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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

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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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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Pricing

Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H360D,H373

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

Certificates of Analysis (COA)

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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
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
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
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
Amanda C Ritter et al.
Comparative medicine, 73(2), 153-172 (2023-03-28)
Mouse kidney parvovirus (MKPV) causes inclusion body nephropathy in severely immunocompromised mice and renal interstitial inflammation in immunocompetent mice. Here we sought to determine the effects of MKPV on pre-clinical murine models that depend on renal function. To assess the
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