Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00059)
Name
Bedaquiline
Synonyms    Click to Show/Hide the Synonyms of This API
Bedaquiline; TMC207; 843663-66-1; Sirturo; TMC-207; R207910; TMC 207; (1R,2S)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol; R 207910; CHEBI:72292; UNII-78846I289Y; R-207910; (1R,2S)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-naphthalen-1-yl-1-phenylbutan-2-ol; 843663-66-1 (free base); MMV689758; 1-(6-Bromo-2-methoxy-quinolin-3-yl)-4-dimethylamino-2-naphthalen-1-yl-1-phenyl-butan-2-ol; 654653-93-7; 78846I289Y; (alphaS,betaR)-6-bromo-alpha-[2-(dimethylamino)ethyl]-2-methoxy-alpha-1-naphthalenyl-beta-phenyl-3-quinolineethanol; (1R,2S)-1-(6-Bromo-2-methoxy-3-quinolyl)-4-dimethylamino-2-(1-naphthyl)-1-phenyl-butan-2-ol; (1R,2S)-1-(6-Bromo-2-methoxy-quinolin-3-yl)-4-methyl-amino-2-naphthalen-1-yl-1-phenyl-butan-2-ol; (1R,2S)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(1-naphthyl)-1-phenylbutan-2-ol; AIDS-222089; Bedaquiline [USAN:INN]; bedaquilina; bedaquilinum; HSDB 8217; (1R,2S)-1-(6-bromo-2-methoxy-3-quinolyl)-4-(dimethylamino)-2-(1-naphthyl)-1-phenyl-butan-2-ol; AIDS 222089; Tube401; Bedaquiline (USAN/INN); AR)-Bedaquiline; Bedaquiline (TMC-207); C32H31BrN2O2; SCHEMBL295482; CHEMBL376488; GTPL11171; DTXSID80903989; AOB87357; EX-A4133; ZINC4655029; BDBM50063995; AKOS022186476; ACN-040787; CCG-270030; DB08903; bromo-2-methoxy-quinolin-3-yl)-4-dimethylamino-2-naphthalen-1-yl-1-phenyl-butan-2-ol; compound 1a [PMID: 17496888]; KS-0000002K; NCGC00348215-01; NCGC00348215-03; NCGC00348215-04; 3-Quinolineethanol, 6-bromo-alpha-(2-(dimethylamino)ethyl)-2-methoxy-alpha-1-naphthalenyl-beta-phenyl-, (alphaR,betaS)-rel-; AC-28385; HY-14881; A12327; D09872; J-500265; Q1257318; R403323; TMC207; R207910; (1R)-(6-Bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2(S)-(1-naphthyl)-1-phenylbutan-2-ol; 1-(1R)-(6-Bromo-2-methoxy-quinolin-3-yl)-4-dimethylamino-2-(2S)-(naphthalen-1-yl)-1-phenyl-butan-2-ol; 3-Quinolineethanol, 6-bromo-alpha-(2-(dimethylamino)ethyl)-2-methoxy-alpha-1-naphthalenyl-beta-phenyl-, (alphaS,betaR)-
Clinical Status
Approved
Disease Indication Pulmonary tuberculosis ICD-11: 1B10 [1]
PubChem CID
5388906
Formula
C32H31BrN2O2
Canonical SMILES
CN(C)CC[C@@](C1=CC=CC2=CC=CC=C21)([C@H](C3=CC=CC=C3)C4=C(N=C5C=CC(=CC5=C4)Br)OC)O
InChI
1S/C32H31BrN2O2/c1-35(2)19-18-32(36,28-15-9-13-22-10-7-8-14-26(22)28)30(23-11-5-4-6-12-23)27-21-24-20-25(33)16-17-29(24)34-31(27)37-3/h4-17,20-21,30,36H,18-19H2,1-3H3/t30-,32-/m1/s1
InChIKey
QUIJNHUBAXPXFS-XLJNKUFUSA-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=5388906"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 555.5 Topological Polar Surface Area 45.6
XlogP 7.2 Complexity 715
Heavy Atom Count 37 Rotatable Bond Count 8
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 4
Full List of Drug Formulations (DFMs) Containing This API
          Bedaquiline Fumarate eq 100mg base 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
Colloidal Silicon Dioxide; Corn Starch; Croscarmellose Sodium; Hypromellose 2910 15 Mpa.S; Lactose Monohydrate; Magnesium Stearate; Microcrystalline Cellulose; Polysorbate 20; Purified Water (Removed During Processing)
                   Dosage Form Tablet
                   Company Janssen Therap
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Hypromellose DIG Info Cytochrome P450 3A5 (IC50 = 19.4 uM) [2]
Polysorbate 20 DIG Info Cytochrome P450 2E1 (IC50 = 64.1 uM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [3]
Pregelatinized starch DIG Info Multidrug resistance protein 1 (Protein expression downregulation) [3]
          Bedaquiline 100 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; Water; Croscarmellose sodium; Polysorbate 20; Silicon dioxide; Hypromellose 2910 (15 mpa.s); Microcrystalline cellulose; Starch, corn
                   Dosage Form Oral Tablet
                   Company Janssen Products
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Polysorbate 20 DIG Info Cytochrome P450 2E1 (IC50 = 64.1 uM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [3]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
          Bedaquiline Fumarate eq 20mg base 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
Colloidal Silicon Dioxide; Crospovidone; Hypromellose 2910 5 Mpa.S; Polysorbate 20; Purified Water (Removed During Processing); Silicified Microcrystalline Cellulose; Sodium Stearyl Fumarate
                   Dosage Form Tablet
                   Company Janssen Therap
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium stearyl fumarate DIG Info Leukemia K562 cells (IC50 = 20.2 ug.mL-1) [4]
Hypromellose DIG Info Cytochrome P450 3A5 (IC50 = 19.4 uM) [2]
Polysorbate 20 DIG Info Cytochrome P450 2E1 (IC50 = 64.1 uM) [2]
Crospovidone DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
References
1 FDA label for approved bedaquiline from the official website of the U.S. Food and Drug Administration.
2 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.
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 Synthesis and evaluation of (-)-Massoialactone and analogues as potential anticancer and anti-inflammatory agents. Eur J Med Chem. 2014 Apr 9; 76:291-300.

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