Determine the necessary mass, volume, or concentration for preparing a solution.
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Moligand™, ≥99% Moligand™ for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
Store at -20°C Ships Ice chest + Ice pads Check lot-specific COA for exact specifications.
SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
Cited in 7 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
Ezetimibe has been reported to be a cholesterol transport inhibitor. Mechanistic studies show that this compound directly affects Niemann-Pick C1-like 1 (NPC1L1) and prevents it from incorporating into clathrin-coated vesicles. NPC1L1 is a polytopic transmembrane protein that facilitates absorption of cholesterol via clathrin/AP2-mediated endocytosis. By binding to NPC1L1, ezetimibe prevents endocytosis of this protein therefore blocking cholesterol transfer across membranes. Ezetimibe is used clinically to lower plasma cholesterol levels.
A cholesterol transport inhibitor that binds to NPC1L1
| ALogP | 4 |
|---|
| Pubchem Sid | 504757332 |
|---|---|
| Pubchem Sid Url | https://pubchem.ncbi.nlm.nih.gov/substance/504757332 |
| Sonrisas canónicas | C1=CC(=CC=C1C2C(C(=O)N2C3=CC=C(C=C3)F)CCC(C4=CC=C(C=C4)F)O)O |
| IUPAC Name | (3R,4S)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)azetidin-2-one |
| InChIKey | OLNTVTPDXPETLC-XPWALMASSA-N |
| 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 |
| Isómeros SMILES | C1=CC(=CC=C1[C@@H]2[C@H](C(=O)N2C3=CC=C(C=C3)F)CC[C@@H](C4=CC=C(C=C4)F)O)O |
| CAS alternativo | 163222-33-1 |
| Términos de entrada MeSH | (1-(4-fluorophenyl)-(3R)-(3-(4-fluorophenyl)-(3S)-hydroxypropyl)-(4S)-(4-hydroxyphenyl)-2-azetidinone);58235, SCH;ezetimib;ezetimibe;Ezetrol;SCH 58235;SCH-58235;SCH58235;Zetia |
| Peso molecular | 409.43 |
| Reaxy-Rn | 11745669 |
| Reaxys-RN_link_address | https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=11745669&ln= |
Comprehensive hazard, handling, storage, and regulatory compliance document.
Download SDS →Lot-specific quality data. Enter your lot number to retrieve the exact COA.
Look up COA →Full quality attributes and acceptance criteria for this grade.
View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organoheterocyclic compounds |
| Clase | Lactams |
| Subclass | Beta lactams |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Monobactams |
| Alternative Parents | Phenylazetidines Fluorobenzenes 1-hydroxy-2-unsubstituted benzenoids Aryl fluorides Tertiary carboxylic acid amides Secondary alcohols Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Organofluorides Organic oxides Hydrocarbon derivatives Carbonyl compounds Aromatic alcohols |
| Molecular Framework | Aromatic heteromonocyclic compounds |
| Substituents | Monobactam - 1-phenylazetidine - 2-phenylazetidine - 1-hydroxy-2-unsubstituted benzenoid - Fluorobenzene - Halobenzene - Phenol - Aryl fluoride - Aryl halide - Monocyclic benzene moiety - Benzenoid - Tertiary carboxylic acid amide - Azetidine - Carboxamide group - Secondary alcohol - Azacycle - Carboxylic acid derivative - Organonitrogen compound - Organofluoride - Organohalogen compound - Hydrocarbon derivative - Organic oxide - Carbonyl group - Organopnictogen compound - Alcohol - Organic oxygen compound - Organooxygen compound - Aromatic alcohol - Organic nitrogen compound - Aromatic heteromonocyclic compound |
| Descripción | This compound belongs to the class of organic compounds known as monobactams. These are compounds comprising beta-lactam ring is alone and not fused to another ring. |
| External Descriptors | organofluorine compound - azetidines - beta-lactam |
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Find and download the COA for your product by matching the lot number on the packaging.
| Lot Number | Certificate Type | Fecha | Articulo |
|---|---|---|---|
| Certificate of Analysis | Aug 21, 2025 | E126609 | |
| Certificate of Analysis | Jun 10, 2025 | E126609 | |
| Certificate of Analysis | Jun 10, 2025 | E126609 | |
| Certificate of Analysis | Jun 10, 2025 | E126609 | |
| Certificate of Analysis | Jun 10, 2025 | E126609 | |
| Certificate of Analysis | Jun 10, 2025 | E126609 | |
| Certificate of Analysis | Jun 10, 2025 | E126609 | |
| Certificate of Analysis | Nov 28, 2024 | E126609 | |
| Certificate of Analysis | Aug 17, 2023 | E126609 | |
| Certificate of Analysis | Aug 07, 2023 | E126609 | |
| Certificate of Analysis | Aug 07, 2023 | E126609 | |
| Certificate of Analysis | Aug 07, 2023 | E126609 | |
| Certificate of Analysis | Aug 07, 2023 | E126609 | |
| Certificate of Analysis | Mar 24, 2023 | E126609 | |
| Certificate of Analysis | Sep 16, 2022 | E126609 | |
| Certificate of Analysis | Nov 11, 2021 | E126609 |
| Solubilidad | Soluble in water (<1 mg/ml at 25 °C), alcohols, DMSO (82 mg/ml at 25 °C), ethanol (82 mg/ml at 25 °C), and methanol. |
|---|---|
| Sensibilidad | Air Sensitive,Heat Sensitive |
| Punto de fusión (°C) | 327.2 - 330.8 °C |
| Peso molecular | 409.400 g/mol |
| XLogP3 | 4.000 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 6 |
| Exact Mass | 409.149 Da |
| Monoisotopic Mass | 409.149 Da |
| Topological Polar Surface Area | 60.800 Ų |
| Heavy Atom Count | 30 |
| Formal Charge | 0 |
| Complexity | 567.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 3 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 0 |
| Covalently-Bonded Unit Count | 1 |
| 1. Chao Meng, Lingye Zhou, Lin Huang, Qi Gu, Xinyue Du, Cheng Wang, Fanglan Liu, Chunhua Xia. (2023) Chlorogenic acid regulates the expression of NPC1L1 and HMGCR through PXR and SREBP2 signaling pathways and their interactions with HSP90 to maintain cholesterol homeostasis. PHYTOMEDICINE, [PMID:38103317] [10.1016/j.phymed.2023.155271] |
| 2. Qiuyao Du, Yunfeng Zhang, Jifen Wang, Bingjie Liu. (2020) Simultaneous determination and quantitation of hypolipidemic drugs in fingerprints by UPLC-Q-TRAP/MS. JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES, [PMID:33991956] [10.1016/j.jchromb.2020.122496] |
| 3. Yao Pan, Ze-Yuan Deng, Xuan Chen, Bing Zhang, Yawei Fan, Hongyan Li. (2020) Synergistic antioxidant effects of phenolic acids and carotenes on H2O2-induced H9c2 cells: Role of cell membrane transporters. FOOD CHEMISTRY, [PMID:33059273] [10.1016/j.foodchem.2020.128000] |
| 4. Ziyao Liu, Xiaohui Zhan, Minggang Yang, Qi Yang, Xianghui Xu, Fang Lan, Yao Wu, Zhongwei Gu. (2016) A magnetic-dependent protein corona of tailor-made superparamagnetic iron oxides alters their biological behaviors. Nanoscale, 8 (14): (7544-7555). [PMID:26949199] [10.1039/C5NR08447D] |
| 5. Juan Zhou, Yi-Qiao Xu, Sheng-Ya Guo, Chun-Qi Li. (2014) Rapid analysis of hypolipidemic drugs in a live zebrafish assay. JOURNAL OF PHARMACOLOGICAL AND TOXICOLOGICAL METHODS, [PMID:25497901] [10.1016/j.vascn.2014.12.002] |
| 6. Wenyue Yu, Yangyu Zhou, Ya Liu, Huan Guo, Lihui Huang, Jinrong Bai, Yue Xiao, Yanping Wu, Kai Zhong, Yina Huang, Hong Gao. (2025) Gut Microbial Catabolism of Prebiotic Theabrownin Yields Bioactive Metabolites for Gut Health and Lipid Homeostasis. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, [PMID:41085220] [10.1021/acs.jafc.5c10211] |
| 7. Xiaoxue He, Tian Liu, Mingjia Sun, Linsheng Wu, Yinghou Wang, Jingdong Xiao, Jin Sun, Qikun Jiang. (2026) Ginsenoside-Engineered Lipid Nanoparticles in Microbeads Enable Oral siRNA Delivery and Targeted Therapy for Ulcerative Colitis. ADVANCED FUNCTIONAL MATERIALS, [PMID:] [10.1002/adfm.202525241] |
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