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Details

Stereochemistry ACHIRAL
Molecular Formula C16H14Br2N6O4S
Molecular Weight 546.1939
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of APROCITENTAN

SMILES

c1cc(ccc1-c2c(=NS(=O)(=O)N)nc[nH]c2OCCOc3ncc(cn3)Br)Br

InChI

InChIKey=DKULOVKANLVDEA-UHFFFAOYSA-N
InChI=1S/C16H14Br2N6O4S/c17-11-3-1-10(2-4-11)13-14(24-29(19,25)26)22-9-23-15(13)27-5-6-28-16-20-7-12(18)8-21-16/h1-4,7-9H,5-6H2,(H2,19,25,26)(H,22,23,24)

HIDE SMILES / InChI

Molecular Formula C16H14Br2N6O4S
Molecular Weight 546.1939
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

ACT-132577 is the major and pharmacologically active metabolite of macitentan (ACT-064992), which is dual ETA/ETB endothelin (ET) receptor antagonist designed for tissue targeting.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
3.4 nM [IC50]
987.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Pharmacology of macitentan, an orally active tissue-targeting dual endothelin receptor antagonist.
2008 Dec
Pharmacokinetic study of ACT-132577 in rat plasma by ultra performance liquid chromatography-tandem mass spectrometry.
2015
TNFα-induced airway smooth muscle cell proliferation depends on endothelin receptor signaling, GM-CSF and IL-6.
2016 Sep 15
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Jun 26 14:13:09 UTC 2021
Edited
by admin
on Sat Jun 26 14:13:09 UTC 2021
Record UNII
MZI81HV01P
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
APROCITENTAN
INN  
USAN   INN  
Official Name English
N-(5-(4-BROMOPHENYL)-6-(2-((5-BROMOPYRIMIDIN-2-YL)OXY)ETHOXY)PYRIMIDIN-4-YL)SULFAMIDE
Systematic Name English
ACT-132577
Code English
SULFAMIDE, N-(5-(4-BROMOPHENYL)-6-(2-((5-BROMO-2-PYRIMIDINYL)OXY)ETHOXY)-4-PYRIMIDINYL)-
Systematic Name English
MACITENTAN METABOLITE M6
Common Name English
N-(5-(4-BROMOPHENYL)-6-(2-((5-BROMOPYRIMIDIN-2-YL)OXY)ETHOXY)PYRIMIDIN-4-YL)SULFURIC DIAMIDE
Systematic Name English
APROCITENTAN [INN]
Common Name English
N-(5-(4-BROMOPHENYL)-6-(2-((5-BROMO-2-PYRIMIDINYL)OXY)ETHOXY)-4-PYRIMIDINYL)-SULFAMIDE
Systematic Name English
APROCITENTAN [USAN]
USAN  
Common Name English
Code System Code Type Description
INN
10552
Created by admin on Sat Jun 26 14:13:09 UTC 2021 , Edited by admin on Sat Jun 26 14:13:09 UTC 2021
PRIMARY
FDA UNII
MZI81HV01P
Created by admin on Sat Jun 26 14:13:09 UTC 2021 , Edited by admin on Sat Jun 26 14:13:09 UTC 2021
PRIMARY
NCI_THESAURUS
C174728
Created by admin on Sat Jun 26 14:13:09 UTC 2021 , Edited by admin on Sat Jun 26 14:13:09 UTC 2021
PRIMARY
DRUG BANK
DB15059
Created by admin on Sat Jun 26 14:13:09 UTC 2021 , Edited by admin on Sat Jun 26 14:13:09 UTC 2021
PRIMARY
PUBCHEM
25099191
Created by admin on Sat Jun 26 14:13:09 UTC 2021 , Edited by admin on Sat Jun 26 14:13:09 UTC 2021
PRIMARY
CAS
1103522-45-7
Created by admin on Sat Jun 26 14:13:09 UTC 2021 , Edited by admin on Sat Jun 26 14:13:09 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
TARGET -> INHIBITOR
METABOLIC ENZYME -> INDUCER
Both ACT-064992 and ACT-132577 can induce CYP3A4 enzymes in vitro.
Related Record Type Details
PARENT -> METABOLITE ACTIVE
Related Record Type Details
ACTIVE MOIETY