UTIBAPRIL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H31N3O5S
Molecular Weight	449.564
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
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)N2N=C(S[C@H]2C(O)=O)C(C)(C)C

InChI

InChIKey=FTYVYAGWBXTWTN-ZVZYQTTQSA-N

InChI=1S/C22H31N3O5S/c1-6-30-20(29)16(13-12-15-10-8-7-9-11-15)23-14(2)17(26)25-18(19(27)28)31-21(24-25)22(3,4)5/h7-11,14,16,18,23H,6,12-13H2,1-5H3,(H,27,28)/t14-,16-,18-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C22H31N3O5S
Molecular Weight	449.564
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://adisinsight.springer.com/drugs/800000394 | https://www.ncbi.nlm.nih.gov/pubmed/9213213

Utibapril (FPL 63547) is an ester prodrug of a novel thiadiazoline ACE inhibitor. Utibapril was undergoing phase II clinical studies in the United Kingdom for the treatment of heart failure and hypertension. Utibapril is an angiotensin-converting enzyme (ACE) inhibitor with a proposed tissue-specific inhibitory profile. This implies that at a certain dose, utibapril should be able to inhibit tissue ACE activity without affecting plasma ACE.

Originator

Approval Year

PubMed

Title	Date	PubMed
Pharmacological properties of FPL 63547, a novel inhibitor of angiotensin-converting enzyme.	1990 May	2164863
Cardiac and aortic effects of angiotensin converting enzyme inhibitors.	1991 Oct	1916997

Sample Use Guides

In Vivo Use Guide

Normal Wistar rats were randomly allocated to oral treatment with different doses of utibapril (0, 2, 10, 50, or 250 ug/kg/day) for 30 days. Utibapril significantly inhibited plasma, renal, and vascular ACE but not ventricular ACE activity. Notably, however, only treatment with the highest dose of utibapril resulted in a significant inhibition of plasma ACE, whereas vascular ACE activity was already significantly inhibited after treatment with a lower dose of utibapril.

Route of Administration: Oral

In Vitro Use Guide

Utibapril (FPL 63547), in its active diacid form, was a potent inhibitor of rabbit lung angiotension converting enzyme (ACE) in vitro (IC50 0.51 nM).

Substance Class	Chemical Created by `admin` on `Sat Dec 16 18:05:26 GMT 2023` Edited by `admin` on `Sat Dec 16 18:05:26 GMT 2023`
Record UNII	87I5H747BC
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

UTIBAPRIL

Official Name

English

Utibapril [WHO-DD]

Common Name

English

utibapril [INN]

Common Name

English

(S)-2-TERT-BUTYL-4-((S)-N-((S)-1-CARBOXY-3-PHENYLPROPYL)ALANYL)-.DELTA.(SUP 2)-1,3,4-THIADIAZOLINE-5-CARBOXYLIC ACID, 4-ETHYL ESTER

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C270