Dexibuprofen Explained
| Watchedfields: | changed |
| Verifiedrevid: | 443586803 |
| Iupac Name: | (2S)-2-[4-(2-methylpropyl)phenyl]propanoic acid |
| Width: | 150px |
| Width2: | 150px |
| Tradename: | Seractil, Deltaran, Ibusoft, Monactil |
| Routes Of Administration: | Oral |
| Cas Number: | 51146-56-6 |
| Atc Prefix: | M01 |
| Atc Suffix: | AE14 |
| Pubchem: | 39912 |
| Chemspiderid: | 36498 |
| Unii: | 671DKG7P5S |
| Kegg: | D03715 |
| Chebi: | 43415 |
| Synonyms: | S(+)Ibuprofen |
| Chembl: | 175 |
| C: | 13 |
| H: | 18 |
| O: | 2 |
| Smiles: | C[C@@H](c1ccc(cc1)CC(C)C)C(=O)O |
| Stdinchi: | 1S/C13H18O2/c1-9(2)8-11-4-6-12(7-5-11)10(3)13(14)15/h4-7,9-10H,8H2,1-3H3,(H,14,15)/t10-/m0/s1 |
| Stdinchikey: | HEFNNWSXXWATRW-JTQLQIEISA-N |
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
Notes and References
- Hardikar MS . Chiral non-steroidal anti-inflammatory drugs--a review . Journal of the Indian Medical Association . 106 . 9 . 615–8, 622, 624 . September 2008 . 19552094 .
- Cahn RS, Ingold C, Prelog V . 1966. Specification of Molecular Chirality . Angewandte Chemie International Edition in English . 5 . 4 . 385–415 . 10.1002/anie.196603851 . 0570-0833.
- Cahn RS, Ingold CK, Prelog V . 1956 . The specification of asymmetric configuration in organic chemistry . Experientia . 12 . 3 . 81–94 . 10.1007/bf02157171 . 43026989 . 0014-4754.
- Caldwell J, Hutt AJ, Fournel-Gigleux S . The metabolic chiral inversion and dispositional enantioselectivity of the 2-arylpropionic acids and their biological consequences . Biochemical Pharmacology . 37 . 1 . 105–114 . January 1988 . 3276314 . 10.1016/0006-2952(88)90762-9 .
- Hutt AJ, Caldwell J . The metabolic chiral inversion of 2-arylpropionic acids--a novel route with pharmacological consequences . The Journal of Pharmacy and Pharmacology . 35 . 11 . 693–704 . November 1983 . 6139449 . 10.1111/j.2042-7158.1983.tb02874.x . 40669413 .
- Adams SS, Bresloff P, Mason CG . 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 . March 1976 . 6706 . 10.1111/j.2042-7158.1976.tb04144.x . 38614295 .
- Hao H, Wang G, Sun J . Enantioselective pharmacokinetics of ibuprofen and involved mechanisms . Drug Metabolism Reviews . 37 . 1 . 215–234 . 2005 . 15747501 . 10.1081/dmr-200047999 . 43433812 .
- Web site: Kannappan V . Dexibuprofen – Chiralpedia . 2022-08-27 . en-US.
