FASIDOTRILAT

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C14H17NO5S
Molecular Weight	311.353
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](CS)CC1=CC=C2OCOC2=C1)C(O)=O

InChI

InChIKey=TXSINLUUGRGAJO-WCBMZHEXSA-N

InChI=1S/C14H17NO5S/c1-8(14(17)18)15-13(16)10(6-21)4-9-2-3-11-12(5-9)20-7-19-11/h2-3,5,8,10,21H,4,6-7H2,1H3,(H,15,16)(H,17,18)/t8-,10+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C14H17NO5S
Molecular Weight	311.353
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
Mixed inhibitors of angiotensin-converting enzyme (EC 3.4.15.1) and enkephalinase (EC 3.4.24.11): rational design, properties, and potential cardiovascular applications of glycopril and alatriopril.	1991 May 15	1851998
Effect of long-term therapy with fasidotril, a mixed inhibitor of neprilysin and angiotensin-converting enzyme (ACE), on survival of rats after myocardial infarction.	1999 Mar	10435026
Antihypertensive effects of fasidotril, a dual inhibitor of neprilysin and angiotensin-converting enzyme, in rats and humans.	2000 May	10818079
Strategies for access to enantiomerically pure ecadotril, dexecadotril and fasidotril: a review.	2002 Jun	12370063

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 `Sat Dec 16 10:58:59 GMT 2023` Edited by `admin` on `Sat Dec 16 10:58:59 GMT 2023`
Record UNII	0N48AL0PRA
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FASIDOTRILAT

Common Name

English

L-ALANINE, N-((2S)-3-(1,3-BENZODIOXOL-5-YL)-2-(MERCAPTOMETHYL)-1-OXOPROPYL)-

Systematic Name

English

FASIDOTRIL DIACID [MI]

Common Name

English

ALATRIOPRILAT

Brand Name

English

Code System Code Type Description

PUBCHEM

9818189