A dual ETA and ETB receptor antagonist and an active metabolite of macitentan
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Parent Compound(s)
23304Macitentan
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Aprocitentan

Item No. 34915

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[5-(4-bromophenyl)-6-[2-[(5-bromo-2-pyrimidinyl)oxy]ethoxy]-4-pyrimidinyl]-sulfamide
CAS Number
1103522-45-7
Synonyms
  • ACT-132577
Molecular Formula
C16H14Br2N6O4S
Formula Weight
546.2
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: soluble
λmax
259 nm
SMILES
O=S(N)(NC1=NC=NC(OCCOC2=NC=C(C=N2)Br)=C1C3=CC=C(C=C3)Br)=O
InChi Code
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)
InChi Key
DKULOVKANLVDEA-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $61

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    5 mg

    $213

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    10 mg

    $303

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    25 mg

    $530

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    Cayman Chemical
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    Product Description

    Aprocitentan is a dual endothelin type A (ETA) and ETB receptor antagonist and an active metabolite of macitentan (Item No. 23304).1 It is formed from macitentan by the cytochrome P450 (CYP) isoform CYP3A4. Aprocitentan inhibits increases in intracellular calcium induced by endothelin-1 (ET-1) in primary human pulmonary arterial smooth muscle cells (HPASMCs; IC50 = 14 nM), ET-1-induced contractions in isolated rat aortic rings (pA2 = 6.7 for ETA), and sarafotoxin S6c-induced contractions of isolated rat tracheal rings (pKB = 5.5 for ETB).2 It reduces ET-1-induced increases in the proliferation of isolated human skin fibroblasts when used at concentrations of 10 and 100 µM.3 Aprocitentan (10-300 mg/kg) increases plasma ET-1 concentrations in normotensive rats and decreases mean arterial pressure (MAP) in DOCA-salt hypertensive rats.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Dingemanse, J., Sidharta, P.N., Maddrey, W.C., et al. Efficacy, safety and clinical pharmacology of macitentan in comparison to other endothelin receptor antagonists in the treatment of pulmonary arterial hypertension. Expert Opin. Drug Saf. 13(3), 391-405 (2013).

    2. Iglarz, M., Binkert, C., Morrison, K., et al. Pharmacology of macitentan, an orally active tissue-targeting dual endothelin receptor antagonist. J. Pharmacol. Exp. Ther. 327(3), 736-745 (2008).

    3. Cutolo, M., Montagna, P., Brizzolara, R., et al. Effects of macitentan and its active metabolite on cultured human systemic sclerosis and control skin fibroblasts. J. Rheumatol. 42(3), 456-463 (2015).

    4. Trensz, F., Bortolamiol, C., Kramberg, M., et al. Pharmacological characterization of aprocitentan, a dual endothelin receptor antagonist, alone and in combination with blockers of the renin angiotensin system, in two models of experimental hypertension. J. Pharmacol. Exp. Ther. 368(3), 462-473 (2019).