captopril
Trade name: capoten
Approved
Apr 6, 1981
Pivalopril (RHC 3659-(S); (S)-N-cyclopentyl-N-(2-methyl-3-pivaloylthiopropionyl) glycine) is an angiotensin-converting enzyme (ACE) inhibitor with antihypertensive activity. Upon hydrolysis, the free SH metabolite of pivopril competitively binds to and inhibits ACE, thereby blocking the conversion of angiotensin I to angiotensin II. This prevents the potent vasoconstrictive actions of angiotensin II and results in vasodilation. Pivopril also decreases angiotensin II-induced aldosterone secretion by the adrenal cortex, which leads to an increase in sodium excretion and subsequently increases water outflow. Pivalopril has been compared to captopril for oral angiotensin-converting enzyme (ACE) inhibition in rats and dogs and antihypertensive activity in rats. In separate groups of conscious normotensive rats, pivalopril (0.03-1.0 mg/kg, orally [p.o.]) produced a dose-related antagonism of angiotensin I (AngI)-induced pressor effects. The ED50 for pivalopriland captopril was 0.1 mg/kg. Pivalopril has being shown to be a potent, orally effective ACE inhibitor and antihypertensive agent. — NCATS
Clinical trial activity
43 trials · 48 clinical orgs · 34 marketing orgs
Earliest trial started Oct 1, 1999 (NCT00004230)
Timeline
1980s
- Apr 6, 1981
Earliest FDA Approval
- Apr 6, 1981
Strides Pharma Science — Marketing Organization
- Apr 6, 1981
Par Pharmaceuticals — NDA Secondary Org
- Apr 6, 1981
Strides Pharma Science — NDA Secondary Org
- Oct 12, 1984
Apothecon — Marketing Organization
- Oct 12, 1984
Apothecon — NDA Secondary Org
1990s
- Nov 9, 1995
Chartwell Pharmaceuticals — Marketing Organization
- Nov 9, 1995
Fosun — Marketing Organization
- Feb 13, 1996
Cosette — Marketing Organization
- Feb 13, 1996
DAVA Pharmaceuticals — Marketing Organization
- Feb 13, 1996
G & W Laboratories Inc. — Marketing Organization
- Feb 13, 1996
Hikma — Marketing Organization
- Feb 13, 1996
Oxford Pharmaceuticals — Marketing Organization
- Feb 13, 1996
Prinston Inc — Marketing Organization
- Feb 13, 1996
Sandoz — Marketing Organization
- Feb 13, 1996
Teva — Marketing Organization
- Feb 13, 1996
Watson Pharmaceuticals — Marketing Organization
- Feb 13, 1996
ACP Nimble — Marketing Organization
- Feb 13, 1996
Aurobindo Pharma — Marketing Organization
- Feb 13, 1996
Novartis — Marketing Organization
- Mar 28, 1997
Atlantide Pharmaceuticals — Marketing Organization
- Mar 28, 1997
Wockhardt — Marketing Organization
- May 29, 1997
Egis — Marketing Organization
- May 30, 1997
Boscogen — Marketing Organization
- May 30, 1997
Kenton — Marketing Organization
- May 30, 1997
Innogenix — Marketing Organization
- Dec 29, 1997
Rising Pharmaceuticals — Marketing Organization
- Dec 29, 1997
Mylan — Marketing Organization
- Dec 29, 1997
Vintage — Marketing Organization
- Oct 28, 1998
Corepharma — Marketing Organization
- Oct 28, 1998
Apotex — Marketing Organization
- Oct 28, 1998
Annora Pharma — Marketing Organization
- Jan 1, 1999
Earliest Phase 3 Sponsor(trial)
2010s
- Oct 30, 2019
Seton Pharm — Marketing Organization
- Dec 13, 2019
Ajanta Pharma Ltd — Marketing Organization
2020s
- Jan 27, 2023
Changzhou Jinyuan Pharmaceutical Manufacturing Co., Ltd. — Marketing Organization
Indications
Approved for
Studied for
- Aortic Valve Stenosis · Phase 4
- Blood Pressure · Early Phase 1
- Cardiotoxicity · Phase 3
- Coronavirus Infections · Phase 2
- COVID-19 · Phase 3
- Diabetes Mellitus · Phase 4
- Diabetes Mellitus, Type 1 · Phase 3
- Diabetes Mellitus, Type 2 · Phase 4
- Drug-Related Side Effects and Adverse Reactions · Phase 2
- Drugs, Investigational · Phase 2
- Essential Hypertension · Phase 3
- Glioblastoma · Phase 1
- Healthy Volunteers · Phase 1
- Heart Diseases · Phase 4
- Hemangioma · Phase 4
- Hyperaldosteronism · Phase 4
- Hypertension, Pulmonary · Phase 1
- Hypotension · Phase 4
- Inflammation · Phase 4
- Kidney Diseases · Phase 4
- Kidney Failure, Chronic · Phase 4
- Leukemia, Myeloid, Acute · Phase 3
- Lung Diseases · Phase 2
- Lung Neoplasms · Phase 2
- Metabolic Syndrome · Phase 4
- Multiple System Atrophy · Phase 1
- Myeloproliferative Disorders · Phase 1/Phase 2
- Neoplasms · Phase 3
- Peripheral Arterial Disease · Phase 3
- Pharmacokinetics · Early Phase 1
- Pneumonia · Phase 2
- Pre-Eclampsia · Phase 4
- Primary Myelofibrosis · Phase 1/Phase 2
- Pure Autonomic Failure · Phase 1
- Radiation Fibrosis Syndrome · Phase 2
- Radiation Pneumonitis · Phase 2
- Renal Insufficiency · Phase 4
- Ventricular Dysfunction, Left · Phase 4
Mechanism of action
- Angiotensin-converting enzymeINHIBITOR
ACE inhibitor
Combination products
capozide
with hydrochlorothiazide
Approval history
- approvedPriority reviewApr 6, 1981
Chemistry & pharmacology
SMILES
C[C@H](CS)C(=O)N1CCC[C@H]1C(O)=O- Mol. weight
- 217.285 g/mol
- Lipinski Ro5
- Pass
- Rule of 3
- Yes
- Chirality
- Single Stereoisomer
- Inorganic
- No
- Polymer
- No
- Delivery
- Oral
- Availability
- Prescription Only
Oral
Yes
Parenteral
No
Topical
No
Sources
- WikipediaCaptopril ↗
- NCATS9G64RSX1XD ↗
- ChEMBLCHEMBL1560 ↗
Also known as
- (2s)-1-[(2s)-2-methyl-3-sulfanylpropanoyl]pyrrolidine-2-carboxylic acid
- (2s)-1-[(2s)-2-methyl-3-sulfanylpropanoyl]pyrrolidine-2-carboxylic acid
- acepress
- acepress
- acepril
- acepril
- apopril
- apopril
- capoten
- capoten
- capoten
- captolane
- captolane
- captomex
- captopril
- captopril
- captopril
- captopril
- captopril
- captopril
- captopril
- captopril
- captopril
- captopril
- captopril
- (-)-captopril
- captoprilum
- captoprilum
- captopryl
- captopryl
- captoril
- captoril
- cesplon
- cesplon
- cp
- cp
- d-2-methyl-3-mercaptopropanoyl-l-proline
- d-2-methyl-3-mercaptopropanoyl-l-proline
- d-3-mercapto-2-methylpropanoyl-l-proline
- d-3-mercapto-2-methylpropanoyl-l-proline
- dilabar
- dilabar
- ecopace
- garranil
- garranil
- hypertil
- hypertil
- hyteneze 12.5
- hyteneze 25
- hyteneze 50
- kaplon
- l-captopril
- l-captopril
- l-captopril
- lopirin
- lopirin
- lopirin
- lopril
- lopril
- noyada
- s-captopril
- sq14225
- sq 14225
- sq-14225
- sq-14225
- sq-14225
- tenosbon
- tenosbon
- tensobon
- tensobon
- tensobon
- tensoprel
- tensoprel
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT07272486 | N/A | Aug 1, 2024 | Ankara Yildirim Beyazıt University |
| NCT06141200 | Phase 3 | Mar 31, 2024 | Natural Wellness Egypt |
| NCT06292091 | Phase 1 | Feb 28, 2024 | Seoul National University |
| NCT06485661 | Early Phase 1 (Phase 1) | Jan 1, 2024 | Ain Shams University |
| NCT06253429 | Phase 3 | Jan 1, 2023 | Ain Shams University |
| NCT04964050 | Phase 1 | Dec 24, 2021 | GlaxoSmithKline |
| NCT04878315 | Phase 1 | Dec 10, 2021 | GlaxoSmithKline |
| NCT04893629 | N/A | May 20, 2021 | Damascus University |
| NCT04629651 | Phase 1/Phase 2 (Phase 2) | Dec 31, 2020 | Case Western Reserve University, University of Rochester |
| NCT04355429 | Phase 2 | May 5, 2020 | Assistance Publique - Hôpitaux de Paris |
| NCT04345406 | Phase 3 | Apr 15, 2020 | Tanta University |
| NCT04485845 | Phase 4 | Nov 1, 2019 | Cairo University |
| NCT04288700 | Phase 4 | Oct 1, 2019 | Ain Shams University, Future University in Egypt |
| NCT03613506 | Phase 2 | Oct 25, 2018 | Wuhan University |
| NCT03370705 | Phase 3 | Sep 1, 2018 | Alfa Wassermann, Poseidon CRO |
| NCT03389724 | Phase 3 | Nov 14, 2017 | Cairo University |
| NCT03147092 | Early Phase 1 (Phase 1) | Jul 1, 2017 | Centro Neurológico de Pesquisa e Reabiitação, Brazil, Hospital Carlos Fernando Malzoni |
| NCT03660293 | N/A | Apr 1, 2017 | Tanta University |
| NCT02770378 | Phase 1 | Nov 1, 2016 | Government of Belgium, Reliable Cancer Therapies, University of Ulm |
| NCT03179163 | Phase 1/Phase 2 (Phase 2) | Jul 20, 2016 | National Heart, Lung, and Blood Institute (NHLBI), Pennsylvania State University |
Organizations
Research & Development (48)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| Ain Shams University | Academic/Hospital | 3 | 3 | 3 | 2019 |
| National Cancer Institute (NCI) | Government | 3 | 0 | 2 | 1999 |
| Northwestern University | Academic/Hospital | 3 | 2 | 2 | 1999 |
| Cairo University | Academic/Hospital | 2 | 2 | 2 | 2017 |
| GlaxoSmithKline | For profit | 2 | 2 | 1 | 2021 |
| Harvard University | Academic/Hospital | 2 | 2 | 2 | 2012 |
| Tanta University | Academic/Hospital | 2 | 2 | 2 | 2017 |
| Vanderbilt University | Academic/Hospital | 2 | 2 | 1 | 2001 |
| Alfa Wassermann | For profit | 1 | 1 | 1 | 2018 |
| Ankara Yildirim Beyazıt University | Academic/Hospital | 1 | 1 | 1 | 2024 |
| Assistance Publique - Hôpitaux de Paris | Academic/Hospital | 1 | 1 | 1 | 2020 |
| AstraZeneca | For profit | 1 | 1 | 1 | 2006 |
| Case Western Reserve University | Academic/Hospital | 1 | 1 | 1 | 2020 |
| Centro Neurológico de Pesquisa e Reabiitação, Brazil | Academic/Hospital | 1 | 1 | 1 | 2017 |
| Damascus University | Academic/Hospital | 1 | 1 | 1 | 2021 |
| Danderyds Hospital | Academic/Hospital | 1 | 0 | 1 | 2006 |
| Federal University of Rio Grande do Sul | Academic/Hospital | 1 | 1 | 1 | 2010 |
| Future University in Egypt | Academic/Hospital | 1 | 0 | 1 | 2019 |
| Government of Belgium | Government | 1 | 0 | 1 | 2016 |
| Government of Mexico | Government | 1 | 1 | 1 | 2009 |
Marketing (40)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| ACP Nimble | For profit | MKTG | Feb 13, 1996 |
| Ajanta Pharma Ltd | For profit | MKTG | Dec 13, 2019 |
| Annora Pharma | For profit | MKTG | Oct 28, 1998 |
| Apotex | For profit | MKTG | Oct 28, 1998 |
| Apothecon | For profit | MKTG | Oct 12, 1984 |
| Apothecon | For profit | NDA2 | Oct 12, 1984 |
| Atlantide Pharmaceuticals | For profit | MKTG | Mar 28, 1997 |
| Aurobindo Pharma | For profit | MKTG | Feb 13, 1996 |
| Boscogen | For profit | MKTG | May 30, 1997 |
| Changzhou Jinyuan Pharmaceutical Manufacturing Co., Ltd. | For profit | MKTG | Jan 27, 2023 |
| Chartwell Pharmaceuticals | For profit | MKTG | Nov 9, 1995 |
| Corepharma | For profit | MKTG | Oct 28, 1998 |
| Cosette | For profit | MKTG | Feb 13, 1996 |
| DAVA Pharmaceuticals | For profit | MKTG | Feb 13, 1996 |
| Egis | For profit | MKTG | May 29, 1997 |
| Fosun | For profit | MKTG | Nov 9, 1995 |
| G & W Laboratories Inc. | For profit | MKTG | Feb 13, 1996 |
| Hikma | For profit | MKTG | Feb 13, 1996 |
| Innogenix | For profit | MKTG | May 30, 1997 |
| Kenton | For profit | MKTG | May 30, 1997 |
| Mylan | For profit | MKTG | Dec 29, 1997 |
| Mylan | For profit | SYN | Feb 13, 1996 |
| Novartis | For profit | MKTG | Feb 13, 1996 |
| Oxford Pharmaceuticals | For profit | MKTG | Feb 13, 1996 |
| Par Pharmaceuticals | For profit | NDA2 | Apr 6, 1981 |
| Prinston Inc | For profit | MKTG | Feb 13, 1996 |
| Puracap Pharmaceutical | For profit | MKTG | — |
| Rising Pharmaceuticals | For profit | MKTG | Dec 29, 1997 |
| Rising Pharmaceuticals | For profit | SYN | Dec 29, 1997 |
| Sandoz | For profit | MKTG | Feb 13, 1996 |
| Seton Pharm | For profit | MKTG | Oct 30, 2019 |
| Squibb | For profit | NDA | — |
| Strides Pharma Science | For profit | MKTG | Apr 6, 1981 |
| Strides Pharma Science | For profit | NDA2 | Apr 6, 1981 |
| Teva | For profit | SYN | Jun 18, 1998 |
| Teva | For profit | MKTG | Feb 13, 1996 |
| Vintage | For profit | MKTG | Dec 29, 1997 |
| Watson Pharmaceuticals | For profit | MKTG | Feb 13, 1996 |
| Wockhardt | For profit | MKTG | Mar 28, 1997 |
| Wockhardt | For profit | SYN | Mar 28, 1997 |