U-18666A

Cayman Chemical Item Number 10009085

(CAS 3039-71-2)

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Description

Impaired trafficking of cholesterol to or from the endoplasmic reticulum (ER) has been implicated in many disease states including Neimann-Pick disease type C (NPC), Alzheimers disease and atherosclerosis. U-18666A is a cell permeable drug that inhibits cholesterol trafficking. It inhibits cholesterol transport from late endosomes/lysosomes to the endoplasmic reticulum (ER), but not cholesterol transport to the plasma membrane as demonstrated in many cell types including macrophages, primary cortical neurons and primary fibroblasts.1,2,3 In macrophages, micromolar concentrations of U-18666A inhibit multiple pathways of cholesterol trafficking from late endosomes, whereas nanomolar concentrations impair cholesterol trafficking to the ER, a response similar to that found in NPC. U-18666A inhibits Oxidosqualene Cyclase at high (>0.5 mM) concentrations and oral doses (10 mg/kg) induces cataracts in rats.1

1. Koh, C.H.V., and Cheung, N.S. Cellular mechanism of U18666A-mediated apoptosis in cultured murine cortical neurons: Bridging Niemann-Pick disease type C and Alzheimer’s disease. Cell Signal 18(11) 1844-1853 (2006).

2. Tabas, I. Apoptosis and plaque destabilization in atherosclerosis: The role of macrophage apoptosis induced by cholesterol. Cell Death Differ 11 S12-S16 (2004).

3. Feng, B., Yao, P.M., Li, Y., et al. The endoplasmic reticulum is the site of cholesterol-induced cytotoxicity in macrophages. Nat Cell Biol 5(9) 781-792 (2003).

Formal Name 3b-​[2-​(diethylamino)ethoxy]-​androst-​5-​en-​17-​one,​ monohydrochloride
CAS Number 3039-71-2
Molecular Formula C25H41NO2 · HCl
Formula Weight 424.1
Formulation A crystalline solid
Purity >95%
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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C[C@]​12C(C[C@@H]​(OCCN(CC)​CC)​CC2)​=CC[C@]​3([H]​)​[C@]​1([H]​)​CC[C@@]​4(C)​[C@@]​3([H]​)​CCC4=O.Cl
InCHI Code
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​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
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GZFYZYBWLCYBMI-MYZJJQSMSA-N

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U-18666A is available in the following screening library:

Size Price Quantity Subtotal
5 mg $38.00 $0.00
10 mg $72.00 $0.00
25 mg $171.00 $0.00
50 mg $304.00 $0.00
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