Ezetimibe | SCH-58235 | CAS#163222-33-1

Ezetimibe
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 317859

CAS#: 163222-33-1

Description: Ezetimibe, also known as SCH 58235, is a drug that lowers plasma cholesterol levels. It acts by decreasing cholesterol absorption in the small intestine. It may be used alone when other cholesterol-lowering medications are not tolerated, or together with statins (e.g., ezetimibe/simvastatin) when statins alone do not control cholesterol. Ezetimibe is recommended as second line therapy for those intolerant of statins or unable to achieve target LDL cholesterol levels on statins alone by several major medical group practice guidelines, but not by those of the American Heart Association and American College of Cardiology.

Chemical Structure

Ezetimibe

CAS# 163222-33-1

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 317859
Name: Ezetimibe
CAS#: 163222-33-1
Chemical Formula: C24H21F2NO3
Exact Mass: 409.15
Molecular Weight: 409.425
Elemental Analysis: C, 70.41; H, 5.17; F, 9.28; N, 3.42; O, 11.72

Price and Availability

Size	Price	Availability
200mg	USD 150	2 weeks
500mg	USD 250	2 weeks
1g	USD 450	2 weeks
2g	USD 650	2 weeks
5g	USD 1350	2 weeks
10g	USD 1950	2 weeks
20g	USD 2950	2 weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: SCH 58235; SCH-58235; SCH58235; Ezetimibe, Zetia, Ezetrol,

IUPAC/Chemical Name: (3R,4S)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)azetidin-2-one

InChi Key: OLNTVTPDXPETLC-XPWALMASSA-N

InChi Code: 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

SMILES Code: O=C1N(C2=CC=C(F)C=C2)[C@H](C3=CC=C(O)C=C3)[C@H]1CC[C@@H](C4=CC=C(F)C=C4)O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:

Product Data

Instruction:

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Biological target:	Ezetimibe (SCH 58235) is a potent cholesterol absorption inhibitor. Ezetimibe is a Niemann-Pick C1-like1 (NPC1L1) inhibitor, and is a potent Nrf2 activator.
In vitro activity:	Although ezetimibe allowed the cells to take up cholesterol normally, the esterification was abolished. Meanwhile, oleic acid esterification was unaffected. Moreover, ezetimibe activated sterol regulatory element-binding protein 2 by approximately 1.5-fold. These results suggest that ezetimibe limited cellular cholesterol mobilization required for lipoprotein assembly. Reference: Biochim Biophys Acta Mol Cell Biol Lipids. 2020 Dec;1865(12):158808. https://pubmed.ncbi.nlm.nih.gov/32860884/
In vivo activity:	In addition, EZ (ezetimibe) also maintained the redox status via decreasing the lipid peroxidation and protein-bound carbonyl content (CC) and increasing the activity of high-density lipoprotein (HDL)-associated-paraoxonase-1 (PON-1) and renal antioxidant enzymes as well as also protected renal histopathological features. This study concludes that EZ exhibits antidiabetic and reno-protective properties in diabetic rats. Reference: Arch Physiol Biochem. 2021 Jan 29:1-16. https://pubmed.ncbi.nlm.nih.gov/33508970/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	65.7	160.40
	DMF	20.0	48.85
	Ethanol	51.0	124.56
	Ethanol:PBS (pH 7.2) (1:4)	0.2	0.49

Preparing Stock Solutions

The following data is based on the product molecular weight 409.43 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:	1. Nakano T, Inoue I, Takenaka Y, Ito R, Kotani N, Sato S, Nakano Y, Hirasaki M, Shimada A, Murakoshi T. Ezetimibe impairs transcellular lipid trafficking and induces large lipid droplet formation in intestinal absorptive epithelial cells. Biochim Biophys Acta Mol Cell Biol Lipids. 2020 Dec;1865(12):158808. doi: 10.1016/j.bbalip.2020.158808. Epub 2020 Aug 27. PMID: 32860884. 2. Osuna-Ramos JF, Reyes-Ruiz JM, Bautista-Carbajal P, Cervantes-Salazar M, Farfan-Morales CN, De Jesús-González LA, Hurtado-Monzón AM, Del Ángel RM. Ezetimibe inhibits dengue virus infection in Huh-7 cells by blocking the cholesterol transporter Niemann-Pick C1-like 1 receptor. Antiviral Res. 2018 Dec;160:151-164. doi: 10.1016/j.antiviral.2018.10.024. Epub 2018 Nov 1. PMID: 30391500. 3. Nabi R, Alvi SS, Shah A, Chaturvedi CP, Faisal M, Alatar AA, Ahmad S, Khan MS. Ezetimibe attenuates experimental diabetes and renal pathologies via targeting the advanced glycation, oxidative stress and AGE-RAGE signalling in rats. Arch Physiol Biochem. 2021 Jan 29:1-16. doi: 10.1080/13813455.2021.1874996. Epub ahead of print. PMID: 33508970. 4. Cho Y, Kim RH, Park H, Wang HJ, Lee H, Kang ES. Effect of Ezetimibe on Glucose Metabolism and Inflammatory Markers in Adipose Tissue. Biomedicines. 2020 Nov 18;8(11):512. doi: 10.3390/biomedicines8110512. PMID: 33217950; PMCID: PMC7698625.
In vitro protocol:	1. Nakano T, Inoue I, Takenaka Y, Ito R, Kotani N, Sato S, Nakano Y, Hirasaki M, Shimada A, Murakoshi T. Ezetimibe impairs transcellular lipid trafficking and induces large lipid droplet formation in intestinal absorptive epithelial cells. Biochim Biophys Acta Mol Cell Biol Lipids. 2020 Dec;1865(12):158808. doi: 10.1016/j.bbalip.2020.158808. Epub 2020 Aug 27. PMID: 32860884. 2. Osuna-Ramos JF, Reyes-Ruiz JM, Bautista-Carbajal P, Cervantes-Salazar M, Farfan-Morales CN, De Jesús-González LA, Hurtado-Monzón AM, Del Ángel RM. Ezetimibe inhibits dengue virus infection in Huh-7 cells by blocking the cholesterol transporter Niemann-Pick C1-like 1 receptor. Antiviral Res. 2018 Dec;160:151-164. doi: 10.1016/j.antiviral.2018.10.024. Epub 2018 Nov 1. PMID: 30391500.
In vivo protocol:	1. Nabi R, Alvi SS, Shah A, Chaturvedi CP, Faisal M, Alatar AA, Ahmad S, Khan MS. Ezetimibe attenuates experimental diabetes and renal pathologies via targeting the advanced glycation, oxidative stress and AGE-RAGE signalling in rats. Arch Physiol Biochem. 2021 Jan 29:1-16. doi: 10.1080/13813455.2021.1874996. Epub ahead of print. PMID: 33508970. 2. Cho Y, Kim RH, Park H, Wang HJ, Lee H, Kang ES. Effect of Ezetimibe on Glucose Metabolism and Inflammatory Markers in Adipose Tissue. Biomedicines. 2020 Nov 18;8(11):512. doi: 10.3390/biomedicines8110512. PMID: 33217950; PMCID: PMC7698625.

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1: Signy J, Signy M. The IMPROVE-IT study and ezetimibe. Br J Community Nurs. 2015 May;20(5):243-4. doi: 10.12968/bjcn.2015.20.5.243. Review. PubMed PMID: 25993373.

2: Gryn SE, Hegele RA. Ezetimibe plus simvastatin for the treatment of hypercholesterolemia. Expert Opin Pharmacother. 2015 Jun;16(8):1255-62. doi: 10.1517/14656566.2015.1041504. Epub 2015 Apr 28. Review. PubMed PMID: 25920750.

3: Averna M. The effect of ezetimibe on NAFLD. Atheroscler Suppl. 2015 Feb;17:27-34. doi: 10.1016/S1567-5688(15)50007-X. Review. PubMed PMID: 25659874.

4: Fazio S. The role of PCSK9 in intestinal lipoprotein metabolism: synergism of statin and ezetimibe. Atheroscler Suppl. 2015 Feb;17:23-6. doi: 10.1016/S1567-5688(15)50006-8. Review. PubMed PMID: 25659873.

5: Federici M. Effect of ezetimibe on cholesterol absorption and lipoprotein composition in diabetes and metabolic syndrome. Atheroscler Suppl. 2015 Feb;17:17-22. doi: 10.1016/S1567-5688(15)50005-6. Review. PubMed PMID: 25659872.

6: Farnier M. Ezetimibe/statin combination therapy to treat patients with type 2 diabetes. Atheroscler Suppl. 2015 Feb;17:2-8. doi: 10.1016/S1567-5688(15)50002-0. Review. PubMed PMID: 25659869.

7: In brief: adding ezetimibe to a statin improves clinical outcomes. Med Lett Drugs Ther. 2014;56(1457):126. Review. PubMed PMID: 25461232.

8: Sumarokov AB, Kukharchuk VV. [Hypolipidemic and pleiotropic effects of a combination of simvastatin and ezetimibe in patients with different types of hyperlipidemia]. Ter Arkh. 2014;86(12):107-15. Review. Russian. PubMed PMID: 25804051.

9: Liptruzet: a combination of ezetimibe and atorvastatin. Med Lett Drugs Ther. 2013 Jun 24;55(1419):49-50. Review. PubMed PMID: 23797796.

10: Couture P, Lamarche B. Ezetimibe and bile acid sequestrants: impact on lipoprotein metabolism and beyond. Curr Opin Lipidol. 2013 Jun;24(3):227-32. doi: 10.1097/MOL.0b013e3283613a55. Review. PubMed PMID: 23571732.

11: Katsiki N, Theocharidou E, Karagiannis A, Athyros VG, Mikhailidis DP. Ezetimibe therapy for dyslipidemia: an update. Curr Pharm Des. 2013;19(17):3107-14. Review. PubMed PMID: 23317398.

12: Institute for Quality and Efficiency in Health Care: Executive Summaries [Internet]. Cologne, Germany: Institute for Quality and Efficiency in Health Care (IQWiG); 2005-. Available from http://www.ncbi.nlm.nih.gov/books/NBK84142/ PubMed PMID: 23101081.

13: Phan BA, Dayspring TD, Toth PP. Ezetimibe therapy: mechanism of action and clinical update. Vasc Health Risk Manag. 2012;8:415-27. doi: 10.2147/VHRM.S33664. Epub 2012 Jul 3. Review. PubMed PMID: 22910633; PubMed Central PMCID: PMC3402055.

14: Huang X, Chen DY. A case study of single-pill combination therapy: the ezetimibe/simvastatin combination for treatment of hyperlipidemia. ChemMedChem. 2012 Nov;7(11):1882-94. doi: 10.1002/cmdc.201200287. Epub 2012 Aug 20. Review. PubMed PMID: 22907901.

15: Doggrell SA. The ezetimibe controversy - can this be resolved by comparing the clinical trials with simvastatin and ezetimibe alone and together? Expert Opin Pharmacother. 2012 Jul;13(10):1469-80. doi: 10.1517/14656566.2012.696098. Review. PubMed PMID: 22725704.

16: Ye Y, Zhao X, Zhai G, Guo L, Tian Z, Zhang S. Effect of high-dose statin versus low-dose statin plus ezetimibe on endothelial function: a meta-analysis of randomized trials. J Cardiovasc Pharmacol Ther. 2012 Dec;17(4):357-65. doi: 10.1177/1074248412449384. Epub 2012 Jun 18. Review. PubMed PMID: 22710021.

17: Green D, Panayotova R, Ritchie JP, O'Riordan E, McDonald J. Lipid-lowering therapy in chronic kidney disease: is there a role for ezetimibe? J Ren Care. 2012 Sep;38(3):138-46. doi: 10.1111/j.1755-6686.2012.00309.x. Epub 2012 May 22. Review. PubMed PMID: 22613701.

18: Morrone D, Weintraub WS, Toth PP, Hanson ME, Lowe RS, Lin J, Shah AK, Tershakovec AM. Lipid-altering efficacy of ezetimibe plus statin and statin monotherapy and identification of factors associated with treatment response: a pooled analysis of over 21,000 subjects from 27 clinical trials. Atherosclerosis. 2012 Aug;223(2):251-61. doi: 10.1016/j.atherosclerosis.2012.02.016. Epub 2012 Feb 16. Review. PubMed PMID: 22410123.

19: Suchy D, Łabuzek K, Stadnicki A, Okopień B. Ezetimibe--a new approach in hypercholesterolemia management. Pharmacol Rep. 2011;63(6):1335-48. Review. PubMed PMID: 22358082.

20: Teramoto T, Kashiwagi A, Ishibashi S, Daida H; Japan Lipid Guideline Achievement Program Investigators. Cross-sectional survey to assess the status of lipid management in high-risk patients with dyslipidemia: clinical impact of combination therapy with ezetimibe. Curr Ther Res Clin Exp. 2012 Feb;73(1-2):1-15. doi: 10.1016/j.curtheres.2012.02.001. Review. PubMed PMID: 24653509; PubMed Central PMCID: PMC3954020.

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