Skip to Content
Merck
All Photos(3)

Key Documents

901558

Sigma-Aldrich

Lenalidomide

≥95%

Synonym(s):

1-Oxo-4-amino-2-(2,6-dioxopiperidin-3-yl)isoindole, 3-(4-Amino-1,3-dihydro-1-oxo-2H-isoindol-2-yl)-2,6-piperidinedione, 3-(4-Amino-1-oxoisoindolin-2-yl)piperidine-2,6-dione, E3 Ligase ligand, Ligand for PROTAC® research

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C13H13N3O3
CAS Number:
Molecular Weight:
259.26
MDL number:
UNSPSC Code:
12352101
NACRES:
NA.22

ligand

lenalidomide

Assay

≥95%

form

powder

reaction suitability

reagent type: ligand

mp

265-268  °C

storage temp.

2-8°C

SMILES string

O=C1N(C2CCC(NC2=O)=O)CC3=C1C=CC=C3N

InChI

1S/C13H13N3O3/c14-9-3-1-2-7-8(9)6-16(13(7)19)10-4-5-11(17)15-12(10)18/h1-3,10H,4-6,14H2,(H,15,17,18)

InChI key

GOTYRUGSSMKFNF-UHFFFAOYSA-N

Looking for similar products? Visit Product Comparison Guide

Application

Lenalidomide is a ligand demonstrated to bind the Cereblon (CRBN) protein. Lenalidomide, along with other thalidomide derivatives, are useful for constructing small molecules for targeted protein degradation and PROTAC (proteolysis-targeting chimeras) technology. Explore protein degrader building blocks, E3 ligase ligand-linker conjugates that simplify the synthesis and library generation of PROTACs.

.

Legal Information

PROTAC is a registered trademark of Arvinas Operations, Inc., and is used under license

related product

Product No.
Description
Pricing

Pictograms

Health hazard

Signal Word

Danger

Hazard Statements

Hazard Classifications

Repr. 1B - STOT RE 2

Target Organs

Blood

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Inchul You et al.
Cell chemical biology, 27(1), 66-73 (2019-12-21)
The PI3K/AKT signaling cascade is one of the most commonly dysregulated pathways in cancer, with over half of tumors exhibiting aberrant AKT activation. Although potent small-molecule AKT inhibitors have entered clinical trials, robust and durable therapeutic responses have not been
Philip P Chamberlain et al.
Nature structural & molecular biology, 21(9), 803-809 (2014-08-12)
The Cul4-Rbx1-DDB1-Cereblon E3 ubiquitin ligase complex is the target of thalidomide, lenalidomide and pomalidomide, therapeutically important drugs for multiple myeloma and other B-cell malignancies. These drugs directly bind Cereblon (CRBN) and promote the recruitment of substrates Ikaros (IKZF1) and Aiolos
Richard J Visconti et al.
Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research, 36(10), 1914-1930 (2021-06-27)
Human myeloma bone disease (MBD) occurs when malignant plasma cells migrate to the bone marrow and commence inimical interactions with stromal cells, disrupting the skeletal remodeling process. The myeloma cells simultaneously suppress osteoblastic bone formation while promoting excessive osteoclastic resorption.
Jan Krönke et al.
Science (New York, N.Y.), 343(6168), 301-305 (2013-12-03)
Lenalidomide is a drug with clinical efficacy in multiple myeloma and other B cell neoplasms, but its mechanism of action is unknown. Using quantitative proteomics, we found that lenalidomide causes selective ubiquitination and degradation of two lymphoid transcription factors, IKZF1
Gang Lu et al.
Science (New York, N.Y.), 343(6168), 305-309 (2013-12-03)
Thalidomide-like drugs such as lenalidomide are clinically important treatments for multiple myeloma and show promise for other B cell malignancies. The biochemical mechanisms underlying their antitumor activity are unknown. Thalidomide was recently shown to bind to, and inhibit, the cereblon

Articles

Partial PROTACs are a collection of crosslinker-E3 ligand conjugates with a pendant functional group for covalent linkage to a target ligand.

Partial PROTACs are a collection of crosslinker-E3 ligand conjugates with a pendant functional group for covalent linkage to a target ligand.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service