CAS 190448-57-8

Ezetimibe glucuronide

Description:

Ezetimibe glucuronide is a metabolite of the cholesterol absorption inhibitor ezetimibe, primarily formed through the process of glucuronidation in the liver. This compound is characterized by its role in enhancing the pharmacological effects of ezetimibe by increasing its solubility and facilitating its excretion. Ezetimibe itself works by selectively inhibiting the intestinal absorption of cholesterol, thereby lowering serum cholesterol levels. The glucuronide form is typically more polar, which can influence its bioavailability and pharmacokinetics. In terms of chemical structure, ezetimibe glucuronide features a glucuronic acid moiety linked to the ezetimibe molecule, which alters its interaction with biological systems. This modification can affect its efficacy and safety profile, making it an important consideration in pharmacotherapy for hyperlipidemia. The compound is generally studied in the context of drug metabolism and pharmacodynamics, contributing to a better understanding of how ezetimibe functions in the body and its potential therapeutic benefits.

Formula: C₃₀H₂₉F₂NO₉

InChI: InChI=1S/C30H29F2NO9/c31-17-5-1-15(2-6-17)22(34)14-13-21-23(33(28(21)38)19-9-7-18(32)8-10-19)16-3-11-20(12-4-16)41-30-26(37)24(35)25(36)27(42-30)29(39)40/h1-12,21-27,30,34-37H,13-14H2,(H,39,40)/t21-,22+,23-,24+,25+,26-,27+,30-/m1/s1

InChI key: InChIKey=UOFYCFMTERCNEW-ADEYADIWSA-N

SMILES: C(C[C@H](O)C1=CC=C(F)C=C1)[C@@H]2[C@H](N(C2=O)C3=CC=C(F)C=C3)C4=CC=C(O[C@@H]5O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]5O)C=C4

Synonyms:

• 4-[(2S,3R)-1-(4-Fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxo-2-azetidinyl]phenyl β-<span class="text-smallcaps">D</span>-glucopyranosiduronic acid
• 4-[(2S,3R)-1-(4-Fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxo-2-azetidinyl]phenyl-D-Glucopyranosiduronic Acid
• Ezetimibe -D-Glucuronide, >85%
• Ezetimibe B-D-Glucuronide
• Ezetimibe glucuronide
• Ezm-G
• Sch 58235 Glucuronide
• Sch 60663
• β-<span class="text-smallcaps">D</span>-Glucopyranosiduronic acid, 4-[(2S,3R)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxo-2-azetidinyl]phenyl
• β-D-Glucopyranosiduronic acid, 4-[(2S,3R)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxo-2-azetidinyl]phenyl
• 4-[(2S,3R)-1-(4-Fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxo-2-azetidinyl]phenyl β-D-glucopyranosiduronic acid

Ezetimibe glucuronide

CAS: 190448-57-8

Formula: C₃₀H₂₉F₂NO₉

Purity: 98%

Color and Shape: Solid

Molecular weight: 585.5494

Ref: IN-DA002EKX

Ezetimibe Phenoxy Glucuronide-d4

CAS: 190448-57-8

Formula: C₃₀H₂₅D₄F₂NO₉

Color and Shape: White To Off-White Solid

Molecular weight: 589.58

Ref: 4Z-E-065

Ezetimibe Phenoxy Glucuronide

CAS: 190448-57-8

Formula: C₃₀H₂₉F₂NO₉

Color and Shape: White To Off-White Solid

Molecular weight: 585.56

Ref: 4Z-E-062

Ezetimibe phenoxy glucuronide

CAS: 190448-57-8

Ezetimibe phenoxy glucuronide (Ezetimibe glucuronide) is the active metabolite of Ezetimibe. Antihyperlipoproteinemic activity.

Formula: C₃₀H₂₉F₂NO₉

Purity: 98%

Color and Shape: Solid

Molecular weight: 585.55

Ref: TM-T11253

Ezetimibe phenoxy glucuronide

CAS: 190448-57-8

Color and Shape: Solid

Molecular weight: 585.557

Ref: 10-F987045

Ezetimibe phenoxy-β-D-glucuronide

CAS: 190448-57-8

Ezetimibe phenoxy-β-D-glucuronide

Purity: 98%

Molecular weight: 585.55g/mol

Ref: 54-BICL2231

Ezetimibe b-D-glucuronide

CAS: 190448-57-8

Ref: 7W-GC0776

Ezetimibe Phenoxy β-D-Glucuronide

Controlled Product

CAS: 190448-57-8

Stability Hygroscopic
Applications Phase-II metabolite of Ezetimibe, an antihyperlipoproteinemic. A Cholesterol absorption inhibitor.This compound is very hygroscopic. Handle with care.
References van Heek, M., at al.: J. Pharmacol. Exp. Ther., 283, 157 (1997), van Heek, M., at al.: Brit. J. Pharmacol., 129, 1748 (2000)

Formula: C₃₀H₂₉F₂NO₉

Color and Shape: White To Light Brown

Molecular weight: 585.55

Ref: TR-E975030

Ezetimibe b-D-glucuronide

CAS: 190448-57-8

Ezetimibe b-D-glucuronide is a glucuronide conjugate of ezetimibe. It can be found in human serum, as well as in the liver and small intestine. Ezetimibe b-D-glucuronide has been shown to inhibit uptake of uridine into Caco2 cells, which may be due to its ability to inhibit the activity of drug transporters such as P-glycoprotein and organic anion transporting polypeptides. This drug also inhibits the production of creatine kinase in the liver and lowers cholesterol levels by inhibiting dietary cholesterol absorption. The drug interactions with statins are still unclear and require further investigation. Ezetimibe b-D-glucuronide is metabolized by glucuronidation in the liver and small intestine.

Formula: C₃₀H₂₉F₂NO₉

Purity: Min. 95%

Color and Shape: Powder

Molecular weight: 585.55 g/mol

Ref: 3D-ME07193

Ezetimibe Phenoxy β-D-Glucuronide

CAS: 190448-57-8

Formula: C₃₀H₂₉F₂NO₉

Molecular weight: 585.56

Ref: ST-EA-CP-E6044