Lenalidomide 191732-72-6 C13H13N3O3
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Lenalidomide Basic information |
Product Name: | Lenalidomide |
Synonyms: | Revlimid;Lenalidomide ,98%;3-(4-amino-1-oxoisoindolin-2-yl)piperidine-2,6-dione;3-(4-amino-1-oxoisoindolin-2-yl)piperidine-2,6-dione,Lenalidomide;LenalidoMide(CC-5013,RevliMid);(3S)-3-(4-Amino-1-oxo-1,3-dihydro-2H-isoindol-2-yl)piperidine-2,6-dione;3-(4-aMino-1-oxo-1,3-dihydro-2H-isoindol-2-yl)piperidine-2,6-dione;(3R)-3-(4-aMino-1-oxo-2,3-dihydro-1H-isoindol-2-yl)piperidine-2,6-dione |
CAS: | 191732-72-6 |
MF: | C13H13N3O3 |
MW: | 259.26062 |
EINECS: | 691-297-1 |
Product Categories: | Intermediates & Fine Chemicals;Pharmaceuticals;Amines;Heterocycles;Inhibitor;CC-5013;Inhibitors;-;Molecular Targeted Antineoplastic;pharmaceutical intermediate |
Mol File: | 191732-72-6.mol |
Lenalidomide Chemical Properties |
Melting point | 269-271°C |
storage temp. | -20°C Freezer |
CAS DataBase Reference | 191732-72-6(CAS DataBase Reference) |
Safety Information |
Risk Statements | 20/21/22 |
Safety Statements | 36/37 |
HazardClass | IRRITANT |
HS Code | 29339900 |
Lenalidomide Usage And Synthesis |
Antitumor Drug |
Lenalidomide is a kind of antitumor drugs that developed by American biological pharmaceutical companies. Its chemical structure is similar with thalidomide. It has many functions such as anti-tumor, immune regulation and anti-angiogenesis. It can inhibit the secretion of inflammatory cytokines, and increase the secretion of peripheral blood mononuclear anti-inflammatory cytokines. Vitro tests show that lenalidomide can inhibit the hyperplasia of some cell lines such as namalwa cell. It can inhibit the growth of patients’ multiple myeloma cells and MM1S cell. In addition, lenalidomide also can inhibit the expression of oxidase-2 (COX-2), but it has no effect on COX-1. Two multicenter randomized double-blind placebo-controlled clinical studies evaluate the safety and curative effect of lenalidomide that is used for multiple myeloma. The primary efficacy end point of the studies is time to progression (TTP). The interim analysis shows that TTP of the combination group is significantly superior to dexamethasone group. Recent clinical research results show that lenalidomide not only has curative effect on treating MDS and MM, but also on treating myeloma, leukemia, metastatic renal cell carcinoma, solid tumor, idiopathic generalized amyloidosis and systemic bone marrow fibrosis disease with marrow unripe. Lenalidomide is a new derivative of thalidomide. But its teratogenic toxicity has not found. Its effectiveness is 100 times stronger than thalidomide. According to the result of three clinical trials, lenalidomide is the most effective drug in the treatment of multiple myeloma. More than half of patients can prolong survival time to more than 3 years after taking the drug. In addition, it is also the only effective drugs to treat myelodysplastic syndrome (MDS). Clinical results find that 64% of the patients with MDS need not use blood transfusion after treated by lenalidomide. In December 2005, the US Food and Drug Administration (FDA) approved lenalidomide to be used in the treatment of myelodysplastic syndrome (MDS). In March 2006, the FDA approved lenalidomide that was produced by American Celgene Biological Pharmaceutical Companies to be used in the treatment of multiple myeloma (MM). On September 23, 2011, the European Medicines Agency (EMA) released information that they have confirmed that the benefits of lenalidomide(trade name: Revlimid) to be used in the treatment of patients group that was approved outweighed the risks. Meanwhile they warned the doctor the risk of the drug to cause new cancer cases. Lenalidomide has been used with dexamethasone to treat adult patients with multiple myeloma that has received at least one treatment. Three new studies show that the incidence of new cancer will be increased in the patients with newly diagnosed multiple myeloma treated by lenalidomide and other combined treatment increased incidence of cancer. The above information is edited by the Chemicalbook Geqian. |
Description | Lenalidomide is a derivative of thalidomide differing in the presence of an amino moiety in the 4-position and removal of one of the carbonyls of the phthaloyl ring. This derivative evolved from a structural-based effort to eliminate the adverse effects (somnolence, neuropathy, and teratogenicity) of thalidomide while maintaining or enhancing the appealing attributes. While the mechanism of action remains to be fully identified, lenalidomide inhibits TNF-a production in stimulated monocytes. In addition to inhibiting TNF-a secretion, the production of other pro-inflammatory cytokines is blocked. Complimentary to inhibition of pro-inflammatory cytokines, lenalidomide also increases the secretion of antiinflammatory cytokines, such as IL-10. Furthermore, lenalidomide inhibits secretion of angiogenic cytokines, VEGF and bFGF. Due to its immunomodulatory and antiangiogenic properties, lenalidomide has the potential for a wide spectrum of therapeutic applications. While other indications are under evaluation, lenalidomide has initially been launched for the treatment of myelodysplastic syndromes (MDS), a set of hematologic disorders that affect the bone marrow and result in a deficiency of mature blood cells. There are various types of MDS, and lenalidomide is approved for the type associated with a truncation of chromosome 5 known as deletion 5q MDS. In combination with dexamethasone, it has also been designated for the second-line treatment of multiple myeloma, a B cell malignancy characterized by excess monotypic plasma cells in the bone marrow. . |
Chemical Properties | Yellow Solid |
Originator | Celgene (US) |
Uses | Immunomodulatory drug; analog of Thalidomide. |
Uses | Lenalidomide (Revlimid, CC-5013) is a TNF-α secretion inhibitor with IC50 of 13 nM. |
Uses | Lovastatin content <1% 98% |
Uses | A Thalidomide analog known to have immunomodulatory properties |
Definition | ChEBI: A dicarboximide that consists of 1-oxoisoindoline bearing an amino substituent at position 4 and a 2,6-dioxopiperidin-3-yl group at position 2. Inhibits the secretion of TNF-alpha. |
Brand name | Revlimid(Celgene). |
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