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Sigma-Aldrich

U 18666A

≥95% (HPLC), lyophilized solid, δ8-sterol isomerase inhibitor, Calbiochem®

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Synonym(s):
U18666A, 3β-(2-Diethylaminoethoxy)androst-5-en-17-one, HCl
Empirical Formula (Hill Notation):
C25H41NO2 · xHCl
CAS Number:
3039-71-2
Molecular Weight:
387.60 (free base basis)
MDL number:
MFCD00210908
UNSPSC Code:
12352200
NACRES:
NA.77

product name

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

Quality Level

100

Assay

≥95% (HPLC)

form

lyophilized solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
desiccated (hygroscopic)

color

white

solubility

water: 10 mg/mL

shipped in

ambient

storage temp.

2-8°C

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

InChI key

ICPRVJHNLABCSA-UHFFFAOYSA-N

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.
A cell-permeable, amphiphilic amino-steroid that alters intracellular membrane protein trafficking by impairing intracellular biosynthesis and transport of LDL-derived cholesterol, presumably via its inhibitory effect on 2,3-oxidosqualene-lanosterol cyclase activity. Also reported to inhibit the activity of Δ8-sterol isomerase.

Biochem/physiol Actions

Cell permeable: yes
Primary Target
Activity of δ8-sterol isomerase
Product does not compete with ATP.
Reversible: no

Packaging

Packaged under inert gas

Warning

Toxicity: Standard Handling (A)

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Other Notes

Hall, A.M., et al. 2003. Pigment Cell Res.16, 149.
Kobayashi, T., et al. 1998. Nature392, 193.
Liscum, L. and Faust, J.R., 1989. J. Biol. Chem.264, 11796.
Sexton, R.C., et al. 1983. Biochemistry22, 5687.
Bierkamper, G.G. and Cenedella, R.J., 1978. Brain Res.150, 343.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Yu-Ting Chiang et al.
International journal of molecular sciences, 24(19) (2023-10-14)
Adipocytes store a significant amount of cholesterol and triglycerides. However, whether cholesterol modulates adipocyte function remains largely unknown. We modulated the cholesterol level in adipocytes to examine its effect on the secretion of adiponectin, an important hormone specifically secreted by
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The study of organelle contact sites has received a great impulse due to increased interest in the understanding of their involvement in many disease conditions. Split-GFP-based contact sites (SPLICS) reporters emerged as essential tools to easily detect changes in a
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The activation of apoptosis signalling by TRAIL (TNF-related apoptosis-inducing ligand) through receptor binding is a fundamental mechanism of cell death induction and is often perturbed in cancer cells to enhance their cell survival and treatment resistance. Ubiquitination plays an important
Malgorzata Wiweger et al.
Frontiers in cellular neuroscience, 15, 647860-647860 (2021-05-15)
Niemann-Pick type C (NPC) disease is an autosomal recessive lysosomal storage disease that is caused by a mutation of the NPC1 or NPC2 gene, in which un-esterified cholesterol and sphingolipids accumulate mainly in the liver, spleen, and brain. Abnormal lysosomal
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