Suxibuzone

Suxibuzone
	Suxibuzone molecule
Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	M02AA22 (WHO) QM01AA90 (WHO);
Identifiers
	IUPAC name 4-[ [4-butyl-3,5-dioxo-1,2-di(phenyl)pyrazolidin-4-yl]methoxy]-4-oxobutanoic acid;
CAS Number	27470-51-5 ;
PubChem CID	5362;
ChemSpider	5169 ;
UNII	86TDZ5WP2B;
KEGG	D01289 ;
ChEMBL	ChEMBL1414320 ;
CompTox Dashboard (EPA)	DTXSID6021296 ;
ECHA InfoCard	100.044.056
Chemical and physical data
Formula	C24H26N2O6
Molar mass	438.480 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(O)CCC(=O)OCC2(C(=O)N(c1ccccc1)N(C2=O)c3ccccc3)CCCC;
	InChI InChI=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) ; Key:ONWXNHPOAGOMTG-UHFFFAOYSA-N ;
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Suxibuzone is an analgesic used for joint and muscular pain. It is a prodrug of the non-steroidal anti-inflammatory drug (NSAID) phenylbutazone,^[1] and is commonly used in horses.^[2]

Synthesis

Suxibuzone is synthesized by the following method:^[3] Patent:^[4] (Precursor:^[5])

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

^ Yasuda Y, Shindo T, Mitani N, Ishida N, Oono F, Kageyama T (1982). "Comparison of the absorption, excretion, and metabolism of suxibuzone and phenylbutazone in humans". Journal of Pharmaceutical Sciences. 71 (5): 565–72. doi:10.1002/jps.2600710521. PMID 7097505.
^ Sabaté D, Homedes J, Salichs M, Sust M, Monreal L (2009). "Multicentre, controlled, randomised and blinded field study comparing efficacy of suxibuzone and phenylbutazone in lame horses". Equine Veterinary Journal. 41 (7): 700–5. doi:10.2746/042516409X464807. PMID 19927590.
^ Esteve, J. et al, Quim. Ind. (Madrid), 1971,17, 107.
^ Esteve Dr Antonio, DE1936747A1 (1970 to Laboratorios Del Dr. Esteve S.A., Barcelona (Spanien)).
^ 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.

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[pmid7097505-1] Yasuda Y, Shindo T, Mitani N, Ishida N, Oono F, Kageyama T (1982). "Comparison of the absorption, excretion, and metabolism of suxibuzone and phenylbutazone in humans". Journal of Pharmaceutical Sciences. 71 (5): 565–72. doi:10.1002/jps.2600710521. PMID 7097505.

[pmid19927590-2] Sabaté D, Homedes J, Salichs M, Sust M, Monreal L (2009). "Multicentre, controlled, randomised and blinded field study comparing efficacy of suxibuzone and phenylbutazone in lame horses". Equine Veterinary Journal. 41 (7): 700–5. doi:10.2746/042516409X464807. PMID 19927590.

[3] Esteve, J. et al, Quim. Ind. (Madrid), 1971,17, 107.

[4] Esteve Dr Antonio, DE1936747A1 (1970 to Laboratorios Del Dr. Esteve S.A., Barcelona (Spanien)).

[5] 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.

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