  4. Hori A: Pharmacotherapy for personality disorders. Psychiatry Clin Neurosci. 1998 Feb;52(1):13-9. [PubMed:9682928 ]
  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:17453885 ]
External Links
ATC CodesN05BA12
AHFS Codes
  • 28:24.08
PDB EntriesNot Available
FDA labelDownload (63.6 KB)
MSDSDownload (47.3 KB)
Interactions
Drug Interactions
Drug
AminophyllineThe therapeutic efficacy of Alprazolam can be decreased when used in combination with Aminophylline.
AprepitantThe serum concentration of Alprazolam can be increased when it is combined with Aprepitant.
AripiprazoleThe serum concentration of Aripiprazole can be increased when it is combined with Alprazolam.
AtazanavirThe serum concentration of Alprazolam can be increased when it is combined with Atazanavir.
AzelastineAlprazolam may increase the central nervous system depressant (CNS depressant) activities of Azelastine.
BaclofenThe risk or severity of adverse effects can be increased when Baclofen is combined with Alprazolam.
BatimastatThe serum concentration of Alprazolam can be increased when it is combined with Batimastat.
BexaroteneThe serum concentration of Alprazolam can be decreased when it is combined with Bexarotene.
BoceprevirThe serum concentration of Alprazolam can be increased when it is combined with Boceprevir.
BosentanThe serum concentration of Alprazolam can be decreased when it is combined with Bosentan.
BrimonidineBrimonidine may increase the central nervous system depressant (CNS depressant) activities of Alprazolam.
BuprenorphineAlprazolam may increase the central nervous system depressant (CNS depressant) activities of Buprenorphine.
ClarithromycinThe serum concentration of Alprazolam can be increased when it is combined with Clarithromycin.
ClozapineThe risk or severity of adverse effects can be increased when Alprazolam is combined with Clozapine.
ConivaptanThe serum concentration of Alprazolam can be increased when it is combined with Conivaptan.
DabrafenibThe serum concentration of Alprazolam can be decreased when it is combined with Dabrafenib.
DarunavirThe serum concentration of Alprazolam can be increased when it is combined with Darunavir.
DasatinibThe serum concentration of Alprazolam can be increased when it is combined with Dasatinib.
DeferasiroxThe serum concentration of Alprazolam can be decreased when it is combined with Deferasirox.
DofetilideThe serum concentration of Dofetilide can be increased when it is combined with Alprazolam.
DoxylamineDoxylamine may increase the central nervous system depressant (CNS depressant) activities of Alprazolam.
DronabinolDronabinol may increase the central nervous system depressant (CNS depressant) activities of Alprazolam.
DroperidolDroperidol may increase the central nervous system depressant (CNS depressant) activities of Alprazolam.
DyphyllineThe therapeutic efficacy of Alprazolam can be decreased when used in combination with Dyphylline.
ErythromycinThe serum concentration of Alprazolam can be increased when it is combined with Erythromycin.
EthanolAlprazolam may increase the central nervous system depressant (CNS depressant) activities of Ethanol.
FlibanserinThe serum concentration of Flibanserin can be increased when it is combined with Alprazolam.
FluconazoleThe metabolism of Alprazolam can be decreased when combined with Fluconazole.
FluvoxamineThe serum concentration of Alprazolam can be increased when it is combined with Fluvoxamine.
FosamprenavirThe serum concentration of Alprazolam can be increased when it is combined with Fosamprenavir.
FosaprepitantThe serum concentration of Alprazolam can be increased when it is combined with Fosaprepitant.
FosphenytoinThe serum concentration of Fosphenytoin can be increased when it is combined with Alprazolam.
Fusidic AcidThe serum concentration of Alprazolam can be increased when it is combined with Fusidic Acid.
Gamma Hydroxybutyric AcidAlprazolam may increase the central nervous system depressant (CNS depressant) activities of Gamma Hydroxybutyric Acid.
HydrocodoneAlprazolam may increase the central nervous system depressant (CNS depressant) activities of Hydrocodone.
HydroxyzineHydroxyzine may increase the central nervous system depressant (CNS depressant) activities of Alprazolam.
IdelalisibThe serum concentration of Alprazolam can be increased when it is combined with Idelalisib.
IndinavirThe serum concentration of Alprazolam can be increased when it is combined with Indinavir.
IsoflurophateThe serum concentration of Alprazolam can be increased when it is combined with Isoflurophate.
ItraconazoleThe serum concentration of Alprazolam can be increased when it is combined with Itraconazole.
IvacaftorThe serum concentration of Alprazolam can be increased when it is combined with Ivacaftor.
KetoconazoleThe serum concentration of Alprazolam can be increased when it is combined with Ketoconazole.
LomitapideThe serum concentration of Lomitapide can be increased when it is combined with Alprazolam.
LorazepamThe risk or severity of adverse effects can be increased when Lorazepam is combined with Alprazolam.
LuliconazoleThe serum concentration of Alprazolam can be increased when it is combined with Luliconazole.
Magnesium SulfateMagnesium Sulfate may increase the central nervous system depressant (CNS depressant) activities of Alprazolam.
MethadoneAlprazolam may increase the central nervous system depressant (CNS depressant) activities of Methadone.
MethotrimeprazineAlprazolam may increase the central nervous system depressant (CNS depressant) activities of Methotrimeprazine.
MetyrosineAlprazolam may increase the sedative activities of Metyrosine.
MifepristoneThe serum concentration of Alprazolam can be increased when it is combined with Mifepristone.
MinocyclineMinocycline may increase the central nervous system depressant (CNS depressant) activities of Alprazolam.
MirtazapineAlprazolam may increase the central nervous system depressant (CNS depressant) activities of Mirtazapine.
MitotaneThe serum concentration of Alprazolam can be decreased when it is combined with Mitotane.
NabiloneNabilone may increase the central nervous system depressant (CNS depressant) activities of Alprazolam.
NelfinavirThe serum concentration of Alprazolam can be increased when it is combined with Nelfinavir.
NetupitantThe serum concentration of Alprazolam can be increased when it is combined with Netupitant.
NimodipineThe serum concentration of Nimodipine can be increased when it is combined with Alprazolam.
OlanzapineThe risk or severity of adverse effects can be increased when Olanzapine is combined with Alprazolam.
OrphenadrineAlprazolam may increase the central nervous system depressant (CNS depressant) activities of Orphenadrine.
PalbociclibThe serum concentration of Alprazolam can be increased when it is combined with Palbociclib.
ParaldehydeAlprazolam may increase the central nervous system depressant (CNS depressant) activities of Paraldehyde.
ParoxetineThe risk or severity of adverse effects can be increased when Alprazolam is combined with Paroxetine.
PerampanelPerampanel may increase the central nervous system depressant (CNS depressant) activities of Alprazolam.
PhenytoinThe serum concentration of Phenytoin can be increased when it is combined with Alprazolam.
PimozideThe serum concentration of Pimozide can be increased when it is combined with Alprazolam.
PramipexoleAlprazolam may increase the sedative activities of Pramipexole.
RitonavirThe serum concentration of Alprazolam can be increased when it is combined with Ritonavir.
RopiniroleAlprazolam may increase the sedative activities of Ropinirole.
RotigotineAlprazolam may increase the sedative activities of Rotigotine.
RufinamideThe risk or severity of adverse effects can be increased when Rufinamide is combined with Alprazolam.
SaquinavirThe serum concentration of Alprazolam can be increased when it is combined with Saquinavir.
SiltuximabThe serum concentration of Alprazolam can be decreased when it is combined with Siltuximab.
SimeprevirThe serum concentration of Alprazolam can be increased when it is combined with Simeprevir.
Sodium oxybateAlprazolam may increase the central nervous system depressant (CNS depressant) activities of Sodium oxybate.
St. John's WortThe serum concentration of Alprazolam can be decreased when it is combined with St. John's Wort.
StiripentolThe serum concentration of Alprazolam can be increased when it is combined with Stiripentol.
SuvorexantAlprazolam may increase the central nervous system depressant (CNS depressant) activities of Suvorexant.
TapentadolTapentadol may increase the central nervous system depressant (CNS depressant) activities of Alprazolam.
TeduglutideThe serum concentration of Alprazolam can be increased when it is combined with Teduglutide.
TelaprevirThe serum concentration of Alprazolam can be increased when it is combined with Telaprevir.
TelithromycinThe serum concentration of Alprazolam can be increased when it is combined with Telithromycin.
ThalidomideAlprazolam may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
TheophyllineThe therapeutic efficacy of Alprazolam can be decreased when used in combination with Theophylline.
TipranavirThe serum concentration of Alprazolam can be increased when it is combined with Tipranavir.
TocilizumabThe serum concentration of Alprazolam can be decreased when it is combined with Tocilizumab.
YohimbineThe therapeutic efficacy of Alprazolam can be decreased when used in combination with Yohimbine.
ZolpidemAlprazolam may increase the central nervous system depressant (CNS depressant) activities of Zolpidem.
Food Interactions
  • Avoid alcohol.
  • Avoid excessive quantities of coffee or tea (Caffeine).
  • Avoid taking with grapefruit juice.
  • Take with food.

Targets

Kind
Protein group
Organism
Human
Pharmacological action
yes
Actions
positive allosteric modulator
General Function:
Inhibitory extracellular ligand-gated ion channel activity
Specific Function:
Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine. Functions as receptor for diazepines and various anesthetics, such as pentobarbital; these are bound at a separate allosteric effector binding site. Functions as ligand-gated chloride channel (By similarity).
Components:
NameUniProt IDDetails
Gamma-aminobutyric acid receptor subunit alpha-1P14867 Details
Gamma-aminobutyric acid receptor subunit alpha-2P47869 Details
Gamma-aminobutyric acid receptor subunit alpha-3P34903 Details
Gamma-aminobutyric acid receptor subunit alpha-4P48169 Details
Gamma-aminobutyric acid receptor subunit alpha-5P31644 Details
Gamma-aminobutyric acid receptor subunit alpha-6Q16445 Details
Gamma-aminobutyric acid receptor subunit beta-1P18505 Details
Gamma-aminobutyric acid receptor subunit beta-2P47870 Details
Gamma-aminobutyric acid receptor subunit beta-3P28472 Details
Gamma-aminobutyric acid receptor subunit deltaO14764 Details
Gamma-aminobutyric acid receptor subunit epsilonP78334 Details
Gamma-aminobutyric acid receptor subunit gamma-1Q8N1C3 Details
Gamma-aminobutyric acid receptor subunit gamma-2P18507 Details
Gamma-aminobutyric acid receptor subunit gamma-3Q99928 Details
Gamma-aminobutyric acid receptor subunit piO00591 Details
Gamma-aminobutyric acid receptor subunit thetaQ9UN88 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.x. Epub 2008 Mar 31. [PubMed:18384456 ]
  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:14978513 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
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:19515014 ]
  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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  3. 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:12124305 ]
  4. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular Weight:
55627.365 Da
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:19515014 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxygen binding
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular Weight:
57108.065 Da
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:19515014 ]
  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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  3. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxygen binding
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A7
Uniprot ID:
P24462
Molecular Weight:
57525.03 Da
References
  1. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
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Drug created on June 13, 2005 07:24 / Updated on July 26, 2016 01:52