Ritonavir Impurity N is a structurally related isomer arising from synthetic divergence during the formation of the naphthalene-thiazole core. It retains the parent drug's bicyclic scaffold but features an alternative substitution pattern on the naphthalene ring, incorporating a 2-aminothiazole moiety linked via a methylene bridge to a cyclohexylmethyl side chain. The compound contains multiple hydrogen bond donors/acceptors, including amide and sulfonamide functionalities, which influence its chromatographic behavior. This impurity serves as a critical HPLC reference standard for quantifying process-related variability in ritonavir formulations.
On RequestCC(C)C1=NC(=CS1)CN(C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC2=CC=CC=C2)[C@H](C[C@H](CC3=CC=CC=C3)NC(=O)OCC4=CN=CS4)O
InChI=1S/C37H48N6O5S2/c1-24(2)33(42-36(46)43(5)20-29-22-49-35(39-29)25(3)4)34(45)41-31(17-27-14-10-7-11-15-27)32(44)18-28(16-26-12-8-6-9-13-26)40-37(47)48-21-30-19-38-23-50-30/h6-15,19,22-25,28,31-33,44H,16-18,20-21H2,1-5H3,(H,40,47)(H,41,45)(H,42,46)/t28-,31-,32-,33-/m0/s1
VRNXMJYSOAQBMK-XGKFQTDJSA-N