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SML1629

Sigma-Aldrich

Ezetimibe

≥98% (HPLC)

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
MDL number:
MFCD00937872
UNSPSC Code:
12352200
PubChem Substance ID:
329825513
NACRES:
NA.77

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 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.
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.

Reconstitution

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)
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

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