Dexibuprofen

{{Short description|Chemical compound}}

{{cs1 config|name-list-style=vanc}}

{{Infobox drug

| Watchedfields = changed

| verifiedrevid = 443586803

| IUPAC_name = (2S)-2-[4-(2-methylpropyl)phenyl]propanoic acid

| image = Dexibuprofen.png

| image_class = skin-invert-image

| image2 = (S)-ibuprofen-3D-balls.png

| width = 200px

| width2 = 200px

| tradename = Seractil, Deltaran, Ibusoft, Monactil

| Drugs.com = {{drugs.com|international|dexibuprofen}}

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU =

| legal_CA =

| legal_UK =

| legal_US =

| legal_status =

| routes_of_administration = Oral

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 51146-56-6

| ATC_prefix = M01

| ATC_suffix = AE14

| PubChem = 39912

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank =

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 36498

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 671DKG7P5S

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D03715

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 43415

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| synonyms = S(+)Ibuprofen

| ChEMBL = 175

| C = 13

| H = 18

| O = 2

| smiles = C[C@@H](c1ccc(cc1)CC(C)C)C(=O)O

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| 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_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = HEFNNWSXXWATRW-JTQLQIEISA-N

}}

Dexibuprofen is a nonsteroidal anti-inflammatory drug (NSAID). It is the active dextrorotatory enantiomer of ibuprofen.{{cite journal | vauthors = Hardikar MS | title = Chiral non-steroidal anti-inflammatory drugs--a review | journal = Journal of the Indian Medical Association | volume = 106 | issue = 9 | pages = 615–8, 622, 624 | date = September 2008 | pmid = 19552094 }} Most ibuprofen formulations, as well as other drugs of the profen drug class, 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.{{Cite journal| vauthors = Cahn RS, Ingold C, Prelog V |date=1966|title=Specification of Molecular Chirality |journal=Angewandte Chemie International Edition in English |volume=5 |issue=4 |pages=385–415 |doi=10.1002/anie.196603851 |issn=0570-0833}}{{Cite journal| vauthors = Cahn RS, Ingold CK, Prelog V |date=1956 |title=The specification of asymmetric configuration in organic chemistry |journal=Experientia |volume=12 |issue=3 |pages=81–94 |doi=10.1007/bf02157171 |s2cid=43026989 |issn=0014-4754}} Dexibuprofen is also called (S)-(+)-ibuprofen.{{Pubchem|39912}}

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.{{cite journal | vauthors = Caldwell J, Hutt AJ, Fournel-Gigleux S | title = The metabolic chiral inversion and dispositional enantioselectivity of the 2-arylpropionic acids and their biological consequences | journal = Biochemical Pharmacology | volume = 37 | issue = 1 | pages = 105–114 | date = January 1988 | pmid = 3276314 | doi = 10.1016/0006-2952(88)90762-9 }}{{cite journal | vauthors = Hutt AJ, Caldwell J | title = The metabolic chiral inversion of 2-arylpropionic acids--a novel route with pharmacological consequences | journal = The Journal of Pharmacy and Pharmacology | volume = 35 | issue = 11 | pages = 693–704 | date = November 1983 | pmid = 6139449 | doi = 10.1111/j.2042-7158.1983.tb02874.x | doi-access = | s2cid = 40669413 }}{{cite journal | vauthors = Adams SS, Bresloff P, Mason CG | title = Pharmacological differences between the optical isomers of ibuprofen: evidence for metabolic inversion of the (-)-isomer | journal = The Journal of Pharmacy and Pharmacology | volume = 28 | issue = 3 | pages = 256–257 | date = March 1976 | pmid = 6706 | doi = 10.1111/j.2042-7158.1976.tb04144.x | s2cid = 38614295 }}{{cite journal | vauthors = Hao H, Wang G, Sun J | title = Enantioselective pharmacokinetics of ibuprofen and involved mechanisms | journal = Drug Metabolism Reviews | volume = 37 | issue = 1 | pages = 215–234 | date = 2005 | pmid = 15747501 | doi = 10.1081/dmr-200047999 | s2cid = 43433812 }}{{Cite web | vauthors = Kannappan V |title= Dexibuprofen – Chiralpedia |url=https://chiralpedia.com/blog/dexibuprofen/ |access-date=2022-08-27 |language=en-US}} That is, when the ibuprofen is administered as a racemate the distomer is converted in vivo into the eutomer while the latter is unaffected.