It07:Ezetimibe

Is an anti-hyperlipemic medication used to lower cholesterol in the blood. It works by reducing aborbtion of cholesterol in the intestines. It is normally taken with other cholesterol lowering drugs (statins eg. ezetimibe/simvastatin) when they are not reducing cholesterol enough or if the patient is unable to take statins. It is produced by Merck and Schering-Plough under the names Ezetrol, Zetia and Zemibe. It was discoved by four Schering-Plough research chemists; Drs. Stuart B. Rosenblum, Duane A. Burnett, John W. Clader and Brian A. McKittrick.

It07:Ezetimibe
It07:Ezetimibe
General
Systematic name	(3R,4S)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4 -hydroxyphenyl)azetidin-2-one
Other names	Ezetimibe,Ezetrol, Zetia and Zemibe
Molecular formula	C24H21F2NO3
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
Molar mass	409.425246 g/mol
Appearance	{{{Appearance}}}
CAS number	{{{CASNo}}}
Properties
Density & phase	{{{Density}}} g/cm³
Solubility in water	{{{Sol_Water}}} g/100 ml (25°C)
Melting point	164-166 K
Boiling point	{{{Bp}}} K
Acidity (pKa)	{{{pKa}}}
Basicity (pKb)	{{{pKb}}}
Chiral rotation [α]D	{{{Rotation}}}°
Viscosity	{{{Viscosity}}} cP at 25°C
Structure
Molecular shape	{{{Mol_Shape}}}
Coordination geometry	{{{Coordination}}}
Crystal structure	{{{Crystal_Structure}}}
Dipole moment	{{{DM}}} D
Hazards
MSDS	External MSDS
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NFPA 704	{{{NFPA}}}
Flash point	{{{Fp}}}°C
R/S statement	R: {{{R-S}}} S: ?
RTECS number	{{{RTECS}}}
Supplementary data page
Structure and properties	n, εr, etc.
Thermodynamic data	Phase behaviour Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
Related compounds
Other anions	{{{Other_anion}}}
Other cations	{{{Ohter_cation}}}
Related compounds	{{{Relative_Compounds}}}
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Structure
Molecular shape	{{{MolShape}}}
Coordination geometry	{{{Coordination}}}
Crystal structure	{{{CrystalStruct}}}
Dipole moment	{{{Dipole}}} D

effects

Ezetimibe is taken by people with high cholestrol levels, normal hypercholesterolaemia. The drug works by reducing the uptake of cholesterol from the small intestines. It works by inhibiting the uptake of cholestrol at the brush border in the small intestines by inhibiting the sterol transporter, Niemann-Pick C1-Like1 (NPC1L1). This reduces the level in the blood while increasing the level of HDL-cholestrol. When combined with a low chloestrol diet and statins cholestrol levels can be lowered sigficiantly. Ezetimibe is precribed when a low cholesterol diet, statines and exercise fail to reduce levels enough. It is precribed because it works in a different way to statins. statins work by reducing cholestrol production in the liver. It is also precribed to hypercholesterolaemia patients, who can't take statins

Doses

ezetimibe is taken oraly

Hyperlipidemias: Children ≥10 years and Adults: 10 mg/day

Sitosterolemia: Adults: 10 mg/day

Elderly: Refer to adult dosing

Risks and side effects

Ezetimibe is not to be taken by any one who is allergic to any of the ingredients, liver diesies or pregnent. Side effects to taking the drug include:

1. Headache

1. Abdominal pain

1. Diarrhoea

1. Constipation

1. Excess gas in the stomach and intestines (flatulence)

1. Nausea

1. Fatigue

1. Allergic skin rash

1. Liver disorders

1. Pain in the muscles or joints (myalgia or arthralgia)

1. Muscle disorders (myopathy or rhabdomyolysis)

1. Inflammation of the pancreas (pancreatitis)

http://www.netdoctor.co.uk/medicines/100004905.html http://www.merck.com/mmpe/lexicomp/ezetimibe.html#N9F8D8

Storage

Store at room temperature and keep dry

Ezetimibe

Unit Cell of crystilline Ezetimibe

Ezetimibe unit cell

http://www.merck.com/mmpe/lexicomp/ezetimibe.html

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IUPAC Systematic name
(3R,4S)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4 -hydroxyphenyl)azetidin-2-one
Ezetimibe
&btnG=Google+Search&meta= Zetia and &btnG=Google+Search&meta= Zemibe]
Indentifiers
ATC Code	{{{ATC_Code}}}
CAS number	{{{CASNo}}}
PubChem (CID)	{{{PubChem}}}
SMILES	{{{SMILES}}}
Chemical Data
Molecular formula	C24H21F2NO3
Molar mass	409.425246 g/mol
Pharmacokinetic Data
Bioavailability	Variable
Protein Binding	>90% to plasma proteins
Metabolism	Undergoes conjugation in the small intestine and liver; forms metabolite (active); may undergo enterohepatic recycling
Half life	22 hours (ezetimibe and metabolite)
Excretion	Feces (78%, 69% as ezetimibe); urine (11%, 9% as metabolite)
Therapeutic considerations
Pregnancy cat.	C
Legal status	{{{Legal_status}}}
Routes	Oral