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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=C(C2)C=CC=C3

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
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

Curator's Comment: # Takeda Chemical Industries, Ltd

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P12821
Gene ID: 1636.0
Gene Symbol: ACE
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
VIVACE

Approved Use

To treat the arterial hypertension.
PubMed

PubMed

TitleDatePubMed
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
Antihypertensive action of a non-sulfhydryl angiotensin converting enzyme inhibitor (CV-3317) in various hypertensive models.
1986 Sep
Inhibition of angiotensin converting enzyme by CV-3317, a non-sulfhydryl compound.
1986 Sep
Effect of delapril hydrochloride on angiotensin II release from isolated rat hind legs.
1990 Aug 2
Long-term effects of delapril on renal function and urinary excretion of kallikrein, prostaglandin E2, and thromboxane B2 in hypertensive patients.
1991 Jan
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
Effects of ACE inhibitors versus calcium antagonists on left ventricular morphology and function in patients with essential hypertension.
1997 Mar
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
Delapril versus manidipine in hypertensive therapy to halt the type-2-diabetes-mellitus-associated nephropathy.
2000 Feb
ACE Inhibitor Delapril Prevents Ca(2+)-Dependent Blunting of IK1 and Ventricular Arrhythmia in Ischemic Heart Disease.
2015
Patents

Sample Use Guides

30 mg per day
Route of Administration: Oral
In Vitro Use Guide
Unknown
Name Type Language
DELAPRILAT
Common Name English
GLYCINE, N-(N-(1-CARBOXY-3-PHENYLPROPYL)-L-ALANYL)-N-(2,3-DIHYDRO-1H-INDEN-2-YL)-, (S)-
Common Name English
DELAPRIL DIACID
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID10232315
Created by admin on Fri Dec 15 20:16:59 UTC 2023 , Edited by admin on Fri Dec 15 20:16:59 UTC 2023
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PUBCHEM
5488746
Created by admin on Fri Dec 15 20:16:59 UTC 2023 , Edited by admin on Fri Dec 15 20:16:59 UTC 2023
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FDA UNII
50A464U6E7
Created by admin on Fri Dec 15 20:16:59 UTC 2023 , Edited by admin on Fri Dec 15 20:16:59 UTC 2023
PRIMARY
CAS
83398-08-7
Created by admin on Fri Dec 15 20:16:59 UTC 2023 , Edited by admin on Fri Dec 15 20:16:59 UTC 2023
PRIMARY