APROCITENTAN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H14Br2N6O4S
Molecular Weight	546.193
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

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

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	546.193
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

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

Primary Target	Pharmacology	Condition	Potency
Endothelin receptor ET-A 22	Antagonist 2,849		3.4 nM [IC50]
Endothelin receptor ET-B 11	Antagonist 2,849		987.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2,596

PubMed

Show entries

Title	Date	PubMed
Pharmacology of macitentan, an orally active tissue-targeting dual endothelin receptor antagonist.	2008 Dec	18780830
Pharmacokinetic study of ACT-132577 in rat plasma by ultra performance liquid chromatography-tandem mass spectrometry.	2015	26770447
TNFα-induced airway smooth muscle cell proliferation depends on endothelin receptor signaling, GM-CSF and IL-6.	2016 Sep 15	27422754

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Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Unknown

Substance Class	Chemical
Record UNII	MZI81HV01P
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

ACT-132577

Preferred Name

English

APROCITENTAN

Official Name

English

N-(5-(4-BROMOPHENYL)-6-(2-((5-BROMOPYRIMIDIN-2-YL)OXY)ETHOXY)PYRIMIDIN-4-YL)SULFAMIDE

Systematic Name

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

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Code System

Code

Type

Description

USAN

GH-03

PRIMARY

SMS_ID

100000184049

PRIMARY

DAILYMED

MZI81HV01P

PRIMARY

INN

10552

PRIMARY

FDA UNII

MZI81HV01P

PRIMARY

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Related Record

Type

Details


					L5QY0GLC6X

Endothelin receptor type B

TARGET -> INHIBITOR

Amount:


					5Q6PN7AC39

ENDOTHELIN-1 RECEPTOR

TARGET -> INHIBITOR

Amount:


					PUO0521HZV

CYTOCHROME P450 3A4

METABOLIC ENZYME -> INDUCER

Comments:

Both ACT-064992 and ACT-132577 can induce CYP3A4 enzymes in vitro.

Amount:

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Related Record

Type

Details


					Z9K9Y9WMVL

MACITENTAN

PARENT -> METABOLITE ACTIVE

Amount:

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Related Record

Type

Details


					MZI81HV01P

APROCITENTAN

ACTIVE MOIETY

Amount:

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SMILES

InChI

Description<div class="info-popup-container"><div><span class="pop-sub-key ">Sources:&nbsp;</span><span class="pop-sub-val"><span class="ext-link"><a target="_self" href="https://www.ncbi.nlm.nih.gov/pubmed/18780830">https://www.ncbi.nlm.nih.gov/pubmed/18780830</a></span></span></div></div>

Approval Year

Targets

Conditions

PubMed

Patents

Sample Use Guides

Description