A derivative of thalidomide
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Lenalidomide

Item No. 14643

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-(4-amino-1,3-dihydro-1-oxo-2H-isoindol-2-yl)-2,6-piperidinedione
CAS Number
191732-72-6
Synonyms
  • CC-5013
Molecular Formula
C13H13N3O3
Formula Weight
259.3
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 16 mg/mlDMF:PBS (pH 7.2) (1:1): 0.5 mg/mlDMSO: 16 mg/ml
λmax
206, 220, 311 nm
SMILES
NC1=C(CN(C2C(NC(CC2)=O)=O)C3=O)C3=CC=C1
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    100 mg

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    Product Description

    Lenalidomide is a derivative of the immunomodulatory compound thalidomide (Item No. 14610).1 It reduces TNF-α production in isolated human peripheral blood mononuclear cells (PBMCs) and whole blood stimulated by LPS from S. minnesota (Item No. 23608; IC50s = 13 and 25 nM, respectively). Lenalidomide has been used as a building block in the synthesis of PROTACs that induce the degradation of Ikaros family zinc finger protein 1 (IKZF1) and IKZF3 in MM.1S multiple myeloma cells.2 Orally administered lenalidomide (250 mg/kg per day) reduces vascularization and total microvascular length in a rat mesenteric window assay.3 Formulations containing lenalidomide have been used in the treatment of myelodysplastic syndrome and multiple myeloma.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Muller, G.W., Chen, R., Huang, S.Y., et al. Amino-substituted thalidomide analogs: Potent inhibitors of TNF-α production. Bioorg. Med. Chem. Lett. 9(11), 1625-1630 (1999).

    2. Krönke, J., Udeshi, N.D., Narla, A., et al. Lenalidomide causes selective degradation of IKZF1 and IKZF3 in multiple myeloma cells. Science 343(6168), 301-305 (2014).

    3. Dredge, K., Horsfall, R., Robinson, S.P., et al. Orally administered lenalidomide (CC-5013) is anti-angiogenic in vivo and inhibits endothelial cell migration and Akt phosphorylation in vitro. Microvasc. Res. 69(1-2), 56-63 (2005).