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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 of UTIBAPRIL

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

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.

Approval Year

PubMed

PubMed

TitleDatePubMed
Pharmacological properties of FPL 63547, a novel inhibitor of angiotensin-converting enzyme.
1990 May
Cardiac and aortic effects of angiotensin converting enzyme inhibitors.
1991 Oct

Sample Use Guides

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
  • Download
Name Type Language
UTIBAPRIL
INN   WHO-DD  
INN  
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
Created by admin on Sat Dec 16 18:05:26 GMT 2023 , Edited by admin on Sat Dec 16 18:05:26 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C81524
Created by admin on Sat Dec 16 18:05:26 GMT 2023 , Edited by admin on Sat Dec 16 18:05:26 GMT 2023
PRIMARY
FDA UNII
87I5H747BC
Created by admin on Sat Dec 16 18:05:26 GMT 2023 , Edited by admin on Sat Dec 16 18:05:26 GMT 2023
PRIMARY
PUBCHEM
9803778
Created by admin on Sat Dec 16 18:05:26 GMT 2023 , Edited by admin on Sat Dec 16 18:05:26 GMT 2023
PRIMARY
CAS
109683-61-6
Created by admin on Sat Dec 16 18:05:26 GMT 2023 , Edited by admin on Sat Dec 16 18:05:26 GMT 2023
PRIMARY
MESH
C065021
Created by admin on Sat Dec 16 18:05:26 GMT 2023 , Edited by admin on Sat Dec 16 18:05:26 GMT 2023
PRIMARY
EVMPD
SUB11391MIG
Created by admin on Sat Dec 16 18:05:26 GMT 2023 , Edited by admin on Sat Dec 16 18:05:26 GMT 2023
PRIMARY
SMS_ID
100000076665
Created by admin on Sat Dec 16 18:05:26 GMT 2023 , Edited by admin on Sat Dec 16 18:05:26 GMT 2023
PRIMARY
INN
6563
Created by admin on Sat Dec 16 18:05:26 GMT 2023 , Edited by admin on Sat Dec 16 18:05:26 GMT 2023
PRIMARY
ChEMBL
CHEMBL138029
Created by admin on Sat Dec 16 18:05:26 GMT 2023 , Edited by admin on Sat Dec 16 18:05:26 GMT 2023
PRIMARY
EPA CompTox
DTXSID80883196
Created by admin on Sat Dec 16 18:05:26 GMT 2023 , Edited by admin on Sat Dec 16 18:05:26 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY