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Basic Information

Molecular Structure:
CAS No.:	163222-33-1
Name:	Ezetimibe
Article Data:	70

Formula:	C₂₄H₂₁F₂NO₃
Molecular Weight:	409.432
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;
EINECS:	682-606-0
Density:	1.334 g/cm³
Melting Point:	164-166 °C
Boiling Point:	654.9 °C at 760 mmHg
Flash Point:	349.9 °C
Appearance:	white powder
Hazard Symbols:	R36/37/38:;
Risk Codes:	36/37/38
Safety:	26-36
PSA:	60.77000
LogP:	4.95330

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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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

Raw Materials

163222-32-0

4397-53-9

371-40-4

406-00-8

350-46-9

190595-65-4

70627-52-0

555-16-8

Downstream Products

163380-20-9

Total:293 Page 1 of 8 1 2 3 4 5 6 …8 Next>>

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Chemistry

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

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

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.

Specification

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