Lenalidomide

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WARNING: This product is for research use only, not for human or veterinary use.

Description:Lenalidomide, also known as CC-5013, is the thalidomide analog with potential antineoplastic activity. Lenalidomide inhibits TNF-alpha production, stimulates T cells, reduces serum levels of the cytokines vascular endothelial growth factor (VEGF) and basic fibroblast growth factor (bFGF), and inhibits angiogenesis. This agent also promotes G1 cell cycle arrest and apoptosis of malignant cells. Lenalidomide is an approved drug.

Price and Availability

Lenalidomide, purity > 98%, is in stock. The same day shipping out after order is received.

Chemical Structure

Theoretical Analysis

MedKoo Cat#: 100500Name: LenalidomideCAS#: 191732-72-6Chemical Formula: C13H13N3O3Exact Mass: 259.09569Molecular Weight: 259.26Elemental Analysis:C, 60.22; H, 5.05; N, 16.21; O, 18.51

Synonym:CC5013; CC-5013; CC 5013; IMiD1; Lenalidomide; US brand name: Revlimid.

IUPAC/Chemical Name:3-(4-amino-1-oxoisoindolin-2-yl)piperidine-2,6-dione

InChi Key:GOTYRUGSSMKFNF-UHFFFAOYSA-N

InChi Code: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)

SMILES Code:O=C(C(N(CC1=C2C=CC=C1N)C2=O)CC3)NC3=O

Technical Data

Additional Information

Chemical structures:Chemical structures of Pomalidomide ; Thalidomide and Lenalidomide are very similar:  Lenalidomide, initially known as CC-5013 and marketed as Revlimid by Celgene, is a derivative of thalidomide introduced in 2004. It was initially intended as a treatment for multiple myeloma, for which thalidomide is an accepted therapeutic modality, but has also shown efficacy in the class of hematological disorders known as myelodysplastic syndromes (MDS). Revlimid is also known as Revamid in the UK.The exact mechanism of the immunomodulatory drugs (i.e., thalidomide, CC-4047/Actimid and lenalidomide) is not known. Apart from interfering with the immune system, they are also thought to act on angiogenesis. Lenalidomide and bortezomib are considered therapeutic breakthroughs in myeloma, which generally carries a poor prognosis. Lenalidomide is an off-white to pale-yellow solid powder. It is soluble in organic solvent/water mixtures, and buffered aqueous solvents. Lenalidomide is more soluble in organic solvents and low pH solutions. Solubility was significantly lower in less acidic buffers, ranging from about 0.4 to 0.5 mg/ml. Lenalidomide has an asymmetric carbon atom and can exist as the optically active forms S(-) and R(+), and is produced as a racemic mixture with a net optical rotation of zero. REVLIMID® (lenalidomide) is available in 5 mg, 10 mg, 15 mg and 25 mg capsules for oral administration. Each capsule contains lenalidomide as the active ingredient and the following inactive ingredients: lactose anhydrous, microcrystalline cellulose, croscarmellose sodium, and magnesium stearate. The 5 mg and 25 mg capsule shell contains gelatin, titanium dioxide and black ink. The 10 mg capsule shell contains gelatin, FD&C blue #2, yellow iron oxide, titanium dioxide and black ink. The 15 mg capsule shell contains gelatin, FD&C blue #2, titanium dioxide and black ink. The mechanism of action of lenalidomide remains to be fully characterized. Lenalidomide possesses antineoplastic, immunomodulatory and antiangiogenic properties. Lenalidomide inhibited the secretion of pro-inflammatory cytokines and increased the secretion of antiinflammatory cytokines from peripheral blood mononuclear cells. Lenalidomide inhibited cell proliferation with varying effectiveness (IC50s) in some but not all cell lines. Of cell lines tested, lenalidomide was effective in inhibiting growth of Namalwa cells (a human B cell lymphoma cell line with a deletion of one chromosome 5) but was much less effective in inhibiting growth of KG-1 cells (human myeloblastic cell line, also with a deletion of one chromosome 5) and other cell lines without chromosome 5 deletions. Lenalidomide inhibited the growth of multiple myeloma cells from patients, as well as MM.1S cells (a human multiple myeloma cell line), by inducing cell cycle arrest and apoptosis. Lenalidomide inhibited the expression of cyclooxygenase-2 (COX-2) but not COX-1 in vitro.  

References

1: Nojkov B, Signori C, Konda A, Fontana RJ.Lenalidomide-associated hepatotoxicity--a case report and literaturereview. Anticancer Res. 2012 Sep;32(9):4117-9. Review. PubMed PMID:22993370.

2: Kimby E. Biological therapy doublets: pairing rituximab withinterferon, lenalidomide, and other biological agents in patients withfollicular lymphoma. Curr Hematol Malig Rep. 2012 Sep;7(3):221-7. doi:10.1007/s11899-012-0133-2. Review. PubMed PMID: 22895878.

3: Bringhen S, Gay F, Pautasso C, Cerrato C, Boccadoro M, Palumbo A.Evaluation of the pharmacokinetics, preclinical, and clinical efficacyof lenalidomide for the treatment of multiple myeloma. Expert Opin DrugMetab Toxicol. 2012 Sep;8(9):1209-22. doi: 10.1517/17425255.2012.712685.Epub 2012 Aug 3. Review. PubMed PMID: 22862790.

4: Brower V. Lenalidomide maintenance for multiple myeloma. Lancet Oncol.2012 Jun;13(6):e238. Review. PubMed PMID: 22833889.

5: Dawar R, Hernandez-Ilizaliturri F. The emerging role of lenalidomidein the management of mantle cell lymphoma (MCL). Best Pract Res ClinHaematol. 2012 Jun;25(2):185-90. doi: 10.1016/j.beha.2012.04.005. Epub2012 May 18. Review. PubMed PMID: 22687454.

6: Dimopoulos MA, Terpos E, Goldschmidt H, Alegre A, Mark T, NiesvizkyR. Treatment with lenalidomide and dexamethasone in patients withmultiple myeloma and renal impairment. Cancer Treat Rev. 2012Dec;38(8):1012-9. doi: 10.1016/j.ctrv.2012.02.009. Epub 2012 May 18.Review. PubMed PMID: 22609463.

7: Segler A, Tsimberidou AM. Lenalidomide in solid tumors. CancerChemother Pharmacol. 2012 Jun;69(6):1393-406. doi:10.1007/s00280-012-1874-2. Epub 2012 May 15. Review. PubMed PMID:22584909.

8: Kunimasa K, Ueda T, Arita M, Maeda T, Hotta M, Ishida T. Drug-inducedinterstitial pneumonitis due to low-dose lenalidomide. Intern Med.2012;51(9):1081-5. Epub 2012 Apr 29. Review. PubMed PMID: 22576392.

9: Komrokji RS, List AF. Lenalidomide for treatment of myelodysplasticsyndromes. Curr Pharm Des. 2012;18(22):3198-203. Review. PubMed PMID:22571699.

10: Barosi G, Merlini G, Billio A, Boccadoro M, Corradini P, MarchettiM, Massaia M, Tosi P, Palumbo A, Cavo M, Tura S. SIE, SIES, GITMOevidence-based guidelines on novel agents (thalidomide, bortezomib, andlenalidomide) in the treatment of multiple myeloma. Ann Hematol. 2012Jun;91(6):875-88. doi: 10.1007/s00277-012-1445-y. Epub 2012 Apr 4.Review. PubMed PMID: 22476884.