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AB254455

Ezetimibe, cholesterol absorption inhibitor

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MW 409.4 Da, Purity >98%. 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.

View Alternative Names

NPC1 LIKE 1, NPC1 Niemann Pick disease type C1 gene like 1, NPC1L1, NPC1L1 splice variant, NPCL1_HUMAN, Niemann Pick disease type C1 gene like 1, Niemann-Pick C1-like protein 1, Truncated Niemann Pick C1 like protein 1

1 Images
Chemical Structure - Ezetimibe, cholesterol absorption inhibitor (AB254455)
  • Chemical Structure

Supplier Data

Chemical Structure - Ezetimibe, cholesterol absorption inhibitor (AB254455)

2D chemical structure image of ab254455, Ezetimibe, cholesterol absorption inhibitor

Key facts

CAS number

163222-33-1

Purity

>98%

Form

Solid

form

Molecular weight

409.4 Da

Molecular formula

C<sub>2</sub><sub>4</sub>H<sub>2</sub><sub>1</sub>F<sub>2</sub>NO<sub>3</sub>

PubChem

150311

Nature

Synthetic

Solubility

Soluble in DMSO to 50 mM

Soluble 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

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Product details

Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months
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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
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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.
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Product protocols

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Assay Kits

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Assay Kits

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