U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C9H15NO3S
Molecular Weight 217.2867
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CAPTOPRIL

SMILES

C[C@]([H])(CS)C(=O)N1CCC[C@@]1([H])C(=O)O

InChI

InChIKey=FAKRSMQSSFJEIM-RQJHMYQMSA-N
InChI=1S/C9H15NO3S/c1-6(5-14)8(11)10-4-2-3-7(10)9(12)13/h6-7,14H,2-5H2,1H3,(H,12,13)/t6-,7+/m1/s1

HIDE SMILES / InChI

Description
Curator's Comment:: Description was created based on several sources, including https://ncit.nci.nih.gov/ncitbrowser/ConceptReport.jsp?dictionary=NCI_Thesaurus&ns=NCI_Thesaurus&code=C66443

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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
CAPOTEN

Approved Use

Hypertension: CAPOTEN (captopril tablets, USP) is indicated for the treatment of hypertension. In using CAPOTEN, consideration should be given to the risk of neutropenia/agranulocytosis. CAPOTEN may be used as initial therapy for patients with normal renal function, in whom the risk is relatively low. In patients with impaired renal function, particularly those with collagen vascular disease, captopril should be reserved for hypertensives who have either developed unacceptable side effects on other drugs, or have failed to respond satisfactorily to drug combinations. CAPOTEN is effective alone and in combination with other antihypertensive agents, especially thiazide­ type diuretics. The blood pressure lowering effects of captopril and thiazides are approximately additive. Heart Failure: CAPOTEN is indicated in the treatment of congestive heart failure usually in combination with diuretics and digitalis. The beneficial effect of captopril in heart failure does not require the presence of digitalis, however, most controlled clinical trial experience with captopril has been in patients receiving digitalis, as well as diuretic treatment. Left Ventricular Dysfunction After Myocardial Infarction: CAPOTEN is indicated to improve survival following myocardial infarction in clinically stable patients with left ventricular dysfunction manifested as an ejection fraction ≤40% and to reduce the incidence of overt heart failure and subsequent hospitalizations for congestive heart failure in these patients. Diabetic Nephropathy: CAPOTEN is indicated for the treatment of diabetic nephropathy (proteinuria >500 mg/day) in patients with type I insulin-dependent diabetes mellitus and retinopathy. CAPOTEN decreases the rate of progression of renal insufficiency and development of serious adverse clinical outcomes (death or need for renal transplantation or dialysis).

Launch Date

3.55276816E11
Primary
CAPOTEN

Approved Use

Hypertension: CAPOTEN (captopril tablets, USP) is indicated for the treatment of hypertension. In using CAPOTEN, consideration should be given to the risk of neutropenia/agranulocytosis. CAPOTEN may be used as initial therapy for patients with normal renal function, in whom the risk is relatively low. In patients with impaired renal function, particularly those with collagen vascular disease, captopril should be reserved for hypertensives who have either developed unacceptable side effects on other drugs, or have failed to respond satisfactorily to drug combinations. CAPOTEN is effective alone and in combination with other antihypertensive agents, especially thiazide­ type diuretics. The blood pressure lowering effects of captopril and thiazides are approximately additive. Heart Failure: CAPOTEN is indicated in the treatment of congestive heart failure usually in combination with diuretics and digitalis. The beneficial effect of captopril in heart failure does not require the presence of digitalis, however, most controlled clinical trial experience with captopril has been in patients receiving digitalis, as well as diuretic treatment. Left Ventricular Dysfunction After Myocardial Infarction: CAPOTEN is indicated to improve survival following myocardial infarction in clinically stable patients with left ventricular dysfunction manifested as an ejection fraction ≤40% and to reduce the incidence of overt heart failure and subsequent hospitalizations for congestive heart failure in these patients. Diabetic Nephropathy: CAPOTEN is indicated for the treatment of diabetic nephropathy (proteinuria >500 mg/day) in patients with type I insulin-dependent diabetes mellitus and retinopathy. CAPOTEN decreases the rate of progression of renal insufficiency and development of serious adverse clinical outcomes (death or need for renal transplantation or dialysis).

Launch Date

3.55276816E11
Primary
CAPOTEN

Approved Use

Hypertension: CAPOTEN (captopril tablets, USP) is indicated for the treatment of hypertension. In using CAPOTEN, consideration should be given to the risk of neutropenia/agranulocytosis. CAPOTEN may be used as initial therapy for patients with normal renal function, in whom the risk is relatively low. In patients with impaired renal function, particularly those with collagen vascular disease, captopril should be reserved for hypertensives who have either developed unacceptable side effects on other drugs, or have failed to respond satisfactorily to drug combinations. CAPOTEN is effective alone and in combination with other antihypertensive agents, especially thiazide­ type diuretics. The blood pressure lowering effects of captopril and thiazides are approximately additive. Heart Failure: CAPOTEN is indicated in the treatment of congestive heart failure usually in combination with diuretics and digitalis. The beneficial effect of captopril in heart failure does not require the presence of digitalis, however, most controlled clinical trial experience with captopril has been in patients receiving digitalis, as well as diuretic treatment. Left Ventricular Dysfunction After Myocardial Infarction: CAPOTEN is indicated to improve survival following myocardial infarction in clinically stable patients with left ventricular dysfunction manifested as an ejection fraction ≤40% and to reduce the incidence of overt heart failure and subsequent hospitalizations for congestive heart failure in these patients. Diabetic Nephropathy: CAPOTEN is indicated for the treatment of diabetic nephropathy (proteinuria >500 mg/day) in patients with type I insulin-dependent diabetes mellitus and retinopathy. CAPOTEN decreases the rate of progression of renal insufficiency and development of serious adverse clinical outcomes (death or need for renal transplantation or dialysis).

Launch Date

3.55276816E11
Primary
CAPOTEN

Approved Use

Hypertension: CAPOTEN (captopril tablets, USP) is indicated for the treatment of hypertension. In using CAPOTEN, consideration should be given to the risk of neutropenia/agranulocytosis. CAPOTEN may be used as initial therapy for patients with normal renal function, in whom the risk is relatively low. In patients with impaired renal function, particularly those with collagen vascular disease, captopril should be reserved for hypertensives who have either developed unacceptable side effects on other drugs, or have failed to respond satisfactorily to drug combinations. CAPOTEN is effective alone and in combination with other antihypertensive agents, especially thiazide­ type diuretics. The blood pressure lowering effects of captopril and thiazides are approximately additive. Heart Failure: CAPOTEN is indicated in the treatment of congestive heart failure usually in combination with diuretics and digitalis. The beneficial effect of captopril in heart failure does not require the presence of digitalis, however, most controlled clinical trial experience with captopril has been in patients receiving digitalis, as well as diuretic treatment. Left Ventricular Dysfunction After Myocardial Infarction: CAPOTEN is indicated to improve survival following myocardial infarction in clinically stable patients with left ventricular dysfunction manifested as an ejection fraction ≤40% and to reduce the incidence of overt heart failure and subsequent hospitalizations for congestive heart failure in these patients. Diabetic Nephropathy: CAPOTEN is indicated for the treatment of diabetic nephropathy (proteinuria >500 mg/day) in patients with type I insulin-dependent diabetes mellitus and retinopathy. CAPOTEN decreases the rate of progression of renal insufficiency and development of serious adverse clinical outcomes (death or need for renal transplantation or dialysis).

Launch Date

3.55276816E11
Primary
Unknown

Approved Use

Unknown
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.9 h
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CAPTOPRIL plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
50 mg 1 times / day multiple, oral
Highest studied dose
Dose: 50 mg, 1 times / day
Route: oral
Route: multiple
Dose: 50 mg, 1 times / day
Sources:
unhealthy, 54 years (range: 39-65 years)
n = 10
Health Status: unhealthy
Condition: essential hypertension
Age Group: 54 years (range: 39-65 years)
Population Size: 10
Sources:
50 mg 1 times / day multiple, oral
Dose: 50 mg, 1 times / day
Route: oral
Route: multiple
Dose: 50 mg, 1 times / day
Sources:
unhealthy, 65 years
n = 1
Health Status: unhealthy
Condition: type 2 diabetes
Age Group: 65 years
Sex: F
Population Size: 1
Sources:
Disc. AE: Eruption lichenoid...
AEs leading to
discontinuation/dose reduction:
Eruption lichenoid (severe, 1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
Eruption lichenoid severe, 1 patient
Disc. AE
50 mg 1 times / day multiple, oral
Dose: 50 mg, 1 times / day
Route: oral
Route: multiple
Dose: 50 mg, 1 times / day
Sources:
unhealthy, 65 years
n = 1
Health Status: unhealthy
Condition: type 2 diabetes
Age Group: 65 years
Sex: F
Population Size: 1
Sources:
PubMed

PubMed

TitleDatePubMed
Effects of the angiotensin-converting enzyme inhibitor alacepril on exercise capacity and neurohormonal factors in patients with mild-to-moderate heart failure.
2002 Dec
Effects of acute and chronic alacepril treatment on exercise capacity and hemodynamics in patients with heart failure: a preliminary study.
2002 Feb
Sialic acid 9-O-acetylesterase catalyzes the hydrolyzing reaction from alacepril to deacetylalacepril.
2003 Aug
The inhibitory effect of alacepril, an angiotensin-converting enzyme inhibitor, on endothelial inflammatory response induced by oxysterol and TNF-alpha.
2004
Long-term plasma levels and dose modulation of alacepril in patients with chronic renal failure.
2008 Jan
[Successful extubation in a patient with alacepril-induced tongue angioedema].
2010 Apr
Evaluation of the effect of an angiotensin-converting enzyme inhibitor, alacepril, on drug-induced renin-angiotensin-aldosterone system activation in normal dogs.
2016 Sep
Pharmacodynamics of alacepril in healthy cats.
2017 Jun
Effects of the angiotensin-converting enzyme inhibitor alacepril in dogs with mitral valve disease.
2018 Aug 10
Effects of high-dose alacepril on left atrial pressure and central aortic pressure in awake dogs with mitral valve regurgitation.
2019 Mar
Patents

Sample Use Guides

Single oral dose (5 - 80 mg)
Route of Administration: Oral
In Vitro Use Guide
Unknown
Name Type Language
CAPTOPRIL
EP   HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
INN   USAN  
Official Name English
CAPTOPRIL [USP]
Common Name English
CAPOTEN
Brand Name English
CAPTOPRIL [WHO-IP]
Common Name English
CAPTOPRIL [MART.]
Common Name English
CAPTOPRIL [USP MONOGRAPH]
Common Name English
SA-333
Code English
GARRANIL
Common Name English
1-((2S)-3-MERCAPTO-2-METHYLPROPIONYL)-L-PROLINE
Systematic Name English
SQ-14225
Code English
TENSIOMIN
Common Name English
CAPTOMAX
Common Name English
CAPTOPRIL [USP-RS]
Common Name English
CAPTOPRIL [WHO-DD]
Common Name English
SQ -14225
Code English
CAPTOPRIL [USAN]
Common Name English
CAPTOPRIL [HSDB]
Common Name English
CAPTOPRILUM [WHO-IP LATIN]
Common Name English
C09AA01
Code English
FARCOPRIL
Common Name English
CAPTOPRIL [EP MONOGRAPH]
Common Name English
CAPTOPRIL [MI]
Common Name English
L-PROLINE, 1-((2S)-3-MERCAPTO-2-METHYL-1-OXOPROPYL)-
Systematic Name English
ZAPTO
Common Name English
APOPRIL
Brand Name English
MEPHA
Common Name English
CAPTOPRIL [VANDF]
Common Name English
CAPTOPRIL [ORANGE BOOK]
Common Name English
NSC-757419
Code English
CAPTOPRIL [JAN]
Common Name English
HYPOPRESS
Common Name English
CAPTOPRIL [INN]
Common Name English
Classification Tree Code System Code
WHO-ATC C09AA01
Created by admin on Fri Jun 25 21:01:01 UTC 2021 , Edited by admin on Fri Jun 25 21:01:01 UTC 2021
WHO-ATC C09BA01
Created by admin on Fri Jun 25 21:01:01 UTC 2021 , Edited by admin on Fri Jun 25 21:01:01 UTC 2021
NDF-RT N0000000181
Created by admin on Fri Jun 25 21:01:01 UTC 2021 , Edited by admin on Fri Jun 25 21:01:01 UTC 2021
NDF-RT N0000175562
Created by admin on Fri Jun 25 21:01:01 UTC 2021 , Edited by admin on Fri Jun 25 21:01:01 UTC 2021
WHO-VATC QC09AA01
Created by admin on Fri Jun 25 21:01:01 UTC 2021 , Edited by admin on Fri Jun 25 21:01:01 UTC 2021
WHO-VATC QC09BA01
Created by admin on Fri Jun 25 21:01:01 UTC 2021 , Edited by admin on Fri Jun 25 21:01:01 UTC 2021
NCI_THESAURUS C247
Created by admin on Fri Jun 25 21:01:01 UTC 2021 , Edited by admin on Fri Jun 25 21:01:01 UTC 2021
LIVERTOX 144
Created by admin on Fri Jun 25 21:01:01 UTC 2021 , Edited by admin on Fri Jun 25 21:01:01 UTC 2021
Code System Code Type Description
MESH
D002216
Created by admin on Fri Jun 25 21:01:01 UTC 2021 , Edited by admin on Fri Jun 25 21:01:01 UTC 2021
PRIMARY
USP_CATALOG
1091200
Created by admin on Fri Jun 25 21:01:01 UTC 2021 , Edited by admin on Fri Jun 25 21:01:01 UTC 2021
PRIMARY USP-RS
NCI_THESAURUS
C340
Created by admin on Fri Jun 25 21:01:01 UTC 2021 , Edited by admin on Fri Jun 25 21:01:01 UTC 2021
PRIMARY
RXCUI
1998
Created by admin on Fri Jun 25 21:01:01 UTC 2021 , Edited by admin on Fri Jun 25 21:01:01 UTC 2021
PRIMARY RxNorm
ECHA (EC/EINECS)
263-607-1
Created by admin on Fri Jun 25 21:01:01 UTC 2021 , Edited by admin on Fri Jun 25 21:01:01 UTC 2021
PRIMARY
MERCK INDEX
M3046
Created by admin on Fri Jun 25 21:01:01 UTC 2021 , Edited by admin on Fri Jun 25 21:01:01 UTC 2021
PRIMARY Merck Index
INN
4373
Created by admin on Fri Jun 25 21:01:01 UTC 2021 , Edited by admin on Fri Jun 25 21:01:01 UTC 2021
PRIMARY
ChEMBL
CHEMBL1560
Created by admin on Fri Jun 25 21:01:01 UTC 2021 , Edited by admin on Fri Jun 25 21:01:01 UTC 2021
PRIMARY
WIKIPEDIA
CAPTOPRIL
Created by admin on Fri Jun 25 21:01:01 UTC 2021 , Edited by admin on Fri Jun 25 21:01:01 UTC 2021
PRIMARY
IUPHAR
5158
Created by admin on Fri Jun 25 21:01:01 UTC 2021 , Edited by admin on Fri Jun 25 21:01:01 UTC 2021
PRIMARY
DRUG CENTRAL
484
Created by admin on Fri Jun 25 21:01:01 UTC 2021 , Edited by admin on Fri Jun 25 21:01:01 UTC 2021
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
CAPTOPRIL
Created by admin on Fri Jun 25 21:01:01 UTC 2021 , Edited by admin on Fri Jun 25 21:01:01 UTC 2021
PRIMARY Description: A white or almost white, crystalline powder. Solubility: Freely soluble in water, dichloromethane R, and methanol R. Category: Cardiovascular agent; angiotensin-converting enzyme inhibitor. Storage: Captopril should be kept in a tightly closed container, protected from light. Additional information: Captopril may exist in different polymorphic forms. Requirement: Captopril contains not less than 98.0% and not more than 102.0% of C9H15NO3S, calculated with reference to the dried substance.
EVMPD
SUB06081MIG
Created by admin on Fri Jun 25 21:01:01 UTC 2021 , Edited by admin on Fri Jun 25 21:01:01 UTC 2021
PRIMARY
HSDB
6527
Created by admin on Fri Jun 25 21:01:01 UTC 2021 , Edited by admin on Fri Jun 25 21:01:01 UTC 2021
PRIMARY
FDA UNII
9G64RSX1XD
Created by admin on Fri Jun 25 21:01:01 UTC 2021 , Edited by admin on Fri Jun 25 21:01:01 UTC 2021
PRIMARY
DRUG BANK
DB01197
Created by admin on Fri Jun 25 21:01:01 UTC 2021 , Edited by admin on Fri Jun 25 21:01:01 UTC 2021
PRIMARY
CAS
62571-86-2
Created by admin on Fri Jun 25 21:01:01 UTC 2021 , Edited by admin on Fri Jun 25 21:01:01 UTC 2021
PRIMARY
EPA CompTox
62571-86-2
Created by admin on Fri Jun 25 21:01:01 UTC 2021 , Edited by admin on Fri Jun 25 21:01:01 UTC 2021
PRIMARY
PUBCHEM
44093
Created by admin on Fri Jun 25 21:01:01 UTC 2021 , Edited by admin on Fri Jun 25 21:01:01 UTC 2021
PRIMARY
LACTMED
Captopril
Created by admin on Fri Jun 25 21:01:01 UTC 2021 , Edited by admin on Fri Jun 25 21:01:01 UTC 2021
PRIMARY