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SML2283

Sigma-Aldrich

Lenalidomide

≥98% (HPLC)

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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
Empirical Formula (Hill Notation):
C13H13N3O3
CAS Number:
Molecular Weight:
259.26
MDL number:

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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This Item
901558P0018T144
Lenalidomide ≥98% (HPLC)

SML2283

Lenalidomide

Lenalidomide ≥95%

901558

Lenalidomide

Pomalidomide ≥98% (HPLC)

P0018

Pomalidomide

(±)-Thalidomide ≥98%, powder

T144

(±)-Thalidomide

form

powder

form

powder

form

powder

form

powder

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

-

solubility

DMSO: 2 mg/mL, clear

solubility

-

solubility

DMSO: ≥14 mg/mL

solubility

DMSO: 20 mg/mL, clear

color

white to beige

color

-

color

yellow

color

white

reaction suitability

reagent type: ligand

reaction suitability

reagent type: ligand

reaction suitability

reagent type: ligand

reaction suitability

reagent type: ligand

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).

related product

Product No.
Description
Pricing

pictograms

Health hazard

signalword

Warning

Hazard Classifications

Repr. 2 - STOT RE 2

target_organs

Blood

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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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
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
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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