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Details

Stereochemistry ACHIRAL
Molecular Formula C19H20Br2N6O4S
Molecular Weight 588.273
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MACITENTAN

SMILES

CCCNS(=O)(=O)NC1=C(C2=CC=C(Br)C=C2)C(OCCOC3=NC=C(Br)C=N3)=NC=N1

InChI

InChIKey=JGCMEBMXRHSZKX-UHFFFAOYSA-N
InChI=1S/C19H20Br2N6O4S/c1-2-7-26-32(28,29)27-17-16(13-3-5-14(20)6-4-13)18(25-12-24-17)30-8-9-31-19-22-10-15(21)11-23-19/h3-6,10-12,26H,2,7-9H2,1H3,(H,24,25,27)

HIDE SMILES / InChI

Description

Macitentan is an orally active, dual endothelin receptor antagonist with tissue targeting properties. Macitentan inhibits both ETA and ETB receptors and prevents them from binding to ET-1. Macitentan displays high affinity and sustained occupancy of the ET receptors in human pulmonary arterial smooth muscle cells. One of the metabolites of macitentan is also pharmacologically active at the ET receptors and is estimated to be about 20% as potent as the parent drug in vitro. Macitentan is approved in the EU (as monotherapy or combination therapy) for the long-term treatment of pulmonary arterial hypertension (PAH) in adults of WHO functional class II or III, and in the USA for the treatment of PAH (WHO group I) to delay disease progression and reduce hospitalization for PAH.

Approval Year

PubMed

PubMed

TitleDatePubMed
The discovery of N-[5-(4-bromophenyl)-6-[2-[(5-bromo-2-pyrimidinyl)oxy]ethoxy]-4-pyrimidinyl]-N'-propylsulfamide (Macitentan), an orally active, potent dual endothelin receptor antagonist.
2012 Sep 13
Endothelin-1 receptor antagonists in fetal development and pulmonary arterial hypertension.
2015 Aug 15
Patents

Sample Use Guides

In Vivo Use Guide
The recommended dosage is 10 mg once daily for oral administration.
Route of Administration: Oral
Name Type Language
MACITENTAN
DASH   INN   MI   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
MACITENTAN [VANDF]
Common Name English
MACITENTAN [JAN]
Common Name English
OPSUMIT
Brand Name English
MACITENTAN [USAN]
Common Name English
ACT 064992
Code English
MACITENTAN [WHO-DD]
Common Name English
MACITENTAN [MI]
Common Name English
N-(5-(4-BROMOPHENYL)-6-(2-((5-BROMOPYRIMIDIN-2-YL)OXY)ETHOXY)PYRIMIDIN-4-YL)-N'-PROPYLSULFAMIDE
Systematic Name English
N-(5-(4-BROMOPHENYL)-6-(2-((5-BROMOPYRIMIDIN-2-YL)OXI)ETHOXY)PYRIMIDIN-4-YL)-N'-PROPYLSULFURIC DIAMIDE
Common Name English
ACT-064992
Code English
SULFAMIDE, N-(5-(4-BROMOPHENYL)-6-(2-((5-BROMO-2-PYRIMIDINYL)OXY)ETHOXY)-4-PYRIMIDINYL)-N'-PROPYL-
Systematic Name English
MACITENTAN [INN]
Common Name English
Classification Tree Code System Code
WHO-ATC C02KX04
Created by admin on Mon Oct 21 20:50:51 UTC 2019 , Edited by admin on Mon Oct 21 20:50:51 UTC 2019
FDA ORPHAN DRUG 580117
Created by admin on Mon Oct 21 20:50:51 UTC 2019 , Edited by admin on Mon Oct 21 20:50:51 UTC 2019
EMA ASSESSMENT REPORTS OPSUMIT (AUTHORIZED: HYPERTENSION, PULMONARY)
Created by admin on Mon Oct 21 20:50:51 UTC 2019 , Edited by admin on Mon Oct 21 20:50:51 UTC 2019
FDA ORPHAN DRUG 282209
Created by admin on Mon Oct 21 20:50:51 UTC 2019 , Edited by admin on Mon Oct 21 20:50:51 UTC 2019
WHO-VATC QC02KX04
Created by admin on Mon Oct 21 20:50:51 UTC 2019 , Edited by admin on Mon Oct 21 20:50:51 UTC 2019
FDA ORPHAN DRUG 509615
Created by admin on Mon Oct 21 20:50:51 UTC 2019 , Edited by admin on Mon Oct 21 20:50:51 UTC 2019
FDA ORPHAN DRUG 574917
Created by admin on Mon Oct 21 20:50:51 UTC 2019 , Edited by admin on Mon Oct 21 20:50:51 UTC 2019
NDF-RT N0000175581
Created by admin on Mon Oct 21 20:50:51 UTC 2019 , Edited by admin on Mon Oct 21 20:50:51 UTC 2019
FDA ORPHAN DRUG 279309
Created by admin on Mon Oct 21 20:50:51 UTC 2019 , Edited by admin on Mon Oct 21 20:50:51 UTC 2019
EU-Orphan Drug EU/3/11/909
Created by admin on Mon Oct 21 20:50:51 UTC 2019 , Edited by admin on Mon Oct 21 20:50:51 UTC 2019
Code System Code Type Description
INN
9018
Created by admin on Mon Oct 21 20:50:51 UTC 2019 , Edited by admin on Mon Oct 21 20:50:51 UTC 2019
PRIMARY
MERCK INDEX
M6975
Created by admin on Mon Oct 21 20:50:51 UTC 2019 , Edited by admin on Mon Oct 21 20:50:51 UTC 2019
PRIMARY Merck Index
PUBCHEM
16004692
Created by admin on Mon Oct 21 20:50:51 UTC 2019 , Edited by admin on Mon Oct 21 20:50:51 UTC 2019
PRIMARY
EVMPD
SUB89247
Created by admin on Mon Oct 21 20:50:51 UTC 2019 , Edited by admin on Mon Oct 21 20:50:51 UTC 2019
PRIMARY
CAS
441798-33-0
Created by admin on Mon Oct 21 20:50:51 UTC 2019 , Edited by admin on Mon Oct 21 20:50:51 UTC 2019
PRIMARY
RXCUI
1442132
Created by admin on Mon Oct 21 20:50:51 UTC 2019 , Edited by admin on Mon Oct 21 20:50:51 UTC 2019
PRIMARY RxNorm
DRUG BANK
DB08932
Created by admin on Mon Oct 21 20:50:51 UTC 2019 , Edited by admin on Mon Oct 21 20:50:51 UTC 2019
PRIMARY
IUPHAR
7352
Created by admin on Mon Oct 21 20:50:51 UTC 2019 , Edited by admin on Mon Oct 21 20:50:51 UTC 2019
PRIMARY
EPA CompTox
441798-33-0
Created by admin on Mon Oct 21 20:50:51 UTC 2019 , Edited by admin on Mon Oct 21 20:50:51 UTC 2019
PRIMARY
ChEMBL
CHEMBL2103873
Created by admin on Mon Oct 21 20:50:51 UTC 2019 , Edited by admin on Mon Oct 21 20:50:51 UTC 2019
PRIMARY
NCI_THESAURUS
C87728
Created by admin on Mon Oct 21 20:50:51 UTC 2019 , Edited by admin on Mon Oct 21 20:50:51 UTC 2019
PRIMARY