U3633

U 18666A

powder

• Synonym(s): (3β)-3-[2-(Diethylamino)ethoxy]androst-5-en-17-one hydrochloride
• Empirical Formula (Hill Notation): C₂₅H₄₁NO₂·HCl
• CAS Number: 3039-71-2
• Molecular Weight: 424.06
• MDL number: MFCD00210908
• UNSPSC Code: 12352200
• PubChem Substance ID: 24724638
• NACRES: NA.77

Properties

• 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

Description

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.

Safety Information

• 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)