Crystal structure of tebipenem pivoxil

• Main Authors: Chao Tang, Li Cai, Shuai Liu, Zhiwei Zheng, Gen Li, Jianli Chen, Qiang Sui
• Format: Article
• Language: English
• Published: International Union of Crystallography 2018-09-01
• Series: Acta Crystallographica Section E: Crystallographic Communications
• Subjects: crystal structure; carbapenem; antibiotics; tebipenem; prodrug; hydrogen bonding
• Online Access: http://scripts.iucr.org/cgi-bin/paper?S2056989018010770

The molecular structure of the first orally active carbapenem antibacterial agent, tebipenem pivoxil (systematic name: (2,2-dimethylpropanoyloxy)methyl (4R,5S,6S)-3-{[1-(4,5-dihydro-1,3-thiazol-2-yl)azetidin-3-yl]sulfanyl}-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate), C22H31N3O6S2, has been determined and the configurations of the four chiral centers validated. The title compound crystallizes in the triclinic space group P1 with one molecule in the unit cell. Three out of the four rings adopt planar conformations while the thiazolinyl ring adopts an enveloped conformation. In the crystal, O—H...N hydrogen bonds link the molecules into chains along [1\overline{1}0].