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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

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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
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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.

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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

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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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

901558-100MG: + 901558-1G: + 901558-5G: + 901558-VAR: + 901558-BULK:

jan

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Certificates of Analysis (COA)

Lot/Batch Number
MKCZ8000
MKCX7379
MKCV5383
MKCV6532
MKCT8216

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Articles

標的タンパク質分解のための分解物ビルディングブロック

タンパク質分解誘導化合物ビルディングブロックは、標的リガンドと共有結合するペンダント基を持つクロスリンカー-E3リガンド複合体です。

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
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
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
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