Suxibuzone - Wikipedia

Suxibuzone
Clinical data
Suxibuzone molecule
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

[edit]

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

[edit]

^ 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.

v t e Non-steroidal anti-inflammatory drugs (NSAIDs) (primarily M01A and M02A, also N02BA)
pyrazolones / pyrazolidines	Aminophenazone Ampyrone Azapropazone Clofezone Difenamizole Famprofazone Feprazone Kebuzone Metamizole Mofebutazone Morazone Nifenazone Oxyphenbutazone Phenazone Phenylbutazone Propyphenazone Sulfinpyrazone Suxibuzone^‡
salicylates	Aspirin (acetylsalicylic acid)^# Aloxiprin Benorylate Carbasalate calcium Diflunisal Dipyrocetyl Ethenzamide Guacetisal Magnesium salicylate Methyl salicylate Salsalate Salicin Salicylamide Salicylic acid (salicylate) Sodium salicylate
acetic acid derivatives and related substances	Aceclofenac Acemetacin Alclofenac Amfenac Bendazac Bromfenac Bufexamac Bumadizone Diclofenac Difenpiramide Etodolac Felbinac Fenclozic acid Fentiazac Indometacin Indometacin farnesil Isoxepac Ketorolac Lonazolac Mofezolac Oxametacin Prodolic acid Proglumetacin Sulindac Tiopinac Tolmetin Zomepirac^†
oxicams	Ampiroxicam Droxicam Isoxicam Lornoxicam Meloxicam Piroxicam Pivoxicam Tenoxicam
propionic acid derivatives (profens)	Alminoprofen Benoxaprofen^† Carprofen^‡ Dexibuprofen Dexketoprofen Fenbufen Fenoprofen Flunoxaprofen Flurbiprofen Ibuprofen^# Ibuproxam Indoprofen^† Ketoprofen Loxoprofen Miroprofen Naproxen Oxaprozin Pelubiprofen Piketoprofen Pirprofen Suprofen Tarenflurbil Tepoxalin^‡ Tiaprofenic acid Vedaprofen^‡ Zaltoprofen COX-inhibiting nitric oxide donator: Naproxcinod
n-arylanthranilic acids (fenamates)	Azapropazone Clonixin Etofenamate Floctafenine Flufenamic acid Flunixin Flutiazin Glafenine^† Meclofenamic acid Mefenamic acid Morniflumate Niflumic acid Tolfenamic acid
COX-2 inhibitors (coxibs)	Apricoxib Celecoxib (+tramadol) Cimicoxib^‡ Deracoxib^‡ Etoricoxib Firocoxib^‡ Lumiracoxib^† Mavacoxib^‡ Parecoxib Robenacoxib^‡ Rofecoxib^† Valdecoxib^†
other	Aminopropionitrile Benzydamine Chondroitin sulfate Diacerein Fluproquazone Glucosamine Glycosaminoglycan Hyperforin Nabumetone Nimesulide Oxaceprol Proquazone Superoxide dismutase / orgotein Tenidap
NSAID combinations	Ibuprofen/famotidine Ibuprofen/hydrocodone Ibuprofen/oxycodone Ibuprofen/paracetamol Meloxicam/bupivacaine Naproxen/diphenhydramine Naproxen/esomeprazole
Key: underline indicates initially developed first-in-class compound of specific group; ^#WHO-Essential Medicines; ^†withdrawn drugs; ^‡veterinary use.
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Topical products for joint and muscular pain (M02)

Anti-inflammatory
preparations,
non-steroids

Pyrazolidines	Clofezone Mofebutazone Oxyphenbutazone Phenylbutazone
Acetic acid derivatives	Diclofenac Fentiazac Tolmetin
Other	Bendazac Benzydamine Bufexamac Etofenamate Felbinac Feprazone Flurbiprofen Ibuprofen Indometacin Ketoprofen Meclofenamic acid Naproxen Nifenazone Niflumic acid Piketoprofen Piroxicam Suxibuzone

Capsaicin derivatives

Zucapsaicin

Other

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