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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

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

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

PubMed

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

Sample Use Guides

BIA 5-1058 (Zamicastat) (5, 25 and 100 mg) tablets
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Sat Dec 16 05:25:37 GMT 2023
Edited
by admin
on Sat Dec 16 05:25:37 GMT 2023
Record UNII
YLU32D0DNV
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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
zamicastat [INN]
Common 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 Sat Dec 16 05:25:37 GMT 2023 , Edited by admin on Sat Dec 16 05:25:37 GMT 2023
NCI_THESAURUS C471
Created by admin on Sat Dec 16 05:25:37 GMT 2023 , Edited by admin on Sat Dec 16 05:25:37 GMT 2023
NCI_THESAURUS C270
Created by admin on Sat Dec 16 05:25:37 GMT 2023 , Edited by admin on Sat Dec 16 05:25:37 GMT 2023
Code System Code Type Description
INN
9684
Created by admin on Sat Dec 16 05:25:37 GMT 2023 , Edited by admin on Sat Dec 16 05:25:37 GMT 2023
PRIMARY
PUBCHEM
25052630
Created by admin on Sat Dec 16 05:25:37 GMT 2023 , Edited by admin on Sat Dec 16 05:25:37 GMT 2023
PRIMARY
SMS_ID
100000177211
Created by admin on Sat Dec 16 05:25:37 GMT 2023 , Edited by admin on Sat Dec 16 05:25:37 GMT 2023
PRIMARY
CAS
1080028-80-3
Created by admin on Sat Dec 16 05:25:37 GMT 2023 , Edited by admin on Sat Dec 16 05:25:37 GMT 2023
PRIMARY
NCI_THESAURUS
C152947
Created by admin on Sat Dec 16 05:25:37 GMT 2023 , Edited by admin on Sat Dec 16 05:25:37 GMT 2023
PRIMARY
FDA UNII
YLU32D0DNV
Created by admin on Sat Dec 16 05:25:37 GMT 2023 , Edited by admin on Sat Dec 16 05:25:37 GMT 2023
PRIMARY
EPA CompTox
DTXSID80148358
Created by admin on Sat Dec 16 05:25:37 GMT 2023 , Edited by admin on Sat Dec 16 05:25:37 GMT 2023
PRIMARY
DRUG BANK
DB12389
Created by admin on Sat Dec 16 05:25:37 GMT 2023 , Edited by admin on Sat Dec 16 05:25:37 GMT 2023
PRIMARY
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