Gemfibrozil 1-O-β-glucuronide

Modify Date: 2024-01-03 06:56:50

Gemfibrozil 1-O-β-glucuronide Structure
Gemfibrozil 1-O-β-glucuronide structure
Common Name Gemfibrozil 1-O-β-glucuronide
CAS Number 91683-38-4 Molecular Weight 426.45800
Density 1.32g/cm3 Boiling Point 611.2ºC at 760mmHg
Molecular Formula C21H30O9 Melting Point N/A
MSDS N/A Flash Point 208.4ºC

 Use of Gemfibrozil 1-O-β-glucuronide


Gemfibrozil 1-O-β-Glucuronide, a metabolite of Gemfibrozil (CI-719; HY-B0258), is a potent and competitive P450 (CYP) isoform CYP2C8 inhibitor with an IC50 of 4.07 μM[1][2].

 Names

Name gemfibrozil 1-o--glucuronide
Synonym More Synonyms

 Gemfibrozil 1-O-β-glucuronide Biological Activity

Description Gemfibrozil 1-O-β-Glucuronide, a metabolite of Gemfibrozil (CI-719; HY-B0258), is a potent and competitive P450 (CYP) isoform CYP2C8 inhibitor with an IC50 of 4.07 μM[1][2].
Related Catalog
Target

CYP2C8:4.07 μM (IC50)

In Vitro Gemfibrozil 1-O-β-Glucuronide significantly inhibits the OATP2 (OATP1B1)-mediated uptake of Cerivastatin (CER; HY-129458) with an IC50 of 24.3 μM[1]. Gemfibrozil 1-O-β-Glucuronide inhibits CYP2C8-mediated M1, M23 formation with IC50s of 5.38 μM, 4.30 μM, and has no effects for CYP2C8-mediated M3 formation[1]. Gemfibrozil 1-O-β-Glucuronide has an IC50 of 243 μM for the CYP3A4- mediated metabolism[1].
References

[1]. Shitara Y, et al. 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. J Pharmacol Exp Ther. 2004 Oct;311(1):228-36.

[2]. Baer BR, et al. Benzylic oxidation of gemfibrozil-1-O-beta-glucuronide by P450 2C8 leads to heme alkylation and irreversible inhibition. Chem Res Toxicol. 2009 Jul;22(7):1298-309.

 Chemical & Physical Properties

Density 1.32g/cm3
Boiling Point 611.2ºC at 760mmHg
Molecular Formula C21H30O9
Molecular Weight 426.45800
Flash Point 208.4ºC
Exact Mass 426.18900
PSA 142.75000
LogP 0.92400
Index of Refraction 1.572

 Synonyms

Gemfibrozilb-D-glucuronide
Gemfibrozil 1-O-b-Glucuronide
gemfibrozil 1-O-acylglucuronide
1-[5-(2,5-Dimethylphenoxy)-2,2-dimethylpentanoate] b-D-Glucopyranuroic Acid, Gemfibrozil Glucuronide
1-[5-(2,5-Dimethylphenoxy)-2,2-dimethylpentanoate]-D-Glucopyranuroic Acid