Febuxostat acyl glucuronide | CAS# 1351692-92-6 | Metabolite

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

MedKoo CAT#: 574276

CAS#: 1351692-92-6

Description: Febuxostat acyl glucuronide is a metabolite of the xanthine oxidoreductase inhibitor febuxostat. Febuxostat acyl glucuronide is formed via glucuronidation of febuxostat by uridine diphosphate-glucuronosyltransferases (UGTs).

Chemical Structure

Febuxostat acyl glucuronide

CAS# 1351692-92-6

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 574276
Name: Febuxostat acyl glucuronide
CAS#: 1351692-92-6
Chemical Formula: C22H24N2O9S
Exact Mass: 492.12
Molecular Weight: 492.500
Elemental Analysis: C, 53.65; H, 4.91; N, 5.69; O, 29.24; S, 6.51

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 305
2mg	USD 585
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Febuxostat acyl glucuronide

IUPAC/Chemical Name: (2S,3S,4S,5R,6S)-6-((2-(3-cyano-4-isobutoxyphenyl)-4-methylthiazole-5-carbonyl)oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylic acid

InChi Key: ZRXRMGPMLDOOKN-FVMGUFKOSA-N

InChi Code: InChI=1S/C22H24N2O9S/c1-9(2)8-31-13-5-4-11(6-12(13)7-23)19-24-10(3)18(34-19)21(30)33-22-16(27)14(25)15(26)17(32-22)20(28)29/h4-6,9,14-17,22,25-27H,8H2,1-3H3,(H,28,29)/t14-,15-,16+,17-,22-/m0/s1

SMILES Code: CC(C)COC1=C(C#N)C=C(C2=NC(C)=C(C(O[C@@H]3O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]3O)=O)S2)C=C1

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: >3 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:	A metabolite of febuxostat.
In vitro activity:	The gene expression level of iNOS was significantly increased by stimulation with IL-18 but greatly suppressed by the introduction of Febuxostat (Figure 4A). The increased release of NO induced by stimulation with IL-18 was significantly inhibited in the presence of Febuxostat (Figure 4B). Reference: Am J Transl Res. 2021; 13(3): 979–987. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8014396/
In vivo activity:	The gingival expression of TNF-α, IL-1β, 4-HNE, and 8-OHdG was up-regulated in rats with periodontitis. Febuxostat significantly reduced alveolar bone loss, proinflammatory cytokine levels, and oxidative stress. Reference: Pharmacology. 2021;106(5-6):294-304. https://pubmed.ncbi.nlm.nih.gov/33735887/

Preparing Stock Solutions

The following data is based on the product molecular weight 492.50 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.

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:	1. Geng Q, Zhang H, Cui Y, Wei Q, Wang S. Febuxostat mitigates IL-18-induced inflammatory response and reduction of extracellular matrix gene. Am J Transl Res. 2021 Mar 15;13(3):979-987. PMID: 33841634; PMCID: PMC8014396. 2. Hao J, Zhang W, Tong R, Huang Z. Febuxostat Prevents the Cytotoxicity of Propofol in Brain Endothelial Cells. ACS Omega. 2021 Feb 15;6(8):5471-5478. doi: 10.1021/acsomega.0c05708. PMID: 33681587; PMCID: PMC7931401. 3. Tsukamoto T, Tsujii M, Odake K, Iino T, Nakamura T, Matsumine A, Sudo A. Febuxostat reduces muscle wasting in tumor-bearing mice with LM8 osteosarcoma cells via inhibition of reactive oxygen species generation. Free Radic Res. 2021 Jul 19:1-11. doi: 10.1080/10715762.2021.1947502. Epub ahead of print. PMID: 34278932. 4. Nessa N, Kobara M, Toba H, Adachi T, Yamamoto T, Kanamura N, Pezzotti G, Nakata T. Febuxostat Attenuates the Progression of Periodontitis in Rats. Pharmacology. 2021;106(5-6):294-304. doi: 10.1159/000513034. Epub 2021 Mar 18. PMID: 33735887.
In vitro protocol:	1. Geng Q, Zhang H, Cui Y, Wei Q, Wang S. Febuxostat mitigates IL-18-induced inflammatory response and reduction of extracellular matrix gene. Am J Transl Res. 2021 Mar 15;13(3):979-987. PMID: 33841634; PMCID: PMC8014396. 2. Hao J, Zhang W, Tong R, Huang Z. Febuxostat Prevents the Cytotoxicity of Propofol in Brain Endothelial Cells. ACS Omega. 2021 Feb 15;6(8):5471-5478. doi: 10.1021/acsomega.0c05708. PMID: 33681587; PMCID: PMC7931401.
In vivo protocol:	1. Tsukamoto T, Tsujii M, Odake K, Iino T, Nakamura T, Matsumine A, Sudo A. Febuxostat reduces muscle wasting in tumor-bearing mice with LM8 osteosarcoma cells via inhibition of reactive oxygen species generation. Free Radic Res. 2021 Jul 19:1-11. doi: 10.1080/10715762.2021.1947502. Epub ahead of print. PMID: 34278932. 2. Nessa N, Kobara M, Toba H, Adachi T, Yamamoto T, Kanamura N, Pezzotti G, Nakata T. Febuxostat Attenuates the Progression of Periodontitis in Rats. Pharmacology. 2021;106(5-6):294-304. doi: 10.1159/000513034. Epub 2021 Mar 18. PMID: 33735887.

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1. Grabowski, B.A., Khosravan, R., Vernillet, L., et al. Metabolism and excretion of [14C] febuxostat, a novel nonpurine selective inhibitor of xanthine oxidase, in healthy male subjects. J. Clin. Pharmacol. 51(2), 189-201 (2011).

2. Kamel, B., Graham, G.G., Williams, K.M., et al. Clinical pharmacokinetics and pharmacodynamics of febuxostat. Clin. Pharmacokinet. 56(5), 459-475 (2017).

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