Avasimibe

Names

[ Name ]:
Avasimibe

[Synonym ]:
2,6-Diisopropylphenyl [(2,4,6-triisopropylphenyl)acetyl]sulfamate
Sulfamic acid, N-[2-[2,4,6-tris(1-methylethyl)phenyl]acetyl]-, 2,6-bis(1-methylethyl)phenyl ester
[2,6-di(propan-2-yl)phenyl] N-[2-[2,4,6-tri(propan-2-yl)phenyl]acetyl]sulfamate
2,6-di(propan-2-yl)phenyl {[2,4,6-tri(propan-2-yl)phenyl]acetyl}sulfamate
Avasimibe
CI-1011

Biological Activity

[Description]:

Avasimibe is an oral inhibitor of acyl-Coenzyme A:cholesterol acyltransferase (ACAT) with IC50s of 24 and 9.2 µM for ACAT1 and ACAT2, respectively.

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> Acyltransferase

Research Areas >> Cancer

[References]

[1]. Tardif JC et al. Effects of the acyl coenzyme A:cholesterol acyltransferase inhibitor avasimibe on human atherosclerotic lesions. Circulation, 2004 Nov 23, 110(21):3372-7.

[2]. Raal FJ et al. Avasimibe, an ACAT inhibitor, enhances the lipid lowering effect of atorvastatin in subjects with homozygousfamilial hypercholesterolemia. Atherosclerosis, 2003 Dec, 171(2):273-9.

[3]. Delsing DJ et al. Acyl-CoA:cholesterol acyltransferase inhibitor avasimibe reduces atherosclerosis in addition to its cholesterol-lowering effect in ApoE*3-Leiden mice. Circulation, 2001 Apr 3, 103(13):1778-86.

[Related Small Molecules]

LCQ-908 | DGAT-3 | A922500 | Xanthohumol | PF-04620110 | AZD7687 | MGAT2-IN-1 | DGAT-1 inhibitor 2 | DGAT1-IN-1 | K-604 dihydrochloride | PF-06471553 | YM17E | ABT-046 | RP 70676 | Furan-2-carboxylic acid

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Melting Point ]:
178-180° (Lee); mp 169.5-170.4° (Dozeman)

[ Molecular Formula ]:
C₂₉H₄₃NO₄S

[ Molecular Weight ]:
501.721

[ Exact Mass ]:
501.291290

[ PSA ]:
80.85000

[ LogP ]:
9.34

[ Appearance of Characters ]:
white to tan

[ Index of Refraction ]:
1.529

[ Storage condition ]:
room temp

[ Water Solubility ]:
DMSO: ≥40mg/mL

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: CY1482550

CHEMICAL NAME :: Benzeneacetamide, N-((2,6-bis(1-methylethyl)phenoxy)sulfonyl)-2,4,6-tri s(1-methylethyl)-

CAS REGISTRY NUMBER :: 166518-60-1

LAST UPDATED :: 199712

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C29-H43-N-O4-S

MOLECULAR WEIGHT :: 501.79

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 137 gm/kg/13W-C

TOXIC EFFECTS :: Behavioral - food intake (animal) Skin and Appendages - hair Nutritional and Gross Metabolic - weight loss or decreased weight gain

REFERENCE :: FAATDF Fundamental and Applied Toxicology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1981- Volume(issue)/page/year: 36(1, Pt 2),274,1997

Safety Information

[ RIDADR ]:
NONH for all modes of transport

[ HS Code ]:
2935009090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2935009090

[ Summary ]:
2935009090 other sulphonamides VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:35.0%

Articles

Statin therapy alone and in combination with an acyl-CoA:cholesterol O-acyltransferase inhibitor on experimental atherosclerosis.

Pathophysiol. Haemost. Thromb. 36(1) , 9-17, (2007)

The ability to modify the enzymatic processes involved in promoting atherosclerotic plaque disruption and to serially monitor atherosclerotic evolution could provide novel information in the managemen...

Coronary circulatory function in patients with the metabolic syndrome.

J. Nucl. Med. 52(9) , 1369-77, (2011)

The metabolic syndrome affects 25% of the U.S. population and greatly increases the risk of diabetes and coronary artery disease (CAD). We tested the hypothesis that the metabolic syndrome is associat...

Avasimibe and atorvastatin synergistically reduce cholesteryl ester content in THP-1 macrophages.

Eur. J. Pharmacol. 451(1) , 11-7, (2002)

Evidence suggests that the inhibition of both acyl-CoA:cholesterol acyltransferase and hydroxymethyl glutaryl-CoA reductase causes a synergistic direct antiatherosclerotic effect on the vessel wall. T...

Related Compounds

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