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Details

Stereochemistry ABSOLUTE
Molecular Formula C16H27NO4S
Molecular Weight 329.455
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIVOPRIL

SMILES

C[C@H](CSC(=O)C(C)(C)C)C(=O)N(CC(O)=O)C1CCCC1

InChI

InChIKey=XRKXJJYSKUIIEN-LLVKDONJSA-N
InChI=1S/C16H27NO4S/c1-11(10-22-15(21)16(2,3)4)14(20)17(9-13(18)19)12-7-5-6-8-12/h11-12H,5-10H2,1-4H3,(H,18,19)/t11-/m1/s1

HIDE SMILES / InChI

Molecular Formula C16H27NO4S
Molecular Weight 329.455
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
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
[Successful extubation in a patient with alacepril-induced tongue angioedema].
2010 Apr
Effects of the angiotensin-converting enzyme inhibitor alacepril in dogs with mitral valve disease.
2018 Aug 10
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 15:15:32 GMT 2023
Edited
by admin
on Fri Dec 15 15:15:32 GMT 2023
Record UNII
3V6I5962EM
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PIVOPRIL
INN   MART.   USAN  
INN   USAN  
Official Name English
USV-3659-(S)
Code English
REV 3659-(S)
Code English
PIVOPRIL [USAN]
Common Name English
USV 3659-(S)
Code English
RHC-3659 (S)
Code English
RHC 3659-(S)
Code English
USV-3659 (S)
Code English
REV-3659 (S)
Code English
PIVOPRIL [MART.]
Common Name English
pivopril [INN]
Common Name English
REV 3569-(S)
Code English
RHC-3659-(S)
Code English
REV-3659-(S)
Code English
Classification Tree Code System Code
NCI_THESAURUS C247
Created by admin on Fri Dec 15 15:15:32 GMT 2023 , Edited by admin on Fri Dec 15 15:15:32 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID501319138
Created by admin on Fri Dec 15 15:15:32 GMT 2023 , Edited by admin on Fri Dec 15 15:15:32 GMT 2023
PRIMARY
NCI_THESAURUS
C66443
Created by admin on Fri Dec 15 15:15:32 GMT 2023 , Edited by admin on Fri Dec 15 15:15:32 GMT 2023
PRIMARY
SMS_ID
100000081910
Created by admin on Fri Dec 15 15:15:32 GMT 2023 , Edited by admin on Fri Dec 15 15:15:32 GMT 2023
PRIMARY
USAN
S-87
Created by admin on Fri Dec 15 15:15:32 GMT 2023 , Edited by admin on Fri Dec 15 15:15:32 GMT 2023
PRIMARY
PUBCHEM
6917956
Created by admin on Fri Dec 15 15:15:32 GMT 2023 , Edited by admin on Fri Dec 15 15:15:32 GMT 2023
PRIMARY
INN
5569
Created by admin on Fri Dec 15 15:15:32 GMT 2023 , Edited by admin on Fri Dec 15 15:15:32 GMT 2023
PRIMARY
ChEMBL
CHEMBL2051970
Created by admin on Fri Dec 15 15:15:32 GMT 2023 , Edited by admin on Fri Dec 15 15:15:32 GMT 2023
PRIMARY
CAS
81045-50-3
Created by admin on Fri Dec 15 15:15:32 GMT 2023 , Edited by admin on Fri Dec 15 15:15:32 GMT 2023
PRIMARY
FDA UNII
3V6I5962EM
Created by admin on Fri Dec 15 15:15:32 GMT 2023 , Edited by admin on Fri Dec 15 15:15:32 GMT 2023
PRIMARY
EVMPD
SUB09952MIG
Created by admin on Fri Dec 15 15:15:32 GMT 2023 , Edited by admin on Fri Dec 15 15:15:32 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY