suxibuzone
{{Short description|Analgesic drug used for joint and muscular pain}}
{{Use dmy dates|date=February 2022}}{{Use British English|date=February 2022}}
{{Infobox drug
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|Watchedfields = changed
|verifiedrevid = 408916457
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|image = Suxibuzone.png
|image_class = skin-invert-image
|alt = Two-dimensional monochrome diagram showing the structure of the molecule of Suxibuzone, uing the hexagonal style to depict a chemical compound.
|caption = Suxibuzone molecule
|tradename=
|Drugs.com= {{Drugs.com|international|suxibuzone}}
|IUPAC_name= 4-[ [4-butyl-3,5-dioxo-1,2-di(phenyl)pyrazolidin-4-yl]methoxy]-4-oxobutanoic acid
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|CAS_number_Ref= {{Cascite|correct|CAS}}
|CAS_number = 27470-51-5
|ATC_prefix= M02
|ATC_suffix= AA22
|ATC_supplemental= {{ATCvet|M01|AA90}}
|PubChem= 5362
|DrugBank_Ref= {{Drugbankcite|correct|drugbank}}
|DrugBank =
|UNII_Ref= {{Fdacite|correct|FDA}}
|UNII = 86TDZ5WP2B
|KEGG_Ref= {{Keggcite|correct|kegg}}
|KEGG = D01289
|ChEMBL_Ref= {{Ebicite|changed|EBI}}
|ChEMBL = 1414320
|ChemSpiderID_Ref= {{Chemspidercite|changed|chemspider}}
|ChemSpiderID = 5169
|smiles= O=C(O)CCC(=O)OCC2(C(=O)N(c1ccccc1)N(C2=O)c3ccccc3)CCCC
|StdInChI_Ref= {{Stdinchicite|changed|chemspider}}
|StdInChI= 1S/C24H26N2O6/c1-2-3-16-24(17-32-21(29)15-14-20(27)28)22(30)25(18-10-6-4-7-11-18)26(23(24)31)19-12-8-5-9-13-19/h4-13H,2-3,14-17H2,1H3,(H,27,28)
|StdInChIKey_Ref= {{Stdinchicite|changed|chemspider}}
|StdInChIKey = ONWXNHPOAGOMTG-UHFFFAOYSA-N
|C=24|H=26|N=2|O=6
}}
Suxibuzone is an analgesic used for joint and muscular pain. It is a prodrug of the non-steroidal anti-inflammatory drug (NSAID) phenylbutazone,{{Cite journal|vauthors=Yasuda Y, Shindo T, Mitani N, Ishida N, Oono F, Kageyama T|date=1982|title=Comparison of the absorption, excretion, and metabolism of suxibuzone and phenylbutazone in humans|journal=Journal of Pharmaceutical Sciences|volume=71|issue=5|pages=565–72|pmid=7097505|doi=10.1002/jps.2600710521}} and is commonly used in horses.{{Cite journal|vauthors=Sabaté D, Homedes J, Salichs M, Sust M, Monreal L|date=2009|title=Multicentre, controlled, randomised and blinded field study comparing efficacy of suxibuzone and phenylbutazone in lame horses|journal=Equine Veterinary Journal|volume=41|issue=7|pages=700–5|pmid=19927590|doi=10.2746/042516409X464807}}
Synthesis
Suxibuzone is synthesized by the following method:Esteve, J. et al, Quim. Ind. (Madrid), 1971,17, 107. Patent:Esteve Dr Antonio, DE1936747A1 (1970 to Laboratorios Del Dr. Esteve S.A., Barcelona (Spanien)). (Precursor:Dhareshwar, Sundeep S.; Stella, Valentino J. (2010). "A Novel Prodrug Strategy for β-Dicarbonyl Carbon Acids: Syntheses and Evaluation of the Physicochemical Characteristics of C-Phosphoryloxymethyl (POM) and Phosphoryloxymethyloxymethyl (POMOM) Prodrug Derivatives". Journal of Pharmaceutical Sciences. 99 (6): 2711–2723. doi:10.1002/jps.22021.)
Phenylbutazone [50-33-9] (1) is hydroxymethylated with formaldehyde giving ~86% 4-butyl-4-(hydroxymethyl)-1,2-diphenylpyrazolidine-3,5-dione [23111-33-3] (2). This is then esterified with succinic anhydride. [108-30-5] (3) to give (4).
References
{{Reflist}}
{{Anti-inflammatory products}}
{{Topical products for joint and muscular pain}}
{{Veterinary medicine}}
{{Authority control}}
Category:Nonsteroidal anti-inflammatory drugs
{{Musculoskeletal-drug-stub}}