The mol-ecular structure of the first orally active carbapenem anti-bacterial agent, tebipenem pivoxil (systematic name: (2,2-di-methyl-propano-yloxy)methyl (4R,5S,6S)-3-{[1-(4,5-di-hydro-1,3-thia-zol-2-yl)azetidin-3-yl]sulfanyl}-6-[(1R)-1-hy-droxy-eth-yl]-4-methyl-7-oxo-1-aza-bicyclo-[3.2.0]hept-2-ene-2-carboxyl-ate), 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 mol-ecule in the unit cell. Three out of the four rings adopt planar conformations while the thia-zolinyl ring adopts an enveloped conformation. In the crystal, O-H⋯N hydrogen bonds link the mol-ecules into chains along [10].
Keywords: antibiotics; carbapenem; crystal structure; hydrogen bonding; prodrug; tebipenem.