Ezetimibe

ChemicalBook > CAS DataBase List > Ezetimibe

Description Indications and Usage Mechanisms of Action References

Product Name: Ezetimibe
CAS No.: 163222-33-1
Chemical Name: Ezetimibe
Synonyms: ZETIA;EzetiMib;Ezetimide;Ezatimibe;(3R,4S)-1-(4-fluorophenyl)-3-((S)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-(4-hydroxyphenyl)azetidin-2-one;Ezetimibe-001;(3R,4S)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)azetidin-2-one;CS-1965;Etimibe;EZETIMIBE
CBNumber: CB7380787
Molecular Formula: C24H21F2NO3
Formula Weight: 409.43
MOL File: 163222-33-1.mol

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Ezetimibe Property

Melting point:: 164-166°C
alpha: D22 -33.9° (c = 3 in methanol)
Boiling point:: 654.9±55.0 °C(Predicted)
Density: 1.334±0.06 g/cm3(Predicted)
storage temp.: 2-8°C
solubility: Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 15 mg/ml)
pka: 9.72±0.30(Predicted)
form: powder
color: White or off-white
BCS Class: 2
Stability:: Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.
InChI: 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
InChIKey: OLNTVTPDXPETLC-XPWALMASSA-N
SMILES: N1(C2=CC=C(F)C=C2)[C@H](C2=CC=C(O)C=C2)[C@@H](CC[C@@H](C2=CC=C(F)C=C2)O)C1=O
CAS DataBase Reference: 163222-33-1(CAS DataBase Reference)
EPA Substance Registry System: 2-Azetidinone, 1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)-, (3R,4S)- (163222-33-1)

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Safety

Risk Statements: 36/37/38
Safety Statements: 26-36-24/25
HS Code: 29337900
Hazardous Substances Data: 163222-33-1(Hazardous Substances Data)

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P273Avoid release to the environment.

P391Collect spillage. Hazardous to the aquatic environment

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: SML1629
Product name: Ezetimibe
Purity: ≥98% (HPLC)
Packaging: 25MG
Price: $128
Updated: 2023/06/20

Sigma-Aldrich

Product number: PHR1866
Product name: Ezetimibe
Purity: Pharmaceutical Secondary Standard; Certified Reference Material
Packaging: 1G
Price: $224
Updated: 2022/05/15

Sigma-Aldrich

Product number: 1269028
Product name: Ezetimibe
Purity: United States Pharmacopeia (USP) Reference Standard
Packaging: 250MG
Price: $704
Updated: 2022/05/15

Cayman Chemical

Product number: 16331
Product name: Ezetimibe
Purity: ≥98%
Packaging: 25mg
Price: $73
Updated: 2024/03/01

Cayman Chemical

Product number: 16331
Product name: Ezetimibe
Purity: ≥98%
Packaging: 50mg
Price: $110
Updated: 2024/03/01

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Ezetimibe Chemical Properties,Usage,Production

Description

Ezetimibe is ananti-hyperlipidemic drug used for lowering the plasma cholesterol levels. It is indicated as an adjunctive therapy to diet for the reduction of high-level total-C, LDL-C, and ApoB in patients suffering primary (heterozygous familial and non-familial) hypercholesterolemia. It is also used in combination therapy with HMG-CoA reductase inhibitors.Ezetimibe does not inhibit the cholesterol synthesis in the liver, or increase bile acid excretion.It takes effect throughacting at the brush border of the small intestine and inhibiting the absorption of cholesterol, further leading to a decrease in the delivery of intestinal cholesterol to the liver. This causes a reduction of hepatic cholesterol stores and an increase in clearance of blood cholesterol.

Indications and Usage

Ezetimibe is a new form of selective cholesterol absorption inhibitor developed in a collaboration between Schering-Plough Co. and Merck Co. This drug is the first cholesterol absorption selective inhibitor to be approved for sale by the American FDA. Its commercial name is Ezetrol.
This drug can be used alone or in combination with HMG-CoA reductase inhibitors (statins) to treat primary (heterozygous familial and non-familial) hypercholesterolemia, homozygous familial hypercholesterolemia (HoFH), homozygous viremia (or phytosterolemia).

Mechanisms of Action

Ezetimibe’s mechanisms of action are different from those of other lipid-lowering drugs (such as statins, cholic acid chelating agents, phenoxy acid derivatives, and plant sterols). This drug binds with the surface proteins on the brush border membrane vesicles of the small intestine (relative molecular mass 145x10^3) to inhibit the small intestine’s absorption of cholesterol in food and bile, thus decreasing the cholesterol content in serum and the liver. Ezetimibe is different from bile acid sequestrants because it does not affect the absorption of cholesterol esters, other steroids (such as bezoar and cholic acid), three triacylglycerol, and fat-soluble vitamins. Its effects are unrelated to whether or not acetyl coenzyme A- cholesterol acetyltransferase (ACAT) is inhibited or whether or not the LDL receptor (scavenger receptor) is expressed. After Ezetimibe is absorbed and binds with glucuronic acid in the liver, it undergoes enterohepatic circulation and almost exclusively targets small intestine mucosa cells.

References

https://en.wikipedia.org/wiki/Ezetimibe
https://pubchem.ncbi.nlm.nih.gov/compound/Ezetimibe#section=Top
https://www.drugbank.ca/drugs/DB00973
Davidson, Michael H, et al. "Ezetimibe coadministered with simvastatin in patients with primary hypercholesterolemia ☆." Journal of the American College of Cardiology 40.12(2002):2125.
Sudhop, T, et al. "Inhibition of intestinal cholesterol absorption by ezetimibe in humans. " Circulation 106.15(2002):1943-8.

Description

Ezetimibe is a once-daily orally active cholesterol absorption inhibitor, launched as a hypolipidemic agent. The one-step diastereo- and enantioselective formation of β-lactams starting from commercially available (3S)-hydroxy-y-lactone is the key point of the asymmetric synthesis of ezetimibe. The 2-azetidinone class was initially designed as acylcoenzyme A: cholesterol acyltransferase (ACAT) inhibitors but experimental data suggest that this compound acts in the intestinal wall to inhibit cholesterol through a novel mechanism with an as yet undiscovered target. Orally administered ezetimibe inhibited increases in plasma cholesterol in four cholesterol-fed animals species (hamster, rats, dogs and rhesus monkeys). In rats cannulated in the intestine and bile duct, [³H]-ezetimibe inhibited cholesterol absorption by more than 95%. In cholesterol-fed LDL receptor+apoE knockout mice, treatment with ezetimibe reduced atherosclerotic lesion cross sectional area by 48% in the aorta and 20% in the carotid artery. Moreover, the plasma cholesterol levels were reduced and the progression of lesions was inhibited. Ezetimibe is highly protein bound and is metabolized by the liver to its glucuronide metabolite, which represents 80-90% of circulating ezetimibe. About 90% of ezetimibe and/or the glucuronide metabolite are excreted in the feces and 10% in the urine. The parent compound and its glucuronide metabolite undergo enterohepatic recirculation; in consequence, the drug is slowly eliminated. In hypercholesterolemic patients, ezetimibe (10 mglday, 12 weeks) reduced LDL cholesterol by 18% and total cholesterol by 12%, with a similar safety profile to placebo. Co-administration of ezetimibe with statins or fenofibrate lowered LDL cholesterol levels more than either monotherapy. Ezetimibe was well tolerated and interaction studies provided evidence that ezetimibe had no significant effect on the activity of major CYP450 drug-metabolizing enzymes. Moreover, no pharmacokinetic/pharmacodynamic interactions were seen between ezetimibe and statins and others frequently administered drugs. .

Chemical Properties

White Solid

Originator

Schering-Plough (USA)

Uses

antibacterial

Uses

A cholesterol transport inhibitor that binds to NPC1L1

Uses

For use as adjunctive therapy to diet for the reduction of elevated total-C, LDL-C, and Apo B in patients with primary (heterozygous familial and non-familial) hypercholesterolemia.

Uses

Ezetimibe (9) was approved as the first hypolipidemic drug to act by blocking the absorption of dietary cholesterol. This drug was discovered by Schering-Plough and is codeveloped and co-marketed by Merck and Schering-Plough for the treatment of hypercholesterolemia and also two less common forms of hyperlipidemia: homozygous familial hypercholesterolemia and homozygous sitosterolemia.

Definition

ChEBI: Ezetimibe is a beta-lactam that is azetidin-2-one which is substituted at 1, 3, and 4 by p-fluorophenyl, 3-(p-fluorophenyl)-3-hydroxypropyl, and 4-hydroxyphenyl groups, respectively (the 3R,3'S,4S enantiomer). It has a role as an anticholesteremic drug, an antilipemic drug and an antimetabolite. It is a member of azetidines, an organofluorine compound and a beta-lactam.

brand name

Zetia (Merck/Schering-Pough);Ezetrol.

Biological Functions

Ezetimibe lowers plasma cholesterol levels by inhibiting the absorption of cholesterol at the brush border of the small intestine. Specifically, it has been proposed to bind to a specific transport protein located in the wall of the small intestine, resulting in a reduction of cholesterol transport and absorption. Ezetimibe appears to be selective in its actions in that it does not interfere with the absorption of triglycerides, lipid-soluble vitamins or other nutrients. The decreased absorption of cholesterol eventually leads to enhanced receptor-mediated LDL uptake similar to that seen with bile acid sequestrants and HMGRIs. When used as monotherapy, the decreased absorption of cholesterol causes a compensatory increase in cholesterol biosynthesis. This is similar to that described for bile acid sequestrants and is insufficient to override the overall LDL lowering effects of ezetimibe.

General Description

Ezetimibe, (3R,4S)-1-(4-fluorophenyl)-3-((3S)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-(4-hydroxyphenyl)-2-azetidinone (Zetia), is an antihyperlipidemicagent that has usefulness in lowering cholesterol levels. Itacts by decreasing cholesterol absorption in the intestine byblocking the absorption of the sterol at the Brush boarder.Specifically, the -lactam binds to the Niemann-Pick C1-Like 1 (NPC1L1) protein on the gastrointestinal tract that isresponsible for cholesterol absorption. Although it may beused alone, it is marketed as a combination product withsimvastatin under the trade name Vytorin.

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.

Pharmacokinetics

Ezetimibe is administered orally; however, its absolute bioavailability cannot be determined because of its aqueous insolubility and the lack of an injectable formulation. Based on area under the curve values, the oral absorption ranges from 35 to 60%. Mean peak concentrations of the active glucuronidated metabolite are reached within 1 to 2 hours. Both ezetimibe and its glucuronide conjugate are extensively bound (>90%) to plasma proteins. The relative plasma concentrations of ezetimibe and its glucuronide conjugate range from 10 to 20% and from 80 to 90%, respectively. Both compounds have a long half-life of approximately 22 hours. The coadministration of food with ezetimibe has no effect on the extent of absorption.

Clinical Use

Ezetimibe is indicated as monotherapy or in combination with an HMGRI for the reduction of elevated total cholesterol, LDL cholesterol, and apoB in patients with primary (heterozygous familial and nonfamilial) hypercholesterolemia. When used as monotherapy, ezetimibe reduces LDL cholesterol by approximately 18%. When used in combination therapy with an HMGRI, LDL levels are reduced by 25 to 65% depending on the dose of the HMGRI inhibitor. Ezetimibe also is indicated for homozygous familial hypercholesterolemia in combination with either atorvastatin or simvastatin and for homozygous familial sitosterolemia. All indications are for patients who have not responded to diet, exercise, and other nonpharmacological methods.

Side effects

Ezetimibe generally is well tolerated. The most common adverse effects are listed above. Whenever ezetimibe is used in combination with an HMGRI, the incidence of myopathy or rhabdomyolysis does not increase above that seen with HMGRI monotherapy.

Synthesis

The synthesis of ezetimibe (9) begins with the one-step diastereoselective and practical synthesis of the trans |?- lactam from commercially available (S)-3-hydroxy-|?-lactone (92). Lactam 95 was obtained by generation of a dianion of lactone 92 with LDA in THF followed by addition of the imine and N,N?ˉ-dimethylpropyleneurea (DMPU) to give predominately adduct 93 (93:94 = 79:21). However, intermediate 93 and 94 did not cyclize to their respective lactams due to formation of stable lithium aggregates.Addition of lithium chloride/DMF was employed to cyclize the intermediates into trans-lactam 95 as the major product (trans:cis = 95:5) in a one-pot process from 92 in 64% yield. The 95:5 ratio of compound 95 was oxidatively cleaved with NaIO4 to give aldehyde 96. Mukaiyama aldol condensation was adopted to elaborate the 4-fluorophenylpropyl side chain to give alcohol 98. Without isolation, the reaction mixture was subjected to dehydration using p-TSA to give enone 99 in 75% yield from compound 96. Reduction of the double bond in 99 with Wilkinson?ˉs catalyst yielded ketone 100, which was subjected to the highly enantioselective CBS reduction to give alcohol 101 with a 98:2 selectivity of S:R at the benzylic position. Catalytic hydrogenation of compound 101 gave ezetimibe (9) in 79% yield. Alternatively, a palladium-catalyzed double reduction in EtOAc/MeOH of both the double bond and the benzyl protecting group in enone 99 produced free phenol 107 in 90% yield. A three-step one-pot procedure was subsequently developed to transform 107 into ezetimibe (9) in 79% yield. That is, free phenol 107 was protected in situ as its TMS ether using BSU followed by a highly selective CBS reduction of the ketone group to give the desired alcohol in 97% ee. The TMS group was removed during acidic workup to give ezetimibe (9). A more convergent approach to this drug was also developed by preparing the (S)-hydroxy side chain before the ring construction. Therefore, p-fluorobenzoylbutyric acid (102) was reacted with pivaloyl chloride and the acid chloride thus obtained was acylated with chiral auxiliary 103 to give the corresponding amide. The ketone group in the amide was reduced with (R)-MeCBS/BH3-THF (104) in the presence of p-TSA to give desired alcohol 105 in high yield (99%) and stereoselectivity (96 % d.e.). Chiral alcohol 105 was then mixed with the imine in the presence of TMSCl and DIPEA to protect the alcohols as TMS ethers. In the same pot, TiCl4 was added to catalyze the condensation reaction and gave compound 106 in 65% yield. Compound 106 was reacted with TBAF and a fluoridecatalyzed cyclization took place to give the corresponding lactam. Finally, the TMS protecting group was removed under acidic conditions to give ezetimibe (9) in 91% yield over two steps.

target

MEK | ERK

Drug interactions

Potentially hazardous interactions with other drugs
Ciclosporin: concentration of both drugs possibly increased.
Lipid lowering agents: avoid with fibrates; concentration of rosuvastatin increased - reduce rosuvastatin dose.

Metabolism

Following oral administration, ezetimibe is rapidly and extensively metabolized in the intestinal wall and the liver to its active metabolite, a corresponding phenol glucuronide. This glucuronide is reexcreted in the bile back to its active site. A small amount (<5%) of ezetimibe undergoes oxidation to covert the benzylic hydroxyl group to a ketone; however, ezetimibe does not appear to exert any significant effect on the activity of CYP450 enzymes.

References

1) Wang?et al. (2007),?Regulation of intestinal cholesterol absorption; Annu. Rev. Physiol.,?69?221 2) Garcia-Calvo?et al. (2005),?The target of ezetimibe is Niemann-Pick C1-Like 1 (NPC1L1); Proc. Natl. Acad. Sci. USA,?102?8132 3) Osuna-Ramos?et al.?(2018),?Ezetimibe inhibits dengue virus infection in Huh-7 cells by blocking the cholesterol transporter Niemann-Pick C1-like 1 receptor; Regulat. Curr. Opin. Cell Biol.,?160?151 4) Kim?et al.?(2017),?Ezetimibe ameliorates steatohepatitis via AMP activated protein kinase-TFEB-mediated activation of autophagy and NLRP3 inflammasome inhibition; Autophagy,?13?1767

Ezetimibe Preparation Products And Raw materials

Raw materials

Preparation Products

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Ezetimibe Suppliers

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Hebei Dangtong Import and export Co LTD

Product: Ezetimibe 163222-33-1
Price: US $65.00-60.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 20Tons
Release date: 2023-10-10

Ouhuang Engineering Materials (Hubei) Co., Ltd

Product: Ezetimibe 163222-33-1
Price: US $10.00/kg
Min. Order: 1kg
Purity: 99.8%
Supply Ability: 10000ton
Release date: 2024-04-29

Sinoway Industrial co., ltd.

Product: Ezetimibe 163222-33-1
Price: US $220.00-120.00/Kg/Bag
Min. Order: 1Kg/Bag
Purity: 98% up / GMP
Supply Ability: 20 tons
Release date: 2023-11-24

163222-33-1, EzetimibeRelated Search:

N,N-Dimethylformamide Propyl butyrate Isopropyl alcohol Polyacrylamide Acrylamide Nicotinamide Etimicin POLY(N-ISOPROPYL ACRYLAMIDE) CHLOROPHOSPHONAZO III Boc-D-Glutamine Etimicin Sulphate Cocamidopropyl betaine Propyl gallate (3R,4S)-4-(4-(Benzyloxy)Phenyl)-1-(4-Fluorophenyl)-3-((S)-3-(4- Fluorophenyl)-3-Hydroxypropyl)Azetidin-2-One ent-EzetiMibe Ezetimibe Impurity 33 Ethyl 2-cyano-3,3-diphenylacrylate Exemestane

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

Ezetimibe-001

Ticagrelor and its interMediate

Ezetimibe 1-(4-Fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxy-propyl]-4-(4-hydroxyphenyl)-azetidin-2-one

Ezatimibe

zetia/vytorin

SCH 60969

Ezetimibe, >=99%

(3R,4S)-1-(4-Fluorophenyl)-3-((S)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-(4-hydroxyphenyl)azeti

1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxy-propyl]-4-(4-hydroxyphenyl)-azetidin-2-one

EZETIMIBE

ZETIA

(3R,4S)-1-(4-Fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)-2-azetidinone, Sch-58235

1-(4-Flurophenyl)-(3R)-3-(4-flurophenyl)-(3S)-hydroxypropyl-(4S)-(4-hydroxyphenyl)-2-azetidinone

Ezetimide

Ezitimibe&Int

EzetimibeC24H21F2N03

CS-1965

SCH-58235

EzetiMib

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

EzitiMibeEzetiMibeC24H21F2N03

2-Azetidinone, 1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)-, (3R,4S)-

EzetiMibe (Zetia)

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

Ezetimibe Tablets

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

Ezetimibe USP/EP/BP

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

Ezetimibe (SCH 58235)

Etimibe

EzetimibeQ: What is Ezetimibe Q: What is the CAS Number of Ezetimibe Q: What is the storage condition of Ezetimibe Q: What are the applications of Ezetimibe

Ezetimibe (1269028)

4'-Methylenediphenol

Ezetimibe CRS

Ezetimib Reference Standard

163222-33-1

163222-31-1

C24H21F2NO3

C24H17F2NO3D4

Isotope

CEDAX

Final material

API

Ezetimibe

Cardiovascular APIs

All Inhibitors

Inhibitors

Intermediates & Fine Chemicals

Pharmaceuticals

163222-33-1