lenalidomide   Click here for help

GtoPdb Ligand ID: 7331

Synonyms: CC-5013 | CDC-501 | Revlimid®
Approved drug Immunopharmacology Ligand
lenalidomide is an approved drug (FDA (2005), EMA (2007))
Compound class: Synthetic organic
Comment: Lenalidomide is a derivative of thalidomide with anti-inflammatory and anti-cancer actions.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

lenalidomide is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 1
Topological polar surface area 95.99
Molecular weight 259.1
XLogP 0.22
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES OC1=NC(=O)C(CC1)N1Cc2c(C1=O)cccc2N
Isomeric SMILES OC1=NC(=O)C(CC1)N1Cc2c(C1=O)cccc2N
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)
InChI Key GOTYRUGSSMKFNF-UHFFFAOYSA-N
No information available.
Summary of Clinical Use Click here for help
Used in combination with anti-inflammatory dexamethasone as a second line therapy to treat multiple myeloma and other myelodysplastic syndromes (in particular, it is a highly effective treatment for myelodysplastic syndrome with deletion of chromosome 5q [1-2]). Lenalidomide is considered an orphan drug as the diseases for which it is indicated are rare.
In February 2015, the US FDA extended approval of the lenalidomide/dexamethasone combination to include use as a first line treatment for patients with newly diagnosed multiple myeloma. In February 2017, the FDA expanded approval for use as maintenance therapy for patients with multiple myeloma following autologous stem cell transplant. Use of lenalidomide in combination with rituximab (or a rituximab biosimilar agent) was FDA approved in May 2019 as therapy for previously treated follicular lymphoma and previously treated marginal zone lymphoma (MZL).
Mechanism Of Action and Pharmacodynamic Effects Click here for help
The precise mechanism of action of this drug has not been fully resolved. Drug action appears to be multi-faceted, exhibiting direct anti-tumour action, anti-angiogenic action, as well as immunomodulatory activity. LIke thalidomide, lenalidomide has been shown to interact with the ubiquitin E3 ligase component, cereblon [5]. When lenalidomide binds to CRBN, the lymphoid transcription factors Ikaros (IKZF1) and Aiolos (IKZF3) are degraded, and in addition casein kinase 1α (CK1α; CSNK1A1) is degraded. Reducing levels of CK1α confers lenalidomide's particular efficacy in treating myelodysplastic syndrome with deletion of chromosome 5q [1-2].
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
Drugs.com
European Medicines Agency (EMA)