Clindamycin-4-phosphate is a phosphorylated derivative of clindamycin, featuring a phosphate ester group appended to the 4-hydroxyl position of the lincosamide core. Its structure retains the 7-chloro-6,7,8-trideoxy-6-(1-methylpropylamino)-1-thioglycosyl moiety characteristic of the parent antibiotic. The phosphate substitution introduces a negatively charged, hydrophilic functionality, distinguishing it from clindamycinβs native hydroxyl group. This impurity arises during synthetic phosphorylation processes or hydrolytic degradation under alkaline conditions. It serves as an HPLC reference standard for quantifying process-related impurities in clindamycin formulations.
On RequestCCC[C@@H]1C[C@H](N(C1)C)C(=O)N[C@@H]([C@@H]2[C@@H]([C@@H]([C@H]([C@H](O2)SC)O)O)OP(=O)(O)O)[C@H](C)Cl
InChI=1S/C18H34ClN2O8PS/c1-5-6-10-7-11(21(3)8-10)17(24)20-12(9(2)19)15-16(29-30(25,26)27)13(22)14(23)18(28-15)31-4/h9-16,18,22-23H,5-8H2,1-4H3,(H,20,24)(H2,25,26,27)/t9-,10+,11-,12+,13+,14+,15+,16+,18+/m0/s1
OZDNESASKLVYBG-OCXYYGTOSA-N