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SML1629

Ezetimibe

Name: Ezetimibe
Brand: SIGMA

≥98% (HPLC), Cholesterol absorption inhibitor, powder

Synonym(s):

(3R,4S)-1-(4-Fluorophenyl)-3-[(S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)azetidin-2-one

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About This Item

Empirical Formula (Hill Notation):

C₂₄H₂₁F₂NO₃

CAS Number:

163222-33-1

Molecular Weight:

409.43

UNSPSC Code:

12352200

PubChem Substance ID:

329825513

NACRES:

NA.77

MDL number:

MFCD00937872

Assay:

≥98% (HPLC)

Form:

powder

Quality level:

200

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Properties

Product Name

Ezetimibe, ≥98% (HPLC)

Quality Level

200

assay

≥98% (HPLC)

form

powder

solubility

DMF: soluble ≥15 mg/mL, DMSO: soluble ≥15 mg/mL, ethanol: soluble ≥15 mg/mL, methanol: soluble ≥15 mg/mL

storage temp.

2-8°C

SMILES string

FC(C=C1)=CC=C1N([C@H](C2=CC=C(O)C=C2)[C@H]3CC[C@H](O)C4=CC=C(F)C=C4)C3=O

InChI

1S/C24H21F2NO3/c25-17-5-1-15(2-6-17)22(29)14-13-21-23(16-3-11-20(28)12-4-16)27(24(21)30)19-9-7-18(26)8-10-19/h1-12,21-23,28-29H,13-14H2/t21-,22+,23-/m1/s1

InChI key

OLNTVTPDXPETLC-XPWALMASSA-N

Description

Biochem/physiol Actions

Ezetimibe is a non statin drug that reduces intestinal cholesterol absorption. In addition, it also has an ability to reduce the risk of cardiovascular events in patients who had had an acute coronary syndrome and whose low-density lipoprotein (LDL) cholesterol values were within guideline recommendations.

Ezetimibe inhibits intestinal cholesterol absorption by preventing cholesterol uptake by Niemann-Pick C1 Like 1 (NPC1L1) protein that was found critical for the intestinal absorption of cholesterol. Ezetimibe selectvely blocks cholesterol absorption without inhibiting pancreatic lipolytic enzyme activities in the intestinal lumen.

Preparation Note

For solubility in aqueous buffer, Ezetimibe should be dissolved in ethanol followed by dilution with the buffer.

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Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Ezetimibe added to statin therapy after acute coronary syndromes.

Cannon C P, et al.

The New England Journal of Medicine, 372(25), 2387-2397 (2015)

Wang, D.Q.

Annual Review of Physiology, 69, 221-248 (2011)

Garcia-Calvo, et al.

Proceedings of the National Academy of Sciences of the USA, 102, 8132-8137 (2005)

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Global Trade Item Number

SKU	GTIN
SML1629-25MG	04061833058664