Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00382)
Name
Macitentan
Synonyms    Click to Show/Hide the Synonyms of This API
Macitentan; 441798-33-0; Opsumit; ACT-064992; ACT 064992; UNII-Z9K9Y9WMVL; ACT064992; N-[5-(4-Bromophenyl)-6-[2-[(5-bromo-2-pyrimidinyl)oxy]ethoxy]-4-pyrimidinyl]-N'-propylsulfamide; Z9K9Y9WMVL; CHEBI:76607; Actelion-1; N-[5-(4-bromophenyl)-6-{2-[(5-bromopyrimidin-2-yl)oxy]ethoxy}pyrimidin-4-yl]-N'- propylsulfamide; Macitentan [USAN:INN]; macitentanum; zlchem 5; Opsumit (TN); Macitentan (JAN/USAN); (non-labelled)Macitentan-d7; MLS006011174; C19H20Br2N6O4S; GTPL7352; SCHEMBL1445625; CHEMBL2103873; DTXSID50196063; EX-A544; ZLA0005; HMS3653N06; HMS3747E09; cas:441798-33-0;Macitentan; AOB87765; BCP05309; ABP001066; BDBM50395626; MFCD17167076; ZINC43202140; AKOS024463406; ACN-034475; AM81244; CCG-270155; CS-0686; DB08932; SB14841; Macitentan (Actelion-1,ACT-064992); NCGC00346456-01; NCGC00346456-05; 5-(4-bromophenyl)-6-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-N-(propylsulfamoyl)pyrimidin-4-amine; AC-30102; AK162704; AS-74590; HY-14184; QC-10426; SMR004702943; AB0007893; DB-070519; FT-0696675; SW219473-1; A11492; ACT 064992; ACT-064992; D10135; S-7749; Q6724151; {[5-(4-BROMOPHENYL)-6-{2-[(5-BROMOPYRIMIDIN-2-YL)OXY]ETHOXY}PYRIMIDIN-4-YL]SULFAMOYL}(PROPYL)AMINE; N-(5-(4-Bromophenyl)-6-(2-((5-bromopyrimidin-2-yl)oxy)ethoxy)pyrimidin-4-yl)-N'-propylsulfamide; N-[5-(4-Bromophenyl)-6-[2-[(5-bromo-2-pyrimidinyl)-oxy]ethoxy]-4-pyrimidinyl]-N'-propylsulfamide; n-[5-(4-bromophenyl)-6-[2-[(5-bromo-2-pyrimidinyl)oxy]ethoxy]-4-pyrimidinyl]-n'-propyl-sulfamide; N-[5-(4-bromophenyl)-6-{2-[(5-bromopyrimidin-2-yl)oxy]ethoxy}pyrimidin-4-yl]-N'-propylsulfuric diamide; Sulfamide, N-[5-(4-bromophenyl)-6-[2-[(5-bromo-2-pyrimidinyl)oxy]ethoxy]-4-pyrimidinyl]-N'-propyl-
Clinical Status
Approved
Disease Indication Pulmonary hypertension ICD-11: BB01 [1]
PubChem CID
16004692
Formula
C19H20Br2N6O4S
Canonical SMILES
CCCNS(=O)(=O)NC1=C(C(=NC=N1)OCCOC2=NC=C(C=N2)Br)C3=CC=C(C=C3)Br
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)
InChIKey
JGCMEBMXRHSZKX-UHFFFAOYSA-N
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=16004692"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 588.3 Topological Polar Surface Area 137
XlogP 3.7 Complexity 642
Heavy Atom Count 32 Rotatable Bond Count 11
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 10
Full List of Drug Formulations (DFMs) Containing This API
          Macitentan 10 mg tablet Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose monohydrate; Magnesium stearate; Talc; Titanium dioxide; Lecithin, soybean; Polysorbate 80; Microcrystalline cellulose; Polyvinyl alcohol, unspecified; Povidone, unspecified; Sodium starch glycolate type a potato; Xanthan gum
                   Dosage Form Oral Tablet
                   Company Actelion Pharmaceuticals US
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Polysorbate 80 DIG Info Prostaglandin G/H synthase 1 (IC50 = 1 uM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
Soybean lecithin DIG Info Albendazole monooxygenase (IC50 = 6.61 mg.mL-1) [4]
References
1 FDA label for approved macitentan from the official website of the U.S. Food and Drug Administration.
2 The activities of drug inactive ingredients on biological targets. Science. 2020 Jul 24;369(6502):403-413.
3 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.
4 Pharmaceutical excipients inhibit cytochrome P450 activity in cell free systems and after systemic administration. Eur J Pharm Biopharm. 2008 Sep;70(1):279-88.

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