Dolutegravir enantiomer is the non-pharmaceutically active stereoisomer of the HIV integrase inhibitor dolutegravir, characterized by inverted configuration at the chiral pyrimidin-4-ylmethyl moiety. Its structure incorporates a substituted pyrimidine core linked to a fluorinated benzamide and a sodium counterion associated with the carboxylate group. The compound exhibits distinct chiral interactions due to its reversed absolute configuration, leading to differential HPLC elution profiles compared to the parent API. This enantiomer serves as a critical chiral HPLC reference standard for quantifying enantiomeric purity in dolutegravir drug substance synthesis.
On RequestC[C@H]1CCO[C@H]2N1C(=O)C3=C(C(=O)C(=CN3C2)C(=O)NCC4=C(C=C(C=C4)F)F)[O-].[Na+]
InChI=1S/C20H19F2N3O5.Na/c1-10-4-5-30-15-9-24-8-13(17(26)18(27)16(24)20(29)25(10)15)19(28)23-7-11-2-3-12(21)6-14(11)22;/h2-3,6,8,10,15,27H,4-5,7,9H2,1H3,(H,23,28);/q;+1/p-1/t10-,15+;/m0./s1
UGWJRRXTMKRYNK-OEQYQXMYSA-M