Tenofovir diphosphate (Crude) is a phosphorylated metabolite of the antiretroviral prodrug tenofovir, featuring a cyclopropylmethyl group linked to a diphosphorylated ribose analog. The structure incorporates two phosphonyl moieties in a 5'-triphosphate configuration, with one terminal phosphate esterified to a hydroxyl group. This compound arises as a synthetic intermediate during the multi-step phosphorylation of tenofovir, reflecting incomplete esterification of the terminal phosphate. Its trivalent phosphorus centers and zwitterionic character contribute to its stability as an API impurity. It serves as an HPLC reference standard for quantifying process-related impurities in tenofovir disoproxil fumarate formulations.
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InChI=1S/C9H16N5O10P3/c1-6(2-14-4-13-7-8(10)11-3-12-9(7)14)22-5-25(15,16)23-27(20,21)24-26(17,18)19/h3-4,6H,2,5H2,1H3,(H,15,16)(H,20,21)(H2,10,11,12)(H2,17,18,19)/t6-/m1/s1
IACQCQDWSIQSRP-ZCFIWIBFSA-N