U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C25H41NO2.ClH
Molecular Weight 424.059
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 3.BETA.-(2-DIETHYLAMINOETHOXY)ANDROST-5-EN-17-ONE HYDROCHLORIDE

SMILES

Cl.[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CC=C4C[C@H](CC[C@]34C)OCCN(CC)CC

InChI

InChIKey=GZFYZYBWLCYBMI-MYZJJQSMSA-N
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

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C25H41NO2
Molecular Weight 387.5985
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

3.beta-3-[2-(Diethylamino)ethoxy]androst-5-en-17-one hydrochloride or U18666A, an amphipathic cationic amine, is a cell permeable research tool drug that inhibits cholesterol synthesis and trafficking, and also a weak inhibitor of hedgehog (Hh) signaling. U18666A had been used in several models both in vivo and in vitro to mimic Niemann-Pick type C disease (NPC) and for assessing the importance of molecular trafficking through the lysosomal pathway in other conditions such as atherosclerosis, Alzheimer's disease, and prion infections. U18666A also provided animal models for such disorders as petite mal (absence) epilepsy and cataracts. U18666A inhibits the enzyme desmosterol reductase responsible for reducing the desmosterol in cholesterol biosynthesis, and also blocks LDL-(low density lipoprotein) cholesterol transport from the lysosomes into the endoplasmic reticulum thereby increasing the level of caveolina-1 located within the plasma membrane caveolae. U18666A was shown to be a potent antagonist of alpha4beta2 neuronal nicotinic acetylcholine receptors and may be useful as a tool in the functional characterization and pharmacological profiling of nAChRs.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Localization of Niemann-Pick C1 protein in astrocytes: implications for neuronal degeneration in Niemann- Pick type C disease.
1999 Feb 16
U18666A inhibits intracellular cholesterol transport and neurotransmitter release in human neuroblastoma cells.
1999 Jan
Cholesterol synthesis inhibitor U18666A and the role of sterol metabolism and trafficking in numerous pathophysiological processes.
2009 Jun
Patents

Sample Use Guides

Acute 10 mg/kg dose of U18666A (3-beta(2-diethylaminoethoxy)androst-5-en-17-one hydrochloride) or chronic injection of 10 mg/kg every 4th day
Route of Administration: Other
U18666A induced neurotoxicity and cholesterol accumulation in mouse primary hippocampal neurons. After 5 days of plating, cultured neurons were treated with 0.1–50 ug/ml U18666A for 24 h or with 5 μg/ml U18666A for 6–96 h. MTT values were significantly attenuated in concentration-dependent (A) and time-dependent (B) manners in U18666A-treated cultures compared with mock-treated cultures.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:20:23 GMT 2023
Edited
by admin
on Fri Dec 15 15:20:23 GMT 2023
Record UNII
V0DPR5J8ZJ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
3.BETA.-(2-DIETHYLAMINOETHOXY)ANDROST-5-EN-17-ONE HYDROCHLORIDE
Systematic Name English
ANDROST-5-EN-17-ONE, 3-(2-(DIETHYLAMINO)ETHOXY)-, HYDROCHLORIDE (1:1), (3.BETA.)-
Systematic Name English
ANDROST-5-EN-17-ONE, 3.BETA.-(2-(DIETHYLAMINO)ETHOXY)-, HYDROCHLORIDE
Systematic Name English
NSC-70801
Code English
Code System Code Type Description
NSC
70801
Created by admin on Fri Dec 15 15:20:23 GMT 2023 , Edited by admin on Fri Dec 15 15:20:23 GMT 2023
PRIMARY
EPA CompTox
DTXSID3046904
Created by admin on Fri Dec 15 15:20:23 GMT 2023 , Edited by admin on Fri Dec 15 15:20:23 GMT 2023
PRIMARY
CAS
3039-71-2
Created by admin on Fri Dec 15 15:20:23 GMT 2023 , Edited by admin on Fri Dec 15 15:20:23 GMT 2023
PRIMARY
FDA UNII
V0DPR5J8ZJ
Created by admin on Fri Dec 15 15:20:23 GMT 2023 , Edited by admin on Fri Dec 15 15:20:23 GMT 2023
PRIMARY
PUBCHEM
9954082
Created by admin on Fri Dec 15 15:20:23 GMT 2023 , Edited by admin on Fri Dec 15 15:20:23 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE