(RS)-lenalidomide

Also known as CC-5013, CDC-501, 1-oxo-2-(2,6-dioxopiperidin-3-yl)-4-aminoisoindoline, IMiD3, CDC 501, IMid-1, 3-(4-amino-1-oxoisoindolin-2-yl)piperidine-2,6-dione, Lenalidomide

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

Key facts

Drug.H: 13
Drug.N: 3
Drug.O: 3
Drug.Watchedfields: changed
Drug.verifiedrevid: 459429828
Drug.image: Lenalidomide enantiomers.svg
Drug.image_class: skin-invert-image
Drug.width: 200
Drug.chirality: Racemic mixture
Drug.tradename: Revlimid, Linamide, others
Drug.MedlinePlus: a608001
Drug.licence_EU: yes
Drug.DailyMedID: Lenalidomide
Drug.pregnancy_AU: X
Drug.routes_of_administration: By mouth
Drug.ATC_prefix: L04
Drug.ATC_suffix: AX04
Drug.legal_AU: S4

via Wikipedia infobox

Chemical data

Formula: C13H13N3O3
Molecular weight: 259.26 g/mol
IUPAC name: 3-(7-amino-3-oxo-1H-isoindol-2-yl)piperidine-2,6-dione
SMILES: C1CC(=O)NC(=O)C1N2CC3=C(C2=O)C=CC=C3N
InChIKey: GOTYRUGSSMKFNF-UHFFFAOYSA-N
XLogP: -0.5
Polar surface area: 92.5 Å²
H-bond donors: 2
H-bond acceptors: 4
Formal charge: 0

via PubChem

Research

57 papers

via PubMed

Wikidata facts

Mass: 259.095691

Show 5 more facts

chemical formula: C₁₃H₁₃N₃O₃
World Health Organisation international non-proprietary name: lenalidomide
canonical SMILES: C1CC(=O)NC(=O)C1N2CC3=C(C2=O)C=CC=C3N
defined daily dose: 10
Commons category: Lenalidomide

Sources (7)

via Wikidata · CC0

~10 min read

Article

19 sections

Contents

Medical uses
Multiple myeloma
Myelodysplastic syndromes
Follicular Lymphoma
Mantle cell lymphoma
AL amyloidosis
Adverse effects
Teratogenicity
Venous thromboembolism
Stevens-Johnson syndrome
FDA ongoing safety review
Mechanism of action
Synthesis
History
Society and culture
Legal status
Economics
Price increases
References

Common side effects include diarrhea, itchiness, joint pain, fever, headache, and trouble sleeping. Severe side effects include low blood platelets, low white blood cells, and blood clots. The dose may need to be adjusted in people with kidney problems. 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.