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Suxibuzone

From Wikipedia, the free encyclopedia
Analgesic drug used for joint and muscular pain

Pharmaceutical compound
Suxibuzone
Two-dimensional monochrome diagram showing the structure of the molecule of Suxibuzone, uing the hexagonal style to depict a chemical compound.
Suxibuzone molecule
Clinical data
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
  • 4-[ [4-butyl-3,5-dioxo-1,2-di(phenyl)pyrazolidin-4-yl]methoxy]-4-oxobutanoic acid
CAS Number
PubChemCID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.044.056Edit this at Wikidata
Chemical and physical data
FormulaC24H26N2O6
Molar mass438.480 g·mol−1
3D model (JSmol)
  • O=C(O)CCC(=O)OCC2(C(=O)N(c1ccccc1)N(C2=O)c3ccccc3)CCCC
  • 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
 ☒NcheckY (what is this?)  (verify)

Suxibuzone is ananalgesic used for joint and muscularpain. It is aprodrug of thenon-steroidal anti-inflammatory drug (NSAID)phenylbutazone,[1] and is commonly used in horses.[2]

Synthesis

[edit]

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

[edit]
  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.
pyrazolones /
pyrazolidines
salicylates
acetic acid derivatives
and related substances
oxicams
propionic acid
derivatives (profens)
n-arylanthranilic
acids (fenamates)
COX-2 inhibitors
(coxibs)
other
NSAID
combinations
Key:underline indicates initially developed first-in-class compound of specific group;#WHO-Essential Medicines;†withdrawn drugs;‡veterinary use.
Topical products forjoint andmuscular pain (M02)
Anti-inflammatory
preparations,
non-steroids
Pyrazolidines
Acetic acid
derivatives
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Capsaicin derivatives
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