Dexibuprofen

Dexibuprofen

Clinical data
Trade names	Seractil, Deltaran, Ibusoft, Monactil
Other names	S(+)Ibuprofen
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	M01AE14 (WHO)
Identifiers
IUPAC name (2S)-2-[4-(2-methylpropyl)phenyl]propanoic acid
CAS Number	51146-56-6^Y
PubChem CID	39912
ChemSpider	36498^Y
UNII	671DKG7P5S
KEGG	D03715^Y
ChEBI	CHEBI:43415^Y
ChEMBL	ChEMBL175^Y
CompTox Dashboard (EPA)	DTXSID9048724
ECHA InfoCard	100.106.960
Chemical and physical data
Formula	C13H18O2
Molar mass	206.285 g·mol^−1
3D model (JSmol)	Interactive image
SMILES C[C@@H](c1ccc(cc1)CC(C)C)C(=O)O
InChI InChI=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^Y Key:HEFNNWSXXWATRW-JTQLQIEISA-N^Y
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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 (S)-(+)-ibuprofen.[4]

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.[5][6][7][8][9] 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

• Chiral switch
• Enantiopure drug
• Chirality
• Eudysmic ratio
• Ibuprofen

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. CID 39912 from PubChem
5. 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.
6. 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.
7. 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.
8. 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.
9. Kannappan V. "Dexibuprofen – Chiralpedia". Retrieved 2022-08-27.