CDS022536
Lenalidomide
Synonym(s):
3-(7-Amino-3-oxo-1H-isoindol-2-yl)piperidine-2,6-dione
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About This Item
Empirical Formula (Hill Notation):
C13H13N3O3
Molecular Weight:
259.26
UNSPSC Code:
12352200
PubChem Substance ID:
MDL number:
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)
SMILES string
O=C1N(C2CCC(NC2=O)=O)CC3=C1C=CC=C3N
InChI key
GOTYRUGSSMKFNF-UHFFFAOYSA-N
description
AldrichCPR
form
powder
Gene Information
human ... CRBN(51185), CUL4A(8451), DDB1(1642), RBX1(9978)
Application
Lenalidomide is a structural analog of thalidomide, which exhibits excellent anticancer activity against multiple myeloma. It can be used in synthesizing multiple derivatives of lenalidomide to study their biological activity. Synthesis of gelator containing lenalidomide, which forms stable gels in 1,4-dioxane has been reported.
Other Notes
Please note that Sigma-Aldrich provides this product to early discovery researchers as part of a collection of unique chemicals. Sigma-Aldrich does not collect analytical data for this product. Buyer assumes responsibility to confirm product identity and/or purity. All sales are final.
NOTWITHSTANDING ANY CONTRARY PROVISION CONTAINED IN SIGMA-ALDRICH′S STANDARD TERMS AND CONDITIONS OF SALE OR AN AGREEMENT BETWEEN SIGMA-ALDRICH AND BUYER, SIGMA-ALDRICH SELLS THIS PRODUCT "AS-IS" AND MAKES NO REPRESENTATION OR WARRANTY WHATSOEVER WITH RESPECT TO THIS PRODUCT, INCLUDING ANY (A) WARRANTY OF MERCHANTABILITY, (B) WARRANTY OF FITNESS FOR A PARTICULAR PURPOSE, OR (C) WARRANTY AGAINST INFRINGEMENT OF INTELLECTUAL PROPERTY RIGHTS OF A THIRD PARTY, WHETHER ARISING BY LAW, COURSE OF DEALING, COURSE OF PERFORMANCE, USAGE OF TRADE OR OTHERWISE.
NOTWITHSTANDING ANY CONTRARY PROVISION CONTAINED IN SIGMA-ALDRICH′S STANDARD TERMS AND CONDITIONS OF SALE OR AN AGREEMENT BETWEEN SIGMA-ALDRICH AND BUYER, SIGMA-ALDRICH SELLS THIS PRODUCT "AS-IS" AND MAKES NO REPRESENTATION OR WARRANTY WHATSOEVER WITH RESPECT TO THIS PRODUCT, INCLUDING ANY (A) WARRANTY OF MERCHANTABILITY, (B) WARRANTY OF FITNESS FOR A PARTICULAR PURPOSE, OR (C) WARRANTY AGAINST INFRINGEMENT OF INTELLECTUAL PROPERTY RIGHTS OF A THIRD PARTY, WHETHER ARISING BY LAW, COURSE OF DEALING, COURSE OF PERFORMANCE, USAGE OF TRADE OR OTHERWISE.
signalword
Warning
hcodes
Hazard Classifications
Repr. 2 - STOT RE 2
target_organs
Blood
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
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Cereblon is a direct protein target for immunomodulatory and antiproliferative activities of lenalidomide and pomalidomide.
Lopez-Girona A E A, et al.
Leukemia, 26(11), 2326-2326 (2012)
Lenalidomide plus dexamethasone for relapsed or refractory multiple myeloma.
Dimopoulos M, et al.
The New England Journal of Medicine, 357(21), 2123-2132 (2007)
Melamine tunable effect in a lenalidomide-based supramolecular self-assembly system via hydrogen bonding.
Gao A, et al.
New. J. Chem., 41(16), 7924-7931 (2017)
Design, synthesis and biological evaluation of Lenalidomide derivatives as tumor angiogenesis inhibitor.
Hu S, et al.
Bioorganic & Medicinal Chemistry Letters, 27(17), 4075-4081 (2017)
Xiaofei He et al.
Experimental hematology, 86, 21-27 (2020-05-22)
Our previous study revealed that expression of G protein-coupled receptor 68 (GPR68) was upregulated in MDSL cells, a cell line representing myelodysplastic syndromes (MDS), in response to lenalidomide (LEN), and mediated a calcium/calpain proapoptotic pathway. Isx, a GPR68 agonist, enhanced
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