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Maleate salts of bedaquiline.
- Source :
-
Acta Crystallographica Section E: Crystallographic Communications . Apr2021, Vol. 77 Issue 4, p433-445. 78p. - Publication Year :
- 2021
-
Abstract
- Bedaquiline is one of two important new drugs for the treatment of drug-resistant tuberculosis (TB). It is marketed in the US as its fumarate salt, but only a few salts of bedaquiline have been structurally described so far. We present here five crystal structures of bedaquilinium maleate {systematic name: [4-(6-bromo-2-methoxyquinolin-3-yl)-3-hydroxy-3-(naphthalen-1-yl)-4-phenylbutyl]di-methylazanium 3-carboxyprop-2-enoate}, C32H32BrN2O2+⋅C4H3O4-, namely, a hemihydrate, a tetrahydrofuran (THF) solvate, a mixed acetone/hexane solvate, an ethyl acetate solvate, and a solvate-free structure obtained from the acetone/hexane solvate by in situ single-crystal-to-single-crystal desolvation. All salts exhibit a 1:1 cation-to-anion ratio, with the anion present as monoanionic hydro-maleate and a singly protonated bedaquilinium cation. The maleate exhibits the strong intramolecular hydrogen bond typical for cis-di-carboxylic acid anions. The conformations of the cations and packing interactions in the maleate salts are compared to those of free base bedaquiline and other bedaquilinium salts. [ABSTRACT FROM AUTHOR]
- Subjects :
- *MALEIC acid
*SALTS
*SALT
*ETHYL acetate
*ACETONE
*HYDROGEN bonding
*CRYSTAL structure
Subjects
Details
- Language :
- English
- ISSN :
- 20569890
- Volume :
- 77
- Issue :
- 4
- Database :
- Academic Search Index
- Journal :
- Acta Crystallographica Section E: Crystallographic Communications
- Publication Type :
- Academic Journal
- Accession number :
- 149698803
- Full Text :
- https://doi.org/10.1107/S2056989021002991