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SML2283

Sigma-Aldrich

Lenalidomide

≥98% (HPLC)

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

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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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).

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Pictograms

Health hazard
GHS08

Signal Word

Warning

Hazard Statements

H361d - H373

Hazard Classifications

Repr. 2 - STOT RE 2

Target Organs

Blood

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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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
Hila Shaim et al.
Frontiers in immunology, 8, 1773-1773 (2018-01-31)
Chronic lymphocytic leukemia (CLL) cells possess regulatory functions comparable to those of normal B10 cells, a regulatory B cell subset that suppresses effector T-cell function through STAT3-mediated IL-10 production. However, the mechanisms governing IL-10 production by CLL cells are not
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
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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