Molecular structure of Gemfibrozil 1-O-β-Glucuronide, CAS Number: 91683-38-4
Gemfibrozil 1-O-β-Glucuronide (CAS 91683-38-4)
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Alternate Names:
Gemfibrozil 1-O-β-Glucuronide also known as 1-O-Gemfibrozil-beta-D-glucuronide; 1-[5-(2,5-Dimethylphenoxy)-2,2-dimethylpentanoate] β-D-Glucopyranuroic Acid; Gemfibrozil Glucuronide
Application:
Gemfibrozil 1-O-β-Glucuronide is an irreversible inhibitor of P450 2C8 and a major metabolite of gemfibrozil
CAS Number:
91683-38-4
Molecular Weight:
426.46
Molecular Formula:
C21H30O9
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.
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SDS & Certificate of Analysis
Gemfibrozil 1-O-β-Glucuronide is an active metabolite formed through the biotransformation of gemfibrozil by the action of glucuronosyltransferase enzymes. In biochemical research, this compound is used to study the chemical kinetics and metabolism of gemfibrozil, as well as the role of glucuronidation in drug clearance. It serves as a key reference substance for the development and validation of analytical methods such as liquid chromatography coupled with mass spectrometry (LC-MS), which are employed to monitor the levels of gemfibrozil and its metabolites in biological samples. Research involving Gemfibrozil 1-O-β-Glucuronide contributes to a broader understanding of the metabolism of lipid-regulating agents and the factors that influence their biotransformation. The compound is also used in in vitro studies to examine the interactions between metabolites and transport proteins, such as those involved in renal and hepatic excretion.
Gemfibrozil 1-O-β-Glucuronide (CAS 91683-38-4) References
- Gemfibrozil and its glucuronide inhibit the organic anion transporting polypeptide 2 (OATP2/OATP1B1:SLC21A6)-mediated hepatic uptake and CYP2C8-mediated metabolism of cerivastatin: analysis of the mechanism of the clinically relevant drug-drug interaction between cerivastatin and gemfibrozil. | Shitara, Y., et al. 2004. J Pharmacol Exp Ther. 311: 228-36. PMID: 15194707
- Atorvastatin glucuronidation is minimally and nonselectively inhibited by the fibrates gemfibrozil, fenofibrate, and fenofibric acid. | Goosen, TC., et al. 2007. Drug Metab Dispos. 35: 1315-24. PMID: 17470524
- Benzylic oxidation of gemfibrozil-1-O-beta-glucuronide by P450 2C8 leads to heme alkylation and irreversible inhibition. | Baer, BR., et al. 2009. Chem Res Toxicol. 22: 1298-309. PMID: 19445523
- Gemfibrozil markedly increases the plasma concentrations of montelukast: a previously unrecognized role for CYP2C8 in the metabolism of montelukast. | Karonen, T., et al. 2010. Clin Pharmacol Ther. 88: 223-30. PMID: 20592724
- Evaluation of CYP2C8 inhibition in vitro: utility of montelukast as a selective CYP2C8 probe substrate. | VandenBrink, BM., et al. 2011. Drug Metab Dispos. 39: 1546-54. PMID: 21697463
- Gemfibrozil is a strong inactivator of CYP2C8 in very small multiple doses. | Honkalammi, J., et al. 2012. Clin Pharmacol Ther. 91: 846-55. PMID: 22472994
- Mechanistic modeling to predict the transporter- and enzyme-mediated drug-drug interactions of repaglinide. | Varma, MV., et al. 2013. Pharm Res. 30: 1188-99. PMID: 23307347
- 2D QSAR Study for Gemfibrozil Glucuronide as the Mechanism-based Inhibitor of CYP2C8. | Taxak, N. and Bharatam, PV. 2013. Indian J Pharm Sci. 75: 680-7. PMID: 24591743
- Quantitative Rationalization of Gemfibrozil Drug Interactions: Consideration of Transporters-Enzyme Interplay and the Role of Circulating Metabolite Gemfibrozil 1-O-β-Glucuronide. | Varma, MV., et al. 2015. Drug Metab Dispos. 43: 1108-18. PMID: 25941268
- Hepatic Disposition of Gemfibrozil and Its Major Metabolite Gemfibrozil 1-O-β-Glucuronide. | Kimoto, E., et al. 2015. Mol Pharm. 12: 3943-52. PMID: 26378985
- Alteration of the intravenous and oral pharmacokinetics of valsartan via the concurrent use of gemfibrozil in rats. | Yang, SJ., et al. 2016. Biopharm Drug Dispos. 37: 245-51. PMID: 26663350
- Role of gemfibrozil as an inhibitor of CYP2C8 and membrane transporters. | Tornio, A., et al. 2017. Expert Opin Drug Metab Toxicol. 13: 83-95. PMID: 27548563
- Utilizing PBPK Modeling to Evaluate the Potential of a Significant Drug-Drug Interaction Between Clopidogrel and Dasabuvir: A Scientific Perspective. | Arya, V., et al. 2017. Clin Pharmacol Ther. 102: 578-580. PMID: 28444890
- Crystalline Sponges as a Sensitive and Fast Method for Metabolite Identification: Application to Gemfibrozil and its Phase I and II Metabolites. | Rosenberger, L., et al. 2020. Drug Metab Dispos. 48: 587-593. PMID: 32434832
- An automated cocktail method for in vitro assessment of direct and time-dependent inhibition of nine major cytochrome P450 enzymes - application to establishing CYP2C8 inhibitor selectivity. | Kahma, H., et al. 2021. Eur J Pharm Sci. 162: 105810. PMID: 33753217
Inhibitor of:
CYP2C8.Ordering Information
| Product Name | Catalog # | UNIT | Price | Qty | FAVORITES | |
Gemfibrozil 1-O-β-Glucuronide, 500 µg | sc-221665C | 500 µg | $326.00 | |||
Gemfibrozil 1-O-β-Glucuronide, 1 mg | sc-221665 | 1 mg | $500.00 | |||
Gemfibrozil 1-O-β-Glucuronide, 1 mg | sc-221665-CW | 1 mg | $653.00 | |||
Gemfibrozil 1-O-β-Glucuronide, 2 mg | sc-221665A | 2 mg | $842.00 | |||
Gemfibrozil 1-O-β-Glucuronide, 5 mg | sc-221665B | 5 mg | $1581.00 | |||
Gemfibrozil 1-O-β-Glucuronide, 5 mg | sc-221665B-CW | 5 mg | $1734.00 | |||
Gemfibrozil 1-O-β-Glucuronide, 10 mg | sc-221665D | 10 mg | $2856.00 | |||
Gemfibrozil 1-O-β-Glucuronide, 25 mg | sc-221665E | 25 mg | $6050.00 |