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 ;
PubChem CID	39912;
ChemSpider	36498 ;
UNII	671DKG7P5S;
KEGG	D03715 ;
ChEBI	CHEBI:43415 ;
ChEMBL	ChEMBL175 ;
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 ; Key:HEFNNWSXXWATRW-JTQLQIEISA-N ;
	(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.

References

^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ Kannappan V. "Dexibuprofen – Chiralpedia". Retrieved 2022-08-27.

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[pmid19552094-1] 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.

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Dexibuprofen

See also

References

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