WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 100500
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.
MedKoo Cat#: 100500
Chemical Formula: C13H13N3O3
Exact Mass: 259.09569
Molecular Weight: 259.26
Elemental 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
Appearance: White solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO, not in water
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 259.26 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
|Concentration / Solvent Volume / Mass||1 mg||5 mg||10 mg|
|1 mM||1.15 mL||5.76 mL||11.51 mL|
|5 mM||0.23 mL||1.15 mL||2.3 mL|
|10 mM||0.12 mL||0.58 mL||1.15 mL|
|50 mM||0.02 mL||0.12 mL||0.23 mL|
1: Nojkov B, Signori C, Konda A, Fontana RJ. Lenalidomide-associated hepatotoxicity--a case report and literature review. Anticancer Res. 2012 Sep;32(9):4117-9. Review. PubMed PMID: 22993370.
2: Kimby E. Biological therapy doublets: pairing rituximab with interferon, lenalidomide, and other biological agents in patients with follicular 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 efficacy of lenalidomide for the treatment of multiple myeloma. Expert Opin Drug Metab 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 lenalidomide in the management of mantle cell lymphoma (MCL). Best Pract Res Clin Haematol. 2012 Jun;25(2):185-90. doi: 10.1016/j.beha.2012.04.005. Epub 2012 May 18. Review. PubMed PMID: 22687454.
6: Dimopoulos MA, Terpos E, Goldschmidt H, Alegre A, Mark T, Niesvizky R. Treatment with lenalidomide and dexamethasone in patients with multiple myeloma and renal impairment. Cancer Treat Rev. 2012 Dec;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. Cancer Chemother 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-induced interstitial 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 myelodysplastic syndromes. Curr Pharm Des. 2012;18(22):3198-203. Review. PubMed PMID: 22571699.
10: Barosi G, Merlini G, Billio A, Boccadoro M, Corradini P, Marchetti M, Massaia M, Tosi P, Palumbo A, Cavo M, Tura S. SIE, SIES, GITMO evidence-based guidelines on novel agents (thalidomide, bortezomib, and lenalidomide) in the treatment of multiple myeloma. Ann Hematol. 2012 Jun;91(6):875-88. doi: 10.1007/s00277-012-1445-y. Epub 2012 Apr 4. Review. PubMed PMID: 22476884.
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.
REVLIMIDÂ® (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.