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enalapril

Trade name: vasotec

Small moleculeapproved

Approved

Dec 24, 1985

Enalapril (marketed as Vasotec in the US, Enaladex and Renitec in some other countries) is an angiotensin-converting-enzyme (ACE) inhibitor used in the treatment of hypertension, diabetic nephropathy, and some types of chronic heart failure. Enalapril, after hydrolysis to enalaprilat, inhibits angiotensin-converting enzyme (ACE) in human subjects and animals. ACE is a peptidyl dipeptidase that catalyzes the conversion of angiotensin I to the vasoconstrictor substance, angiotensin II. Angiotensin II also stimulates aldosterone secretion by the adrenal cortex. The beneficial effects of enalapril in hypertension and heart failure appear to result primarily from suppression of the renin-angiotensin-aldosterone system. Inhibition of ACE results in decreased plasma angiotensin II, which leads to decreased vasopressor activity and to decrease aldosterone secretion. — NCATS

Clinical trial activity

126 trials · 153 clinical orgs · 38 marketing orgs

Phase 1
9
Phase 2
51
Phase 3
39
Phase 4
38

Earliest trial started Jul 1, 1985 (NCT00000516)

Timeline

1980s

  1. Jan 1, 1985

    Earliest Phase 2 Sponsor(trial)

  2. Jan 1, 1985

    Earliest Phase 3 Sponsor(trial)

  3. Dec 24, 1985

    Earliest FDA Approval

  4. Dec 24, 1985

    Bausch Health Companies — NDA Secondary Org

  5. Oct 31, 1986

    Bausch Health Companies — Marketing Organization

  6. Feb 9, 1988

    Biovail — NDA Secondary Org

1990s

  1. Oct 4, 1996

    Biovail — Marketing Organization

  2. Dec 27, 1996

    AstraZeneca — Marketing Organization

  3. Dec 27, 1996

    AstraZeneca — NDA Secondary Org

2000s

  1. Aug 22, 2000

    Aurobindo Pharma — Marketing Organization

  2. Aug 22, 2000

    Apothecon — Marketing Organization

  3. Aug 22, 2000

    Athenex, Inc. — Marketing Organization

  4. Aug 22, 2000

    Beximco — Marketing Organization

  5. Aug 22, 2000

    Heritage Pharma — Marketing Organization

  6. Aug 22, 2000

    Hospira — Marketing Organization

  7. Aug 22, 2000

    Krka — Marketing Organization

  8. Aug 22, 2000

    Mylan — Marketing Organization

  9. Aug 22, 2000

    Sandoz — Marketing Organization

  10. Aug 22, 2000

    Sun Pharmaceuticals — Marketing Organization

  11. Aug 22, 2000

    Teva — Marketing Organization

  12. Aug 22, 2000

    Watson Pharmaceuticals — Marketing Organization

  13. Aug 22, 2000

    Wockhardt — Marketing Organization

  14. Aug 22, 2000

    Novartis — Marketing Organization

  15. Jan 23, 2001

    Taro Pharmaceuticals — Marketing Organization

  16. Mar 23, 2001

    Apotex — Marketing Organization

  17. Mar 23, 2001

    Nostrum Laboratories — Marketing Organization

  18. Mar 23, 2001

    AiPing Pharm Inc — Marketing Organization

  19. Sep 18, 2001

    Rising Pharmaceuticals — Marketing Organization

  20. Sep 18, 2001

    ACP Nimble — Marketing Organization

  21. Sep 18, 2001

    G & W Laboratories Inc. — Marketing Organization

  22. Sep 18, 2001

    Cosette — Marketing Organization

  23. Sep 19, 2001

    Chartwell Pharmaceuticals — Marketing Organization

  24. Sep 19, 2001

    Upsher-Smith Laboratories — Marketing Organization

  25. Oct 15, 2001

    Dr. Reddy's Laboratories — Marketing Organization

  26. Dec 23, 2008

    Hikma — Marketing Organization

  27. Jan 1, 2009

    Earliest Phase 1 Sponsor(trial)

2010s

  1. Aug 13, 2013

    Silvergate Pharmaceuticals — NDA Secondary Org

  2. Sep 20, 2016

    Azurity — Marketing Organization

  3. Sep 20, 2016

    Azurity — NDA Secondary Org

2020s

  1. Apr 29, 2021

    Annora Pharma — Marketing Organization

  2. Aug 10, 2021

    Bionpharma Inc — Marketing Organization

  3. Mar 30, 2022

    Alkem Labs Ltd — Marketing Organization

  4. Jun 29, 2022

    Amneal Pharmaceuticals — Marketing Organization

  5. Jul 7, 2022

    Prinston Inc — Marketing Organization

  6. Sep 19, 2024

    Unique Pharmaceuticals Ltd, India — Marketing Organization

Indications

Approved for

Studied for

Mechanism of action

Combination products

Approval history

  • approvedPriority reviewDec 24, 1985

Chemistry & pharmacology

Loading structure…

SMILES

C[C@H](N[C@@H](CCc1ccccc1)C(=O)O)C(=O)N1CCC[C@H]1C(=O)O.O.O
Mol. weight
384.43 g/mol
Lipinski Ro5
Pass
Rule of 3
No
Chirality
Single Stereoisomer
Inorganic
No
Polymer
No
Delivery
Parenteral
Availability
Prescription Only

Oral

No

Parenteral

Yes

Topical

No

Black box warning

Sources

Also known as

  • 1-(n-((s)-1-carboxy-3-phenylpropyl)-l-alanyl)-l-proline 1'-ethyl ester
  • 1-(n-((s)-1-carboxy-3-phenylpropyl)-l-alanyl)-l-proline 1'-ethyl ester
  • analapril
  • analapril
  • ednyt
  • ednyt
  • enalapril
  • enalapril
  • enalapril
  • enalapril
  • enalapril
  • enalapril
  • enalapril
  • enalapril
  • enalapril
  • enalapril
  • enalaprila
  • enalaprila
  • enalapril acid
  • enalaprilat
  • enalaprilat
  • enalaprilat
  • enalaprilat
  • enalaprilat
  • enalaprilat
  • enalaprilat
  • enalaprilat
  • enalaprilat
  • enalaprilat
  • enalaprilat anhydrous
  • enalaprilat anhydrous
  • enalaprilat dihydrate
  • enalaprilate
  • enalaprilat hydrate
  • enalaprilat hydrate
  • enalaprilat hydrate
  • enalaprilic acid
  • enalapril maleate
  • enalapril maleate
  • enalapril maleate
  • enalapril maleate
  • enalapril maleate
  • enalaprilum
  • enalaprilum
  • enapren
  • enapren
  • enarenal
  • innovace
  • innovace
  • lexxel
  • lexxel
  • mk-421
  • mk-421
  • mk-422
  • mk-422
  • pralenal 10
  • pralenal 20
  • pralenal 2.5
  • pralenal 5
  • renitec
  • renitec
  • (s)-1-(n-(1-(ethoxycarbonyl)-3-phenylpropyl)-l-alanyl)-l-proline
  • (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
  • (s)-1-{(s)-2-[1-((s)-ethoxycarbonyl)-3-phenyl-propylamino]-propionyl}-pyrrolidine-2-carboxylic acid
  • vaseretic
  • vaseretic
  • vasotec
  • vasotec
  • vasotec
  • xanef
  • xanef

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT07222852Phase 3Nov 15, 2025Brown University
NCT07023003Phase 4Jul 11, 2025Nebraska Methodist Health System
NCT06788314Phase 2Feb 1, 2025University of Oslo
NCT06187493N/AJan 1, 2024Assiut University
NCT05373004Phase 2/Phase 3 (Phase 3)Mar 31, 2023Hamad General Hospital
NCT05711810Phase 4Jan 2, 2023University of Pennsylvania
NCT05259137Phase 2/Phase 3 (Phase 3)Aug 31, 2022Government of Canada
NCT05487261Phase 4Aug 31, 2022Government of Poland, K. Marcinkowski University of Medical Sciences, Medical University of Bialystok, Medical University of Gdansk, Silesian University of Medicine, University of Opole
NCT05232370Phase 2Jan 1, 2022Unidad de Investigacion Medica en Enfermedades Renales
NCT04912167Phase 3Nov 30, 2021Sichuan University
NCT05271448N/AJun 1, 2021An-Najah National University
NCT04853758Phase 3May 6, 2021University of Sao Paulo
NCT04591210Phase 3Oct 30, 2020University of Ottawa
NCT04484350Phase 2Oct 23, 2020Hamilton Health Sciences Corporation, McMaster University
NCT04345406Phase 3Apr 15, 2020Tanta University
NCT04183101Phase 2Jan 31, 2020Region Skane
NCT04236258N/AJan 31, 2020Harvard University
NCT04023227Phase 4Dec 16, 2019Novartis
NCT04103554Phase 4Nov 30, 2019University of Zagreb
NCT03949075N/AMay 15, 2019Novo Nordisk, University of Copenhagen
Showing 20 of 126 trials
Page 1 / 7

Organizations

Research & Development (153)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
NovartisFor profit171522005
National Heart, Lung, and Blood Institute (NHLBI)Government6321985
Vanderbilt UniversityAcademic/Hospital5522008
Erasmus University RotterdamAcademic/Hospital4122015
Ethicare GmbHFor profit4422014
MerckFor profit4321990
Peking UniversityAcademic/Hospital4022005
University of LondonAcademic/Hospital4122004
University of PennsylvaniaAcademic/Hospital4121994
University of ViennaAcademic/Hospital4022016
Anhui Medical UniversityAcademic/Hospital3122005
Boehringer IngelheimFor profit3321997
Chulalongkorn UniversityAcademic/Hospital3312009
Harvard UniversityAcademic/Hospital3132003
Shenzhen Ausa Pharmed Co.,LtdFor profit3312008
Southern Medical UniversityAcademic/Hospital3022008
University of CopenhagenAcademic/Hospital3322005
University of MinnesotaAcademic/Hospital3321985
University of Sao PauloAcademic/Hospital3322005
University of VigoAcademic/Hospital3312000
153 organizations
Page 1 / 8

Marketing (52)

OrganizationOrg typeRelationshipDate
ACP NimbleFor profitMKTGSep 18, 2001
AiPing Pharm IncFor profitMKTGMar 23, 2001
Alkem Labs LtdFor profitMKTGMar 30, 2022
Amneal PharmaceuticalsFor profitMKTGJun 29, 2022
Annora PharmaFor profitMKTGApr 29, 2021
ApotexFor profitMKTGMar 23, 2001
ApotexFor profitSYNOct 27, 2004
ApotheconFor profitMKTGAug 22, 2000
AstraZenecaFor profitMKTGDec 27, 1996
AstraZenecaFor profitNDA2Dec 27, 1996
Athenex, Inc.For profitMKTGAug 22, 2000
Aurobindo PharmaFor profitMKTGAug 22, 2000
Aurobindo PharmaFor profitSYNJan 8, 2024
AzurityFor profitMKTGSep 20, 2016
AzurityFor profitNDA2Sep 20, 2016
Bausch Health CompaniesFor profitNDA2Dec 24, 1985
Bausch Health CompaniesFor profitSYNDec 24, 1985
Bausch Health CompaniesFor profitMKTGOct 31, 1986
BeximcoFor profitMKTGAug 22, 2000
Bionpharma IncFor profitMKTGAug 10, 2021
Bionpharma IncFor profitSYNAug 10, 2021
BiovailFor profitNDA2Feb 9, 1988
BiovailFor profitMKTGOct 4, 1996
Chartwell PharmaceuticalsFor profitMKTGSep 19, 2001
Chartwell PharmaceuticalsFor profitSYNAug 22, 2000
CosetteFor profitMKTGSep 18, 2001
Dr. Reddy's LaboratoriesFor profitSYNAug 22, 2000
Dr. Reddy's LaboratoriesFor profitMKTGOct 15, 2001
G & W Laboratories Inc.For profitMKTGSep 18, 2001
Heritage PharmaFor profitMKTGAug 22, 2000
HikmaFor profitMKTGDec 23, 2008
HospiraFor profitMKTGAug 22, 2000
KrkaFor profitMKTGAug 22, 2000
MerckFor profitNDA—
MylanFor profitMKTGAug 22, 2000
Nostrum LaboratoriesFor profitMKTGMar 23, 2001
NovartisFor profitMKTGAug 22, 2000
Prinston IncFor profitMKTGJul 7, 2022
Rising PharmaceuticalsFor profitMKTGSep 18, 2001
Rising PharmaceuticalsFor profitSYNSep 18, 2001
SandozFor profitMKTGAug 22, 2000
SandozFor profitSYNAug 22, 2000
Silvergate PharmaceuticalsFor profitNDA2Aug 13, 2013
Sun PharmaceuticalsFor profitMKTGAug 22, 2000
Taro PharmaceuticalsFor profitMKTGJan 23, 2001
Taro PharmaceuticalsFor profitSYNSep 18, 2001
TevaFor profitSYNAug 22, 2000
TevaFor profitMKTGAug 22, 2000
Unique Pharmaceuticals Ltd, IndiaFor profitMKTGSep 19, 2024
Upsher-Smith LaboratoriesFor profitMKTGSep 19, 2001
Watson PharmaceuticalsFor profitMKTGAug 22, 2000
WockhardtFor profitMKTGAug 22, 2000