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  Y
PubChem CID	5362
ChemSpider	5169  N
UNII	86TDZ5WP2B
KEGG	D01289  Y
ChEMBL	ChEMBL1414320  N
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) N Key:ONWXNHPOAGOMTG-UHFFFAOYSA-N N
NY  (what is this?)    (verify)

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

1. 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.
2. 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.
3. 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.