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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H26N2O5S
Molecular Weight 406.496
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ALACEPRIL

SMILES

C[C@H](CSC(C)=O)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CC2=CC=CC=C2)C(O)=O

InChI

InChIKey=FHHHOYXPRDYHEZ-COXVUDFISA-N
InChI=1S/C20H26N2O5S/c1-13(12-28-14(2)23)19(25)22-10-6-9-17(22)18(24)21-16(20(26)27)11-15-7-4-3-5-8-15/h3-5,7-8,13,16-17H,6,9-12H2,1-2H3,(H,21,24)(H,26,27)/t13-,16+,17+/m1/s1

HIDE SMILES / InChI

Molecular Formula C20H26N2O5S
Molecular Weight 406.496
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

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

1981
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

1981
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

1981
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

1981
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
Angiotensin-converting enzyme inhibitors. New orally active antihypertensive (mercaptoalkanoyl)- and [(acylthio)alkanoyl]glycine derivatives.
1985 Jan
Spatial and temporal analysis of left ventricular filling flow propagation in hypertensive patients before and after regression of myocardial hypertrophy with alacepril therapy.
2001 Aug
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
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:19:04 GMT 2023
Edited
by admin
on Fri Dec 15 16:19:04 GMT 2023
Record UNII
X39TL7JDPF
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ALACEPRIL
INN   MART.   MI   WHO-DD  
INN  
Official Name English
ALACEPRIL [MI]
Common Name English
DU-1219
Code English
N-(1-((S)-3-MERCAPTO-2-METHYLPROPIONYL)-L-PROLYL)-3-PHENYL-L-ALANINE ACETATE (ESTER)
Common Name English
alacepril [INN]
Common Name English
1-((2S)-3-(ACETYLTHIO)-2-METHYL-1-OXOPROPYL)-L-PROLYL-L-PHENYLALANINE
Systematic Name English
ALACEPRIL [MART.]
Common Name English
1-(D-3-ACETYLTHIO-2-METHYLPROPANOYL)-L-PROLYL-L-PHENYLALANINE
Common Name English
CETAPRIL
Brand Name English
ALACEPRIL [JAN]
Common Name English
Alacepril [WHO-DD]
Common Name English
NSC-338157
Code English
Classification Tree Code System Code
NCI_THESAURUS C247
Created by admin on Fri Dec 15 16:19:04 GMT 2023 , Edited by admin on Fri Dec 15 16:19:04 GMT 2023
Code System Code Type Description
DRUG CENTRAL
101
Created by admin on Fri Dec 15 16:19:04 GMT 2023 , Edited by admin on Fri Dec 15 16:19:04 GMT 2023
PRIMARY
INN
5458
Created by admin on Fri Dec 15 16:19:04 GMT 2023 , Edited by admin on Fri Dec 15 16:19:04 GMT 2023
PRIMARY
NCI_THESAURUS
C75021
Created by admin on Fri Dec 15 16:19:04 GMT 2023 , Edited by admin on Fri Dec 15 16:19:04 GMT 2023
PRIMARY
MERCK INDEX
m1463
Created by admin on Fri Dec 15 16:19:04 GMT 2023 , Edited by admin on Fri Dec 15 16:19:04 GMT 2023
PRIMARY Merck Index
CAS
74258-86-9
Created by admin on Fri Dec 15 16:19:04 GMT 2023 , Edited by admin on Fri Dec 15 16:19:04 GMT 2023
PRIMARY
WIKIPEDIA
ALACEPRIL
Created by admin on Fri Dec 15 16:19:04 GMT 2023 , Edited by admin on Fri Dec 15 16:19:04 GMT 2023
PRIMARY
MESH
C046835
Created by admin on Fri Dec 15 16:19:04 GMT 2023 , Edited by admin on Fri Dec 15 16:19:04 GMT 2023
PRIMARY
FDA UNII
X39TL7JDPF
Created by admin on Fri Dec 15 16:19:04 GMT 2023 , Edited by admin on Fri Dec 15 16:19:04 GMT 2023
PRIMARY
ChEMBL
CHEMBL2103775
Created by admin on Fri Dec 15 16:19:04 GMT 2023 , Edited by admin on Fri Dec 15 16:19:04 GMT 2023
PRIMARY
EPA CompTox
DTXSID3048576
Created by admin on Fri Dec 15 16:19:04 GMT 2023 , Edited by admin on Fri Dec 15 16:19:04 GMT 2023
PRIMARY
PUBCHEM
71992
Created by admin on Fri Dec 15 16:19:04 GMT 2023 , Edited by admin on Fri Dec 15 16:19:04 GMT 2023
PRIMARY
SMS_ID
100000087692
Created by admin on Fri Dec 15 16:19:04 GMT 2023 , Edited by admin on Fri Dec 15 16:19:04 GMT 2023
PRIMARY
EVMPD
SUB05288MIG
Created by admin on Fri Dec 15 16:19:04 GMT 2023 , Edited by admin on Fri Dec 15 16:19:04 GMT 2023
PRIMARY
NSC
338157
Created by admin on Fri Dec 15 16:19:04 GMT 2023 , Edited by admin on Fri Dec 15 16:19:04 GMT 2023
PRIMARY
Related Record Type Details
METABOLITE -> PARENT
Related Record Type Details
ACTIVE MOIETY