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Revision as of 12:06, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 477065977 of page Oxyphenbutazone for the Chem/Drugbox validation project (updated: 'DrugBank', 'ChEMBL').  Latest revision as of 18:08, 21 October 2024 edit JWBE (talk | contribs)Extended confirmed users10,126 edits removed Category:Phenols; added Category:4-Hydroxyphenyl compounds using HotCat 
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{{Short description|Chemical compound}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] 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
| chirality = ]
| imagename = 1 : 1 mixture (racemate)
<!--Clinical data-->| tradename = Tandearil, Tanderil
| drug_name = Oxyphenbutazone
⚫ | Drugs.com = {{drugs.com|international|oxyphenbutazone}}
⚫ | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
⚫ | pregnancy_US = <!-- A / B / C / D / X -->
| legal_US_comment = Withdrawn
⚫ | legal_UK = Withdrawn
| legal_AU = Withdrawn
⚫ <!--Identifiers-->| CAS_number_Ref = {{cascite|correct|??}}
⚫ | CAS_number = 129-20-4
⚫ | ATC_prefix = M01
⚫ | ATC_suffix = AA03
⚫ | ATC_supplemental = {{ATC|M02|AA04}} {{ATC|S01|BC02}}
⚫ | PubChem = 104811
⚫ | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
⚫ | DrugBank = DB03585
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | ChemSpiderID = 94610
⚫ | UNII_Ref = {{fdacite|correct|FDA}}
⚫ | UNII = A7D84513GV
⚫ | KEGG_Ref = {{keggcite|correct|kegg}}
⚫ | KEGG = D08324
⚫ | ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 76258
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1228
<!--Chemical data-->| C = 19
| H = 20
| N = 2
| O = 3
⚫ | smiles = O=C2N(c1ccc(O)cc1)N(C(=O)C2CCCC)c3ccccc3.O
⚫ | 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
⚫ | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
⚫ | StdInChIKey = CNDQSXOVEQXJOE-UHFFFAOYSA-N
⚫ }}


'''Oxyphenbutazone''' is a ] (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 ] of ].<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>
<!--Clinical data-->
| tradename =
⚫ | Drugs.com = {{drugs.com|international|oxyphenbutazone}}
⚫ | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
⚫ | pregnancy_US = <!-- A / B / C / D / X -->
| legal_AU = <!-- Unscheduled / S2 / S4 / S8 -->
⚫ | legal_UK = <!-- GSL / P / POM / CD -->
| legal_US = <!-- OTC / Rx-only -->


It was withdrawn from markets worldwide in mid-1980s due to bone marrow suppression and the risk of ].<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>
<!--Identifiers-->

| CASNo_Ref = {{cascite|correct|CAS}}
In '']'', the word "oxyphenbutazone" is the present highest scoring word resulting in 1,780 points based on the ] of 2006.<ref>{{cite web |last=Wood |first=Dave |name-list-style=vanc |date=22 May 2008 |title=Record for the Highest Scoring Scrabble Move |url=https://www.scrabulizer.com/blog/post/3#blog_post_break |url-status=live |archive-url=https://web.archive.org/web/20230511235136/https://www.scrabulizer.com/blog/post/3 |archive-date=11 May 2023 |work=Scrabulizer}}</ref>
⚫ | CAS_number_Ref = {{cascite|correct|??}}

⚫ | CAS_number = 129-20-4
== References ==
⚫ | ATC_prefix = M01
{{reflist}}
⚫ | ATC_suffix = AA03

⚫ | ATC_supplemental = {{ATC|M02|AA04}} {{ATC|S01|BC02}}
{{Anti-inflammatory and antirheumatic products}}
⚫ | PubChem = 104811
{{Topical products for joint and muscular pain}}
⚫ | DrugBank_Ref = {{drugbankcite|changed|drugbank}}

⚫ | DrugBank = DB03585
]
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
]
⚫ | ChemSpiderID = 94610
]
⚫ | UNII_Ref = {{fdacite|correct|FDA}}
]
⚫ | UNII = A7D84513GV

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

⚫ | KEGG = D08324
{{musculoskeletal-drug-stub}}
⚫ | ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = <!-- blanked - oldvalue: 1228 -->
| 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
| 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 = 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
⚫ | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
⚫ | StdInChIKey = CNDQSXOVEQXJOE-UHFFFAOYSA-N
⚫ }}