Suxibuzone
Suxibuzone molecule | |
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| ECHA InfoCard | 100.044.056 |
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| Formula | C24H26N2O6 |
| Molar mass | 438.480 g·mol−1 |
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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]
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 (May 1982). "Comparison of the absorption, excretion, and metabolism of suxibuzone and phenylbutazone in humans". Journal of Pharmaceutical Sciences. 71 (5): 565–572. Bibcode:1982JPhmS..71..565Y. doi:10.1002/jps.2600710521. PMID 7097505.
- ^ Sabaté D, Homedes J, Salichs M, Sust M, Monreal L (September 2009). "Multicentre, controlled, randomised and blinded field study comparing efficacy of suxibuzone and phenylbutazone in lame horses". Equine Veterinary Journal. 41 (7): 700–705. doi:10.2746/042516409X464807. PMID 19927590.
- ^ Esteve J, Parés J, Roser R, Rodriguez L (1971). "Synthesis and characterization of suxibuzone. Blood levels in man after oral and rectal administration". Quimica e Industria. 17. Madrid: 107.