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MedKoo Cat#: 326874 | Name: Suxibuzone
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Suxibuzone, also known as AE-17 is a analgesic used for joint and muscular pain. It is a prodrug of the non-steroidal anti-inflammatory drug phenylbutazone, and is commonly used in horses.

Chemical Structure

Suxibuzone
Suxibuzone
CAS#27470-51-5

Theoretical Analysis

MedKoo Cat#: 326874

Name: Suxibuzone

CAS#: 27470-51-5

Chemical Formula: C24H26N2O6

Exact Mass: 438.1791

Molecular Weight: 438.48

Elemental Analysis: C, 65.74; H, 5.98; N, 6.39; O, 21.89

Price and Availability

Size Price Availability Quantity
100mg USD 350.00
500mg USD 700.00
5g USD 4,500.00
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Related CAS #
No Data
Synonym
AE-17; AE17; AE 17; Suxibuzone; Flamilon; Flogos; Solurol.
IUPAC/Chemical Name
4-((4-butyl-3,5-dioxo-1,2-diphenylpyrazolidin-4-yl)methoxy)-4-oxobutanoic acid
InChi Key
ONWXNHPOAGOMTG-UHFFFAOYSA-N
InChi Code
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)
SMILES Code
O=C(OCC1(CCCC)C(N(C2=CC=CC=C2)N(C3=CC=CC=C3)C1=O)=O)CCC(O)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
The biological target of suxibuzone is primarily the inhibition of cyclooxygenase (COX) enzymes. Specifically, suxibuzone inhibits COX-1 and COX-2 enzymes, which are responsible for the production of prostaglandins from arachidonic acid. By inhibiting these enzymes, suxibuzone exerts its anti-inflammatory, analgesic, and antipyretic effects, similar to other non-steroidal anti-inflammatory drugs (NSAIDs) like aspirin and ibuprofen.
In vitro activity:
In an in vitro study, a high-performance liquid chromatographic method was developed to simultaneously detect suxibuzone and its metabolites, including 4-hydroxymethylphenylbutazone, phenylbutazone, oxyphenbutazone, and gamma-hydroxyphenylbutazone, in plasma and urine. The method involved extraction of acidified plasma or urine with benzenecyclohexane, followed by drying and redissolving the residue in methanol. Chromatography on a reversed-phase column with a methanol-0.5 M KH2PO4 gradient (0 to 100% methanol over 8% min) was used, with detection limits of 0.10 microgram/ml for suxibuzone and 4-hydroxymethylphenylbutazone, and 0.05 microgram/ml for the other metabolites, using a UV absorbance detector at 254 nm. Reference: Marunaka T, Shibata T, Minami Y, Umeno Y, Shindo T. Simultaneous high-performance liquid chromatographic determination of suxibuzone and its metabolites in plasma and urine. J Pharm Sci. 1980 Nov;69(11):1258-61.
In vivo activity:
Suxibuzone (SXB), an anti-inflammatory drug, was studied using a high performance liquid chromatographic method to analyze its major metabolites, phenylbutazone (PBZ) and oxyphenbutazone (OPBZ), in equine plasma and urine. Intravenous (i.v.) or oral (p.o.) administration of SXB at 6 mg/kg did not detect the parent drug in plasma or urine, suggesting rapid metabolism or elimination. After oral administration, PBZ and OPBZ were detected in plasma and urine, with peak PBZ concentrations occurring at 6 hours post-dosing and detectable levels in urine for at least 36 hours. The study discourages i.v. use of SXB in horses due to severe side effects and highlights the significant first-pass effect in equines, where SXB is rapidly hydrolyzed by liver enzymes. Reference: Delbeke FT, Vynckier L, Debackere M. The disposition of suxibuzone in the horse. J Vet Pharmacol Ther. 1993 Sep;16(3):283-90.

Preparing Stock Solutions

The following data is based on the product molecular weight 438.48 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
Delbeke FT, Vynckier L, Debackere M. The disposition of suxibuzone in the horse. J Vet Pharmacol Ther. 1993 Sep;16(3):283-90. doi: 10.1111/j.1365-2885.1993.tb00175.x. PMID: 8230399. Jaraiz MV, Rodriguez C, San Andres MD, Gonzalez F, San Andres MI. Disposition and tolerance of suxibuzone in horses. Equine Vet J. 1999 Sep;31(5):411-6. doi: 10.1111/j.2042-3306.1999.tb03841.x. PMID: 10505957. Marunaka T, Shibata T, Minami Y, Umeno Y, Shindo T. Simultaneous high-performance liquid chromatographic determination of suxibuzone and its metabolites in plasma and urine. J Pharm Sci. 1980 Nov;69(11):1258-61. doi: 10.1002/jps.2600691106. PMID: 7452452. Caturla MC, Cusido E. Solid-phase extraction for the high-performance liquid chromatographic determination of indomethacin, suxibuzone, phenylbutazone and oxyphenbutazone in plasma, avoiding degradation of compounds. J Chromatogr. 1992 Oct 2;581(1):101-7. doi: 10.1016/0378-4347(92)80452-v. PMID: 1429991.
In vitro protocol:
Marunaka T, Shibata T, Minami Y, Umeno Y, Shindo T. Simultaneous high-performance liquid chromatographic determination of suxibuzone and its metabolites in plasma and urine. J Pharm Sci. 1980 Nov;69(11):1258-61. doi: 10.1002/jps.2600691106. PMID: 7452452. Caturla MC, Cusido E. Solid-phase extraction for the high-performance liquid chromatographic determination of indomethacin, suxibuzone, phenylbutazone and oxyphenbutazone in plasma, avoiding degradation of compounds. J Chromatogr. 1992 Oct 2;581(1):101-7. doi: 10.1016/0378-4347(92)80452-v. PMID: 1429991.
In vivo protocol:
Delbeke FT, Vynckier L, Debackere M. The disposition of suxibuzone in the horse. J Vet Pharmacol Ther. 1993 Sep;16(3):283-90. doi: 10.1111/j.1365-2885.1993.tb00175.x. PMID: 8230399. Jaraiz MV, Rodriguez C, San Andres MD, Gonzalez F, San Andres MI. Disposition and tolerance of suxibuzone in horses. Equine Vet J. 1999 Sep;31(5):411-6. doi: 10.1111/j.2042-3306.1999.tb03841.x. PMID: 10505957.
1: Emmerich IU. Neue Arzneimittel für Großtiere 2022 [New drugs for horses and food-producing animals in 2022]. Tierarztl Prax Ausg G Grosstiere Nutztiere. 2023 Apr;51(2):93-96. German. doi: 10.1055/a-2062-7397. Epub 2023 May 25. PMID: 37230144. 2: Emmerich IU. Neue Arzneimittel für Pferde und landwirtschaftliche Nutztiere 2012 [New drugs for horses and production animals in 2012]. Tierarztl Prax Ausg G Grosstiere Nutztiere. 2013;41(4):247-52. German. PMID: 23959620. 3: Andrews FM, Reinemeyer CR, Longhofer SL. Effects of top-dress formulations of suxibuzone and phenylbutazone on development of gastric ulcers in horses. Vet Ther. 2009 Fall;10(3):113-20. PMID: 20037965. 4: Armengou L, Añor S, Climent F, Shelton GD, Monreal L. Antemortem diagnosis of a distal axonopathy causing severe stringhalt in a horse. J Vet Intern Med. 2010 Jan-Feb;24(1):220-3. doi: 10.1111/j.1939-1676.2009.0437.x. PMID: 20002548. 5: Sabaté D, Homedes J, Salichs M, Sust M, Monreal L. Multicentre, controlled, randomised and blinded field study comparing efficacy of suxibuzone and phenylbutazone in lame horses. Equine Vet J. 2009 Sep;41(7):700-5. doi: 10.2746/042516409x464807. PMID: 19927590. 6: Dowling G, Gallo P, Malone E, Regan L. Rapid confirmatory analysis of non- steroidal anti-inflammatory drugs in bovine milk by rapid resolution liquid chromatography tandem mass spectrometry. J Chromatogr A. 2009 Nov 13;1216(46):8117-31. doi: 10.1016/j.chroma.2009.05.004. Epub 2009 May 13. PMID: 19501363. 7: Longhofer SL, Reinemeyer CR, Radecki SV. Evaluation of the palatability of three nonsteroidal antiinflammatory top-dress formulations in horses. Vet Ther. 2008 Summer;9(2):122-7. PMID: 18597250. 8: Monreal L, Sabaté D, Segura D, Mayós I, Homedes J. Lower gastric ulcerogenic effect of suxibuzone compared to phenylbutazone when administered orally to horses. Res Vet Sci. 2004 Apr;76(2):145-9. doi: 10.1016/j.rvsc.2003.10.004. PMID: 14672858. 9: Maurer HH, Tauvel FX, Kraemer T. Screening procedure for detection of non- steroidal anti-inflammatory drugs and their metabolites in urine as part of a systematic toxicological analysis procedure for acidic drugs and poisons by gas chromatography-mass spectrometry after extractive methylation. J Anal Toxicol. 2001 May-Jun;25(4):237-44. doi: 10.1093/jat/25.4.237. PMID: 11386636. 10: Jaraiz MV, Rodriguez C, San Andres MD, Gonzalez F, San Andres MI. Disposition and tolerance of suxibuzone in horses. Equine Vet J. 1999 Sep;31(5):411-6. doi: 10.1111/j.2042-3306.1999.tb03841.x. PMID: 10505957. 11: Jaraiz V, Rodriguez C, San Andres MD, Gonzalez F, San Andres MI. Pharmacokinetics and bioequivalence of two suxibuzone oral dosage forms in horses. J Vet Pharmacol Ther. 1999 Aug;22(4):247-54. doi: 10.1046/j.1365-2885.1999.00219.x. PMID: 10499236. 12: Delbeke FT, Vynckier L, Debackere M. The disposition of suxibuzone in the horse. J Vet Pharmacol Ther. 1993 Sep;16(3):283-90. doi: 10.1111/j.1365-2885.1993.tb00175.x. PMID: 8230399. 13: Caturla MC, Cusido E. Solid-phase extraction for the high-performance liquid chromatographic determination of indomethacin, suxibuzone, phenylbutazone and oxyphenbutazone in plasma, avoiding degradation of compounds. J Chromatogr. 1992 Oct 2;581(1):101-7. doi: 10.1016/0378-4347(92)80452-v. PMID: 1429991. 14: Delbeke FT, Debackere M, Vynckier L. Disposition of human drug preparations in the horse. I. Rectally administered indomethacin. J Vet Pharmacol Ther. 1991 Jun;14(2):145-9. doi: 10.1111/j.1365-2885.1991.tb00816.x. PMID: 1920602. 15: Yanagi S, Sakamoto M, Takahashi S, Tsutsumi M, Konishi Y, Shibata K, Kamiya T. Promotion of hepatocarcinogenesis by suxibuzone in rats initiated with 3'-methyl-4-dimethylaminoazobenzene. Cancer Lett. 1987 Jul;36(1):11-8. doi: 10.1016/0304-3835(87)90097-8. PMID: 3107799. 16: Mizushima Y. Pro-drugs of non-steroidal anti-inflammatory agents. Eur J Rheumatol Inflamm. 1983;6(2):141-2. PMID: 6370701. 17: Mizushima Y, Shiokawa Y, Honma M, Kageyama T. A double-blind comparison of phenylbutazone and suxibuzone, a prodrug of phenylbutazone, in rheumatoid arthritis. Int J Tissue React. 1983;5(1):35-9. PMID: 6345427. 18: Yasuda Y, Shindo T, Mitani N, Ishida N, Oono F, Kageyama T. Comparison of the absorption, excretion, and metabolism of suxibuzone and phenylbutazone in humans. J Pharm Sci. 1982 May;71(5):565-72. doi: 10.1002/jps.2600710521. PMID: 7097505. 19: Mizushima Y. Basic and clinical studies of prodrugs of nonsteroidal anti- inflammatory drugs. Pharmacology. 1982;25 Suppl 1:39-45. doi: 10.1159/000137776. PMID: 7111381. 20: Marunaka T, Shibata T, Minami Y, Umeno Y, Shindo T. Simultaneous high- performance liquid chromatographic determination of suxibuzone and its metabolites in plasma and urine. J Pharm Sci. 1980 Nov;69(11):1258-61. doi: 10.1002/jps.2600691106. PMID: 7452452.

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