Ritonavir Impurity F is a structurally related synthetic byproduct arising from the amidation step in Ritonavir production. It retains the core naphthalene sulfonamide scaffold and pyrazine-fused tetrahydrofuran ring system but features an additional methylene group (-CH2-) in the side chain adjacent to the sulfonamide linkage, resulting from a failed cyclization event. This impurity exhibits a truncated ester functionality compared to the parent drug, replacing the critical ฮณ-lactam moiety with a saturated carbonyl-terminated aliphatic chain. The compound demonstrates moderate hydrophobicity due to its extended aliphatic substituents and serves as a critical HPLC reference standard for monitoring process consistency in antiretroviral drug manufacturing.
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InChI=1S/C29H34N4O5S/c1-19(2)26-27(35)33(28(36)32-26)22(13-20-9-5-3-6-10-20)15-25(34)24(14-21-11-7-4-8-12-21)31-29(37)38-17-23-16-30-18-39-23/h3-12,16,18-19,22,24-26,34H,13-15,17H2,1-2H3,(H,31,37)(H,32,36)/t22-,24-,25-,26-/m0/s1
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