DELAPRIL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C26H32N2O5
Molecular Weight	452.5427
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N(CC(O)=O)C2CC3=C(C2)C=CC=C3

InChI

InChIKey=WOUOLAUOZXOLJQ-MBSDFSHPSA-N

InChI=1S/C26H32N2O5/c1-3-33-26(32)23(14-13-19-9-5-4-6-10-19)27-18(2)25(31)28(17-24(29)30)22-15-20-11-7-8-12-21(20)16-22/h4-12,18,22-23,27H,3,13-17H2,1-2H3,(H,29,30)/t18-,23-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C26H32N2O5
Molecular Weight	452.5427
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.medjchem.com/images/stories/V3N4/mjcbenamar2.pdf

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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Angiotensin-converting enzyme 94 Target ID: P12821 Gene ID: 1636.0 Gene Symbol: ACE Target Organism: Homo sapiens (Human) Sources: https://www.jstage.jst.go.jp/article/cpb1958/34/7/34_7_2852/_pdf	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Arterial hypertension 5 Sources: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4053015/pdf/main.pdf	Primary		Approved 8583	VIVACE Approved Use To treat the arterial hypertension.

C_max

Value	Dose	Analyte	Population
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

Value	Dose	Analyte	Population
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

T_1/2

Value	Dose	Co-administered	Analyte	Population
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

Dose	Population	Adverse 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

Title	Date	PubMed
ACE Inhibitor Delapril Prevents Ca(2+)-Dependent Blunting of IK1 and Ventricular Arrhythmia in Ischemic Heart Disease.	2015	26321755
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	21931073
Delapril versus manidipine in hypertensive therapy to halt the type-2-diabetes-mellitus-associated nephropathy.	2000-02	10670908
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	9890202
Effects of ACE inhibitors versus calcium antagonists on left ventricular morphology and function in patients with essential hypertension.	1997-03	9101306
Pharmacokinetic and pharmacologic properties of delapril, a lipophilic nonsulfhydryl angiotensin-converting enzyme inhibitor.	1995-06-16	7778536
Bioavailability and pharmacokinetics of a fixed combination of delapril/indapamide following single and multiple dosing in healthy volunteers.	1994-01-01	7957454
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	1286488
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	1959233
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	2009151
Long-term effects of delapril on renal function and urinary excretion of kallikrein, prostaglandin E2, and thromboxane B2 in hypertensive patients.	1991-01	2009149
Effect of delapril hydrochloride on angiotensin II release from isolated rat hind legs.	1990-08-02	2209711
Antihypertensive action of a non-sulfhydryl angiotensin converting enzyme inhibitor (CV-3317) in various hypertensive models.	1986-09	3025485
Inhibition of angiotensin converting enzyme by CV-3317, a non-sulfhydryl compound.	1986-09	3025487
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	3021350

Patents

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 18:24:09 GMT 2025` Edited by `admin` on `Mon Mar 31 18:24:09 GMT 2025`
Record UNII	W77UAL9THI
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

DELAPRIL [MI]

Preferred Name

English

DELAPRIL

Official Name

English

ETHYL (S)-2-(((S)-1-((CARBOXYMETHYL)-2-INDANYLCARBAMOYL)ETHYL)AMINO)-4-PHENYLBUTYRATE

Systematic Name

English

delapril [INN]

Common Name

English

Delapril [WHO-DD]

Common Name

English

GLYCINE, N-(2,3-DIHYDRO-1H-INDEN-2-YL)-N-(N-(1-(ETHOXYCARBONYL)-3-PHENYLPROPYL)-L-ALANYL)-, (S)-

Common Name

English

Classification Tree Code System Code

WHO-ATC

C09BB12