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Lenalidomide

CAT: 0804-HY-A0003-04Size: 1 gDry Ice: NoHazardous: No
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Description
Lenalidomide (CC-5013), a derivative of Thalidomide, acts as molecular glue. Lenalidomide is an orally active immunomodulator. Lenalidomide (CC-5013) is a ligand of ubiquitin E3 ligase cereblon (CRBN), and it causes selective ubiquitination and degradation of two lymphoid transcription factors, IKZF1 and IKZF3, by the CRBN-CRL4 ubiquitin ligase. Lenalidomide (CC-5013) specifically inhibits growth of mature B-cell lymphomas, including multiple myeloma, and induces IL-2 release from T cells[1][2].
CAS Number
191732-72-6
Product Name Alternative
CC-5013
UNSPSC
12352005
Hazard Statement
H361, H373
Target
Apoptosis; Ligands for E3 Ligase; Molecular Glues
Type
Reference compound
Related Pathways
Apoptosis; PROTAC
Applications
Cancer-Kinase/protease
Field of Research
Cancer; Inflammation/Immunology
Assay Protocol
https://www.medchemexpress.com/Lenalidomide.html
Purity
99.98
Solubility
DMSO : 100 mg/mL (ultrasonic)
Smiles
O=C1C2=CC=CC(N)=C2CN1C(C(N3)=O)CCC3=O
Molecular Formula
C13H13N3O3
Molecular Weight
259.26
Precautions
H361, H373
References & Citations
[1]Omran A, et al. Effects of MRP8, LPS, and lenalidomide on the expressions of TNF-α , brain-enriched, and inflammation-related microRNAs in the primary astrocyte culture. ScientificWorldJournal. 2013 Sep 21;2013:208309.|[2]Kotla V, et al. Mechanism of action of lenalidomide in hematological malignancies. J Hematol Oncol. 2009 Aug 12;2:36.|[3]Lopez-Girona A, et al. Cereblon is a direct protein target for immunomodulatory and antiproliferative activities of lenalidomide and pomalidomide. Leukemia. 2012 Nov;26 (11) :2326-35.|[4]Rozewski DM, et al. Pharmacokinetics and tissue disposition of lenalidomide in mice. AAPS J. 2012 Dec;14 (4) :872-82.|[5]Minzel W, et al. Small Molecules Co-targeting CKIα and the Transcriptional Kinases CDK7/9 Control AML in Preclinical Models. Cell. 2018 Sep 20;175 (1) :171-185.e25.|[6]Nagashima, Takeyuki, et al. PHARMACEUTICAL COMPOSITION COMPRISING BICYCLIC NITROGEN-CONTAINING AROMATIC HETEROCYCLIC AMIDE COMPOUND AS ACTIVE INGREDIENT. Patent. 20170360780A1.|[7]Krönke J, et al. Lenalidomide induces degradation of IKZF1 and IKZF3. Oncoimmunology. 2014 Jul 3;3 (7) :e941742.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Reference compound1
Clinical Information
Launched
Isoform
Cereblon
Citation 01
ACS Omega. 2024 Dec 3;9 (50) :49739-49748.|ACS Pharmacol Transl Sci. 2021 Feb 26;4 (2) :941-952.|Acta Pharmacol Sin. 2020 Sep;41 (9) :1246-1254.|Acta Pharmacol Sin. 2025 Aug;46 (8) :2296-2309.|Am J Pathol. 2015 Jun;185 (6) :1783-94. |Biochim Biophys Acta Mol Basis Dis. 2022 Oct 1;1868 (10) :166472.|Bioengineering (Basel) . 2025 Oct 19;12 (10) :1121.|bioRxiv. 2024 June 12.|bioRxiv. 2024 October 19.|bioRxiv. April.|Cancer Cell. 2022 Nov 14;40 (11) :1294-1305.e4.|Cancer Res. 2025 Jan 2;85 (1) :101-117.|Cancer Sci. 2019 Dec;110 (12) :3802-3810.|Cancers (Basel) . 2024 Mar 28, 16 (7), 1319.|Cell Rep Med. 2024 Mar 19;5 (3) :101472.|Cell Rep Med. 2025 Apr 2:102053.|Cell Rep Methods. 2023 Oct 23;3 (10) :100599.|Cell Rep. 2024 May 8;43 (5) :114211.|Cell Syst. 2018 Apr 25;6 (4) :424-443.e7.|Cell. 2018 Sep 20;175 (1) :171-185.e25.|Chemrxiv. 2025 Nov 17.|Clin Chim Acta. 2024 Jan 15:553:117707.|Elife. 2018 Aug 1;7:e38430. |Eur J Pharmacol. 2025 Dec 5:1008:178303.|Exp Cell Res. 2020 Aug 1;393 (1) :112054.|Faculty of Science, Masaryk University. Department of Experimental Biology.2014. |Food Chem Toxicol. 2019 Mar:125:392-402.|Free Radic Biol Med. 2023 Jul:203:86-101.|Front Cell Infect Microbiol. 2022 Jul 28;12:954814.|Harvard Medical School LINCS LIBRARY|Harvard University. 2025.|Inflammation. 2019 Feb;42 (1) :221-234. |Int Immunopharmacol. 2025 May 14:158:114831.|Int J Mol Sci. 2023 Sep 14;24 (18) :14097.|iScience. 2022 Jul 19;25 (8) :104781.|J Transl Med. 2024 Dec 3;22 (1) :1095.|Leukemia. 2025 Mar;39 (3) :720-733.|Microbiome. 2025 Feb 28;13 (1) :56.|Mol Ther Oncol. 2025 Feb 20;33 (1) :200952.|Nat Cancer. 2022 May;3 (5) :595-613.|Nat Chem Biol. 2021 Jun;17 (6) :711-717.|Nat Commun. 2017 May 22;8:15398. |Nat Commun. 2025 Nov 6;16 (1) :9805.|Nat Commun. 2025 Sep 1;16 (1) :8155.|Nature. 2024 Sep;633 (8030) :670-677.|Neoplasia. 2025 Oct 27:70:101243.|Oncol Rep. 2018 Jun;39 (6) :2873-2880. |Oxid Med Cell Longev. 2021 Dec 29:2021:8302831.|Patent. US20170360780A1.|Patent. US20180263995A1.|Patent. US20210379039A1.|Patent. US20220332776A1.|Patent. US20240261246A1.|Universidad de Navarra. 2024 Feb 28.|University of Washington. The Columbian College of Arts and Sciences. August 31, 2021.|Cell Commun Signal. 2025 May 7;23 (1) :216.|Food Chem Toxicol. 2019 Mar:125:392-402.

Chemical Information

Lenalidomide

Lenalidomide is a dicarboximide that consists of 1-oxoisoindoline bearing an amino substituent at position 4 and a 2,6-dioxopiperidin-3-yl group at position 2. Inhibits the secretion of TNF-alpha. It has a role as an antineoplastic agent, an angiogenesis inhibitor and an immunomodulator. It is a member of isoindoles, an aromatic amine, a dicarboximide and a member of piperidones.

CAS Number191732-72-6
PubChem CID216326
IUPAC Name3-(7-amino-3-oxo-1H-isoindol-2-yl)piperidine-2,6-dione
Molecular FormulaC13H13N3O3
Molecular Weight259.26
XLogP-0.5
Topological Polar Surface Area92.5
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count1
Heavy Atom Count19
Formal Charge0
Complexity437
SMILES
C1CC(=O)NC(=O)C1N2CC3=C(C2=O)C=CC=C3N
InChI
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)
InChIKey
GOTYRUGSSMKFNF-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of Lenalidomide
CAS: 191732-72-6
CID: 216326
Formula: C13H13N3O3
MW: 259.26
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight259.26
XLogP3-0.5
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count1
Exact Mass259.09569129
Monoisotopic Mass259.09569129
Topological Polar Surface Area92.5 Ų
Heavy Atom Count19
Formal Charge0
Complexity437
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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CatalogName
FL24864-01Lenalidomide

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