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SML1629

Ezetimibe

≥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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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

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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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000440669
0000440669
0000369430
0000340751
0000369430

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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)
Wojciech G Garbacz et al.
Molecular pharmacology, 94(4), 1145-1154 (2018-07-27)
Cholesterol is essential for numerous biologic functions and processes, but an excess of intracellular cholesterol can be toxic. Intestinal cholesterol absorption is a major determinant of plasma cholesterol level. The liver X receptor (LXR) is a nuclear receptor known for
Jing Yu et al.
Oxidative medicine and cellular longevity, 2020, 4717258-4717258 (2020-01-31)
Oxidative stress and neuroinflammation play essential roles in ischemic stroke-induced brain injury. Previous studies have reported that Ezetimibe (Eze) exerts antioxidative stress and anti-inflammatory properties in hepatocytes. In the present study, we investigated the effects of Eze on oxidative stress
View All Related Papers

Global Trade Item Number

SKUGTIN
SML1629-25MG04061833058664

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