U3633
U 18666A
≥98% (HPLC), cholesterol synthesis inhibitor, powder
Synonym(s):
(3β)-3-[2-(Diethylamino)ethoxy]androst-5-en-17-one hydrochloride
Sign In to View Organizational & Contract Pricing.
Select a Size
Change View
About This Item
Empirical Formula (Hill Notation):
C25H41NO2·HCl
CAS Number:
Molecular Weight:
424.06
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
MDL number:
Product Name
U 18666A, powder
assay
≥98% (HPLC)
Quality Level
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
General description
U18666A, a cationic amphiphile/sterol, has a diethylaminoethyl chain linked to the 3-hydroxyl. It is an androstenolone derivative.
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.
U 18666A has been used:
- as a competitive inhibitor of the Niemann-Pick disease, type C (NPC2) binding partner Niemann-Pick C1 (NPC1) to treat symbiotic and aposymbiotic adult Aiptasia to study the effect of global sterol transport inhibition
- in treating seminiferous tubules to study its effects on the localization pattern of VPS35-positive vesicles
- to study the U18666A treatment effects on early endosomes and late endosomes/multivesicular bodies (MVBs)
- as an NPC1 inhibitor to test its in vivo efficacy and study its effects on filovirus entry and infection
Biochem/physiol Actions
Inhibitor of cholesterol synthesis (inhibits desmosterol Δ24-reductase). Weak inhibitor of hedgehog (hh) signaling.
U18666A, a Niemann-Pick phenotype inducer, can inhibit the lysosomal cholesterol export and Ebola infection.
Preparation Note
U 18666A is soluble in water at 10 mg/ml.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Choose from one of the most recent versions:
Already Own This Product?
Find documentation for the products that you have recently purchased in the Document Library.
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
Takashi Takano et al.
Journal of hepatology, 55(3), 512-521 (2010-12-28)
We characterized the role of 24-dehydrocholesterol reductase (DHCR24) in hepatitis C virus infection (HCV). DHCR24 is a cholesterol biosynthetic enzyme and cholesterol is a major component of lipid rafts, which is reported to play an important role in HCV replication.
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