ZAMICASTAT

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H21F2N3OS
Molecular Weight	401.473
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

FC1=CC(F)=C2OC[C@@H](CC2=C1)N3C(=S)NC=C3CCNCC4=CC=CC=C4

InChI

InChIKey=ZSSLCFLHEFXANG-GOSISDBHSA-N

InChI=1S/C21H21F2N3OS/c22-16-8-15-9-18(13-27-20(15)19(23)10-16)26-17(12-25-21(26)28)6-7-24-11-14-4-2-1-3-5-14/h1-5,8,10,12,18,24H,6-7,9,11,13H2,(H,25,28)/t18-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C21H21F2N3OS
Molecular Weight	401.473
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/30401628 | https://clinicaltrials.gov/ct2/show/NCT02151994 |

Zamicastat (also known as BIA 5-1058) is a dopamine β-hydroxylase (DβH) inhibitor that decreases noradrenaline and increases dopamine levels in peripheral sympathetically innervated tissues. It is known that the use of DβH inhibitors is a promising approach to treat hypertension, heart failure and cardiovascular diseases where a reduction in the sympathetic tone has beneficial effects. Zamicastat participated in phase II clinical trials in pulmonary arterial hypertension as adjuvant therapy in Austria. In addition, the drug successfully completed phase I in patients with hypertension and chronic heart failure.

Approval Year

PubMed

Title	Date	PubMed
A new PAMPA model using an in-house brain lipid extract for screening the blood-brain barrier permeability of drug candidates.	2016-03-30	26836708

Patents

Sample Use Guides

In Vivo Use Guide

BIA 5-1058 (Zamicastat) (5, 25 and 100 mg) tablets

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:29:26 GMT 2025` Edited by `admin` on `Mon Mar 31 21:29:26 GMT 2025`
Record UNII	YLU32D0DNV
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

zamicastat [INN]

Preferred Name

English

ZAMICASTAT

Official Name

English

5-(2-(BENZYLAMINO)ETHYL)-1-((3R)-6,8-DIFLUORO-3,4-DIHYDRO- 2H-1-BENZOPYRAN-3-YL)-1,3-DIHYDRO-2H-IMIDAZOLE-2-THIONE

Systematic Name

English

2H-IMIDAZOLE-2-THIONE, 1-((3R)-6,8-DIFLUORO-3,4-DIHYDRO-2H-1-BENZOPYRAN-3-YL)-1,3-DIHYDRO-5-(2-((PHENYLMETHYL)AMINO)ETHYL)-

Systematic Name

English

(R)-5-(2-(BENZYLAMINO)ETHYL)-1-(6,8-DIFLUOROCHROMAN-3-YL)-1H-IMIDAZOLE-2(3H)-THIONE

Systematic Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

693619