Lenalidomide

Lenalidomide
Clinical data
Pronunciation/ˌlɛnəˈlɪdoʊmaɪd/
Trade namesRevlimid, Linamide, others
AHFS/Drugs.comMonograph
MedlinePlusa608001
License data
Pregnancy
category
  • AU: X (High risk)[1]
Routes of
administration		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityUndetermined
Protein binding30%
MetabolismUndetermined
Elimination half-life3 hours
ExcretionKidney (67% unchanged)
Identifiers
  • (3RS)-3-(4-Amino-1-oxo-1,3-dihydro-2H-isoindol-2-yl)piperidine-2,6-dione
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.218.924 Edit this at Wikidata
Chemical and physical data
FormulaC13H13N3O3
Molar mass259.265 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
  • O=C1NC(=O)CCC1N3C(=O)c2cccc(c2C3)N
  • 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) checkY
  • Key:GOTYRUGSSMKFNF-UHFFFAOYSA-N checkY
  (verify)

Lenalidomide, sold under the brand name Revlimid among others, is a medication used to treat multiple myeloma, smoldering myeloma, and myelodysplastic syndromes (MDS).[8] For multiple myeloma, it is a first line treatment, and is given with dexamethasone.[8] It is taken by mouth.[8]

Common side effects include diarrhea, itchiness, joint pain, fever, headache, and trouble sleeping.[8] Severe side effects include low blood platelets, low white blood cells, and blood clots.[8] The dose may need to be adjusted in people with kidney problems.[8] Lenalidomide is closely related to thalidomide, which is known to cause severe birth defects, so its use during pregnancy is very likely to harm the fetus.[8]

Lenalidomide belongs to a class of drugs known as immunomodulatory imide drugs (IMiDs) or Cereblon E3 ligase modulators, which includes thalidomide and its analogs.[9] In lymphocytes, these drugs target an E3 ubiquitin ligase and change its specificity to include new targets.[9] This results in the rapid degradation of several disease-related proteins including IKZF1, IKZF3, and CSNK1A1.[9]

Lenalidomide was approved for medical use in the United States in 2005.[8] It is on the World Health Organization's List of Essential Medicines.[10]

  1. ^ "Lenalidomide (Revlimid) Use During Pregnancy". Drugs.com. 13 March 2020. Archived from the original on 9 October 2020. Retrieved 13 August 2020.
  2. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  3. ^ "LENALIDOMIDE VIATRIS (Alphapharm Pty Ltd)". Department of Health and Ages Care. Archived from the original on 13 November 2022. Retrieved 1 April 2023.
  4. ^ "Lenalidomide Sun/Lenalidomide Rbx/Lenalidomide Ran (Sun Pharma ANZ Pty Ltd)". Department of Health and Ages Care. Archived from the original on 18 March 2023. Retrieved 1 April 2023.
  5. ^ Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 15 August 2023.
  6. ^ Cite error: The named reference PI2019 was invoked but never defined (see the help page).
  7. ^ "Revlimid EPAR". European Medicines Agency. 14 June 2007. Retrieved 2 July 2024.
  8. ^ a b c d e f g h "Lenalidomide Monograph for Professionals". Drugs.com. Archived from the original on 4 March 2016. Retrieved 27 October 2019.
  9. ^ a b c Fink EC, Ebert BL (November 2015). "The novel mechanism of lenalidomide activity". Blood. 126 (21): 2366–2369. doi:10.1182/blood-2015-07-567958. PMC 4653765. PMID 26438514.
  10. ^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.