Certain pharmaceutical drugs undergo racemization or stereoconversion in vivo
Certain pharmaceutical drugs undergo racemization or stereoconversion in vivo, as demonstrated by studies on agents like thalidomide and ibuprofen that invert between their enantiomeric forms.
The claim is specific, empirical, and contestable. Multiple retrieved papers explicitly discuss and confirm the in vivo racemization or chiral inversion of specific pharmaceutical drugs (such as thalidomide, ibuprofen, and acidic methine compounds). Therefore, the evidence clearly supports the claim.
Tommy Eriksson, Sven Bjöurkman, Bodil Roth, Årsa Fyge, Peter Höuglund. Stereospecific determination, chiral inversion in vitro and pharmacokinetics in humans of the enantiomers of thalidomide. 1995. https://doi.org/10.1002/chir.530070109
Demonstrates the rapid chiral inversion of thalidomide enantiomers in human blood and in vivo.
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Yu ZJ, Morfin C, Paul T, Kyne H, Zhang X, Thomas-Tran R, Venkataramani C, Ghaffari H, Subramanian M, Murray B, Liu X, Subramanian R. Hydrogen/Deuterium Exchange for Chiral Stability Assessment in Acidic Methine-Containing Compounds.. 2025. https://doi.org/10.1021/acs.analchem.5c04777
Discusses racemization driven by keto-enol tautomerization in acidic methine-containing drugs such as glutarimide derivatives and thiazolidinediones.
Hiroyuki Ikuta, Atsushi Kawase, Masahiro Iwaki. Stereoselective Pharmacokinetics and Chiral Inversion of Ibuprofen in Adjuvant-induced Arthritic Rats.. 2017. https://doi.org/10.1124/dmd.116.073239
Shows that the inactive R-enantiomer of ibuprofen undergoes unidirectional chiral inversion to the active S-enantiomer in vivo.
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