| Identification | More | [Name]
Lenalidomide | [CAS]
191732-72-6 | [Synonyms]
3-(7-amino-3-oxo-1h-isoindol-2-yl)piperidine-2,6-dione
lenalidomide
LenalidomideLenalidomide
1-Oxo-2-(2,6-dioxopiperidin-3-yl)-4-aminoisoindoline
3-(4-Amino-1,3-dihydro-1-oxo-2H-isoindol-2-yl)-2,6-piperidinedione
CC-5013
Revlimi
Lenalidomide(other anti-cancers)
Revlimid
Lenalidomide ,98% | [EINECS(EC#)]
691-297-1 | [Molecular Formula]
C13H13N3O3 | [MDL Number]
29339900 | [Molecular Weight]
259.261 | [MOL File]
191732-72-6.mol | [References]
http://www.sigmaaldrich.com/catalog/product/aldrich/70170?lang=en®ion=US https://pubchem.ncbi.nlm.nih.gov/compound/Naphazoline_nitrate J. JosephCharles, and M. Bertucat. "Simultaneous Determination of Naphazoline Nitrate and Tetramethylthionine Base in Eye Drops by First-Derivative UV Spectrophotometry." Analytical Letters 32.2(1999):373-382.
Hayasaka, Y, et al. "Effects of Topical Mydriatics and Vasoconstrictors on Prostaglandin-E2-Induced Aqueous Flare Elevation in Pigmented Rabbits." Ophthalmic Research 35.5(2003):256-260.
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| Chemical Properties | Back Directory | [Appearance]
Yellow Solid | [Melting point ]
265-268 °C | [Boiling point ]
614.0±55.0 °C(Predicted) | [density ]
1.460±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
Soluble in DMSO (up to 30 mg/ml) | [form ]
solid | [pka]
10.75±0.40(Predicted) | [color ]
White | [Usage]
Immunomodulatory drug; analog of Thalidomide. | [Detection Methods]
HPLC,NMR | [Stability:]
Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months. | [InChI]
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) | [InChIKey]
GOTYRUGSSMKFNF-UHFFFAOYSA-N | [SMILES]
N1C(=O)CCC(N2CC3=C(C2=O)C=CC=C3N)C1=O | [CAS DataBase Reference]
191732-72-6(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Description]
Lenalidomide(191732-72-6) 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) | [History]
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. | [Uses]
A Thalidomide analog known to have immunomodulatory properties | [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% | [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). | [benefits]
Lenalidomide(191732-72-6) is used to treat various types of cancers. It works by slowing or stopping the growth of cancer cells. It is also used to treat anemia in patients with certain blood/bone marrow disorders (myelodysplastic syndromes-MDS). Lenalidomide may lessen the need for blood transfusions.
| [Biochem/physiol Actions]
Lenalidomide(191732-72-6), a derivative of thalidomide, is an immunomodulatory agent that is approved drug for treatment of multiple myeloma. Apparently Lenalidomide is a ligand of ubiquitin E3 ligase cereblon that induces the enzyme to degrade the Ikaros transcription factors IKAROS family zinc finger 1 (IKZF1) and IKZF3. Lenalidomide possess pleiotropic antitumor effects. It is used in the treatment of 5q-deletion associated myelodysplastic syndrome (del(5q)-MDS).
| [Mechanism of action]
Lenalidomide acts by a novel drug mechanism—modulation of the substrate specificity of the CRL4CRBN E3 ubiquitin ligase. In multiple myeloma, lenalidomide induces the ubiquitination of IKZF1 and IKZF3 by CRL4CRBN. Subsequent proteasomal degradation of these transcription factors kills multiple myeloma cells. | [Clinical Use]
#N/A | [target]
TNF-α | [Drug interactions]
Lenalidomide is poorly metabolised as 82% of the dose
is excreted unchanged in urine. Hydroxy-lenalidomide
and N-acetyl-lenalidomide represent 4.59% and 1.83%
of the excreted dose, respectively. The renal clearance
of lenalidomide exceeds the glomerular filtration rate
and therefore is at least actively secreted to some extent.
Approximately 4% of lenalidomide is eliminated in faeces. | [Metabolism]
Lenalidomide is poorly metabolised as 82% of the dose
is excreted unchanged in urine. Hydroxy-lenalidomide
and N-acetyl-lenalidomide represent 4.59% and 1.83%
of the excreted dose, respectively. The renal clearance
of lenalidomide exceeds the glomerular filtration rate
and therefore is at least actively secreted to some extent.
Approximately 4% of lenalidomide is eliminated in faeces. | [storage]
Store at -20°C | [Clinical claims and research]
Lenalidomide(191732-72-6) 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.
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