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

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 97 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 8297

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 8429	VIVACE Approved Use To treat the arterial hypertension.

PubMed

Title	Date	PubMed
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 Jul	3021350
Antihypertensive action of a non-sulfhydryl angiotensin converting enzyme inhibitor (CV-3317) in various hypertensive models.	1986 Sep	3025485
Inhibition of angiotensin converting enzyme by CV-3317, a non-sulfhydryl compound.	1986 Sep	3025487
Effect of delapril hydrochloride on angiotensin II release from isolated rat hind legs.	1990 Aug 2	2209711
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 Jan	2009151
Long-term effects of delapril on renal function and urinary excretion of kallikrein, prostaglandin E2, and thromboxane B2 in hypertensive patients.	1991 Jan	2009149
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 Sep	1959233
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 Nov-Dec	1286488
Bioavailability and pharmacokinetics of a fixed combination of delapril/indapamide following single and multiple dosing in healthy volunteers.	1994 Jan-Mar	7957454
Pharmacokinetic and pharmacologic properties of delapril, a lipophilic nonsulfhydryl angiotensin-converting enzyme inhibitor.	1995 Jun 16	7778536
Effects of ACE inhibitors versus calcium antagonists on left ventricular morphology and function in patients with essential hypertension.	1997 Mar	9101306
Long-term effects of delapril hydrochloride on procollagen type III amino-terminal peptide, left ventricular mass and left ventricular function in hypertensive patients.	1998 Dec	9890202
Delapril versus manidipine in hypertensive therapy to halt the type-2-diabetes-mellitus-associated nephropathy.	2000 Feb	10670908
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 Nov	21931073
ACE Inhibitor Delapril Prevents Ca(2+)-Dependent Blunting of IK1 and Ventricular Arrhythmia in Ischemic Heart Disease.	2015	26321755

Patents

Sample Use Guides

In Vivo Use Guide

30 mg per day

Route of Administration: Oral

In Vitro Use Guide

Unknown

Name

Type

Language

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 [MI]

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