FASIDOTRIL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H25NO6S
Molecular Weight	443.513
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@H](NC(=O)[C@@H](CSC(C)=O)CC1=CC=C2OCOC2=C1)C(=O)OCC3=CC=CC=C3

InChI

InChIKey=KKBIUAUSZKGNOA-HNAYVOBHSA-N

InChI=1S/C23H25NO6S/c1-15(23(27)28-12-17-6-4-3-5-7-17)24-22(26)19(13-31-16(2)25)10-18-8-9-20-21(11-18)30-14-29-20/h3-9,11,15,19H,10,12-14H2,1-2H3,(H,24,26)/t15-,19+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C23H25NO6S
Molecular Weight	443.513
Charge	0
Count

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

Description
Sources: https://adisinsight.springer.com/drugs/800003997 | https://onlinelibrary.wiley.com/doi/pdf/10.1111/j.1527-3466.2000.tb00030.x | https://www.ncbi.nlm.nih.gov/pubmed/14582457

Fasidotril is a diester prodrug of the active metabolite fasidotrilat. Fasidotrilat inhibited both angiotensin I converting enzyme (ACE, EC 3.4.25.1) and neprilysin (NEP, EC 3.4.24.11, also named neutral endopeptidase, enkephalinase, or atriopeptidase) at nanomolar concentrations (Ki = 9.8 nM against ACE and 5.1 nM against NEP) Fasidotril was being developed for the treatment of myocardial infarction, congestive heart failure and myocardial infarction.

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.ncbi.nlm.nih.gov/pubmed/1851998	Inhibitor 8297		9.8 nM [Ki]
Neprilysin 29 Target ID: P08473 Gene ID: 4311.0 Gene Symbol: MME Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/1851998	Inhibitor 8297		5.1 nM [Ki]

PubMed

Title	Date	PubMed
Hemodynamic effects of acute and chronic treatment with aladotril, a mixed inhibitor of neutral endopeptidase and angiotensin I-converting enzyme, in conscious rats with myocardial infarction.	1995 Dec	8531099

Patents

Sample Use Guides

In Vivo Use Guide

After a 4-week placebo run-in period, 57 patients with essential hypertension were included in a randomized double-blind, placebo-controlled, parallel-group study and received orally either fasidotril (100 mg twice daily) or placebo for 6 weeks.

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:29:19 GMT 2023` Edited by `admin` on `Fri Dec 15 16:29:19 GMT 2023`
Record UNII	BIB7HG2V9E
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FASIDOTRIL

Official Name

English

L-ALANINE, N-(3-(ACETYLTHIO)-2-(1,3-BENZODIOXOL-5-YLMETHYL)-1-OXOPROPYL)-, PHENYLMETHYL ESTER, (S)-

Systematic Name

English

ALATRIOPRIL

Common Name

English

ALADOTRIL

Common Name

English

BP-1137

Code

English

fasidotril [INN]

Common Name

English

Fasidotril [WHO-DD]

Common Name

English

FASIDOTRIL [MI]

Common Name

English

L-ALANINE, N-((2S)-3-(ACETYLTHIO)-2-(1,3-BENZODIOXOL-5-YLMETHYL)-1-OXOPROPYL)-, PHENYLMETHYL ESTER

Systematic Name

English

N-((S)-.ALPHA.-(MERCAPTOMETHYL)-3,4-(METHYLENEDIOXY)HYDROCINNAMOYL)-L-ALANINE, BENZYL ESTER ACETATE (ESTER)

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C783