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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v t e Non-steroidal anti-inflammatory drugs (NSAIDs) (primarily M01A and M02A, also N02BA)
pyrazolones / pyrazolidines	Aminophenazone Ampyrone Azapropazone Clofezone Difenamizole Famprofazone Feprazone Kebuzone Metamizole Mofebutazone Morazone Nifenazone Oxyphenbutazone Phenazone Phenylbutazone Propyphenazone Sulfinpyrazone Suxibuzone^‡
salicylates	Aspirin (acetylsalicylic acid)^# Aloxiprin Benorylate Carbasalate calcium Diflunisal Dipyrocetyl Ethenzamide Guacetisal Magnesium salicylate Methyl salicylate Salsalate Salicin Salicylamide Salicylic acid (salicylate) Sodium salicylate
acetic acid derivatives and related substances	Aceclofenac Acemetacin Alclofenac Amfenac Bendazac Bromfenac Bufexamac Bumadizone Diclofenac Difenpiramide Etodolac Felbinac Fenclozic acid Fentiazac Indometacin Indometacin farnesil Isoxepac Ketorolac Lonazolac Mofezolac Oxametacin Prodolic acid Proglumetacin Sulindac Tiopinac Tolmetin Zomepirac^†
oxicams	Ampiroxicam Droxicam Isoxicam Lornoxicam Meloxicam Piroxicam Pivoxicam Tenoxicam
propionic acid derivatives (profens)	Alminoprofen Benoxaprofen^† Carprofen^‡ Dexibuprofen Dexketoprofen Fenbufen Fenoprofen Flunoxaprofen Flurbiprofen Ibuprofen^# Ibuproxam Indoprofen^† Ketoprofen Loxoprofen Miroprofen Naproxen Oxaprozin Pelubiprofen Piketoprofen Pirprofen Suprofen Tarenflurbil Tepoxalin^‡ Tiaprofenic acid Vedaprofen^‡ Zaltoprofen COX-inhibiting nitric oxide donator: Naproxcinod
n-arylanthranilic acids (fenamates)	Azapropazone Clonixin Etofenamate Floctafenine Flufenamic acid Flunixin Flutiazin Glafenine^† Meclofenamic acid Mefenamic acid Morniflumate Niflumic acid Tolfenamic acid
COX-2 inhibitors (coxibs)	Apricoxib Celecoxib (+tramadol) Cimicoxib^‡ Deracoxib^‡ Etoricoxib Firocoxib^‡ Lumiracoxib^† Mavacoxib^‡ Parecoxib Robenacoxib^‡ Rofecoxib^† Valdecoxib^†
other	Aminopropionitrile Benzydamine Chondroitin sulfate Diacerein Fluproquazone Glucosamine Glycosaminoglycan Hyperforin Nabumetone Nimesulide Oxaceprol Proquazone Superoxide dismutase / orgotein Tenidap
NSAID combinations	Ibuprofen/famotidine Ibuprofen/hydrocodone Ibuprofen/oxycodone Ibuprofen/paracetamol Meloxicam/bupivacaine Naproxen/diphenhydramine Naproxen/esomeprazole
Key: underline indicates initially developed first-in-class compound of specific group; ^#WHO-Essential Medicines; ^†withdrawn drugs; ^‡veterinary use.
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See also

References