Skip to Content
Merck

Key Documents

View All Documentation

901558

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 In to View Organizational & Contract Pricing.

Select a Size

Change View

About This Item

Empirical Formula (Hill Notation):
C13H13N3O3
CAS Number:
191732-72-6
Molecular Weight:
259.26
UNSPSC Code:
12352101
NACRES:
NA.22
MDL number:
MFCD07772307
Assay:
≥95%
Form:
powder
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

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

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.

.

Other Notes

Technology Spotlight: Degrader Building Blocks for Targeted Protein Degradation

Portal: Building PROTAC® Degraders for Targeted Protein Degradation

Structure of the human Cereblon–DDB1–lenalidomide complex reveals basis for responsiveness to thalidomide analogs

Lenalidomide causes selective degradation of IKZF1 and IKZF3 in multiple myeloma cells

The myeloma drug lenalidomide promotes the cereblon-dependent destruction of Ikaros proteins

Legal Information

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

Still not finding the right product?

Explore all of our products under Lenalidomide

pictograms

Health hazard
GHS08

signalword

Danger

Hazard Classifications

Repr. 1B - STOT RE 2

target_organs

Blood

Storage Class

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

It looks like we've run into a problem, but you can still download Certificates of Analysis from our Documents section.

If you need assistance, please contact Customer Support

Already Own This Product?

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

Visit the Document Library

Articles

Partial PROTACs for Targeted Protein Degradation

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

Degrader Building Blocks for Targeted Protein Degradation

Protein Degrader Building Blocks are a collection of crosslinker-E3 ligand conjugates with a pendant functional group for covalent linkage to a target ligand.

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.
View All Related Papers

Global Trade Item Number

SKUGTIN
901558-5G04061838382528
901558-100MG04061835333608
901558-1G04061838382511