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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 of FASIDOTRILAT

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

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P12821
Gene ID: 1636.0
Gene Symbol: ACE
Target Organism: Homo sapiens (Human)
9.8 nM [Ki]
Target ID: P08473
Gene ID: 4311.0
Gene Symbol: MME
Target Organism: Homo sapiens (Human)
5.1 nM [Ki]
PubMed

PubMed

TitleDatePubMed
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
Patents

Sample Use Guides

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
  • Download
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
Created by admin on Sat Dec 16 10:58:59 GMT 2023 , Edited by admin on Sat Dec 16 10:58:59 GMT 2023
PRIMARY
CAS
135038-59-4
Created by admin on Sat Dec 16 10:58:59 GMT 2023 , Edited by admin on Sat Dec 16 10:58:59 GMT 2023
PRIMARY
FDA UNII
0N48AL0PRA
Created by admin on Sat Dec 16 10:58:59 GMT 2023 , Edited by admin on Sat Dec 16 10:58:59 GMT 2023
PRIMARY
EPA CompTox
DTXSID20159221
Created by admin on Sat Dec 16 10:58:59 GMT 2023 , Edited by admin on Sat Dec 16 10:58:59 GMT 2023
PRIMARY
MERCK INDEX
m1152
Created by admin on Sat Dec 16 10:58:59 GMT 2023 , Edited by admin on Sat Dec 16 10:58:59 GMT 2023
PRIMARY Merck Index
Related Record Type Details
TARGET -> INHIBITOR
TARGET -> INHIBITOR
Related Record Type Details
PRODRUG -> METABOLITE ACTIVE
Related Record Type Details
ACTIVE MOIETY