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Activity Type | Activity Value -log(M) | Mechanism of Action | Activity Reference | Publications (PubMed IDs) |
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SKU | Size | Availability | Price | Qty |
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E126609-50mg | 50mg | In stock | $86.90 | |
E126609-250mg | 250mg | In stock | $391.90 | |
E126609-1g | 1g | In stock | $1,409.90 | |
E126609-5g | 5g | In stock | $6,342.90 | |
E126609-25g | 25g | In stock | $28,540.90 |
Potent selective cholesterol absorption inhibitor
Synonyms | Ezetimibe | 163222-33-1 | Zetia | Ezetrol | Ezedoc | Sch 58235 | SCH58235 | (3R,4S)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)azetidin-2-one | SCH-58235 | (-)-Sch 58235 | ezetimiba | ezetimibum | UNII-EOR26LQQ24 | (3R,4S)-1-(4-fluorophenyl)- |
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Specifications & Purity | Moligand™, ≥99% |
Biochemical and Physiological Mechanisms | Ezetimibe inhibits intestinal cholesterol absorption by preventing cholesterol uptake by Niemann-Pick C1 Like 1 (NPC1L1) protein that was found critical for the intestinal absorption of cholesterol. Ezetimibe selectvely blocks cholesterol absorption witho |
Storage Temp | Store at -20°C |
Shipped In | Ice chest + Ice pads |
Grade | Moligand™ |
Action Type | ANTAGONIST, INHIBITOR |
Mechanism of action | Niemann-Pick C1-like protein 1 inhibitor |
Note | Toxic, refer to SDS for further information. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details. |
Product Description | 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. |
ALogP | 4 |
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IUPAC Name | (3R,4S)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)azetidin-2-one |
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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 |
InChi Key | OLNTVTPDXPETLC-XPWALMASSA-N |
Canonical SMILES | C1=CC(=CC=C1C2C(C(=O)N2C3=CC=C(C=C3)F)CCC(C4=CC=C(C=C4)F)O)O |
Isomeric 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 |
Alternate CAS | 163222-33-1 |
PubChem CID | 150311 |
MeSH Entry Terms | (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 |
Molecular Weight | 409.43 |
DrugBank Ligand | DB00973 |
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PubChem CID | 150311 |
CAS Registry No. | 163222-33-1 |
ChEMBL Ligand | CHEMBL1138 |
Wikipedia | Ezetimibe |
PEP | ezetimibe |
RCSB PDB Ligand | H56 |
DrugCentral Ligand | 1125 |
Enter Lot Number to search for COA:
To view the certificate results,please click on a Lot number.For Lot numbers from past orders,please use our order status section
Lot Number | Certificate Type | Date | Item |
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H2330365 | Certificate of Analysis | Aug 17, 2023 | E126609 |
H2330366 | Certificate of Analysis | Aug 17, 2023 | E126609 |
H2330369 | Certificate of Analysis | Aug 17, 2023 | E126609 |
H2330371 | Certificate of Analysis | Aug 17, 2023 | E126609 |
H2330373 | Certificate of Analysis | Aug 17, 2023 | E126609 |
H2330400 | Certificate of Analysis | Aug 17, 2023 | E126609 |
K2104154 | Certificate of Analysis | Aug 07, 2023 | E126609 |
K2104155 | Certificate of Analysis | Aug 07, 2023 | E126609 |
K2104243 | Certificate of Analysis | Aug 07, 2023 | E126609 |
K2104245 | Certificate of Analysis | Aug 07, 2023 | E126609 |
C2320442 | Certificate of Analysis | Mar 24, 2023 | E126609 |
B1527007 | Certificate of Analysis | Sep 16, 2022 | E126609 |
D2301019 | Certificate of Analysis | Nov 11, 2021 | E126609 |
Solubility | 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. |
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Sensitivity | Air Sensitive,Heat Sensitive |
Melt Point(°C) | 327.2 - 330.8 °C |
Pictogram(s) | GHS09 |
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Signal | Warning |
Hazard Statements | H410:Very toxic to aquatic life with long lasting effects |
Precautionary Statements | P273:Avoid release to the environment. P501:Dispose of contents/container to ... P391:Collect spillage. |
1. Chao Meng, Lingye Zhou, Lin Huang, Qi Gu, Xinyue Du, Cheng Wang, Fanglan Liu, Chunhua Xia. (2024) 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, 123 (155271). [PMID:38103317] |
1. Oswald S, König J, Lütjohann D, Giessmann T, Kroemer HK, Rimmbach C, Rosskopf D, Fromm MF, Siegmund W. (2008) Disposition of ezetimibe is influenced by polymorphisms of the hepatic uptake carrier OATP1B1.. Pharmacogenet Genomics, 18 (7): (559-68). [PMID:18551036] |
2. Huang CS, Yu X, Fordstrom P, Choi K, Chung BC, Roh SH, Chiu W, Zhou M, Min X, Wang Z. (2020) Cryo-EM structures of NPC1L1 reveal mechanisms of cholesterol transport and ezetimibe inhibition.. Sci Adv, 6 (25): (eabb1989). [PMID:32596471] |
3. Chao Meng, Lingye Zhou, Lin Huang, Qi Gu, Xinyue Du, Cheng Wang, Fanglan Liu, Chunhua Xia. (2024) 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, 123 (155271). [PMID:38103317] |