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Identification
NameEnalapril
Accession NumberDB00584  (APRD00510)
TypeSmall Molecule
GroupsApproved, Vet Approved
Description

Enalapril is a prodrug that belongs to the angiotensin-converting enzyme (ACE) inhibitor class of medications. It is rapidly metabolized in the liver to enalaprilat following oral administration. Enalaprilat is a potent, competitive inhibitor of ACE, the enzyme responsible for the conversion of angiotensin I (ATI) to angiotensin II (ATII). ATII regulates blood pressure and is a key component of the renin-angiotensin-aldosterone system (RAAS). Enalapril may be used to treat essential or renovascular hypertension and symptomatic congestive heart failure.

Structure
Thumb
Synonyms
(S)-1-(N-(1-(Ethoxycarbonyl)-3-phenylpropyl)-L-alanyl)-L-proline
(S)-1-{(S)-2-[1-((S)-ethoxycarbonyl)-3-phenyl-propylamino]-propionyl}-pyrrolidine-2-carboxylic acid
1-(N-((S)-1-Carboxy-3-phenylpropyl)-L-alanyl)-L-proline 1'-ethyl ester
Analapril
Enalapril
Enalaprila
Enalaprilum
External Identifiers
  • L 154739-01 D
  • MK 421
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act Enalapriltablet2 mgoralActavis Pharma Company2007-10-17Not applicableCanada
Act Enalapriltablet4 mgoralActavis Pharma Company2007-10-17Not applicableCanada
Act Enalapriltablet16 mgoralActavis Pharma Company2007-10-17Not applicableCanada
Act Enalapriltablet8 mgoralActavis Pharma Company2007-10-17Not applicableCanada
Ava-enalapriltablet10.0 mgoralAvanstra Inc2011-10-112014-08-21Canada
Ava-enalapriltablet20.0 mgoralAvanstra Inc2011-10-112014-08-21Canada
Ava-enalapriltablet5.0 mgoralAvanstra Inc2011-10-112014-08-21Canada
Ava-enalapriltablet2.5 mgoralAvanstra Inc2011-10-112014-08-21Canada
Dom-enalapriltablet16 mgoralDominion PharmacalNot applicableNot applicableCanada
Dom-enalapriltablet8 mgoralDominion PharmacalNot applicableNot applicableCanada
Dom-enalapriltablet4 mgoralDominion PharmacalNot applicableNot applicableCanada
Dom-enalapriltablet2.0 mgoralDominion PharmacalNot applicableNot applicableCanada
Enalapriltablet16 mgoralFrosst A Division Of Merck Canada IncNot applicableNot applicableCanada
Enalapriltablet8 mgoralFrosst A Division Of Merck Canada IncNot applicableNot applicableCanada
Enalapriltablet4 mgoralFrosst A Division Of Merck Canada IncNot applicableNot applicableCanada
Enalapriltablet16 mgoralSivem Pharmaceuticals Ulc2015-08-10Not applicableCanada
Enalapriltablet2 mgoralFrosst A Division Of Merck Canada IncNot applicableNot applicableCanada
Enalapriltablet16 mgoralSanis Health Inc2013-02-13Not applicableCanada
Enalapriltablet8 mgoralSivem Pharmaceuticals Ulc2015-08-10Not applicableCanada
Enalapriltablet16 mgoralCobalt Pharmaceuticals CompanyNot applicableNot applicableCanada
Enalapriltablet8 mgoralSanis Health Inc2013-02-13Not applicableCanada
Enalapriltablet4 mgoralSivem Pharmaceuticals Ulc2015-08-10Not applicableCanada
Enalapriltablet8.0 mgoralCobalt Pharmaceuticals CompanyNot applicableNot applicableCanada
Enalapriltablet4 mgoralSanis Health Inc2013-02-13Not applicableCanada
Enalapriltablet2 mgoralSivem Pharmaceuticals Ulc2015-08-10Not applicableCanada
Enalapriltablet4.0 mgoralCobalt Pharmaceuticals CompanyNot applicableNot applicableCanada
Enalapriltablet2 mgoralSanis Health Inc2013-02-13Not applicableCanada
Enalapriltablet2.0 mgoralCobalt Pharmaceuticals CompanyNot applicableNot applicableCanada
Enalapril Maleatetablet2.5 mg/1oralOceanside Pharmaceuticals1988-07-26Not applicableUs
Enalapril Maleatetablet20 mg/1oralOceanside Pharmaceuticals1985-12-24Not applicableUs
Enalapril Maleatetablet10 mg/1oralOceanside Pharmaceuticals1985-12-24Not applicableUs
Enalapril Maleatetablet5 mg/1oralOceanside Pharmaceuticals1985-12-24Not applicableUs
EpanedkitSilvergate Pharmaceuticals, Inc.2013-08-22Not applicableUs
Ipg-enalapriltablet10 mgoralInternational Pharmaceutical Generics LtdNot applicableNot applicableCanada
Ipg-enalapriltablet20 mgoralInternational Pharmaceutical Generics LtdNot applicableNot applicableCanada
Mylan-enalapriltablet4 mgoralMylan Pharmaceuticals Ulc2007-10-17Not applicableCanada
Mylan-enalapriltablet2.0 mgoralMylan Pharmaceuticals Ulc2007-10-17Not applicableCanada
Mylan-enalapriltablet16 mgoralMylan Pharmaceuticals Ulc2007-10-17Not applicableCanada
Mylan-enalapriltablet8 mgoralMylan Pharmaceuticals Ulc2007-10-17Not applicableCanada
Ntp-enalapriltablet8 mgoralTeva Canada LimitedNot applicableNot applicableCanada
Ntp-enalapriltablet4 mgoralTeva Canada LimitedNot applicableNot applicableCanada
Ntp-enalapriltablet2 mgoralTeva Canada LimitedNot applicableNot applicableCanada
Ntp-enalapriltablet32 mgoralTeva Canada LimitedNot applicableNot applicableCanada
Ntp-enalapriltablet16 mgoralTeva Canada LimitedNot applicableNot applicableCanada
Nu-enalapriltablet20 mgoralNu Pharm IncNot applicableNot applicableCanada
Nu-enalapriltablet10 mgoralNu Pharm IncNot applicableNot applicableCanada
Nu-enalapriltablet5 mgoralNu Pharm IncNot applicableNot applicableCanada
Nu-enalapriltablet2.5 mgoralNu Pharm IncNot applicableNot applicableCanada
PMS-enalapriltablet16 mgoralPharmascience Inc2007-11-23Not applicableCanada
PMS-enalapriltablet8 mgoralPharmascience Inc2007-11-23Not applicableCanada
PMS-enalapriltablet4 mgoralPharmascience Inc2007-11-23Not applicableCanada
PMS-enalapriltablet2.0 mgoralPharmascience Inc2007-11-23Not applicableCanada
Pro-enalapril - 10tablet10 mgoralPro Doc Limitee2008-07-04Not applicableCanada
Pro-enalapril - 2.5tablet2.5 mgoralPro Doc Limitee2008-07-04Not applicableCanada
Pro-enalapril - 20tablet20 mgoralPro Doc Limitee2008-07-04Not applicableCanada
Pro-enalapril - 5tablet5 mgoralPro Doc Limitee2008-07-04Not applicableCanada
Ran-enalapriltablet8 mgoralRanbaxy Pharmaceuticals Canada Inc.2010-08-01Not applicableCanada
Ran-enalapriltablet4 mgoralRanbaxy Pharmaceuticals Canada Inc.2010-08-01Not applicableCanada
Ran-enalapriltablet2 mgoralRanbaxy Pharmaceuticals Canada Inc.2010-08-01Not applicableCanada
Ran-enalapriltablet16 mgoralRanbaxy Pharmaceuticals Canada Inc.2010-08-01Not applicableCanada
Ratio-enalapriltablet8.0 mgoralRatiopharm Inc Division Of Teva Canada Limited2007-10-172014-09-19Canada
Ratio-enalapriltablet4.0 mgoralRatiopharm Inc Division Of Teva Canada Limited2007-10-172014-09-19Canada
Ratio-enalapriltablet2.0 mgoralRatiopharm Inc Division Of Teva Canada Limited2007-10-172014-09-19Canada
Ratio-enalapriltablet16 mgoralRatiopharm Inc Division Of Teva Canada Limited2007-10-172014-09-19Canada
Riva-enalapriltablet16 mgoralLaboratoire Riva Inc2007-10-20Not applicableCanada
Riva-enalapriltablet8.0 mgoralLaboratoire Riva Inc2007-10-20Not applicableCanada
Riva-enalapriltablet4.0 mgoralLaboratoire Riva Inc2007-10-20Not applicableCanada
Riva-enalapriltablet2.0 mgoralLaboratoire Riva Inc2007-10-20Not applicableCanada
Sandoz Enalapriltablet16 mgoralSandoz Canada Incorporated2007-10-17Not applicableCanada
Sandoz Enalapriltablet8.0 mgoralSandoz Canada Incorporated2007-10-17Not applicableCanada
Sandoz Enalapriltablet4.0 mgoralSandoz Canada Incorporated2007-10-17Not applicableCanada
Sandoz Enalapriltablet2.0 mgoralSandoz Canada Incorporated2007-10-17Not applicableCanada
Sig-enalapriltablet16 mgoralSigmacon Lifesciences Inc2009-04-302015-08-02Canada
Sig-enalapriltablet8.0 mgoralSigmacon Lifesciences Inc2009-04-302015-08-02Canada
Sig-enalapriltablet4.0 mgoralSigmacon Lifesciences Inc2009-04-302015-08-02Canada
Sig-enalapriltablet2.0 mgoralSigmacon Lifesciences Inc2009-04-302015-08-02Canada
Taro-enalapriltablet4 mgoralTaro Pharmaceuticals Inc2007-11-06Not applicableCanada
Taro-enalapriltablet8 mgoralTaro Pharmaceuticals Inc2007-11-06Not applicableCanada
Taro-enalapriltablet2.0 mgoralTaro Pharmaceuticals Inc2007-11-06Not applicableCanada
Taro-enalapriltablet16 mgoralTaro Pharmaceuticals Inc2007-11-06Not applicableCanada
Teva-enalapriltablet16 mgoralTeva Canada Limited2007-10-17Not applicableCanada
Teva-enalapriltablet32 mgoralTeva Canada Limited2009-09-15Not applicableCanada
Teva-enalapriltablet8 mgoralTeva Canada Limited1998-08-31Not applicableCanada
Teva-enalapriltablet4 mgoralTeva Canada Limited1998-08-31Not applicableCanada
Teva-enalapriltablet2.0 mgoralTeva Canada Limited2007-10-17Not applicableCanada
Vasotectablet2.5 mg/1oralValeant Pharmaceuticals North America LLC1988-07-26Not applicableUs
Vasotectablet5 mg/1oralREMEDYREPACK INC.2015-02-25Not applicableUs
Vasotectablet20 mg/1oralREMEDYREPACK INC.2015-02-25Not applicableUs
Vasotectablet4 mgoralMerck Canada Inc1987-12-31Not applicableCanada
Vasotectablet10 mg/1oralREMEDYREPACK INC.2014-10-24Not applicableUs
Vasotectablet2 mgoralMerck Canada Inc1990-12-31Not applicableCanada
Vasotectablet16 mgoralMerck Canada Inc1987-12-31Not applicableCanada
Vasotectablet20 mg/1oralValeant Pharmaceuticals North America LLC1985-12-24Not applicableUs
Vasotectablet8 mgoralMerck Canada Inc1987-12-31Not applicableCanada
Vasotectablet10 mg/1oralValeant Pharmaceuticals North America LLC1985-12-24Not applicableUs
Vasotectablet5 mg/1oralValeant Pharmaceuticals North America LLC1985-12-24Not applicableUs
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-enalapril Tab 10mgtablet10 mgoralApotex Inc1993-12-31Not applicableCanada
Apo-enalapril Tab 2.5mgtablet2.5 mgoralApotex Inc1993-12-31Not applicableCanada
Apo-enalapril Tab 20mgtablet20 mgoralApotex Inc1993-12-31Not applicableCanada
Apo-enalapril Tab 5mgtablet5 mgoralApotex Inc1993-12-31Not applicableCanada
Enalapril Maleatetablet20 mg/1oralREMEDYREPACK INC.2013-05-15Not applicableUs
Enalapril Maleatetablet2.5 mg/1oralTaro Pharmaceuticals U.S.A., Inc.2001-01-23Not applicableUs
Enalapril Maleatetablet2.5 mg/1oralMajor Pharmaceuticals2004-02-03Not applicableUs
Enalapril Maleatetablet5 mg/1oralMylan Institutional Inc.2000-11-15Not applicableUs
Enalapril Maleatetablet2.5 mg/1oralNcs Health Care Of Ky, Inc Dba Vangard Labs2009-12-11Not applicableUs
Enalapril Maleatetablet5 mg/1oralCardinal Health2010-10-13Not applicableUs
Enalapril Maleatetablet2.5 mg/1oralTeva Pharmaceuticals USA Inc2000-08-23Not applicableUs
Enalapril Maleatetablet2.5 mg/1oralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs
Enalapril Maleatetablet5 mg/1oralbryant ranch prepack2009-12-11Not applicableUs
Enalapril Maleatetablet10 mg/1oralREMEDYREPACK INC.2013-05-23Not applicableUs
Enalapril Maleatetablet5 mg/1oralGolden State Medical Supply, Inc.2013-11-04Not applicableUs
Enalapril Maleatetablet20 mg/1oralAmerican Health Packaging2009-05-26Not applicableUs
Enalapril Maleatetablet10 mg/1oralPd Rx Pharmaceuticals, Inc.2009-12-11Not applicableUs
Enalapril Maleatetablet10 mg/1oralREMEDYREPACK INC.2013-06-14Not applicableUs
Enalapril Maleatetablet5 mg/1oralContract Pharmacy Services Pa2010-08-02Not applicableUs
Enalapril Maleatetablet2.5 mg/1oralNorthstar Rx LLC2015-08-06Not applicableUs
Enalapril Maleatetablet, soluble2.5 mg/1oralApace Packaging2009-08-22Not applicableUs
Enalapril Maleatetablet2.5 mg/1oralbryant ranch prepack2009-12-11Not applicableUs
Enalapril Maleatetablet10 mg/1oralMajor Pharmaceuticals2004-02-03Not applicableUs
Enalapril Maleatetablet5 mg/1oralGolden State Medical Supply, Inc.2011-05-122015-11-30Us
Enalapril Maleatetablet2.5 mg/1oralMylan Institutional Inc.2000-11-15Not applicableUs
Enalapril Maleatetablet2.5 mg/1oralLegacy Pharmaceutical Packaging, Llc2009-12-11Not applicableUs
Enalapril Maleatetablet20 mg/1oralTaro Pharmaceuticals U.S.A., Inc.2001-01-232016-02-06Us
Enalapril Maleatetablet, soluble5 mg/1oralApace Packaging2009-08-22Not applicableUs
Enalapril Maleatetablet20 mg/1oralREMEDYREPACK INC.2013-03-15Not applicableUs
Enalapril Maleatetablet20 mg/1oralMylan Pharmaceuticals Inc.2000-08-22Not applicableUs
Enalapril Maleatetablet10 mg/1oralCardinal Health2010-10-13Not applicableUs
Enalapril Maleatetablet2.5 mg/1oralState of Florida DOH Central Pharmacy2013-01-01Not applicableUs
Enalapril Maleatetablet10 mg/1oralDIRECT RX2015-12-03Not applicableUs
Enalapril Maleatetablet2.5 mg/1oralGolden State Medical Supply, Inc.2013-11-04Not applicableUs
Enalapril Maleatetablet10 mg/1oralAmerican Health Packaging2009-05-26Not applicableUs
Enalapril Maleatetablet10 mg/1oralREMEDYREPACK INC.2013-11-12Not applicableUs
Enalapril Maleatetablet20 mg/1oralDispensing Solutions, Inc.2009-12-11Not applicableUs
Enalapril Maleatetablet10 mg/1oralSTAT Rx USA LLC2009-12-11Not applicableUs
Enalapril Maleatetablet5 mg/1oralREMEDYREPACK INC.2016-01-22Not applicableUs
Enalapril Maleatetablet2.5 mg/1oralGolden State Medical Supply, Inc.2011-05-122015-11-30Us
Enalapril Maleatetablet5 mg/1oralUnit Dose Services2009-12-11Not applicableUs
Enalapril Maleatetablet10 mg/1oralTaro Pharmaceuticals U.S.A., Inc.2001-01-232016-02-06Us
Enalapril Maleatetablet5 mg/1oralREMEDYREPACK INC.2013-05-09Not applicableUs
Enalapril Maleatetablet20 mg/1oralNorthwind Pharmaceuticals, LLC2014-12-09Not applicableUs
Enalapril Maleatetablet5 mg/1oralMajor Pharmaceuticals2004-02-03Not applicableUs
Enalapril Maleatetablet5 mg/1oralSt Marys Medical Park Pharmacy2014-04-21Not applicableUs
Enalapril Maleatetablet20 mg/1oralWockhardt Limited2009-12-11Not applicableUs
Enalapril Maleatetablet5 mg/1oralAmerican Health Packaging2009-05-26Not applicableUs
Enalapril Maleatetablet20 mg/1oralRebel Distributors Corp2009-12-11Not applicableUs
Enalapril Maleatetablet5 mg/1oralTYA Pharmaceuticals2009-12-11Not applicableUs
Enalapril Maleatetablet20 mg/1oralBlenheim Pharmacal, Inc.2014-02-20Not applicableUs
Enalapril Maleatetablet20 mg/1oralREMEDYREPACK INC.2011-04-08Not applicableUs
Enalapril Maleatetablet5 mg/1oralPreferred Pharmaceuticals, Inc.2012-01-17Not applicableUs
Enalapril Maleatetablet10 mg/1oralUnit Dose Services2009-12-11Not applicableUs
Enalapril Maleatetablet5 mg/1oralTaro Pharmaceuticals U.S.A., Inc.2001-01-232016-02-06Us
Enalapril Maleatetablet5 mg/1oralREMEDYREPACK INC.2012-10-03Not applicableUs
Enalapril Maleatetablet20 mg/1oralMed Health Pharma, LLC2011-01-01Not applicableUs
Enalapril Maleatetablet20 mg/1oralNcs Health Care Of Ky, Inc Dba Vangard Labs2000-08-22Not applicableUs
Enalapril Maleatetablet10 mg/1oralMylan Pharmaceuticals Inc.2000-08-22Not applicableUs
Enalapril Maleatetablet5 mg/1oralCardinal Health2004-02-03Not applicableUs
Enalapril Maleatetablet2.5 mg/1oralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs
Enalapril Maleatetablet10 mg/1oralPreferred Pharmaceuticals, Inc.2012-01-17Not applicableUs
Enalapril Maleatetablet2.5 mg/1oralUnit Dose Services2009-12-11Not applicableUs
Enalapril Maleatetablet2.5 mg/1oralTaro Pharmaceuticals U.S.A., Inc.2001-01-232016-02-06Us
Enalapril Maleatetablet20 mg/1oralREMEDYREPACK INC.2013-03-14Not applicableUs
Enalapril Maleatetablet10 mg/1oralMed Health Pharma, LLC2011-01-01Not applicableUs
Enalapril Maleatetablet10 mg/1oralNcs Health Care Of Ky, Inc Dba Vangard Labs2000-08-22Not applicableUs
Enalapril Maleatetablet5 mg/1oralMylan Pharmaceuticals Inc.2000-08-22Not applicableUs
Enalapril Maleatetablet10 mg/1oralCardinal Health2004-02-03Not applicableUs
Enalapril Maleatetablet20 mg/1oralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs
Enalapril Maleatetablet20 mg/1oralSt Marys Medical Park Pharmacy2014-04-21Not applicableUs
Enalapril Maleatetablet10 mg/1oralWockhardt Limited2009-12-11Not applicableUs
Enalapril Maleatetablet20 mg/1oralContract Pharmacy Services Pa2010-08-02Not applicableUs
Enalapril Maleatetablet10 mg/1oralRebel Distributors Corp2009-12-11Not applicableUs
Enalapril Maleatetablet20 mg/1oralWockhardt USA LLC.2009-12-11Not applicableUs
Enalapril Maleatetablet10 mg/1oralBlenheim Pharmacal, Inc.2014-02-20Not applicableUs
Enalapril Maleatetablet5 mg/1oralREMEDYREPACK INC.2013-03-11Not applicableUs
Enalapril Maleatetablet5 mg/1oralMed Health Pharma, LLC2011-01-01Not applicableUs
Enalapril Maleatetablet5 mg/1oralNcs Health Care Of Ky, Inc Dba Vangard Labs2000-08-22Not applicableUs
Enalapril Maleatetablet2.5 mg/1oralMylan Pharmaceuticals Inc.2000-08-22Not applicableUs
Enalapril Maleatetablet10 mg/1oralPhysicians Total Care, Inc.2000-11-29Not applicableUs
Enalapril Maleatetablet20 mg/1oralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs
Enalapril Maleatetablet2.5 mg/1oralSt Marys Medical Park Pharmacy2014-01-23Not applicableUs
Enalapril Maleatetablet5 mg/1oralWockhardt Limited2009-12-11Not applicableUs
Enalapril Maleatetablet10 mg/1oralContract Pharmacy Services Pa2010-08-02Not applicableUs
Enalapril Maleatetablet5 mg/1oralRebel Distributors Corp2009-12-11Not applicableUs
Enalapril Maleatetablet10 mg/1oralWockhardt USA LLC.2009-12-11Not applicableUs
Enalapril Maleatetablet5 mg/1oralBlenheim Pharmacal, Inc.2013-12-10Not applicableUs
Enalapril Maleatetablet20 mg/1oralPreferred Pharmaceuticals, Inc.2012-01-17Not applicableUs
Enalapril Maleatetablet2.5 mg/1oralUnit Dose Services2009-12-11Not applicableUs
Enalapril Maleatetablet5 mg/1oralLake Erie Medical DBA Quality Care Products LLC2009-12-11Not applicableUs
Enalapril Maleatetablet20 mg/1oralTaro Pharmaceuticals U.S.A., Inc.2001-01-23Not applicableUs
Enalapril Maleatetablet2.5 mg/1oralMed Health Pharma, LLC2011-01-01Not applicableUs
Enalapril Maleatetablet20 mg/1oralNcs Health Care Of Ky, Inc Dba Vangard Labs2009-12-11Not applicableUs
Enalapril Maleatetablet20 mg/1oralTeva Pharmaceuticals USA Inc2000-08-23Not applicableUs
Enalapril Maleatetablet5 mg/1oralPhysicians Total Care, Inc.2000-11-29Not applicableUs
Enalapril Maleatetablet10 mg/1oralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs
Enalapril Maleatetablet10 mg/1oralSt Marys Medical Park Pharmacy2014-01-23Not applicableUs
Enalapril Maleatetablet2.5 mg/1oralWockhardt Limited2009-12-11Not applicableUs
Enalapril Maleatetablet20 mg/1oralContract Pharmacy Services Pa2010-06-28Not applicableUs
Enalapril Maleatetablet20 mg/1oralNorthstar Rx LLC2015-08-06Not applicableUs
Enalapril Maleatetablet5 mg/1oralWockhardt USA LLC.2009-12-11Not applicableUs
Enalapril Maleatetablet10 mg/1oralBlenheim Pharmacal, Inc.2013-11-25Not applicableUs
Enalapril Maleatetablet20 mg/1oralLegacy Pharmaceutical Packaging, Llc2009-12-11Not applicableUs
Enalapril Maleatetablet20 mg/1oralUnit Dose Services2009-12-11Not applicableUs
Enalapril Maleatetablet20 mg/1oralLake Erie Medical DBA Quality Care Products LLC2009-12-11Not applicableUs
Enalapril Maleatetablet10 mg/1oralTaro Pharmaceuticals U.S.A., Inc.2001-01-23Not applicableUs
Enalapril Maleatetablet20 mg/1oralMylan Institutional Inc.2000-11-15Not applicableUs
Enalapril Maleatetablet10 mg/1oralNcs Health Care Of Ky, Inc Dba Vangard Labs2009-12-11Not applicableUs
Enalapril Maleatetablet10 mg/1oralTeva Pharmaceuticals USA Inc2000-08-23Not applicableUs
Enalapril Maleatetablet2.5 mg/1oralPhysicians Total Care, Inc.2002-09-12Not applicableUs
Enalapril Maleatetablet5 mg/1oralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs
Enalapril Maleatetablet20 mg/1oralGolden State Medical Supply, Inc.2013-11-04Not applicableUs
Enalapril Maleatetablet20 mg/1oralPd Rx Pharmaceuticals, Inc.2009-12-11Not applicableUs
Enalapril Maleatetablet10 mg/1oralContract Pharmacy Services Pa2010-04-07Not applicableUs
Enalapril Maleatetablet10 mg/1oralNorthstar Rx LLC2015-08-06Not applicableUs
Enalapril Maleatetablet2.5 mg/1oralWockhardt USA LLC.2009-12-11Not applicableUs
Enalapril Maleatetablet10 mg/1oralBlenheim Pharmacal, Inc.2011-04-18Not applicableUs
Enalapril Maleatetablet10 mg/1oralLegacy Pharmaceutical Packaging, Llc2009-12-11Not applicableUs
Enalapril Maleatetablet2.5 mg/1oralREMEDYREPACK INC.2011-10-11Not applicableUs
Enalapril Maleatetablet, soluble20 mg/1oralApace Packaging2009-08-22Not applicableUs
Enalapril Maleatetablet10 mg/1oralLake Erie Medical DBA Quality Care Products LLC2009-12-11Not applicableUs
Enalapril Maleatetablet5 mg/1oralTaro Pharmaceuticals U.S.A., Inc.2001-01-23Not applicableUs
Enalapril Maleatetablet10 mg/1oralMylan Institutional Inc.2000-11-15Not applicableUs
Enalapril Maleatetablet5 mg/1oralNcs Health Care Of Ky, Inc Dba Vangard Labs2009-12-11Not applicableUs
Enalapril Maleatetablet5 mg/1oralTeva Pharmaceuticals USA Inc2000-08-23Not applicableUs
Enalapril Maleatetablet20 mg/1oralPhysicians Total Care, Inc.2002-01-02Not applicableUs
Enalapril Maleatetablet10 mg/1oralREMEDYREPACK INC.2014-06-03Not applicableUs
Enalapril Maleatetablet10 mg/1oralGolden State Medical Supply, Inc.2013-11-04Not applicableUs
Enalapril Maleatetablet5 mg/1oralPd Rx Pharmaceuticals, Inc.2009-12-11Not applicableUs
Enalapril Maleatetablet5 mg/1oralContract Pharmacy Services Pa2010-04-07Not applicableUs
Enalapril Maleatetablet5 mg/1oralNorthstar Rx LLC2015-08-06Not applicableUs
Enalapril Maleatetablet10 mg/1oralbryant ranch prepack2009-12-11Not applicableUs
Enalapril Maleatetablet20 mg/1oralMajor Pharmaceuticals2004-02-03Not applicableUs
Enalapril Maleatetablet10 mg/1oralGolden State Medical Supply, Inc.2011-05-122015-11-30Us
Enalapril Maleatetablet5 mg/1oralLegacy Pharmaceutical Packaging, Llc2009-12-11Not applicableUs
Enalapril Maleatetablet2.5 mg/1oralREMEDYREPACK INC.2011-10-05Not applicableUs
Enalapril Maleatetablet, soluble10 mg/1oralApace Packaging2009-08-22Not applicableUs
Enalapril Maleatetablet2.5 mg/1oralLake Erie Medical DBA Quality Care Products LLC2000-08-22Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AcetecAlphapharm
AcetensilGrünenthal
AlaprenRanbaxy
AmotacMass Pharma
AmpraceMerck Sharp & Dohme
DilvasCipla
DiotensilMintlab
DrepatilFada
EnaceAbbott
EnaHexalSandoz
EnalEast West
EnalapotenDel Bel
EnprilWockhardt
FeliberalSilanes
GadoprilGador (Argentina)
GliotenBago
KinfilNova Argentia (Argentina)
Vasotec IVSandoz (Canada)
Brand mixtures
NameLabellerIngredients
Apo-enalapril Maleate/hctzApotex Inc
Enalapril Maleate and HydrochlorothiazideTeva Pharmaceuticals USA Inc
Enalapril/hctzFrosst A Division Of Merck Canada Inc
Teva-enalapril/hctzTeva Canada Limited
VasereticValeant Pharmaceuticals North America LLC
Salts
Name/CASStructureProperties
Enalapril maleate
ThumbNot applicableDBSALT001036
Enalapril sodium
ThumbNot applicableDBSALT001143
Categories
UNII69PN84IO1A
CAS number75847-73-3
WeightAverage: 376.4467
Monoisotopic: 376.199822016
Chemical FormulaC20H28N2O5
InChI KeyInChIKey=GBXSMTUPTTWBMN-XIRDDKMYSA-N
InChI
InChI=1S/C20H28N2O5/c1-3-27-20(26)16(12-11-15-8-5-4-6-9-15)21-14(2)18(23)22-13-7-10-17(22)19(24)25/h4-6,8-9,14,16-17,21H,3,7,10-13H2,1-2H3,(H,24,25)/t14-,16-,17-/m0/s1
IUPAC Name
(2S)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]pyrrolidine-2-carboxylic acid
SMILES
CCOC(=O)[[email protected]](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N1CCC[[email protected]]1C(O)=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentPeptides
Alternative Parents
Substituents
  • Alpha peptide
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Alpha-amino acid ester
  • Alpha-amino acid amide
  • Phenylpropylamine
  • Alpha-amino acid or derivatives
  • N-substituted-alpha-amino acid
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine carboxylic acid
  • N-acylpyrrolidine
  • Aralkylamine
  • Fatty acid ester
  • Fatty acyl
  • Benzenoid
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Tertiary amine
  • Carboxylic acid ester
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Secondary aliphatic amine
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationFor the treatment of essential or renovascular hypertension and symptomatic congestive heart failure. It may be used alone or in combination with thiazide diuretics.
PharmacodynamicsEnalapril is a prodrug that is rapidly metabolized by liver esterases to enalaprilat following oral administration. Enalapril itself has little pharmacologic activity. Enalaprilat lowers blood pressure by antagonizing the effect of the RAAS. The RAAS is a homeostatic mechanism for regulating hemodynamics, water and electrolyte balance. During sympathetic stimulation or when renal blood pressure or blood flow is reduced, renin is released from the granular cells of the juxtaglomerular apparatus in the kidneys. In the blood stream, renin cleaves circulating angiotensinogen to ATI, which is subsequently cleaved to ATII by ACE. ATII increases blood pressure using a number of mechanisms. First, it stimulates the secretion of aldosterone from the adrenal cortex. Aldosterone travels to the distal convoluted tubule (DCT) and collecting tubule of nephrons where it increases sodium and water reabsorption by increasing the number of sodium channels and sodium-potassium ATPases on cell membranes. Second, ATII stimulates the secretion of vasopressin (also known as antidiuretic hormone or ADH) from the posterior pituitary gland. ADH stimulates further water reabsorption from the kidneys via insertion of aquaporin-2 channels on the apical surface of cells of the DCT and collecting tubules. Third, ATII increases blood pressure through direct arterial vasoconstriction. Stimulation of the Type 1 ATII receptor on vascular smooth muscle cells leads to a cascade of events resulting in myocyte contraction and vasoconstriction. In addition to these major effects, ATII induces the thirst response via stimulation of hypothalamic neurons. ACE inhibitors inhibit the rapid conversion of ATI to ATII and antagonize RAAS-induced increases in blood pressure. ACE (also known as kininase II) is also involved in the enzymatic deactivation of bradykinin, a vasodilator. Inhibiting the deactivation of bradykinin increases bradykinin levels and may sustain the effects of enalaprilat by causing increased vasodilation and decreased blood pressure.
Mechanism of actionThere are two isoforms of ACE: the somatic isoform, which exists as a glycoprotein comprised of a single polypeptide chain of 1277; and the testicular isoform, which has a lower molecular mass and is thought to play a role in sperm maturation and binding of sperm to the oviduct epithelium. Somatic ACE has two functionally active domains, N and C, which arise from tandem gene duplication. Although the two domains have high sequence similarity, they play distinct physiological roles. The C-domain is predominantly involved in blood pressure regulation while the N-domain plays a role in hematopoietic stem cell differentiation and proliferation. ACE inhibitors bind to and inhibit the activity of both domains, but have much greater affinity for and inhibitory activity against the C-domain. Enalaprilat, the principle active metabolite of enalapril, competes with ATI for binding to ACE and inhibits and enzymatic proteolysis of ATI to ATII. Decreasing ATII levels in the body decreases blood pressure by inhibiting the pressor effects of ATII as described in the Pharmacology section above. Enalapril also causes an increase in plasma renin activity likely due to a loss of feedback inhibition mediated by ATII on the release of renin and/or stimulation of reflex mechanisms via baroreceptors. Enalaprilat's affinity for ACE is approximately 200,000 times greater than that of ATI and 300-1000 times greater than that enalapril.
Related Articles
Absorption55-75%, absorption is unaffected by food; enalaprilat (clinically administered IV) is poorly absorbed, 3-12%, due to its high polarity.
Volume of distributionNot Available
Protein binding50-60% of enalaprilat is bound to plasma proteins
Metabolism

~ 60% of absorbed dose is extensively hydrolyzed to enalaprilat, primarily by liver esterases

SubstrateEnzymesProduct
Enalapril
Not Available
EnalaprilatDetails
Route of eliminationExcretion of enalapril is primarily renal.
Half life< 2 hours for unchanged enalapril in health individuals, may be increased in those with congestive heart failure (3.4 and 5.8 hours for single 5- and 10-mg doses, respectively). The average terminal half life of enalaprilat is 35-38 hours. The effective half life following multiple doses is 11-14 hours.
ClearanceNot Available
ToxicityOverdosage may result in marked hypotension and stupor. Most common adverse effects include hypotension, headache, dizziness and fatigue.
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Enalapril Action PathwayDrug actionSMP00148
Enalapril Metabolism PathwayDrug metabolismSMP00593
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.7428
Blood Brain Barrier-0.9659
Caco-2 permeable-0.8956
P-glycoprotein substrateSubstrate0.7691
P-glycoprotein inhibitor INon-inhibitor0.6681
P-glycoprotein inhibitor IINon-inhibitor0.5136
Renal organic cation transporterNon-inhibitor0.8442
CYP450 2C9 substrateNon-substrate0.8632
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.5696
CYP450 1A2 substrateNon-inhibitor0.9125
CYP450 2C9 inhibitorNon-inhibitor0.9154
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6825
Ames testNon AMES toxic0.9383
CarcinogenicityNon-carcinogens0.9216
BiodegradationNot ready biodegradable0.8686
Rat acute toxicity1.8269 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9719
hERG inhibition (predictor II)Non-inhibitor0.7456
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Apotex inc
  • Apothecon inc div bristol myers squibb
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Krka dd novo mesto
  • Lek pharmaceuticals d d
  • Mylan pharmaceuticals inc
  • Ranbaxy laboratories ltd
  • Sandoz inc
  • Taro pharmaceutical industries ltd
  • Teva pharmaceuticals usa inc
  • Watson laboratories inc
  • Wockhardt americas inc
  • Biovail laboratories international srl
  • Bedford laboratories div ben venue laboratories inc
  • Hikma farmaceutica (portugal) sa
  • Hospira inc
  • Teva parenteral medicines inc
Packagers
Dosage forms
FormRouteStrength
Tabletoral10 mg
Tabletoral2.5 mg
Tabletoral20 mg
Tabletoral5 mg
Tabletoral10.0 mg
Tabletoral20.0 mg
Tabletoral5.0 mg
Tabletoral10 mg/1
Tabletoral2.5 mg/1
Tabletoral20 mg/1
Tabletoral5 mg/1
Tablet, solubleoral10 mg/1
Tablet, solubleoral2.5 mg/1
Tablet, solubleoral20 mg/1
Tablet, solubleoral5 mg/1
Tabletoral
Kit
Tabletoral2.0 mg
Tabletoral4.0 mg
Tabletoral8.0 mg
Tabletoral16 mg
Tabletoral32 mg
Tabletoral4 mg
Tabletoral8 mg
Tabletoral2 mg
Prices
Unit descriptionCostUnit
Enalapril maleate powder9.18USD g
Enalaprilat 1.25 mg/ml vial3.6USD ml
Vasotec 20 mg tablet3.36USD tablet
Vaseretic 10-25 mg tablet3.15USD tablet
Vasotec 10 mg tablet2.63USD tablet
Vasotec 5 mg tablet2.08USD tablet
Vasotec 2.5 mg tablet1.65USD tablet
Enalapril maleate 20 mg tablet1.56USD tablet
Vaseretic 5-12.5 mg tablet1.49USD tablet
Vasotec 20 mg Tablet1.34USD tablet
Vasotec 10 mg Tablet1.11USD tablet
Enalapril maleate 10 mg tablet1.09USD tablet
Enalapril maleate 5 mg tablet1.03USD tablet
Vasotec 5 mg Tablet0.92USD tablet
Enalapril maleate 2.5 mg tablet0.82USD tablet
Vasotec 2.5 mg Tablet0.78USD tablet
Apo-Enalapril 20 mg Tablet0.75USD tablet
Co Enalapril 20 mg Tablet0.75USD tablet
Mylan-Enalapril 20 mg Tablet0.75USD tablet
Novo-Enalapril 20 mg Tablet0.75USD tablet
Pms-Enalapril 20 mg Tablet0.75USD tablet
Ratio-Enalapril 20 mg Tablet0.75USD tablet
Sandoz Enalapril 20 mg Tablet0.75USD tablet
Taro-Enalapril 20 mg Tablet0.75USD tablet
Apo-Enalapril 10 mg Tablet0.62USD tablet
Co Enalapril 10 mg Tablet0.62USD tablet
Mylan-Enalapril 10 mg Tablet0.62USD tablet
Novo-Enalapril 10 mg Tablet0.62USD tablet
Pms-Enalapril 10 mg Tablet0.62USD tablet
Ratio-Enalapril 10 mg Tablet0.62USD tablet
Sandoz Enalapril 10 mg Tablet0.62USD tablet
Taro-Enalapril 10 mg Tablet0.62USD tablet
Apo-Enalapril 5 mg Tablet0.52USD tablet
Co Enalapril 5 mg Tablet0.52USD tablet
Mylan-Enalapril 5 mg Tablet0.52USD tablet
Novo-Enalapril 5 mg Tablet0.52USD tablet
Pms-Enalapril 5 mg Tablet0.52USD tablet
Ratio-Enalapril 5 mg Tablet0.52USD tablet
Sandoz Enalapril 5 mg Tablet0.52USD tablet
Taro-Enalapril 5 mg Tablet0.52USD tablet
Apo-Enalapril 2.5 mg Tablet0.44USD tablet
Co Enalapril 2.5 mg Tablet0.44USD tablet
Mylan-Enalapril 2.5 mg Tablet0.44USD tablet
Novo-Enalapril 2.5 mg Tablet0.44USD tablet
Pms-Enalapril 2.5 mg Tablet0.44USD tablet
Ratio-Enalapril 2.5 mg Tablet0.44USD tablet
Sandoz Enalapril 2.5 mg Tablet0.44USD tablet
Taro-Enalapril 2.5 mg Tablet0.44USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US8568747 No2012-11-062032-11-06Us
US8778366 No2012-11-062032-11-06Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point143-144.5 °CNot Available
water solubility1.64E+004 mg/L (at 25 °C)MCFARLAND,JW ET AL. (2001)
logP0.07HANSCH,C ET AL. (1995)
Caco2 permeability-5.64ADME Research, USCD
pKa2.97 (the carboxyl group) and 5.35 (the amine group) at 25°CNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.213 mg/mLALOGPS
logP0.19ALOGPS
logP0.59ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)3.67ChemAxon
pKa (Strongest Basic)5.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area95.94 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity99.57 m3·mol-1ChemAxon
Polarizability40.41 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

K. S. Keshava Murthy, Andrew Burchat, Gamini Weeratunga, “Sodium enalapril complex and the use thereof to make sodium enalapril.” U.S. Patent US5637730, issued February, 1983.

US5637730
General References
  1. Florey, Klaus;Al-Badr, Abdullah A.;Brenner, Gerald S. (1987). Analytical Profiles of Drug Substances (16th ed.). Elsevier Science & Technology Books. [ISBN:978-0-12-260816-2 ]
External Links
ATC CodesC09AA02C09BA02C09BB02C09BB06
AHFS Codes
  • 24:32.04
PDB Entries
FDA labelDownload (939 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
Acetylsalicylic acidAcetylsalicylic acid may decrease the antihypertensive activities of Enalapril.
AldesleukinThe risk or severity of adverse effects can be increased when Aldesleukin is combined with Enalapril.
AlfuzosinAlfuzosin may increase the hypotensive activities of Enalapril.
AliskirenAliskiren may increase the hyperkalemic activities of Enalapril.
AllopurinolThe risk of a hypersensitivity reaction to Allopurinol is increased when it is combined with Enalapril.
AmifostineEnalapril may increase the hypotensive activities of Amifostine.
AprotininAprotinin may decrease the antihypertensive activities of Enalapril.
ArdeparinArdeparin may increase the hyperkalemic activities of Enalapril.
AzathioprineEnalapril may increase the myelosuppressive activities of Azathioprine.
BrimonidineBrimonidine may increase the antihypertensive activities of Enalapril.
ButabarbitalButabarbital may increase the hypotensive activities of Enalapril.
ButethalButethal may increase the hypotensive activities of Enalapril.
CanagliflozinCanagliflozin may increase the hyperkalemic activities of Enalapril.
CiprofloxacinEnalapril may increase the arrhythmogenic activities of Ciprofloxacin.
DapoxetineDapoxetine may increase the orthostatic hypotensive activities of Enalapril.
DiazoxideDiazoxide may increase the hypotensive activities of Enalapril.
DrospirenoneEnalapril may increase the hyperkalemic activities of Drospirenone.
DuloxetineEnalapril may increase the orthostatic hypotensive activities of Duloxetine.
EplerenoneEplerenone may increase the hyperkalemic activities of Enalapril.
EverolimusThe risk or severity of adverse effects can be increased when Everolimus is combined with Enalapril.
HeparinHeparin may increase the hyperkalemic activities of Enalapril.
HeptabarbitalHeptabarbital may increase the hypotensive activities of Enalapril.
HexobarbitalHexobarbital may increase the hypotensive activities of Enalapril.
IcatibantIcatibant may decrease the antihypertensive activities of Enalapril.
InfliximabThe risk or severity of adverse effects can be increased when Enalapril is combined with Infliximab.
IronThe risk or severity of adverse effects can be increased when Enalapril is combined with Iron.
Iron DextranThe risk or severity of adverse effects can be increased when Enalapril is combined with Iron Dextran.
LanthanumThe serum concentration of Enalapril can be decreased when it is combined with Lanthanum.
LevodopaEnalapril may increase the orthostatic hypotensive activities of Levodopa.
LithiumThe serum concentration of Lithium can be increased when it is combined with Enalapril.
MethohexitalMethohexital may increase the hypotensive activities of Enalapril.
MethylphenidateMethylphenidate may decrease the antihypertensive activities of Enalapril.
MolsidomineMolsidomine may increase the hypotensive activities of Enalapril.
MoxonidineMoxonidine may increase the hypotensive activities of Enalapril.
NicorandilNicorandil may increase the hypotensive activities of Enalapril.
ObinutuzumabEnalapril may increase the hypotensive activities of Obinutuzumab.
PentobarbitalPentobarbital may increase the hypotensive activities of Enalapril.
PentoxifyllinePentoxifylline may increase the hypotensive activities of Enalapril.
PhenelzinePhenelzine may increase the orthostatic hypotensive activities of Enalapril.
PregabalinThe risk or severity of adverse effects can be increased when Enalapril is combined with Pregabalin.
PrimidonePrimidone may increase the hypotensive activities of Enalapril.
QuinineQuinine may increase the hypotensive activities of Enalapril.
RisperidoneEnalapril may increase the hypotensive activities of Risperidone.
RituximabEnalapril may increase the hypotensive activities of Rituximab.
SacubitrilThe risk or severity of adverse effects can be increased when Enalapril is combined with Sacubitril.
SecobarbitalSecobarbital may increase the hypotensive activities of Enalapril.
SirolimusThe risk or severity of adverse effects can be increased when Sirolimus is combined with Enalapril.
SitagliptinThe risk or severity of adverse effects can be increased when Sitagliptin is combined with Enalapril.
Sodium aurothiomalateThe risk or severity of adverse effects can be increased when Enalapril is combined with Sodium aurothiomalate.
TadalafilTadalafil may increase the antihypertensive activities of Enalapril.
TemsirolimusThe risk or severity of adverse effects can be increased when Temsirolimus is combined with Enalapril.
TizanidineTizanidine may increase the hypotensive activities of Enalapril.
TolvaptanTolvaptan may increase the hyperkalemic activities of Enalapril.
TorasemideTorasemide may increase the hypotensive activities of Enalapril.
TranylcypromineTranylcypromine may increase the orthostatic hypotensive activities of Enalapril.
TreprostinilTreprostinil may increase the hypotensive activities of Enalapril.
TriamtereneTriamterene may increase the hyperkalemic activities of Enalapril.
TrichlormethiazideTrichlormethiazide may increase the hypotensive activities of Enalapril.
TrimethoprimTrimethoprim may increase the hyperkalemic activities of Enalapril.
ValsartanThe risk or severity of adverse effects can be increased when Valsartan is combined with Enalapril.
VardenafilVardenafil may increase the antihypertensive activities of Enalapril.
YohimbineYohimbine may decrease the antihypertensive activities of Enalapril.
Food Interactions
  • Enalapril decreases the excretion of potassium. Salt substitutes containing potassium increase the risk of hyperkalemia.
  • Herbs that may attenuate the antihypertensive effect of enalapril include: bayberry, blue cohash, cayenne, ephedra, ginger, ginseng (American), kola and licorice.
  • High salt intake may attenuate the antihypertensive effect of enalapril.
  • Take without regard to meals.

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Zinc ion binding
Specific Function:
Converts angiotensin I to angiotensin II by release of the terminal His-Leu, this results in an increase of the vasoconstrictor activity of angiotensin. Also able to inactivate bradykinin, a potent vasodilator. Has also a glycosidase activity which releases GPI-anchored proteins from the membrane by cleaving the mannose linkage in the GPI moiety.
Gene Name:
ACE
Uniprot ID:
P12821
Molecular Weight:
149713.675 Da
References
  1. Andujar-Sanchez M, Jara-Perez V, Camara-Artigas A: Thermodynamic determination of the binding constants of angiotensin-converting enzyme inhibitors by a displacement method. FEBS Lett. 2007 Jul 24;581(18):3449-54. Epub 2007 Jun 27. [PubMed:17618628 ]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  3. Liu YH, Liu LY, Wu JX, Chen SX, Sun YX: Comparison of captopril and enalapril to study the role of the sulfhydryl-group in improvement of endothelial dysfunction with ACE inhibitors in high dieted methionine mice. J Cardiovasc Pharmacol. 2006 Jan;47(1):82-8. [PubMed:16424790 ]
  4. Natesh R, Schwager SL, Evans HR, Sturrock ED, Acharya KR: Structural details on the binding of antihypertensive drugs captopril and enalaprilat to human testicular angiotensin I-converting enzyme. Biochemistry. 2004 Jul 13;43(27):8718-24. [PubMed:15236580 ]

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. 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 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Xenobiotic-transporting atpase activity
Specific Function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular Weight:
141477.255 Da
References
  1. Takara K, Kakumoto M, Tanigawara Y, Funakoshi J, Sakaeda T, Okumura K: Interaction of digoxin with antihypertensive drugs via MDR1. Life Sci. 2002 Feb 15;70(13):1491-500. [PubMed:11895100 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Proton-dependent oligopeptide secondary active transmembrane transporter activity
Specific Function:
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products.
Gene Name:
SLC15A1
Uniprot ID:
P46059
Molecular Weight:
78805.265 Da
References
  1. Han H, de Vrueh RL, Rhie JK, Covitz KM, Smith PL, Lee CP, Oh DM, Sadee W, Amidon GL: 5'-Amino acid esters of antiviral nucleosides, acyclovir, and AZT are absorbed by the intestinal PEPT1 peptide transporter. Pharm Res. 1998 Aug;15(8):1154-9. [PubMed:9706043 ]
  2. Han HK, Rhie JK, Oh DM, Saito G, Hsu CP, Stewart BH, Amidon GL: CHO/hPEPT1 cells overexpressing the human peptide transporter (hPEPT1) as an alternative in vitro model for peptidomimetic drugs. J Pharm Sci. 1999 Mar;88(3):347-50. [PubMed:10052994 ]
  3. Temple CS, Boyd CA: Proton-coupled oligopeptide transport by rat renal cortical brush border membrane vesicles: a functional analysis using ACE inhibitors to determine the isoform of the transporter. Biochim Biophys Acta. 1998 Aug 14;1373(1):277-81. [PubMed:9733984 ]
  4. Tsuji A: Transporter-mediated Drug Interactions. Drug Metab Pharmacokinet. 2002;17(4):253-74. [PubMed:15618677 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS) (By similarity). Mediates the sodium-in...
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
Molecular Weight:
61815.78 Da
References
  1. Kuze K, Graves P, Leahy A, Wilson P, Stuhlmann H, You G: Heterologous expression and functional characterization of a mouse renal organic anion transporter in mammalian cells. J Biol Chem. 1999 Jan 15;274(3):1519-24. [PubMed:9880528 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenadine. Transports benzylpenicillin (PCG), estrone-3-sulfate (E1S), cimetidine (CMD), 2,4-dichloro-phenoxyacetate (2,4-D), p-amino-hippurate (PAH), acyclovir (ACV) and ochratoxin (OTA).
Gene Name:
SLC22A8
Uniprot ID:
Q8TCC7
Molecular Weight:
59855.585 Da
References
  1. Kobayashi Y, Ohshiro N, Tsuchiya A, Kohyama N, Ohbayashi M, Yamamoto T: Renal transport of organic compounds mediated by mouse organic anion transporter 3 (mOat3): further substrate specificity of mOat3. Drug Metab Dispos. 2004 May;32(5):479-83. [PubMed:15100168 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Mediates sodium-independent multispecific organic anion transport. Transport of prostaglandin E2, prostaglandin F2, tetracycline, bumetanide, estrone sulfate, glutarate, dehydroepiandrosterone sulfate, allopurinol, 5-fluorouracil, paclitaxel, L-ascorbic acid, salicylate, ethotrexate, and alpha-ketoglutarate.
Gene Name:
SLC22A7
Uniprot ID:
Q9Y694
Molecular Weight:
60025.025 Da
References
  1. Kobayashi Y, Ohshiro N, Shibusawa A, Sasaki T, Tokuyama S, Sekine T, Endou H, Yamamoto T: Isolation, characterization and differential gene expression of multispecific organic anion transporter 2 in mice. Mol Pharmacol. 2002 Jul;62(1):7-14. [PubMed:12065749 ]
  2. Sekine T, Cha SH, Tsuda M, Apiwattanakul N, Nakajima N, Kanai Y, Endou H: Identification of multispecific organic anion transporter 2 expressed predominantly in the liver. FEBS Lett. 1998 Jun 12;429(2):179-82. [PubMed:9650585 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids (By similarity). Selectively inhibited by the grapefruit juice component naringin.
Gene Name:
SLCO1A2
Uniprot ID:
P46721
Molecular Weight:
74144.105 Da
References
  1. Abu-Zahra TN, Wolkoff AW, Kim RB, Pang KS: Uptake of enalapril and expression of organic anion transporting polypeptide 1 in zonal, isolated rat hepatocytes. Drug Metab Dispos. 2000 Jul;28(7):801-6. [PubMed:10859154 ]
  2. Pang KS, Wang PJ, Chung AY, Wolkoff AW: The modified dipeptide, enalapril, an angiotensin-converting enzyme inhibitor, is transported by the rat liver organic anion transport protein. Hepatology. 1998 Nov;28(5):1341-6. [PubMed:9794920 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on May 25, 2016 02:17