SCH 60969
Ezetimibe
CAS: 163222-33-1
Molecular Formula: C24H21F2NO3
SCH 60969 - Names and Identifiers
| Name | Ezetimibe |
| Synonyms | ZETIA Ezetimide Ezatimibe SCH 60969 Ezetimibe Ezetimibe-001 EzetimibeC24H21F2N03 Ticagrelor and its interMediate 1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxy-propyl]-4-(4-hydroxyphenyl)-azetidin-2-one 1-(4-Flurophenyl)-(3R)-3-(4-flurophenyl)-(3S)-hydroxypropyl-(4S)-(4-hydroxyphenyl)-2-azetidinone (3R,4S)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)azetidin-2-one Ezetimibe 1-(4-Fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxy-propyl]-4-(4-hydroxyphenyl)-azetidin-2-one (3R,4S)-1-(4-Fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)-2-azetidinone, Sch-58235 |
| CAS | 163222-33-1 |
| EINECS | 682-606-0 |
| InChI | InChI=1/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 |
SCH 60969 - Physico-chemical Properties
| Molecular Formula | C24H21F2NO3 |
| Molar Mass | 409.43 |
| Density | 1.334±0.06 g/cm3(Predicted) |
| Melting Point | 164-166°C |
| Boling Point | 654.9±55.0 °C(Predicted) |
| Specific Rotation(α) | D22 -33.9° (c = 3 in methanol) |
| Flash Point | 349.9°C |
| Solubility | Soluble in water (<1 mg/ml at 25 °C), alcohols, DMSO (82 mg/ml at 25 °C), ethanol (8 |
| Vapor Presure | 4.83E-18mmHg at 25°C |
| Appearance | powder |
| Color | White or off-white |
| pKa | 9.72±0.30(Predicted) |
| Storage Condition | 2-8°C |
| 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. |
| Refractive Index | 1.623 |
| In vitro study | Ezetimibe significantly reduced total cholesterol, LDL cholesterol and triglycerides, and moderately increased high-density lipoprotein cholesterol. In Caco-2 cells, Ezetimibe reduced cholesterol transport by 31%, but did not affect yellow alcohol transport. Ezetimibe causes the surface receptor SR-BI,Niemann-Pick type C1 analog protein 1,ATP-binding cassette transporter, subfamily A(ABCA1) and the nuclear receptor retinoic acid receptor (RAR) gamma, the mRNA expression of sterol regulatory element binding proteins (SREBPs)-1 and -2, the beta subunit of Liver X receptor (LXR), is significantly reduced. |
| In vivo study | In Western-style, low-fat, cholesterol-free mice, Ezetimibe reduced plasma cholesterol levels from 964 to 374 mg/dL, from 726 to 231 mg/dL, and from 516 to 178 mg/dL. Ezetimibe reduced the surface area of aortic atherosclerotic lesions from 20.2% in the control group to 4.1% in the Western diet group and 7.0% in the mice on the low fat cholesterol diet. Ezetimibe reduced the cross-sectional area of carotid atherosclerotic lesions by 97% in the Western and low-fat cholesterol diet groups and 91% in cholesterol-free mice. In Western, low-fat and cholesterol-free mice, Ezetimibe inhibited cholesterol absorption, decreased plasma cholesterol, increased high-density lipoprotein levels, and inhibited atherosclerosis. In preclinical animal models, Ezetimibe effectively inhibits cholesterol transport across the intestinal wall, thereby reducing plasma cholesteremia. In rats, Ezetimibe eliminates the pancreatic exocrine function of the intestine while maintaining bile flow. In cholesterol-fed hamsters, Ezetimibe reduced plasma cholesterol and liver cholesterol accumulation with an ED50 of 0.04 mg/kg. |
SCH 60969 - Risk and Safety
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. S24/25 - Avoid contact with skin and eyes. |
| HS Code | 29337900 |
SCH 60969 - Reference Information
| introduction | ezetimibe is a white crystalline powder, easily soluble in ethanol, methanol and acetone, insoluble in water, melting point is about 163 ℃, stable at normal temperature. Ezetimibe only acts on the small intestine, reducing the transport of intestinal cholesterol to the liver and reducing its storage by inhibiting the absorption of cholesterol; it can strengthen the clearance of cholesterol in the blood, thereby reducing plasma cholesterol levels. |
| pharmacological action | ezetimibe is orally absorbed and combines with glucuronide to form an active substance, ezetimibe-glucuronide, which is excreted through bile and kidney. After oral administration, the blood drug peak concentration is reached within 4~12h, Cmax is 3.4~5.5 mg/mL, bioavailability is between 35% ~ 60%, t1/2 is about 22h. Ezetimibe mainly acts on exogenous cholesterol, while statins mainly act on the synthesis of cholesterol in the liver, so the two drugs have a synergistic effect. The combination of ezetimibe and statin lipid-lowering drugs is 8 times the cholesterol-lowering effect of statins alone. |
| use | ezetimibe is a new type of selective cholesterol absorption inhibitor, which inhibits the absorption of cholesterol in the diet and in the intestine by combining with the small intestinal brush border membrane vesicle membrane protein (relative molecular mass 145X103), reduce the cholesterol content in serum and liver. Hyperlipidemia is one of the high-risk factors for coronary heart disease. The drugs for clinical treatment of hyperlipidemia mainly include cholesterol synthesis inhibitors (such as statins), phenoxy acids (such as fibrates), bile acid chelating agent (such as cholestyramine) and other (such as nicotinic acid analogs), etc. |
| cholesterol-lowering drug | ezetimibe, also known as ezetimibe and etimibe, is the first selective cholesterol absorption inhibitor jointly developed by Schering-Plough and Merck. This product is the first cholesterol absorption selective inhibitor drug approved by the US FDA. The trade name is "Yishi Chun" and "EZETROL". Ezetimibe is a new type of selective cholesterol absorption inhibitor, and it is also the first selective inhibitor of intestinal cholesterol absorption. Its mechanism of action is different from other lipid-lowering drugs (such as: statins, Cholic acid chelating agent, phenoxyacid derivative and plant-based sterol esterification), this product is combined with the small intestine brush border membrane vesicle membrane protein (relative molecular mass 145X103), inhibits the small intestine's absorption of cholesterol in the diet and transported into the intestine through bile, and reduces the cholesterol content in serum and liver. Unlike cholic acid chelating agents, ezetimibe does not affect the absorption of cholesterol esters, other steroids (such as taurocholic acid), triacylglycerol and fat-soluble vitamins. Its pharmacological effect has nothing to do with the inhibition of acetyl-CoA-cholesterol acetyltransferase (ACAT) and the expression of LDL receptor (scavenger receptor). After being absorbed, ezetimibe is combined with glucuronic acid in the liver and then circulates through the liver and intestines, and is almost specifically located in small intestinal mucosal cells. This product can be used alone or in combination with HMG-CoA reductase inhibitors (statins) to treat primary (heterozygous familial or non-familial) hypercholesterolemia, homozygous familial hypercholesterolemia (HoFH), homozygous sitosterolemia (or phytosterolemia). Andy edited and sorted out the above information. |
| biological activity | Ezetimibe (SCH-58235) is an effective and selective cholesterol absorption inhibitor used to reduce cholesterol. |
| target | TargetValue NPC1L1 |
| Target | Value | in vitro studies | Ezetimibe significantly reduce total cholesterol, LDL cholesterol and triglycerides, and moderately increase high density lipoprotein cholesterol. In Caco-2 cells, Ezetimibe reduces 31% cholesterol transport, but does not affect flavol transport. Ezetimibe leads to surface receptor SR-BI,Niemann-Pick type C1-like protein 1,ATP binding cassette transporter, subgroup A(ABCA1) and nuclear receptor retinoic acid receptor (RAR) gamma, sterol regulatory element binding protein (SREBP)-1 and -2, liver X receptor (LXR) beta subunit mRNA expression is significantly reduced. |
| in vivo studies | western-style mice with a low-fat and cholesterol-free diet Ezetimibe reduce plasma cholesterol levels from 964 to 374 mg/dL, from 726 to 231 mg/dL, and from 516 to 178 mg/dL, respectively. Ezetimibe reduced the surface area of aortic atherosclerotic lesions, from 20.2% in the control group to 7.0% in 4.1% and low-fat cholesterol diet mice in the western diet group. Ezetimibe reducing the cross-sectional area of carotid atherosclerotic lesions, it was 97% in the western and low-fat cholesterol diet group and 91% in cholesterol-free mice. In mice on a western, low-fat and cholesterol-free diet, Ezetimibe inhibited cholesterol absorption, lowered plasma cholesterol, increased high-density lipoprotein levels, and inhibited atherosclerosis. In preclinical animal models, Ezetimibe effectively inhibit cholesterol transport through the intestinal wall, thereby reducing plasma cholesterolemia. In rats, pancreatic exocrine function of the intestine was Ezetimibe eliminated while bile flow was maintained. In cholesterol-fed hamsters, plasma cholesterol and liver cholesterol accumulation were Ezetimibe reduced with an ED50 of 0.04 mg/kg. |
| EPA chemical information | The information is: ofmpub.epa.gov provides (external link) |
| toxic substance data | The information is: pubchem.ncbi.nlm.nih.gov Provide (external link) |
Last Update：2024-04-09 21:54:55
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