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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 of ZAMICASTAT

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

Description

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

Unknown
149124
PubMed

PubMed

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

Patents

08481582
3
20100137390
2

Sample Use Guides

In Vivo Use Guide
BIA 5-1058 (Zamicastat) (5, 25 and 100 mg) tablets
Route of Administration: Oral
Name Type Language
zamicastat [INN]
Preferred Name English
ZAMICASTAT
INN  
INN  
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
Created by admin on Mon Mar 31 21:29:26 GMT 2025 , Edited by admin on Mon Mar 31 21:29:26 GMT 2025
NCI_THESAURUS C471
Created by admin on Mon Mar 31 21:29:26 GMT 2025 , Edited by admin on Mon Mar 31 21:29:26 GMT 2025
NCI_THESAURUS C270
Created by admin on Mon Mar 31 21:29:26 GMT 2025 , Edited by admin on Mon Mar 31 21:29:26 GMT 2025
Code System Code Type Description
INN
9684
Created by admin on Mon Mar 31 21:29:26 GMT 2025 , Edited by admin on Mon Mar 31 21:29:26 GMT 2025
PRIMARY
PUBCHEM
25052630
Created by admin on Mon Mar 31 21:29:26 GMT 2025 , Edited by admin on Mon Mar 31 21:29:26 GMT 2025
PRIMARY
SMS_ID
100000177211
Created by admin on Mon Mar 31 21:29:26 GMT 2025 , Edited by admin on Mon Mar 31 21:29:26 GMT 2025
PRIMARY
CAS
1080028-80-3
Created by admin on Mon Mar 31 21:29:26 GMT 2025 , Edited by admin on Mon Mar 31 21:29:26 GMT 2025
PRIMARY
NCI_THESAURUS
C152947
Created by admin on Mon Mar 31 21:29:26 GMT 2025 , Edited by admin on Mon Mar 31 21:29:26 GMT 2025
PRIMARY
FDA UNII
YLU32D0DNV
Created by admin on Mon Mar 31 21:29:26 GMT 2025 , Edited by admin on Mon Mar 31 21:29:26 GMT 2025
PRIMARY
EPA CompTox
DTXSID80148358
Created by admin on Mon Mar 31 21:29:26 GMT 2025 , Edited by admin on Mon Mar 31 21:29:26 GMT 2025
PRIMARY
DRUG BANK
DB12389
Created by admin on Mon Mar 31 21:29:26 GMT 2025 , Edited by admin on Mon Mar 31 21:29:26 GMT 2025
PRIMARY
ACTIVE MOIETY
Structure of ZAMICASTAT
NIH
NCATS
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