Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Oxyphenbutazone: Difference between pages

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Saving copy of the {{drugbox}} taken from revid 477065977 of page Oxyphenbutazone for the Chem/Drugbox validation project (updated: 'DrugBank', 'ChEMBL').
 
 
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{{Short description|Chemical compound}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid [{{fullurl:Oxyphenbutazone|oldid=477065977}} 477065977] of page [[Oxyphenbutazone]] with values updated to verified values.}}
{{Infobox drug
{{Drugbox
| Verifiedfields = changed
| Verifiedfields = changed
| verifiedrevid = 462267573
| verifiedrevid = 477171011
| IUPAC_name = (''RS'')-4-butyl-1-(4-hydroxyphenyl)-2-phenylpyrazolidine-3,5-dione
| IUPAC_name = (''RS'')-4-butyl-1-(4-hydroxyphenyl)-2-phenylpyrazolidine-3,5-dione
| image = oxyphenbutazone.png
| image = oxyphenbutazone.svg
| width = 250px
| width = 250px
| imagename = 1 : 1 mixture (racemate)
| chirality = [[Racemic mixture]]
| drug_name = Oxyphenbutazone

<!--Clinical data-->
<!--Clinical data-->
| tradename =
| tradename = Tandearil, Tanderil
| Drugs.com = {{drugs.com|international|oxyphenbutazone}}
| Drugs.com = {{drugs.com|international|oxyphenbutazone}}
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| legal_US_comment = Withdrawn
| legal_AU = <!-- Unscheduled / S2 / S4 / S8 -->
| legal_UK = <!-- GSL / P / POM / CD -->
| legal_UK = Withdrawn
| legal_AU = Withdrawn
| legal_US = <!-- OTC / Rx-only -->

<!--Identifiers-->
<!--Identifiers-->
| CASNo_Ref = {{cascite|correct|CAS}}
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 129-20-4
| CAS_number = 129-20-4
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| ATC_supplemental = {{ATC|M02|AA04}} {{ATC|S01|BC02}}
| ATC_supplemental = {{ATC|M02|AA04}} {{ATC|S01|BC02}}
| PubChem = 104811
| PubChem = 104811
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB03585
| DrugBank = DB03585
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
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| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D08324
| KEGG = D08324
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 76258
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = <!-- blanked - oldvalue: 1228 -->
| ChEMBL = 1228
<!--Chemical data-->
| C=19 | H=20 | N=2 | O=3
| C=19 | H=20 | N=2 | O=3
| molecular_weight = 324.379 g/mol
| smiles = O=C2N(c1ccc(O)cc1)N(C(=O)C2CCCC)c3ccccc3.O
| smiles = O=C2N(c1ccc(O)cc1)N(C(=O)C2CCCC)c3ccccc3.O
| InChI = 1/C19H20N2O3.H2O/c1-2-3-9-17-18(23)20(14-7-5-4-6-8-14)21(19(17)24)15-10-12-16(22)13-11-15;/h4-8,10-13,17,22H,2-3,9H2,1H3;1H2
| InChIKey = CNDQSXOVEQXJOE-UHFFFAOYAR
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C19H20N2O3.H2O/c1-2-3-9-17-18(23)20(14-7-5-4-6-8-14)21(19(17)24)15-10-12-16(22)13-11-15;/h4-8,10-13,17,22H,2-3,9H2,1H3;1H2
| StdInChI = 1S/C19H20N2O3.H2O/c1-2-3-9-17-18(23)20(14-7-5-4-6-8-14)21(19(17)24)15-10-12-16(22)13-11-15;/h4-8,10-13,17,22H,2-3,9H2,1H3;1H2
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| StdInChIKey = CNDQSXOVEQXJOE-UHFFFAOYSA-N
| StdInChIKey = CNDQSXOVEQXJOE-UHFFFAOYSA-N
}}
}}

'''Oxyphenbutazone''' is a [[nonsteroidal anti-inflammatory drug]] (NSAID).<ref>{{cite journal | vauthors = Singh N, Jabeen T, Somvanshi RK, Sharma S, Dey S, Singh TP | title = Phospholipase A2 as a target protein for nonsteroidal anti-inflammatory drugs (NSAIDS): crystal structure of the complex formed between phospholipase A2 and oxyphenbutazone at 1.6 A resolution | journal = Biochemistry | volume = 43 | issue = 46 | pages = 14577–83 | date = November 2004 | pmid = 15544328 | doi = 10.1021/bi0483561 }}</ref> It is a [[metabolite]] of [[phenylbutazone]].<ref>{{cite journal | vauthors = Matthews NS, Peck KE, Taylor TS, Mealey KL | title = Pharmacokinetics of phenylbutazone and its metabolite oxyphenbutazone in miniature donkeys | journal = American Journal of Veterinary Research | volume = 62 | issue = 5 | pages = 673–5 | date = May 2001 | pmid = 11341383 | doi = 10.2460/ajvr.2001.62.673 | doi-access = free }}</ref>

It was withdrawn from markets worldwide in mid-1980s due to bone marrow suppression and the risk of [[Stevens–Johnson syndrome]].<ref name=Fung-2001>{{cite journal| vauthors = Fung M, Thornton A, Mybeck K, Wu JH, Hornbuckle K, Muniz E |title=Evaluation of the Characteristics of Safety Withdrawal of Prescription Drugs from Worldwide Pharmaceutical Markets-1960 to 1999 |journal=Therapeutic Innovation & Regulatory Science |date= January 2001 |volume=35 |issue=1 |pages=293–317 |doi=10.1177/009286150103500134 |s2cid=73036562 }}</ref><ref>{{cite journal | vauthors = Biron P | title = Withdrawal of oxyphenbutazone: what about phenylbutazone? | journal = CMAJ | volume = 134 | issue = 10 | pages = 1119–20 | date = May 1986 | pmid = 3697857 | pmc = 1491052 }}</ref>

== References ==
{{reflist}}

{{Anti-inflammatory and antirheumatic products}}
{{Topical products for joint and muscular pain}}

[[Category:Nonsteroidal anti-inflammatory drugs]]
[[Category:Pyrazolidindiones]]
[[Category:Phenols]]
[[Category:Withdrawn drugs]]


{{musculoskeletal-drug-stub}}
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