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.

Product information

CAS Number: 91683-38-4

Molecular Weight: 426.46

Formula: C21H30O9

Chemical Name: (2S,3S,4S,5R,6S)-6-{[5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

Smiles: CC1C=C(OCCCC(C)(C)C(=O)O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)C(C)=CC=1

InChiKey: CJMNXSKEVNPQOK-LVEJAMMSSA-N

InChi: InChI=1S/C21H30O9/c1-11-6-7-12(2)13(10-11)28-9-5-8-21(3,4)20(27)30-19-16(24)14(22)15(23)17(29-19)18(25)26/h6-7,10,14-17,19,22-24H,5,8-9H2,1-4H3,(H,25,26)/t14-,15-,16+,17-,19-/m0/s1

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: Soluble in DMSO

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

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. 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. Gemfibrozil 1-O-β-Glucuronide has an IC50 of 243 μM for the CYP3A4- mediated metabolism.

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.

Products are for research use only. Not for human use.