U 18666A
- CAS No.
- 3039-71-2
- Chemical Name:
- U 18666A
- Synonyms
- U 18666A;U18666A,HCl;U18666A, 10 mM in DMSO;U18666A - CAS 3039-71-2 - Calbiochem;U-18666A, cholesterol transport inhibitor;3BETA-(2-DIETHYLAMINOETHOXY)-ANDROSTENONE HCL;3BETA-(2-DIETHYLAMINOETHOXY)ANDROST-5-EN-17 ONE, HCL;3BETA-(2-DIETHYLAMINO-ETHOXY)ANDROSTENONE HYDROCHLORIDE;3β-(2-Diethylaminoethoxy)androst-5-en-17-one hydrochloride;(3β)-3-[2-(Diethylamino)ethoxy]androst-5-en-17-onehydrochloride
- CBNumber:
- CB1467459
- Molecular Formula:
- C25H41NO2.ClH
- Molecular Weight:
- 424.06
- MDL Number:
- MFCD00210908
- MOL File:
- 3039-71-2.mol
- MSDS File:
- SDS
- TDS File:
- TDS
| Melting point | 195-196.5 °C(lit.) |
|---|---|
| storage temp. | 2-8°C |
| solubility | H2O: 9 mg/mL at ≤60 °C |
| form | crystalline |
| color | white |
| Water Solubility | Soluble in water at 10mg/ml |
| Stability | Stable for 2 years from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20°C for up to 1 week. |
| InChI | 1S/C25H41NO2.ClH/c1-5-26(6-2)15-16-28-19-9-7-18-8-10-20-21-11-12-23(27)24(21,3)14-13-22(20)25(18,4)17-19;/h8,19-22H,5-7,9-17H2,1-4H3;1H |
| InChIKey | ICPRVJHNLABCSA-UHFFFAOYSA-N |
| SMILES | [Cl-].N(CCOC1CC2(C3C(C4C(CC3)(C(=O)CC4)C)CC=C2CC1)C)(CC)CC.[H+] |
| FDA UNII | V0DPR5J8ZJ |
| UNSPSC Code | 12352200 |
| NACRES | NA.77 |
SAFETY
Risk and Safety Statements
| Safety Statements | 22-24/25 |
|---|---|
| WGK Germany | 3 |
| Storage Class | 11 - Combustible Solids |
U 18666A price More Price(58)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | U3633 | U 18666A powder | 3039-71-2 | 5mg | $141 | 2026-04-30 | Buy |
| Sigma-Aldrich | 662015 | U18666A | 3039-71-2 | 10mg | $199 | 2026-04-30 | Buy |
| Cayman Chemical | 10009085 | U-18666A ≥95% | 3039-71-2 | 5mg | $53 | 2026-04-30 | Buy |
| Cayman Chemical | 10009085 | U-18666A ≥95% | 3039-71-2 | 10mg | $98 | 2026-04-30 | Buy |
| Cayman Chemical | 10009085 | U-18666A ≥95% | 3039-71-2 | 25mg | $231 | 2026-04-30 | Buy |
U 18666A Chemical Properties, Uses, Production
Description
U-18666A (3039-71-2) is an oxidosqualene reductase inhibitor.1 Inhibits the egress of cholesterol from late endosomes and lysosomes.2 U-18666A is also used to study Niemann-Pick disease and for assessing the importance of molecular trafficking through the lysosomal pathway in other conditions.3
Uses
U 18666A is a cell-permeable amphiphilic amino-steroid.
Definition
ChEBI: 3beta-(2-diethylaminoethoxy)androst-5-en-17-one hydrochloride is a hydrochloride obtained by reaction of 3beta-(2-diethylaminoethoxy)androst-5-en-17-one with one equivalent of hydrochloric acid. It is a cholesterol synthesis and transport inhibitor. It has a role as an EC 1.3.1.72 (Delta(24)-sterol reductase) inhibitor, a nicotinic antagonist, a sterol biosynthesis inhibitor, an antiviral agent and a Hedgehog signaling pathway inhibitor. It contains a 3beta-(2-diethylaminoethoxy)androst-5-en-17-one(1+).
General Description
A cell-permeable, amphiphilic amino-steroid that alters intracelluar membrane protein trafficking by impairing intracellular biosynthesis and transport of LDL-derived cholesterol. Reported to exert its effects via the inhibition of 2,3-oxidosqualene-lanosterol cyclase activity. Also reported to inhibit the activity of Δ8-sterol isomerase.
Biological Activity
Inhibitor of cholesterol synthesis and cellular transport, and weak inhibitor of hedgehog (Hh) signaling. Reduces serum sterol levels in rats in vivo .
Biochem/physiol Actions
Cell permeable: yes
storage
Desiccate at RT
Background
U-18666A is a cell permeable drug that inhibits cholesterol transport. This small molecule inhibits low density lipoprotein-derived cholesterol transport, blocking cholesterol esterification, and suppressing LDL receptor activities. Studies have shown that impaired cholesterol trafficking is associated with neurological diseases such as Alzheimer’s disease, Niemann-Pick disease type C, and atherosclerosis. The mechanisms of neurodegeneration for these diseases are mostly unknown so studies using U-18666A to simulate intracellular cholesterol accumulation may provide greater insight into these pathologies. Cholesterol levels play a role in the body’s response to viral infection and the ability of a virus to enter and replicate within a host cell, making U-18666A an important compound when studying different viral diseases.
References
[1] RUSSELL C. SEXTON. Effects of 3.beta.-[2-(diethylamino)ethoxy]androst-5-en-17-one on the synthesis of cholesterol and ubiquinone in rat intestinal epithelial cell cultures[J]. Biochemistry Biochemistry, 1983, 22 25: 5687-5692. DOI:10.1021/bi00294a001
[2] L LISCUM J R F. The intracellular transport of low density lipoprotein-derived cholesterol is inhibited in Chinese hamster ovary cells cultured with 3-beta-[2-(diethylamino)ethoxy]androst-5-en-17-one.[J]. The Journal of Biological Chemistry, 1989, 264 20: 11796-11806.
[3] CENEDELLA R J. Cholesterol Synthesis Inhibitor U18666A and the Role of Sterol Metabolism and Trafficking in Numerous Pathophysiological Processes[J]. Lipids, 2009, 44 6: 477-487. DOI:10.1007/s11745-009-3305-7
U 18666A Preparation Products And Raw materials
Raw materials
Preparation Products
U 18666A Suppliers
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| 3B Pharmachem (Wuhan) International Co.,Ltd. | 18930552037 | 3bsc@sina.com | China | 15813 | 69 |
| Dalian Meilun Biotech Co., Ltd. | 0411-62910999 13889544652 | sales@meilune.com | China | 4765 | 58 |
| Guangzhou Isun Pharmaceutical Co., Ltd | 020-39119399 18927568969 | isunpharm@qq.com | China | 4773 | 55 |
| Sigma-Aldrich | 021-61415566 800-8193336 | orderCN@merckgroup.com | China | 51389 | 80 |
| Shanghai Lollane Biological Technology Co.,Ltd. | 021-52996696，15000506266 15000506266 | China | 4859 | 55 | |
| EMMX Biotechnology LLC | 888-539-0666 | info@emmx.com | United States | 8435 | 60 |
| Shanghai EFE Biological Technology Co., Ltd. | 021-65675885 18964387627 | info@efebio.com | China | 9799 | 58 |
| Shanghai YuanYe Biotechnology Co., Ltd. | 15026964105 | 2881489226@qq.com | China | 89667 | 60 |
| ShangHai Biochempartner Co.,Ltd | 177-54423994 17754423994 | 2853530910@QQ.com | China | 8000 | 62 |
| Shanghai Rechem science Co., Ltd. | 021-31433387 15618786686 | sales@rechemscience.com | China | 2970 | 58 |
