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91683-38-4,MFCD00870898
Catalog No.:AA006R6I

91683-38-4 | (2S,3S,4S,5R,6S)-6-((5-(2,5-Dimethylphenoxy)-2,2-dimethylpentanoyl)oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylic acid

Pack Size
Purity
Availability
Price(USD)
Quantity
  
1mg
95%
in stock  
$443.00   $310.00
- +
5mg
95%
in stock  
$1,458.00   $1,021.00
- +
10mg
95%
in stock  
$2,231.00   $1,562.00
- +
  • Technical Information
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  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA006R6I
Chemical Name:
(2S,3S,4S,5R,6S)-6-((5-(2,5-Dimethylphenoxy)-2,2-dimethylpentanoyl)oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylic acid
CAS Number:
91683-38-4
Molecular Formula:
C21H29O4
Molecular Weight:
345.4526
MDL Number:
MFCD00870898
SMILES:
C[C@@H]1[CH][CH][CH][C@@H](O1)OC(=O)C(CCCOc1cc(C)ccc1C)(C)C
Properties
Properties
 
Storage:
-20 ℃;Inert atmosphere;  

Computed Properties
 
Complexity:
593  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
5  
Heavy Atom Count:
30  
Hydrogen Bond Acceptor Count:
9  
Hydrogen Bond Donor Count:
4  
Rotatable Bond Count:
9  
XLogP3:
2.2  

Literature

Title: Mechanism-based inactivation (MBI) of cytochrome P450 enzymes: structure-activity relationships and discovery strategies to mitigate drug-drug interaction risks.

Journal: Journal of medicinal chemistry 20120614

Title: Mechanism-based inactivation of CYP2C8 by gemfibrozil occurs rapidly in humans.

Journal: Clinical pharmacology and therapeutics 20110401

Title: The CYP2C8 inhibitor gemfibrozil does not affect the pharmacokinetics of zafirlukast.

Journal: European journal of clinical pharmacology 20110201

Title: CYP2C8 activity recovers within 96 hours after gemfibrozil dosing: estimation of CYP2C8 half-life using repaglinide as an in vivo probe.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20091201

Title: Construction of triple-transfected cells [organic anion-transporting polypeptide (OATP) 1B1/multidrug resistance-associated protein (MRP) 2/MRP3 and OATP1B1/MRP2/MRP4] for analysis of the sinusoidal function of MRP3 and MRP4.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20091001

Title: Benzylic oxidation of gemfibrozil-1-O-beta-glucuronide by P450 2C8 leads to heme alkylation and irreversible inhibition.

Journal: Chemical research in toxicology 20090701

Title: The effect of gemfibrozil on repaglinide pharmacokinetics persists for at least 12 h after the dose: evidence for mechanism-based inhibition of CYP2C8 in vivo.

Journal: Clinical pharmacology and therapeutics 20080901

Title: Glucuronidation converts gemfibrozil to a potent, metabolism-dependent inhibitor of CYP2C8: implications for drug-drug interactions.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20060101

Title: The effects of the phytoestrogenic isoflavone genistein on the hepatic disposition of preformed and hepatically generated gemfibrozil 1-O-acyl glucuronide in the isolated perfused rat liver.

Journal: The Journal of pharmacy and pharmacology 20031001

Title: Self-micellization of gemfibrozil 1-O-beta acyl glucuronide in aqueous solution.

Journal: Pharmaceutical research 20030301

Title: 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.

Title: 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.

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Tags:91683-38-4 Molecular Formula|91683-38-4 MDL|91683-38-4 SMILES|91683-38-4 (2S,3S,4S,5R,6S)-6-((5-(2,5-Dimethylphenoxy)-2,2-dimethylpentanoyl)oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylic acid