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Details

Stereochemistry ACHIRAL
Molecular Formula C19H20Br2N6O4S
Molecular Weight 588.273
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MACITENTAN

SMILES

CCCNS(=O)(=O)NC1=NC=NC(OCCOC2=NC=C(Br)C=N2)=C1C3=CC=C(Br)C=C3

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.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.5 nM [IC50]
391.0 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
OPSUMIT

Cmax

ValueDoseCo-administeredAnalytePopulation
227 ng/mL
10 mg single, oral
MACITENTAN blood
Homo sapiens
178 ng/mL
10 mg single, oral
APROCITENTAN blood
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
5759 ng × h/mL
10 mg single, oral
MACITENTAN blood
Homo sapiens
19749 ng × h/mL
10 mg single, oral
APROCITENTAN blood
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
14.1 h
10 mg single, oral
MACITENTAN blood
Homo sapiens
46.7 h
10 mg single, oral
APROCITENTAN blood
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
The recommended dosage is 10 mg once daily for oral administration.
Route of Administration: Oral
In Vitro Use Guide
Unknown