Ibuprofen is an α-arylpropionic acid used largely in the treatment of
rheumatoid arthritis and widely used over-the counter drug for headache and minor pains. This drug has a
chiral center and exists as a pair of
enantiomers. (S)-Ibuprofen, the
eutomer, is responsible for the desired therapeutic effect. The inactive (R)-enantiomer, the
distomer, undergoes a unidirectional chiral inversion to give the active (S)-enantiomer, the former acting as a
prodrug for the latter.[4][5][6][7][8] That is, when the ibuprofen is administered as a racemate the distomer is converted in vivo into the eutomer while the latter is unaffected.
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^Caldwell J, Hutt AJ, Fournel-Gigleux S (January 1988). "The metabolic chiral inversion and dispositional enantioselectivity of the 2-arylpropionic acids and their biological consequences". Biochemical Pharmacology. 37 (1): 105–114.
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^Adams SS, Bresloff P, Mason CG (March 1976). "Pharmacological differences between the optical isomers of ibuprofen: evidence for metabolic inversion of the (-)-isomer". The Journal of Pharmacy and Pharmacology. 28 (3): 256–257.
doi:
10.1111/j.2042-7158.1976.tb04144.x.
PMID6706.
S2CID38614295.
^Hao H, Wang G, Sun J (2005). "Enantioselective pharmacokinetics of ibuprofen and involved mechanisms". Drug Metabolism Reviews. 37 (1): 215–234.
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