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SML3386

Sigma-Aldrich

Macitentan

≥98% (HPLC)

Synonym(s):

ACT 064992, ACT-064992, ACT064992, Actelion-1, N-[5-(4-Bromophenyl)-6-[2-[(5-bromo-2-pyrimidinyl)oxy]ethoxy]-4-pyrimidinyl]-N′-propyl-sulfamide

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About This Item

Empirical Formula (Hill Notation):
C19H20Br2N6O4S
CAS Number:
441798-33-0
Molecular Weight:
588.27
MDL number:
MFCD17167076
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

SMILES string

BrC1=CC=C(C=C1)C2=C(N=CN=C2OCCOC3=NC=C(C=N3)Br)NS(NCCC)(=O)=O

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)

InChI key

JGCMEBMXRHSZKX-UHFFFAOYSA-N

Biochem/physiol Actions

Macitentan (ACT-064992; actelion-1) is an orally active, potent endothelin (ET) receptor antagonist that blocks ET-1-induced cellular calicum response (IC50 in nM = 0.9/HPASMC, 0.8/RASMC, 1.84/m3T3), as well as ET-1-induced contractions of rat aortic rings (ETA) and S6c-induced rat tracheal rings (ETB) ex vivo (pA2 = 7.6 and 5.9, respectively). Macitentan displays therapeutic efficacy in rat hypertension models in vivo (0.3-100 mg/kg p.o. via single or daily dosing).

pictograms

Health hazard
GHS08

signalword

Danger

hcodes

H360FD

Hazard Classifications

Repr. 1B

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Marc Iglarz et al.
The Journal of pharmacology and experimental therapeutics, 327(3), 736-745 (2008-09-11)
Macitentan, also called Actelion-1 or ACT-064992 [N-[5-(4-bromophenyl)-6-(2-(5-bromopyrimidin-2-yloxy)ethoxy)-pyrimidin-4-yl]-N'-propylaminosulfonamide], is a new dual ET(A)/ET(B) endothelin (ET) receptor antagonist designed for tissue targeting. Selection of macitentan was based on inhibitory potency on both ET receptors and optimization of physicochemical properties to achieve high
Hao-Chen Liu et al.
Acta pharmacologica Sinica, 41(5), 719-728 (2020-01-15)
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Extracellular vesicles (EVs) carrying tumor cell-derived programmed death-ligand 1 (PD-L1) interact with programmed death 1 (PD-1)-producing T cells, thus significantly lowering a patient's response to immune checkpoint blockade drugs. No drug that reinvigorates CD8+ T cells by suppressing EV PD-L1
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Alexander Treiber et al.
Pharmacology research & perspectives, 8(4), e00619-e00619 (2020-07-03)
The dual endothelin receptor antagonist macitentan was approved in 2013 for the treatment of pulmonary arterial hypertension. Macitentan is an inducer of cytochrome P450 expression in vivo in animal species but not in man. In rat and dog, changes in
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