Medroxyprogesterone impurity F is a synthetic byproduct formed via side-chain oxidation during the alkylation of 17Ξ±-hydroxyprogesterone. It retains the core 17Ξ±-hydroxy-pregn-4-ene-3,20-dione scaffold of the parent drug but incorporates an additional hydroxyl group at C6 and a truncated side chain lacking the 17Ξ²-acetyl moiety. This impurity exhibits a 6Ξ²-hydroxy configuration and a saturated A-ring, distinguishing it from the parent compoundβs Ξ4 double bond. It functions as an HPLC reference standard for monitoring process-related impurities in medroxyprogesterone acetate synthesis.
On RequestC[C@H]1C[C@@H]2[C@H](CC[C@]3([C@H]2CC[C@@]3(C(=O)C)OC(=O)C)C)[C@@]4([C@H]1CC(=O)CC4)C
InChI=1S/C24H36O4/c1-14-12-18-19(22(4)9-6-17(27)13-21(14)22)7-10-23(5)20(18)8-11-24(23,15(2)25)28-16(3)26/h14,18-21H,6-13H2,1-5H3/t14-,18+,19-,20-,21-,22+,23-,24-/m0/s1
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