Chemistry:Suxibuzone
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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
- ↑ "Comparison of the absorption, excretion, and metabolism of suxibuzone and phenylbutazone in humans". Journal of Pharmaceutical Sciences 71 (5): 565–72. 1982. doi:10.1002/jps.2600710521. PMID 7097505. Bibcode: 1982JPhmS..71..565Y.
- ↑ "Multicentre, controlled, randomised and blinded field study comparing efficacy of suxibuzone and phenylbutazone in lame horses". Equine Veterinary Journal 41 (7): 700–5. 2009. 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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