Ezetimibe

Description

N-(4-(Benzyloxy)benzylidene)-4-fluoroaniline · CAS 163222-33-1 · C24H21F2NO3. UNII EOR26LQQ24. Melting Point: 163°C; Melting Point: 164-166 °C; Solubility: 8.46e-03 g/L.

Identification

CAS Registry Number	163222-33-1
PubChem CID	150311
Molecular formula	C24H21F2NO3
IUPAC name	(3R,4S)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)azetidin-2-one
UNII (FDA)	EOR26LQQ24

Computed Descriptors

Molecular Weight	409.4
XLogP3	4
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	6
Exact Mass	409.14894986
Monoisotopic Mass	409.14894986
Topological Polar Surface Area	60.8
Heavy Atom Count	30
Formal Charge	0

Physical & Chemical Properties

Melting Point	163°C
Melting Point	164-166 °C
Solubility	8.46e-03 g/L
LogP	4.5
LogP	3.64

Physical description & handling notes

• Solid
• White solid
• Practically insoluble
• Specific optical rotation: -33.9 degrees at 22 °C/D (c = 3 in methanol)
• 191.17 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
• 188.72 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

GHS Hazard Classification

Reported hazard statements	H410 (85%)

Documented Uses

• So far only one cholesterol absorption inhibitor has reached the market: Ezetimibe. Although the detailed mechanism of action is not yet quite clear, /Ezetimibe/ inhibits the intestinal absorption of cholesterol and as a consequence lowers total plasma cholesterol.
• Use (kg; approx.) in Germany (2009): >1000
• Consumption (g per capita; approx.) in Germany (2009): 0.0122
• Preparation: S.B. Rosenblum et al., WO 9508532; eidem US 5767115 (1995, 1998 both to Schering)
• Ezetimibe is a dyslipidemic agent used to treat people with hyperlipidemia. It was FDA-approved in 2002. Ezetimibe is the most commonly used nonstatin agent, which lowers LDL-C levels by 13% to 20%. Ezetimibe is an inhibitor of intestinal cholesterol absorption. It is indicated to reduce total cholesterol, low-density lipoprotein (LDL), apolipoprotein B (apo B), and non-high-density lipoprotein (HDL) in patients with primary hyperlipidemia, mixed hyperlipidemia, familial hypercholesterolemia (HoFH), and homozygous
• Ezetimibe is an inhibitor of intestinal cholesterol absorption that is widely used in the therapy of hypercholesterolemia, usually in combination with other agents. Ezetimibe therapy is associated with a low rate of serum aminotransferase elevations and clinically apparent liver injury due to ezetimibe occurs, but is rare.

Synonyms

Ezetimibe; 163222-33-1; Zetia; Ezetrol; Ezedoc; (3R,4S)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)azetidin-2-one; Sch 58235; SCH-58235; SCH58235; ezetimiba; EOR26LQQ24; ezetimibum; DTXSID1044223; 2-Azetidinone, 1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)-, (3R,4S)-; MK0653; NSC-758923

Frequently Asked Questions

What are the CAS number and molecular formula of N-(4-(Benzyloxy)benzylidene)-4-fluoroaniline?

CAS 163222-33-1; molecular formula C24H21F2NO3; molecular weight — g/mol.

What other names is N-(4-(Benzyloxy)benzylidene)-4-fluoroaniline known by?

Ezetimibe, 163222-33-1, Zetia, Ezetrol, Ezedoc, (3R,4S)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)azetidin-2-one.

Is N-(4-(Benzyloxy)benzylidene)-4-fluoroaniline classified as hazardous?

Hazard statements reported: H410.

What are the key physical properties of N-(4-(Benzyloxy)benzylidene)-4-fluoroaniline?

Melting Point: 163°C; Melting Point: 164-166 °C; Solubility: 8.46e-03 g/L; LogP: 4.5.

Facts on this page are taken from PubChem (US National Library of Medicine) and Wikidata. Grade-specific data — assay, moisture, particle size, packaging, shelf life — is issued per batch on the COA and is not published here.