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U3633

Sigma-Aldrich

U 18666A

powder

Synonym(s):

(3β)-3-[2-(Diethylamino)ethoxy]androst-5-en-17-one hydrochloride

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$131.00
25 MG
$496.00

About This Item

Empirical Formula (Hill Notation):
C25H41NO2·HCl
CAS Number:
Molecular Weight:
424.06
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

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$131.00


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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

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This Item
662015A8423U6881
U 18666A powder

U3633

U 18666A

U18666A A cell-permeable, amphiphilic amino-steroid that alters intracellular membrane protein trafficking by impairing intracellular biosynthesis and transport of LDL-derived cholesterol.

662015

U18666A

U-73343

U6881

U-73343

assay

≥98% (HPLC)

assay

≥95% (HPLC)

assay

≥98%

assay

≥98% (HPLC)

form

powder

form

lyophilized solid

form

powder

form

powder

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

-

solubility

H2O: 10 mg/mL≥

solubility

water: 10 mg/mL

solubility

-

solubility

DMSO: soluble

color

white to off-white

color

white

color

-

color

white

mp

195-196.5 °C (lit.)

mp

-

mp

-

mp

-

General description

U18666A, a cationic amphiphile/sterol, has a diethylaminoethyl chain linked to the 3-hydroxyl. It is an androstenolone derivative.[1]

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[2].
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[3]
  • in treating seminiferous tubules to study its effects on the localization pattern of VPS35-positive vesicles[4]
  • to study the U18666A treatment effects on early endosomes and late endosomes/multivesicular bodies (MVBs)[4]
  • as an NPC1 inhibitor to test its in vivo efficacy and study its effects on filovirus entry and infection[5]

Biochem/physiol Actions

Inhibitor of cholesterol synthesis (inhibits desmosterol Δ24-reductase). Weak inhibitor of hedgehog (hh) signaling.
U18666A, a Niemann-Pick phenotype inducer[5], can inhibit the lysosomal cholesterol export and Ebola infection.[1]

Preparation Note

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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