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SML2283

Sigma-Aldrich

Lenalidomide

≥98% (HPLC), powder, cereblon binder

Synonym(s):

Lenalidomide, 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)piperidin-2,6-dione, 3-(4-Amino-1-oxoisoindolin-2-yl)piperidine-2,6-dione, CC 5013, CC-5013

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About This Item

Empirical Formula (Hill Notation):
C13H13N3O3
CAS Number:
191732-72-6
Molecular Weight:
259.26
MDL number:
MFCD07772307
UNSPSC Code:
12352200
NACRES:
NA.77

Key Documents

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Product Name

Lenalidomide, ≥98% (HPLC)

ligand

lenalidomide

assay

≥98% (HPLC)

form

powder

reaction suitability

reagent type: ligand

color

white to beige

solubility

DMSO: 2 mg/mL, clear

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

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Related Categories

Biochem/physiol Actions

Lenalidomide, a derivative of thalidomide, is an immunomodulatory agent that is approved drug for treatment of multiple myeloma. Apparently Lenalidomide is a ligand of ubiquitin E3 ligase cereblon that induces the enzyme to degrade the Ikaros transcription factors IKAROS family zinc finger 1 (IKZF1) and IKZF3. Lenalidomide possess pleiotropic antitumor effects. It is used in the treatment of 5q-deletion associated myelodysplastic syndrome (del(5q)-MDS).

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000413531
0000413531
0000396751
0000396751
0000237541

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Yuan Xiao Zhu et al.
Blood, 118(18), 4771-4779 (2011-08-24)
The precise molecular mechanism of action and targets through which thalidomide and related immunomodulatory drugs (IMiDs) exert their antitumor effects remains unclear. We investigated the role of cereblon (CRBN), a primary teratogenic target of thalidomide, in the antimyeloma activity of
Georg Petzold et al.
Nature, 532(7597), 127-130 (2016-02-26)
Thalidomide and its derivatives, lenalidomide and pomalidomide, are immune modulatory drugs (IMiDs) used in the treatment of haematologic malignancies. IMiDs bind CRBN, the substrate receptor of the CUL4-RBX1-DDB1-CRBN (also known as CRL4(CRBN)) E3 ubiquitin ligase, and inhibit ubiquitination of endogenous
Li Du et al.
Cancer gene therapy (2022-03-27)
Despite the potent effect of lenalidomide (Len) in multiple myeloma (MM) treatment, patients develop Len resistance leading to progressive disease, demanding an urgent need to investigate the mechanisms mediating Len resistance. Our study identified SUMOylation as a potential mechanism regulating
Thalidomide promotes degradation of SALL4, a transcription factor implicated in Duane Radial Ray syndrome
Donovan KA, et al.
eLife, 7, e38430-e38430 (2018)
Antoine Domenger et al.
Frontiers in oncology, 13, 1110916-1110916 (2023-02-14)
Multiple Myeloma (MM) is an incurable neoplasm of mature B cells and the second most prevalent hematological malignancy worldwide. While combinations of proteasome inhibitors like bortezomib (Bz) and immunomodulators (IMiDs) like lenalinomide (Len) are generally effective in newly diagnosed patients
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