Major General James G. Blunt

Dexibuprofen is a nonsteroidal anti-inflammatory drug (NSAID). It is the active dextrorotatory enantiomer of ibuprofen.[1] Most ibuprofen formulations contain a racemic mixture of both isomers.

Dexibuprofen is a chiral switch of racemic ibuprofen. The chiral carbon in dexibuprofen is assigned an absolute configuration of (S) per the Cahn–Ingold–Prelog rules.[2][3] Dexibuprofen is also called as S(+)Ibuprofen.

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.


See also

References

  1. ^ Hardikar MS (September 2008). "Chiral non-steroidal anti-inflammatory drugs--a review". Journal of the Indian Medical Association. 106 (9): 615–8, 622, 624. PMID 19552094.
  2. ^ Cahn RS, Ingold C, Prelog V (1966). "Specification of Molecular Chirality". Angewandte Chemie International Edition in English. 5 (4): 385–415. doi:10.1002/anie.196603851. ISSN 0570-0833.
  3. ^ Cahn RS, Ingold CK, Prelog V (1956). "The specification of asymmetric configuration in organic chemistry". Experientia. 12 (3): 81–94. doi:10.1007/bf02157171. ISSN 0014-4754. S2CID 43026989.
  4. ^ 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. doi:10.1016/0006-2952(88)90762-9. PMID 3276314.
  5. ^ Hutt AJ, Caldwell J (November 1983). "The metabolic chiral inversion of 2-arylpropionic acids--a novel route with pharmacological consequences". The Journal of Pharmacy and Pharmacology. 35 (11): 693–704. doi:10.1111/j.2042-7158.1983.tb02874.x. PMID 6139449. S2CID 40669413.
  6. ^ 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. PMID 6706. S2CID 38614295.
  7. ^ Hao H, Wang G, Sun J (2005). "Enantioselective pharmacokinetics of ibuprofen and involved mechanisms". Drug Metabolism Reviews. 37 (1): 215–234. doi:10.1081/dmr-200047999. PMID 15747501. S2CID 43433812.
  8. ^ Kannappan V. "Dexibuprofen – Chiralpedia". Retrieved 2022-08-27.
source: https://en.wikipedia.org/wiki/Dexibuprofen