U 18666A Chemical Properties

Melting point:

195-196.5 °C(lit.)

storage temp. 

2-8°C

solubility 

H₂O: 9 mg/mL at ≤60 °C

form 

crystalline

color 

white

Water Solubility 

Soluble in water at 10mg/ml

Stability:

Stable for 2 years from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20°C for up to 1 week.

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

MSDS

• Language:English Provider:SigmaAldrich

U 18666A Usage And Synthesis

Description

U-18666A (3039-71-2) is an oxidosqualene reductase inhibitor.1 Inhibits the egress of cholesterol from late endosomes and lysosomes.2 U-18666A is also used to study Niemann-Pick disease and for assessing the importance of molecular trafficking through the lysosomal pathway in other conditions.3

Uses

U 18666A is a cell-permeable amphiphilic amino-steroid.

Definition

ChEBI: 3beta-(2-diethylaminoethoxy)androst-5-en-17-one hydrochloride is a hydrochloride obtained by reaction of 3beta-(2-diethylaminoethoxy)androst-5-en-17-one with one equivalent of hydrochloric acid. It is a cholesterol synthesis and transport inhibitor. It has a role as an EC 1.3.1.72 (Delta(24)-sterol reductase) inhibitor, a nicotinic antagonist, a sterol biosynthesis inhibitor, an antiviral agent and a Hedgehog signaling pathway inhibitor. It contains a 3beta-(2-diethylaminoethoxy)androst-5-en-17-one(1+).

General Description

A cell-permeable, amphiphilic amino-steroid that alters intracelluar membrane protein trafficking by impairing intracellular biosynthesis and transport of LDL-derived cholesterol. Reported to exert its effects via the inhibition of 2,3-oxidosqualene-lanosterol cyclase activity. Also reported to inhibit the activity of Δ⁸-sterol isomerase.

Biological Activity

Inhibitor of cholesterol synthesis and cellular transport, and weak inhibitor of hedgehog (Hh) signaling. Reduces serum sterol levels in rats in vivo .

Biochem/physiol Actions

Cell permeable: yes

storage

Desiccate at RT

References

1) Sexton et al. (1983) Effects of 3.beta.-[2-(diethylamino)ethoxy]androst-5-en-17-one on the synthesis of cholesterol and ubiquinone in rat intestinal epithelial cell cultures; Biochemistry 22 5687 2) Liscum and Faust (1989) The intracellular transport of low density lipoprotein-derived cholesterol is inhibited in Chinese hamster ovary cells cultured with 3-?-[2-(diethylamino)ethoxy]androst-5-en-17-one; J. Biol. Chem. 264 11796 3) Cenedella, (2009) Cholesterol synthesis inhibitor U18666A and the role of sterol metabolism and trafficking in numerous pathophysiological processes; Lipids 44 477

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