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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2D Structure
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Physico-chemical Properties
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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
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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)
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].
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