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Details

Stereochemistry ABSOLUTE
Molecular Formula C24H28N2O5
Molecular Weight 424.4895
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DELAPRILAT

SMILES

C[C@H](N[C@@H](CCC1=CC=CC=C1)C(O)=O)C(=O)N(CC(O)=O)C2CC3=CC=CC=C3C2

InChI

InChIKey=PHASTBJLWIZXKB-KKSFZXQISA-N
InChI=1S/C24H28N2O5/c1-16(25-21(24(30)31)12-11-17-7-3-2-4-8-17)23(29)26(15-22(27)28)20-13-18-9-5-6-10-19(18)14-20/h2-10,16,20-21,25H,11-15H2,1H3,(H,27,28)(H,30,31)/t16-,21-/m0/s1

HIDE SMILES / InChI
Molecular Formula C24H28N2O5
Molecular Weight 424.4895
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Delapril is a lipophilic nonsulfhydryl angiotensin-converting enzyme (ACE) inhibitor, which has been shown to exert potent ACE inhibitory activity and is marketed as an antihypertensive drug. Delapril has been shown to exist in solution as a mixture of s-cis and s-trans conformational isomers, as a result of restricted rotation about the amide bond.

Originator

Takeda Chemical Industries
29
Curator's Comment: # Takeda Chemical Industries, Ltd

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Angiotensin-converting enzyme
94
Target ID: P12821
Gene ID: 1636.0
Gene Symbol: ACE
Target Organism: Homo sapiens (Human)
Inhibitor
8504
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
VIVACE

Approved Use

To treat the arterial hypertension.
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
221 ng/mL
CLINICAL TRIAL
https://pubmed.ncbi.nlm.nih.gov/14558436/
30 mg single, oral
dose: 30 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DELAPRIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
489 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3802709/
30 mg single, oral
dose: 30 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DELAPRIL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
173 ng/mL
CLINICAL TRIAL
https://pubmed.ncbi.nlm.nih.gov/13677245/
30 mg single, oral
dose: 30 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DELAPRIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
136 ng/mL
CLINICAL TRIAL
https://pubmed.ncbi.nlm.nih.gov/13677245/
30 mg single, oral
dose: 30 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DELAPRIL HYDROCHLORIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
206 ng × h/mL
CLINICAL TRIAL
https://pubmed.ncbi.nlm.nih.gov/14558436/
30 mg single, oral
dose: 30 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DELAPRIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
572 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3802709/
30 mg single, oral
dose: 30 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DELAPRIL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
206 ng × h/mL
CLINICAL TRIAL
https://pubmed.ncbi.nlm.nih.gov/13677245/
30 mg single, oral
dose: 30 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DELAPRIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
218 ng × h/mL
CLINICAL TRIAL
https://pubmed.ncbi.nlm.nih.gov/13677245/
30 mg single, oral
dose: 30 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DELAPRIL HYDROCHLORIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
0.45 h
CLINICAL TRIAL
https://pubmed.ncbi.nlm.nih.gov/14558436/
30 mg single, oral
dose: 30 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DELAPRIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
0.3 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3802709/
30 mg single, oral
dose: 30 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DELAPRIL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
90 mg 1 times / day multiple, oral
Highest studied dose
Dose: 90 mg, 1 times / day
Route: oral
Route: multiple
Dose: 90 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/2009145/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: unknown
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/2009145/
Sources:
https://pubmed.ncbi.nlm.nih.gov/2009145/
PubMed

PubMed

TitleDatePubMed
ACE Inhibitor Delapril Prevents Ca(2+)-Dependent Blunting of IK1 and Ventricular Arrhythmia in Ischemic Heart Disease.
2015
Effects of manidipine and delapril in hypertensive patients with type 2 diabetes mellitus: the delapril and manidipine for nephroprotection in diabetes (DEMAND) randomized clinical trial.
2011-11
Delapril versus manidipine in hypertensive therapy to halt the type-2-diabetes-mellitus-associated nephropathy.
2000-02
Long-term effects of delapril hydrochloride on procollagen type III amino-terminal peptide, left ventricular mass and left ventricular function in hypertensive patients.
1998-12
Effects of ACE inhibitors versus calcium antagonists on left ventricular morphology and function in patients with essential hypertension.
1997-03
Pharmacokinetic and pharmacologic properties of delapril, a lipophilic nonsulfhydryl angiotensin-converting enzyme inhibitor.
1995-06-16
Bioavailability and pharmacokinetics of a fixed combination of delapril/indapamide following single and multiple dosing in healthy volunteers.
1994-01-01
Effects of manidipine and delapril on serum lipids, lipoproteins, and apolipoproteins in patients with mild to moderate essential hypertension: a randomized trial with one-year follow-up.
1992-11-01
Effect of delapril on the vascular angiotensin II release in isolated hind legs of the spontaneously hypertensive rat: evidence for potential relevance of vascular angiotensin II to the maintenance of hypertension.
1991-09
The antihypertensive mechanism of delapril, a newly developed converting enzyme inhibitor, is related to the suppression of vascular angiotensin II release in the spontaneously hypertensive rat.
1991-01
Long-term effects of delapril on renal function and urinary excretion of kallikrein, prostaglandin E2, and thromboxane B2 in hypertensive patients.
1991-01
Effect of delapril hydrochloride on angiotensin II release from isolated rat hind legs.
1990-08-02
Antihypertensive action of a non-sulfhydryl angiotensin converting enzyme inhibitor (CV-3317) in various hypertensive models.
1986-09
Inhibition of angiotensin converting enzyme by CV-3317, a non-sulfhydryl compound.
1986-09
Design and synthesis of N-[N-[(S)-1-ethoxycarbonyl-3-phenylpropyl]-L -alanyl]-N-(indan-2-yl)glycine (CV-3317), a new, potent angiotensin converting enzyme inhibitor.
1986-07
Patents

Patents

JP1066130A
10
JP2000219639A
8
JP2002536332A
39
JP2002538172A
23
JP2002541233A
406
JP2003503381A
36
JP2003515526A
470
JP2005527462A
22
JP2007514770A
77
JP2007520453A
36
JP2008069139A
3
JP2011524416A
146
JP4729259B2
38
JPH02121922A
14
JPS6466130A
5

Sample Use Guides

In Vivo Use Guide
30 mg per day
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 20:06:22 GMT 2025
Edited
by admin
on Mon Mar 31 20:06:22 GMT 2025
Record UNII
50A464U6E7
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DELAPRILAT
Common Name English
DELAPRIL DIACID
Preferred Name English
GLYCINE, N-(N-(1-CARBOXY-3-PHENYLPROPYL)-L-ALANYL)-N-(2,3-DIHYDRO-1H-INDEN-2-YL)-, (S)-
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID10232315
Created by admin on Mon Mar 31 20:06:22 GMT 2025 , Edited by admin on Mon Mar 31 20:06:22 GMT 2025
PRIMARY
PUBCHEM
5488746
Created by admin on Mon Mar 31 20:06:22 GMT 2025 , Edited by admin on Mon Mar 31 20:06:22 GMT 2025
PRIMARY
FDA UNII
50A464U6E7
Created by admin on Mon Mar 31 20:06:22 GMT 2025 , Edited by admin on Mon Mar 31 20:06:22 GMT 2025
PRIMARY
CAS
83398-08-7
Created by admin on Mon Mar 31 20:06:22 GMT 2025 , Edited by admin on Mon Mar 31 20:06:22 GMT 2025
PRIMARY
Related Record Type Details
Structure of DELAPRIL
PRODRUG -> METABOLITE ACTIVE
NIH
NCATS
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