Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00074)
Name
Bosentan
Synonyms    Click to Show/Hide the Synonyms of This API
Bosentan; 147536-97-8; Tracleer; Ro 47-0203; Ro-47-0203; C27H29N5O6S; Bosentan [USAN:INN:BAN]; 4-tert-butyl-N-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-pyrimidin-2-ylpyrimidin-4-yl]benzenesulfonamide; UNII-XUL93R30K2; p-tert-Butyl-N-(6-(2-hydroxyethoxy)-5-(o-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl)benzenesulfonamide; CHEMBL957; XUL93R30K2; Actelion; CHEBI:51450; 147536-97-8 (free); NCGC00167440-01; bosentan anhydrous; DSSTox_CID_26627; DSSTox_RID_81776; DSSTox_GSID_46627; 4-(1,1-Dimethylethyl)-N-(6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-(2,2'-bipyrimidin)-4-yl) benzenesulfornamide; 4-(tert-butyl)-N-(6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-[2,2'-bipyrimidin]-4-yl)benzenesulfonamide; 4-tert-butyl-N-[6-(2-hydroxyethyloxy)-5-(2-methoxyphenoxy)-2-pyrimidin-2-yl-pyrimidin-4-yl]benzenesulfonamide; Benzenesulfonamide, 4-(1,1-dimethylethyl)-N-(6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)(2,2'-bipyrimidin)-4-yl)-; bosentanum; Bosentan (INN); 4-tert-butyl-N-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2,2'-bipyrimidin-4-yl]benzenesulfonamide; Benzenesulfonamide, 4-(1,1-dimethylethyl)-N-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)[2,2'-bipyrimidin]-4-yl]-; CAS-147536-97-8; Ro 47-0203/039; SR-05000001532; Ro 47-0203/029; 4-tert-butyl-n-(6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2,2'-bipyrimidin-4-yl)benzenesulfonamide; 4-(1,1-Dimethylethyl)-N-(6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-(2,2'-bipyrimidin)-4-yl)benzenesulfornamide; KS-5062; PubChem19119; Ro-47-0203/029; Ro-47-0203/039; SCHEMBL4218; N-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-pyrimidin-2-yl-pyrimidin-4-yl]-4-tert-butyl-benzenesulfonamide; GTPL3494; DTXSID7046627; HMS2090N14; HMS3652F15; HMS3715N05; HMS3750A13; BCP05202; HY-A0013; ZINC1538857; Tox21_112444; ABP001094; AC-148; BDBM50061101; PDSP1_001731; PDSP2_001714; AKOS015852063; Tox21_112444_1; ACN-048487; AM84442; BCP9000445; CCG-221182; CS-0381; DB00559; MCULE-3074160312; SB17356; VA10428; NCGC00167440-02; 174227-18-0; AB0018010; Ro-470203029; FT-0658809; SW199648-3; Ro-47-0203-029; D07538; W-5165; AB01275536-01; 144096-EP2287165A2; 144096-EP2287166A2; 144096-EP2292620A2; 212B550; A808658; L001086; Q419769; J-008366; SR-05000001532-1; SR-05000001532-2; SR-05000001532-4; Z1541632805; 1174918-31-0; 4-(1,1-Dimethylethyl)-N-(6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-(2,2''-bipyrimidin)-4-yl) benzenesulfornamide; 4-(1,1-dimethylethyl)-n-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)[2,2'-bipyrimidin]-4-yl]benzenesulfonamide; 4-(tert-Butyl)-N-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)[2,2'-bipyrimidin]-4-yl]benzenesulfonamide; 4-tert butyl-N-[4-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)pyrimidin-6-yl]benzenesulphonamide; 4-tert-Butyl-N-[6-(2-hydroxy-ethoxy)-5-(2-methoxy-phenoxy)-[2,2']bipyrimidinyl-4-yl]-benzenesulfonamide; 4-tert-butyl-N-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-[2,2'-bipyrimidine]-4-yl]benzene-1-sulfonamide; 4-tert-butyl-N-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2,2''-bipyrimidin-4-yl]benzenesulfonamide; 4-tert-butyl-N-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]benzenesulfonamide; 4-tert-butyl-N-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-(pyrimidin-2-yl)pyrimidin-4-yl]benzene-1-sulfonamide; 4-tert-Butyl-N-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-(pyrimidin-2-yl)pyrimidin-4-yl]benzenesulfonamide
Clinical Status
Approved
Disease Indication Pulmonary hypertension ICD-11: BB01 [1]
PubChem CID
104865
Formula
C27H29N5O6S
Canonical SMILES
CC(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC2=C(C(=NC(=N2)C3=NC=CC=N3)OCCO)OC4=CC=CC=C4OC
InChI
1S/C27H29N5O6S/c1-27(2,3)18-10-12-19(13-11-18)39(34,35)32-23-22(38-21-9-6-5-8-20(21)36-4)26(37-17-16-33)31-25(30-23)24-28-14-7-15-29-24/h5-15,33H,16-17H2,1-4H3,(H,30,31,32)
InChIKey
GJPICJJJRGTNOD-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=104865"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 551.6 Topological Polar Surface Area 154
XlogP 3.8 Complexity 839
Heavy Atom Count 39 Rotatable Bond Count 11
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 11
Full List of Drug Formulations (DFMs) Containing This API
          Bosentan 32 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
Phenylalanine; Acesulfame potassium; Aspartame; Magnesium stearate; Tartaric acid; Anhydrous dibasic calcium phosphate; Croscarmellose sodium; Silicon dioxide; Microcrystalline cellulose
                   Dosage Form Tablet for Oral Suspension
                   Company Actelion Pharmaceuticals US
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Phenylalanine DIG Info Calcium channel alpha-2/delta-1 (Ki = 977.24 nM) [2]
Acesulfame DIG Info Carbonic anhydrase IX (Ki = 2400 nM) [3]
Aspartame DIG Info Pregnane X receptor (Ki = 13 uM) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Calcium hydrogenphosphate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [5]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
          Bosentan 125 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
Glyceryl dibehenate; Magnesium stearate; Ferric oxide red; Ferric oxide yellow; Talc; Titanium dioxide; Triacetin; Ethylcellulose, unspecified; Hypromellose, unspecified; Povidone k90; Sodium starch glycolate type a potato; Starch, corn
                   Dosage Form Oral Tablet
                   Company Actelion Pharmaceuticals US
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
          Bosentan 62.5 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
Glyceryl dibehenate; Magnesium stearate; Ferric oxide red; Ferric oxide yellow; Talc; Titanium dioxide; Triacetin; Ethylcellulose, unspecified; Hypromellose, unspecified; Povidone k90; Sodium starch glycolate type a potato; Starch, corn
                   Dosage Form Oral Tablet
                   Company Actelion Pharmaceuticals US
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
References
1 FDA label for approved bosentan from the official website of the U.S. Food and Drug Administration.
2 Structure-activity relationships of alpha-amino acid ligands for the alpha2delta subunit of voltage-gated calcium channels. Bioorg Med Chem Lett. 2006 Mar 1; 16(5):1138-41.
3 Sweet Binders: Carbonic Anhydrase IX in Complex with Sucralose. ACS Med Chem Lett. 2018 May 10; 9(7):657-661.
4 The activities of drug inactive ingredients on biological targets. Science. 2020 Jul 24;369(6502):403-413.
5 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.

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