Description
Key facts
CAS number:163222-33-1,
Purity:>98%,
Form:SolidSee storage information,
Molecular weight:409.4 Da,
Molecular formula:C24H21F2NO3,
PubChem:150311,
Nature:Synthetic,
Solubility:Soluble in DMSO to 50 mMSoluble in ethanol to 25 mM,
Biochemical name:Ezetimibe,
Biological description:Potent selective cholesterol absorption inhibitor. Inhibits cholesterol absorption in the intestine by preventing uptake by the Niemann-Pick C1-like 1 (NPC1L1) protein, a cholesterol transporter. Ezetimibe reduces plasma cholesterol levels from 964 to 374 mg/dL, from 726 to 231 mg/dL, and from 516 to 178 mg/dL in the western, low-fat, and cholesterol-free diet mice, respectively.,
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,
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,
IUPAC Name:(3R,4S)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)azetidin-2-one
Product details:
Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months
Properties and Storage Information:
Shipped at conditions-Ambient - Cannot Ship with Ice, Appropriate short-term storage conditions-Ambient, Appropriate long-term storage conditions-Ambient, Storage information-Store under desiccating conditions
Supplementary Information:
This supplementary information is collated from multiple sources and compiled automatically.
Niemann Pick C1 Like 1 (NPC1L1) also known simply as NPC1L1 is a protein that plays a critical role in the intestinal absorption of dietary cholesterol. NPC1L1 is a multi-pass membrane protein located in the brush border of small intestine enterocytes and also present in the liver. It consists of approximately 1334 amino acids giving it a mass of around 148 kDa. This protein serves as a conduit for cholesterol as it moves across the cell membrane taking part in the cholesterol uptake mechanism.
Biological function summary
NPC1L1 is essential for maintaining cholesterol homeostasis within the body. It is not part of a larger protein complex but works closely with other proteins to facilitate lipid incorporation into chylomicrons. Inhibitors of NPC1L1 such as ezetimibe effectively reduce blood cholesterol levels by blocking this absorption route. The presence of NPC1L1 on the apical surface of enterocytes emphasizes its function in the body's cholesterol metabolism impacting systemic lipid levels.
Pathways
NPC1L1 is involved with cholesterol absorption pathways an important component of lipid homeostasis. This pathway involves other important proteins such as the Niemann-Pick C1 protein (NPC1) and ATP-binding cassette transporters like ABCG5 and ABCG8. These proteins along with NPC1L1 coordinate the regulation of cholesterol levels by balancing absorption and excretion aiding in maintaining overall homeostasis in the body.
NPC1L1's role in cholesterol regulation links it directly to atherosclerosis and hypercholesterolemia. Elevated levels of cholesterol can lead to plaque formation in arteries contributing to coronary artery disease. Ezetimibe a drug targeting NPC1L1 demonstrates this connection as it helps lower cholesterol levels by inhibiting NPC1L1 function. Moreover interactions with other proteins like APOB (Apolipoprotein B) and LDL receptor exemplify the broader implication of NPC1L1 in lipid metabolism disorders.
