4-Hydroxy Atorvastatin Lactone is a degradation byproduct of Atorvastatin, characterized by a hydroxyl substitution at the 4-position of the lactone ring, which disrupts the parent drug's core HMG-CoA reductase inhibitory scaffold. The molecule retains the fluorinated phenyl group and pyrrole-fused indane moiety of Atorvastatin but features an oxidized lactone ring and a 4-hydroxyl group, introducing steric and electronic asymmetry. This impurity arises via hydrolytic cleavage and subsequent oxidation of the Atorvastatin lactone, forming a stable cyclic ester with altered pharmacokinetic properties. It serves as a critical HPLC reference standard for quantifying oxidative degradation pathways in Atorvastatin formulations.
On RequestCC(C)C1=C(C(=C(N1CC[C@@H]2C[C@H](CC(=O)O2)O)C3=CC=C(C=C3)F)C4=CC=CC=C4)C(=O)NC5=CC=C(C=C5)O
InChI=1S/C33H33FN2O5/c1-20(2)31-30(33(40)35-24-12-14-25(37)15-13-24)29(21-6-4-3-5-7-21)32(22-8-10-23(34)11-9-22)36(31)17-16-27-18-26(38)19-28(39)41-27/h3-15,20,26-27,37-38H,16-19H2,1-2H3,(H,35,40)/t26-,27-/m1/s1
KDJMDZSAAFACAM-KAYWLYCHSA-N