| Revision as of 23:28, 7 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{drugbox}} (changes to verified and watched fields - added verified revid - updated 'DrugBank_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report [[Misplaced Pages talk:WikiProject_Pharmac← Previous edit |
Latest revision as of 07:12, 15 April 2024 edit undoحسن علي البط (talk | contribs)Extended confirmed users, Pending changes reviewers19,940 edits added Category:Benzene derivatives using HotCat |
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{{Short description|Chemical compound}} |
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{{Drugbox |
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{{cs1 config|name-list-style=vanc}} |
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{{Infobox drug |
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| Watchedfields = changed |
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| verifiedrevid = 414417007 |
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| IUPAC_name = (2S)-2-propanoic acid |
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| verifiedrevid = 443586803 |
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| IUPAC_name = (2''S'')-2-propanoic acid |
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| image = Dexibuprofen Structural Formulae V.1.svg |
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| image = Dexibuprofen_Structural_Formulae_v2.png |
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| image2 = (S)-ibuprofen-3D-balls.png |
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| image2 = (S)-ibuprofen-3D-balls.png |
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| width = 150px |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| width2 = 150px |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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<!--Clinical data-->| tradename = Seractil, Deltaran, Ibusoft, Monactil |
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| ChemSpiderID = 36498 |
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| Drugs.com = {{drugs.com|international|dexibuprofen}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| UNII = 671DKG7P5S |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| InChI = 1/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 |
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| pregnancy_category = |
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| smiles = C(c1ccc(cc1)CC(C)C)C(=O)O |
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> |
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| InChIKey = HEFNNWSXXWATRW-JTQLQIEIBT |
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| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> |
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| ChEMBL = 175 |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| legal_status = |
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| 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 |
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| routes_of_administration = Oral |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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<!--Pharmacokinetic data-->| bioavailability = |
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| StdInChIKey = HEFNNWSXXWATRW-JTQLQIEISA-N |
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| CAS_number = 51146-56-6 |
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| protein_bound = |
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| ATC_prefix = M01 |
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| metabolism = |
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| ATC_suffix = AE14 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 43415 |
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| PubChem = 39912 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D03715 |
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| C=13|H=18|O=2 |
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| molecular_weight = 206.28082 g/mol |
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| bioavailability = |
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| protein_bound = |
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| metabolism = |
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| elimination_half-life = |
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| elimination_half-life = |
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| excretion = |
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| excretion = <!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| CAS_number = 51146-56-6 |
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| ATC_prefix = M01 |
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| pregnancy_category= |
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| ATC_suffix = AE14 |
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> |
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| PubChem = 39912 |
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| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> |
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| DrugBank = |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| legal_status = |
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| ChemSpiderID = 36498 |
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| routes_of_administration = Oral, Other ROAs Unknown |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 671DKG7P5S |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D03715 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 43415 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| synonyms = S(+)Ibuprofen |
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| ChEMBL = 175 |
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<!--Chemical data-->| C = 13 |
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| H = 18 |
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| O = 2 |
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| smiles = C(c1ccc(cc1)CC(C)C)C(=O)O |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| 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 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = HEFNNWSXXWATRW-JTQLQIEISA-N |
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}} |
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}} |
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'''Dexibuprofen''' is a ]. It is the active ] ] of ]. Most ibuprofen formulations contain a ] of dexibuprofen and (−)-ibuprofen. |
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'''Dexibuprofen''' is a ] (NSAID). It is the active ] ] of ].<ref name=pmid19552094>{{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 }}</ref> Most ibuprofen formulations contain a ] of both isomers. |
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Dexibuprofen is a ] of racemic ibuprofen. The chiral carbon in dexibuprofen is assigned an absolute configuration of (''S'') per the ].<ref>{{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}}</ref><ref>{{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}}</ref> Dexibuprofen is also called as '''.''' |
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{{Anti-inflammatory and antirheumatic products}} |
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{{NSAIDs}} |
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Ibuprofen is an α-arylpropionic acid used largely in the treatment of ] and widely used over-the counter drug for headache and minor pains. This drug has a ] and exists as a pair of ]. (''S'')-Ibuprofen, the ], is responsible for the desired therapeutic effect. The inactive (''R'')-enantiomer, the ], undergoes a unidirectional chiral inversion to give the active (''S'')-enantiomer, the former acting as a ] for the latter.<ref>{{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 }}</ref><ref>{{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 }}</ref><ref>{{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 }}</ref><ref>{{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 }}</ref><ref>{{Cite web | vauthors = Kannappan V |title= Dexibuprofen – Chiralpedia |url=https://chiralpedia.com/blog/dexibuprofen/ |access-date=2022-08-27 |language=en-US}}</ref> That is, when the ibuprofen is administered as a racemate the distomer is converted ''in vivo'' into the eutomer while the latter is unaffected. |
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== See also == |
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{{musculoskeletal-drug-stub}} |
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* ] |
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== References == |
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{{Reflist|2}} |
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{{Anti-inflammatory products}} |
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{{Prostanoid signaling modulators}} |
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{{Musculoskeletal-drug-stub}} |
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