Abstract
2-Arylpropionic acid nonsteroidal anti-inflammatory drugs (NSAIDs) provide one of the most demonstrated pharmaceutical examples of chiral inversion. Chiral inversion depends on various factors (viz. biological-, solvent-, light-, temperature-induced, etc.) and the energy barrier associated with the stereogenic element present in the chiral molecule. The pharmacological properties of chiral drugs depend on the activity of one enantiomer or both the enantiomers targeting different biological targets. Consequently, chiral inversion can alter the biological activities of the pharmaceutical drug. Hence a better understanding of chiral inversion, factors facilitating such inversion, and the tools employed to determine chiral inversion are of great significance from a pharmacological and toxicological perspective.
Graphical Abstract
[http://dx.doi.org/10.1201/9781003000167-3]
[http://dx.doi.org/10.1007/s002280100320] [PMID: 11599654]
[PMID: 23674971]
[http://dx.doi.org/10.1016/0006-2952(88)90762-9] [PMID: 3276314]
[http://dx.doi.org/10.5603/MRJ.2017.0001]
[http://dx.doi.org/10.2174/1389200043335360] [PMID: 15578945]
[http://dx.doi.org/10.2174/138920012799320392] [PMID: 22304623]
[http://dx.doi.org/10.1016/0009-8981(83)90319-4] [PMID: 6851137]
[http://dx.doi.org/10.1016/j.watres.2021.117871] [PMID: 34872028]
[http://dx.doi.org/10.1248/cpb.38.180] [PMID: 2337941]
[http://dx.doi.org/10.1002/jps.2600780902] [PMID: 2685226]
[http://dx.doi.org/10.1023/A:1016245101389] [PMID: 8592665]
[http://dx.doi.org/10.1016/S0024-3205(01)01287-5] [PMID: 11589520]
[http://dx.doi.org/10.1211/0022357021778574] [PMID: 11902799]
[PMID: 11095576]
[http://dx.doi.org/10.1046/j.1365-2885.2002.00373.x]
[http://dx.doi.org/10.1002/chir.530060211] [PMID: 8204414]
[http://dx.doi.org/10.1002/chir.10180] [PMID: 12520506]
[http://dx.doi.org/10.1002/(SICI)1520-636X(1998)10:8<747:AID-CHIR5>3.0.CO;2-B] [PMID: 9803530]
[http://dx.doi.org/10.1042/bj0271257] [PMID: 16745220]
[http://dx.doi.org/10.1007/BF00541922] [PMID: 6092093]
[http://dx.doi.org/10.1002/chir.20397] [PMID: 17393472]
[http://dx.doi.org/10.1124/mol.51.4.576] [PMID: 9106621]
[http://dx.doi.org/10.1016/S0021-9673(00)82013-0]
[PMID: 1865366]
[http://dx.doi.org/10.1111/j.2042-7158.1983.tb02874.x] [PMID: 6139449]
[http://dx.doi.org/10.5863/1551-6776-19.1.25] [PMID: 24782688]
[http://dx.doi.org/10.1039/C6OB02415G]
[http://dx.doi.org/10.1039/D0CC07008D] [PMID: 33231225]
[http://dx.doi.org/10.1111/j.1472-8206.1990.tb00042.x] [PMID: 2096103]
[http://dx.doi.org/10.1007/978-3-0348-9160-8_7] [PMID: 3142235]
[http://dx.doi.org/10.1111/jcpt.12015] [PMID: 23167572]
[http://dx.doi.org/10.1039/b502508g] [PMID: 15965541]
[http://dx.doi.org/10.1016/S0021-9673(03)00238-3] [PMID: 12877200]
[http://dx.doi.org/10.1016/j.watres.2017.08.003] [PMID: 28806704]
[http://dx.doi.org/10.1016/j.ijms.2019.06.008]
[http://dx.doi.org/10.1002/anie.199516351]