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Ezetimibe
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Name

Ezetimibe

 EINECS 682-606-0
CAS No. 163222-33-1 Density 1.334 g/cm3
PSA 60.77000 LogP 4.95330
Solubility N/A Melting Point 164-166 °C
Formula C24H21F2NO3 Boiling Point 654.9 °C at 760 mmHg
Molecular Weight 409.432 Flash Point 349.9 °C
Transport Information N/A Appearance white powder
Safety 26-36 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 163222-33-1 (Ezetimibe) Hazard Symbols R36/37/38:;
Synonyms

(-)-Sch 58235;Zetia (TN);Zetia;Ezetimibe 1-(4-flurophenyl)-(3R)-[3-(4-flurophenyl)-(3S)-hydroxypropyl]-(4S)-(4-hydroxyphenyl)-2-azetidinone;2-Azetidinone,1-(4-fluorophenyl)-3-[(3S)-3- (4-fluorophenyl)-3-hydroxypropyl]-4-(4- hydroxyphenyl)-,(3R,4S)-;Sch 58235;Vytorin;Ezedoc;(3R,4S)-1-(4-Fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)-2-azetidinone;

Article Data 70

Ezetimibe Synthetic route

163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

163222-33-1

ezetemibe

Conditions
ConditionsYield
With 10 wt% Pd(OH)2 on carbon; hydrogen In methanol; cyclohexane at 70℃; under 760.051 Torr; for 3h;99%
With 5%-palladium/activated carbon; hydrogen In tetrahydrofuran; ethanol at 50 - 55℃; under 37.5038 - 75.0075 Torr;90.3%
With palladium 10% on activated carbon; ammonium formate; acetic acid for 6h; Reflux;90%
873205-85-7

1-(4-fluorophenyl)-3(R)-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4(S)-(4-hydroxyphenyl)-2-azetidinone hydrate

163222-33-1

ezetemibe

Conditions
ConditionsYield
In n-heptane; tert-butyl methyl ether at 20℃; Product distribution / selectivity; Heating / reflux;99%
In Isopropyl acetate at 20℃; Product distribution / selectivity; Heating / reflux;
With acetic acid at 20℃; Product distribution / selectivity; Heating / reflux;

(3R,4S)-1-(4-fluorophenyl)-3-((S)-3-(4-fluorophenyl)-3-(trimethylsilyloxy)propanyl)-4-(4-(trimethylsiloxy)phenyl)azetidinone

163222-33-1

ezetemibe

Conditions
ConditionsYield
With sulfuric acid In water; isopropyl alcohol at 20 - 25℃; for 1h;95%
With perchloric acid at 40℃; for 3h; Temperature; Solvent;92%
With sulfuric acid In water; isopropyl alcohol at 20℃; for 1h;91.5%

C30H35F2NO3Si

163222-33-1

ezetemibe

Conditions
ConditionsYield
With pyridine hydrofluoride In tetrahydrofuran; pyridine at 20℃; for 24h;93%
1232148-26-3

4-((2S,3R)-1-(4-fluorophenyl)-3-((S)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-oxoazetidin-2-yl)phenyl pivalate

163222-33-1

ezetemibe

Conditions
ConditionsYield
Stage #1: 4-((2S,3R)-1-(4-fluorophenyl)-3-((S)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-oxoazetidin-2-yl)phenyl pivalate With sodium hydroxide In tetrahydrofuran; methanol at -15℃;
Stage #2: With hydrogenchloride; water In ethyl acetate		92%

C39H45ClF2N2O5Si2

163222-33-1

ezetemibe

Conditions
ConditionsYield
With N,O-bis-(trimethylsilyl)-acetamide; tetrabutyl ammonium fluoride In tert-butyl methyl ether at 20℃; for 0.25h;91%
191330-56-0

[14C]-Sch 57871

163222-33-1

ezetemibe

Conditions
ConditionsYield
With dimethylsulfide borane complex; trifluoroacetic anhydride; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In dichloromethane; toluene at -25 - -20℃; for 3h; Inert atmosphere;90%
With glucose dehydrogenase; alpha-D-glucopyranose; NADP; KRED-128 In water; isopropyl alcohol at 35℃; for 1.5h; pH=7; Product distribution / selectivity; Phosphate buffer;89.26%
With glucose dehydrogenase; potassium phosphate; alpha-D-glucopyranose; DL-dithiothreitol; NADP; magnesium sulfate; KRED-118 In methanol; water at 30℃; pH=7.0; Product distribution / selectivity;87.59%

C28H29F2NO5

163222-33-1

ezetemibe

Conditions
ConditionsYield
With hydrogen bromide In isopropyl alcohol at 20℃; for 4h;87%
1004520-48-2

(3R,4S)-1-(4-fluorophenyl)-3-((S)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)azetidin-2-one

163222-33-1

ezetemibe

Conditions
ConditionsYield
With dihydrogen peroxide In acetic acid at 20℃; for 2h; Time;86.23%
With dihydrogen peroxide In water; isopropyl alcohol at 20℃; for 0.5h;

(3R,4S)-1-(4-fluorophenyl)-[3(S)-hydroxy-3-(4-fluorophenyl)propyl]-[4-(phenylmethoxy)phenyl]-2-azetidinone

163222-33-1

ezetemibe

Conditions
ConditionsYield
With palladium on activated charcoal; hydrogen; acetic acid In ethanol at 25℃; for 4h; pH=3;85.4%

Ezetimibe Chemical Properties

Name: Ezetimibe
Synonyms: 1-(4-Fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxy-propyl]-4-(4-hydroxyphenyl)-azetidin-2-one
CAS Registry Number: 163222-33-1
Molecular Formula: C24H21F2NO3
Molecular Weight: 409.43
Molecular Structure:
Mp: 164-166°C

Ezetimibe Uses

Ezetimibe is an anti-hyperlipidemic medication which is used to lower Cholesterol levels. It acts by decreasing Cholesterol absorption in the intestine. It could be used alone when other Cholesterol-lowering medications are not tolerated, or when Cholesterol levels are unable to be controlled on statins alone, ezetimibe could be used together with statins

Ezetimibe Safety Profile

Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing.
Use cautiously in:
1)breastfeeding patients
2)children younger than age 10
3)pregnant patients not receiving HMG-CoA reductase inhibitors
4)renal or hepatic impairment
5)elderly patients.

Ezetimibe Specification

Patient monitoring:
1)Monitor hepatic and lipid profiles
2)Assess for and report unexplained muscle pain.

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