ETAMICASTAT

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C14H15F2N3OS
Molecular Weight	311.35
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NCCC1=CNC(=S)N1[C@H]2COC3=C(C2)C=C(F)C=C3F

InChI

InChIKey=CWWWTTYMUOYSQA-LLVKDONJSA-N

InChI=1S/C14H15F2N3OS/c15-9-3-8-4-11(7-20-13(8)12(16)5-9)19-10(1-2-17)6-18-14(19)21/h3,5-6,11H,1-2,4,7,17H2,(H,18,21)/t11-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C14H15F2N3OS
Molecular Weight	311.35
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16451083 | https://adisinsight.springer.com/drugs/800034724 | https://www.ncbi.nlm.nih.gov/pubmed/25854989

Etamicastat (BIA 5453) is a peripherally selective chromanyl imidazolethione-based inhibitor of dopamine beta-hydroxylase, the enzyme that catalyzes the conversion of dopamine to noradrenaline in the sympathetic nerves. Prolonged downregulation of sympathetic drive with etamicastat results in a sustained decrease in the systolic blood pressure and the diastolic blood pressure. Etamicastat was being studied by BIAL for the oral treatment of hypertension and congestive heart failure. Etamicastat development has been discontinued.

Originator

Approval Year

PubMed

Title	Date	PubMed
Synthesis and biological evaluation of novel, peripherally selective chromanyl imidazolethione-based inhibitors of dopamine beta-hydroxylase.	2006 Feb 9	16451083

Patents

Sample Use Guides

In Vivo Use Guide

the randomized, double-blind, placebo-controlled study was conducted in male patients aged between 18 and 65 years with mild to moderate hypertension. Participants received once-daily doses of etamicastat 50, 100, or 200 mg or placebo for 10 days. Etamicastat was well tolerated and showed a pharmacokinetic profile consistent with a once-daily regimen. The antihypertensive effect of etamicastat was dose dependent up to 100 mg.

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:16:16 GMT 2023` Edited by `admin` on `Fri Dec 15 16:16:16 GMT 2023`
Record UNII	9X96V6DBU4
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ETAMICASTAT

Official Name

English

etamicastat [INN]

Common Name

English

5-(2-AMINOETHYL)-1-((3R)-6,8-DIFLUORO-3,4-DIHYDRO-2H-CHROMEN-3-YL)-1,3-DIHYDRO-2H-IMIDAZOLE-2-THIONE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C471