All Photos(1)

U3633

Sigma-Aldrich

U 18666A

powder

Synonym(s):
(3β)-3-[2-(Diethylamino)ethoxy]androst-5-en-17-one hydrochloride
Empirical Formula (Hill Notation):
C25H41NO2·HCl
CAS Number:
Molecular Weight:
424.06
MDL number:
PubChem Substance ID:
NACRES:
NA.77

assay

≥98% (HPLC)

form

powder

color

white to off-white

mp

195-196.5 °C (lit.)

solubility

H2O: 10 mg/mL≥

storage temp.

2-8°C

SMILES string

Cl[H].[H][C@@]12CC=C3C[C@H](CC[C@]3(C)[C@@]1([H])CC[C@]4(C)C(=O)CC[C@@]24[H])OCCN(CC)CC

InChI

1S/C25H41NO2.ClH/c1-5-26(6-2)15-16-28-19-11-13-24(3)18(17-19)7-8-20-21-9-10-23(27)25(21,4)14-12-22(20)24;/h7,19-22H,5-6,8-17H2,1-4H3;1H/t19-,20-,21-,22-,24-,25-;/m0./s1

InChI key

GZFYZYBWLCYBMI-MYZJJQSMSA-N

Application

U 18666A has been used in fibroblast controls to study the mechanism of increase in autophagy in Niemann-Pick Disease Type C (NPC) cells.

Packaging

5, 25 mg in glass bottle

Biochem/physiol Actions

Inhibitor of cholesterol synthesis (inhibits desmosterol Δ24-reductase). Weak inhibitor of hedgehog (hh) signaling.

Preparation Note

U 18666A is soluble in water at 10 mg/ml.

Storage Class Code

13 - Non Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

John J Reiners et al.
Free radical biology & medicine, 50(2), 281-294 (2010-11-16)
Reactive oxygen species (ROS) can induce lysosomal membrane permeabilization (LMP). Photoirradiation of murine hepatoma 1c1c7 cultures preloaded with the photosensitizer NPe6 generates singlet oxygen within acidic organelles and causes LMP and the activation of procaspases. Treatment with the cationic amphiphilic...
Mee Kian Poh et al.
Antiviral research, 93(1), 191-198 (2011-12-08)
The level of cholesterol in host cells has been shown to affect viral infection. However, it is still not understood why this level of regulation is important for successful infection. We have shown in this study that dengue virus infection...
Hanna Appelqvist et al.
The American journal of pathology, 178(2), 629-639 (2011-02-02)
In the past decade, lysosomal membrane permeabilization (LMP) has emerged as a significant component of cell death signaling. The mechanisms by which lysosomal stability is regulated are not yet fully understood, but changes in the lysosomal membrane lipid composition have...
Anton I Rosenbaum et al.
Proceedings of the National Academy of Sciences of the United States of America, 107(12), 5477-5482 (2010-03-10)
Niemann-Pick type C disease (NPC) is a lysosomal storage disorder causing accumulation of unesterified cholesterol in lysosomal storage organelles. Recent studies have shown that hydroxypropyl-beta-cyclodextrin injections in npc1(-/-) mice are partially effective in treating this disease. Using cultured fibroblasts, we...
Elena Piccoli et al.
Biochemical pharmacology, 82(9), 1234-1249 (2011-09-01)
Patients treated with amiodarone accumulate lysobisphosphatidic acid (LBPA), also known as bis(monoacylglycero)phosphate, in airway secretions and develop in different tissues vacuoles and inclusion bodies thought to originate from endosomes. To clarify the origin of these changes, we studied in vitro...

Articles

Cholesterol Biosynthesis Regulation

The amount of cholesterol that is synthesized in the liver is tightly regulated by dietary cholesterol levels. LDL receptors regulate the cellular transport of lipid rich low density lipoprotein (LDL) particles.

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