Tigecycline Epimer (Crude) is a stereoisomeric impurity arising from stereochemical inversion at a chiral center within the glycylcycline scaffold of the parent drug, Tigecycline. This epimer retains the core tetracycline backbone with a glycylamido substituent at position 9 but exhibits altered configuration at a critical chiral carbon, disrupting the parent compound's pharmacophoric alignment. The molecule contains multiple hydroxyl, amino, and amide functional groups, with the epimeric modification influencing its solubility and chromatographic behavior. Synthetically, it emerges as a byproduct during asymmetric synthesis steps, necessitating its quantification in API purity profiling. This crude form serves as an HPLC reference standard for detecting epimeric impurities in Tigecycline drug substance batches.
On RequestC(C)(C)(C)NCC(=O)NC1=CC(=C2C[C@H]3C[C@H]4[C@H](C(=C(C([C@]4(C(=C3C(C2=C1O)=O)O)O)=O)C(=O)N)O)N(C)C)N(C)C
InChI=1S/C29H39N5O8/c1-28(2,3)31-11-17(35)32-15-10-16(33(4)5)13-8-12-9-14-21(34(6)7)24(38)20(27(30)41)26(40)29(14,42)25(39)18(12)23(37)19(13)22(15)36/h10,12,14,21,31,36,38-39,42H,8-9,11H2,1-7H3,(H2,30,41)(H,32,35)/t12-,14-,21+,29-/m0/s1
FPZLLRFZJZRHSY-RXEYFDPISA-N