Chemistry:Dexibuprofen
 | |
-ibuprofen-3D-balls.png) | |
| Clinical data | |
|---|---|
| Trade names | Seractil, Deltaran, Ibusoft, Monactil |
| Other names | S(+)Ibuprofen |
| AHFS/Drugs.com | International Drug Names |
| Routes of administration | Oral |
| ATC code | |
| Identifiers | |
| |
| CAS Number | |
| PubChem CID | |
| ChemSpider | |
| UNII | |
| KEGG | |
| ChEBI | |
| ChEMBL | |
| Chemical and physical data | |
| Formula | C13H18O2 |
| Molar mass | 206.285 g·mol−1 |
| 3D model (JSmol) | |
| |
| |
| (verify) | |
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
- ↑ "Chiral non-steroidal anti-inflammatory drugs--a review". Journal of the Indian Medical Association 106 (9): 615–8, 622, 624. September 2008. PMID 19552094.
- ↑ "Specification of Molecular Chirality". Angewandte Chemie International Edition in English 5 (4): 385–415. 1966. doi:10.1002/anie.196603851. ISSN 0570-0833.
- ↑ "The specification of asymmetric configuration in organic chemistry". Experientia 12 (3): 81–94. 1956. doi:10.1007/bf02157171. ISSN 0014-4754.
- ↑ "The metabolic chiral inversion and dispositional enantioselectivity of the 2-arylpropionic acids and their biological consequences". Biochemical Pharmacology 37 (1): 105–114. January 1988. doi:10.1016/0006-2952(88)90762-9. PMID 3276314.
- ↑ "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. doi:10.1111/j.2042-7158.1983.tb02874.x. PMID 6139449.
- ↑ "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. doi:10.1111/j.2042-7158.1976.tb04144.x. PMID 6706.
- ↑ "Enantioselective pharmacokinetics of ibuprofen and involved mechanisms". Drug Metabolism Reviews 37 (1): 215–234. 2005. doi:10.1081/dmr-200047999. PMID 15747501.
- ↑ "Dexibuprofen – Chiralpedia" (in en-US). https://chiralpedia.com/blog/dexibuprofen/.
 |  |
