Ezetimibe - CAS 163222-33-1
Catalog number:
163222-33-1
Category:
Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C24H21F2NO3
Molecular Weight:
409.4
COA:
Inquire
Targets:
Others
Description:
Ezetimibe produces a significant reduction in total cholesterol, LDL cholesterol, and triglycerides as well as a small but significant increase in HDL cholesterol.
Publictions citing BOC Sciences Products
  • >> More
Purity:
>98%
Synonyms:
SCH-58235
MSDS:
Inquire
1. Heterocyclic ring scaffolds as small-molecule cholesterol absorption inhibitors
Tobias Ritter, Lisbet Kværnø, Moritz Werder, Helmut Hauser and Erick M. Carreira*. Org. Biomol. Chem. , 2005, 3 , 3514–3523
The oxazolidinone scaffold 2 has previously been suggested to serve as a structuralmimic of the β-lactamof ezetimibe (1). Our ab initio geometry optimizations (Fig. 2) additionally suggested that the isoxazoline 3 and the pyrazoline 4 position three out of plane exit vectors in a manner that corresponds well to the b-lactam ring of ezetimibe. The excellent overlaps of the substituents are illustrated by superposition of each of the three heterocycles 2–4 with the b-lactam core found in ezetimibe. In order to focus on the exit vectors from the heterocyclic core, the flexible hydroxypropyl side chain in ezetimibe, which is not expected to strongly favor any single conformation,was replaced by a methyl group in the calculations.
2. Metabolism-guided drug design
Antonia F. Stepan, Vincent Mascitti, Kevin Beaumont and Amit S. Kalgutkar*. Med. Chem. Commun., 2013, 4, 631–652
An excellent example of drug design via an understanding of the bioactivity profile of drug metabolites becomes evident with the cholesterol absorption inhibitor ezetimibe (124) (Fig. 33). Discovery efforts that ultimately led to ezetimibe initially began as a program to discover novel inhibitors of acyl coenzyme A cholesterol acyltransferase (ACAT) using rodent animal models as a pharmacology screen (in the absence of relevant in vitro assays to rank order intrinsic potency). An interesting finding in this effort was the robust reduction of serum cholesterol and blockade of hepatic cholesterol accumulation by certain azetidinone derivatives (e.g.,(-)-SCH48461, 119), which had virtually no inhibitory activity against ACAT. A substantial part of the discovery effort was next devoted to the understanding of the molecular target of 119, which was further confounded by the fact that 119 is extensively metabolized in vivo, making it unclear as to what the active species is. Bioactivity profiling using bile from animals dosed with [14C]-119 led to the characterization of several active metabolites of 119, which included phenols (compounds 120–122) derived from the mono- and bis-O-demethylation and even a glucuronide conjugate (123).
3. Black rice and anthocyanins induce inhibition of cholesterol absorption in vitro
Shu-Long Yao, Ying Xu, Yan-Yan Zhang and Yan-Hua Lu*. Food Funct., 2013, 4, 1602–1608
To examine the effect of anthocyanins on cholesterol uptake in enterocytes, Caco-2 cells were used as an in vitro model. In this study, Ezetimibe, an inhibitor of cholesterol uptake across the gut wall, was used as a positive control, and it caused a substantial depression of cholesterol uptake. In Fig. 7, it is shown that both Cy-3-G and Pn-3-G significantly and in a dose dependent manner suppressed cholesterol uptake. At 40 mgmL-1, Pn-3-G resulted in virtually equivalent reduction of cholesterol uptake compared with Ezetimibe.
4. Synthesis of a fluorinated Ezetimibe analogue using radical allylation of α-bromo-α-fluoro-β-lactam
Atsushi Tarui, Ayumi Tanaka, Masakazu Ueo, Kazuyuki Sato, Masaaki Omote and Akira Ando*. New J. Chem., 2015, 39, 9325—9329
Ezetimibe has been attractive as a novel type of antihyperlipidemic agent for a modern adult disease. This type of drug inhibits a transporter for intestinal cholesterol absorption, Niemann–Pick C1 like 1 (NPC1L1). NPC1L1 is known to provide a main route of cholesterol absorption, therefore Ezetimibe has provided a new course of medication different from HMG-CoA reductase inhibitors such as statins. The backbone structure of Ezetimibe has aβ-lactam core and an alkyl side chain at the C3 position of the β-lactam ring (Fig. 1). Many structure–activity relationship (SAR) studies of several azetidinone compounds have been reported during the past two decades, since these compounds are candidate cholesterol absorption inhibitors. Among the candidate compounds, Clader and co-workers have reported that a 3-fluoroazetidinone compound (1) worked well (Fig. 1). However, the synthetic method for the 3-fluoroazetinone core was not described clearly, and there are no reports on the bioactivity of 3-fluoroazetidinone analogues. Nowadays, organofluorine compounds are important in medicinal chemistry, therefore this type of structuremodification is accepted as a standard target modification in modern SAR studies. In this paper, we describe an effective and short synthetic route for a fluorine-containing Ezetimibe analogue on aβ-lactam core using a-brα-bromo-α-fluoro-β-lactam as a key in termediate.
Molecular Weight Calculator Molarity Calculator Solution Dilution Calculator

Related Products


Epothilone F
(CAS: 208518-52-9)

Epothilone F, an active metabolite of Epothilone D, prevents cancer cells from dividing by interfering with tubulin.

RSL3
(CAS: 1219810-16-8)

RSL3, a glutathione peroxidase 4 inhibitor, has been found to show selective response to tumor cells with oncogenic RAS.

CAS 36062-04-1 Tetrahydrocurcumin

Tetrahydrocurcumin
(CAS: 36062-04-1)

Tetrahydrocurcumin is being studied for the treatment of cancer and dementia. It has antioxidant and anti-inflammatory properties. Tetrahydrocurcumin has been s...

CAS 502-55-6 Dixanthogen

Dixanthogen
(CAS: 502-55-6)

Dixanthogen is the dominant species of xanthate adsorption on pyrite used as an ectoparasiticide.

CAS 23496-41-5 Peimine

Peimine
(CAS: 23496-41-5)

Anti-inflammatory agent. MAPK inhibitor. Inhibits p38, ERK and JNK phosphorylation. Inhibits NFκB activation. Shows antitussive, expectorant and anti-inflammato...

D-Melphalan
(CAS: 13045-94-8)

D-Melphalan is an isomer of melphalan. Melphalan is Alkylating agent and DNA synthesis inhibitor using for the treatment of Multiple myeloma.

CAS 4754-39-6 Deoxyadenosine

Deoxyadenosine
(CAS: 4754-39-6)

Deoxyadenosine is a substrate of bacterial methylthioadenosine/S-adenosylhomocysteine (MTA/SAH) nucleosidase and a product inhibitor produced by radical SAM enz...

CAS 6859-01-4 Isorhynchophylline

Isorhynchophylline
(CAS: 6859-01-4)

Rhynchophylline and isorhynchophylline act as noncompetitive antagonists of the NMDA receptor and that this property may contribute to the neuroprotective and a...

Vadadustat
(CAS: 1000025-07-9)

Vadadustat is a potent Hypoxia-inducible factor-proline dioxygenase inhibitor, which leads to stabilization and increased levels of HIFα. It is used for the tre...

DPY-2103
(CAS: 4792-10-3)

DPY-2103 is a useful intermediate for chemical synthesis of a number of biologically active drugs.

EBI-907
(CAS: 1581764-31-9)

EBI-907, an isoquinolin derivative, has been found to be a B-RafV600E inhibitor and exhibit activities against some oncogenic kinases at some extent. The resear...

EPZ020411
(CAS: 1700663-41-7)

EPZ020411, with potent anticancer activity, is an orally bioactive, selective inhibitor of PRMT6/8/1 with over 100-fold selective for other histone methyltransf...

Presatovir
(CAS: 1353625-73-6)

Presatovir is a viral fusion protein inhibitor originated by Gilead Sciences with EC50 value of 0.43 nM. GS-5806 can inhibit a broad range of respiratory syncyt...

CAS 68278-23-9 Eflornithine hydrochloride

Eflornithine hydrochloride
(CAS: 68278-23-9)

Eflornithine hydrochloride is a drug found to be effective in the treatment of facial hirsutism. It is a "suicide inhibitor," irreversibly binding to Ornithine ...

CAS 840-80-2 Acroteben

Acroteben
(CAS: 840-80-2)

Acroteben is a bio-active chemical but no detailed information has been published yet.

RO 5263397
(CAS: 1357266-05-7)

RO5263397 is a selective trace amine-associated receptor 1(TAAR1) agonist. TAAR1 is a drug discovery target for cocaine addiction. RO5263397 is efficacious in r...

CAS 72432-03-2 Miglitol

Miglitol
(CAS: 72432-03-2)

Miglitol is an oral anti-diabetic drug.

AT-61
(CAS: 300669-68-5)

AT-61 is a nonnucleoside analogue inhibitors of hepatitis B virus (HBV) replication.

CAS 150-13-0 4-Aminobenzoic Acid

4-Aminobenzoic Acid
(CAS: 150-13-0)

4-Aminobenzoic Acid, also called as PABA, was used as sunscreening agent at the past due to its UV absorption and antifibrotic properties.

JNJ-42259152
(CAS: 1301167-87-2)

This molecular is a phosphodiesterase 10A PET tracer. Related studies show that PDE10A activity can be reliably quantified and simplified using a reference tiss...

Chemical Structure

CAS 163222-33-1 Ezetimibe

Quick Inquiry

Verification code

Featured Items