Roxithromycin Impurity C
Roxithromycin Impurity C is a degradation derivative arising from oxidative cleavage of the 14-membered macrolactone core of roxithromycin, featuring a desosamine sugar moiety and a 9-cladinose substituent. The compound exhibits a carbonyl group at the C-6 position, replacing the parent drug's hydroxyl functionality, and retains the characteristic methyl ester at C-12. Structural analysis confirms a loss of the glycosidic linkage at C-3, resulting in a linearized lactone fragment. This impurity is specifically employed as an HPLC reference standard for quantifying oxidative degradation pathways in roxithromycin formulations.
On Request
IUPAC Name
6-[4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-10-hydroxyimino-4-(5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl)oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan-2-one
📝 Synonyms
Roxithromycin Impurity C
Erythromycin Impurity 58
CHEBI:201479
CHEBI:201822
PD121742
(10Z)-6-[4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-10-hydroxyimino-4-(5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl)oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan-2-one
6-((4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-14-ethyl-7,12,13-trihydroxy-4-((5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl)oxy)-10-(hydroxyimino)-3,5,7,9,11,13-hexamethyloxacyclotetradecan-2-one
🔬 Chemical Identifiers
CCC1C(C(C(C(=NO)C(CC(C(C(C(C(C(=O)O1)C)OC2CC(C(C(O2)C)O)(C)OC)C)OC3C(C(CC(O3)C)N(C)C)O)(C)O)C)C)O)(C)O
InChI=1S/C37H68N2O13/c1-14-25-37(10,45)30(41)20(4)27(38-46)18(2)16-35(8,44)32(52-34-28(40)24(39(11)12)15-19(3)48-34)21(5)29(22(6)33(43)50-25)51-26-17-36(9,47-13)31(42)23(7)49-26/h18-26,28-32,34,40-42,44-46H,14-17H2,1-13H3
KYTWXIARANQMCA-UHFFFAOYSA-N
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