Compound: Lenalidomide
SMILES: O=C1NC(=O)CCC1N2C(=O)c3cccc(c3C2)N
InChIKey: GOTYRUGSSMKFNF-UHFFFAOYSA-N
Synonyms: Lenalidomide, 191732-72-6, Revlimid, Revimid, 3-(4-Amino-1-oxoisoindolin-2-yl)piperidine-2,6-dione, CC-5013, 2,6-Piperidinedione, 3-(4-amino-1,3-dihydro-1-oxo-2H-isoindol-2-yl)-, CDC 501, CDC-501, 3-(4-Amino-1-oxo-1,3-dihydro-2H-isoindol-2-yl)piperidine-2,6-dione, Lenalidomida, DTXSID8046664, NSC-747972, F0P408N6V4, 1-oxo-2-(2,6-dioxopiperidin-3-yl)-4-aminoisoindoline, SYP-1512, 3-(4-amino-1-oxo-2,3-dihydro-1H-isoindol-2-yl)piperidine-2,6-dione, DTXCID6026664, CHEBI:63791, 4-amino-2-(6-hydroxy-2-oxo-2,3,4,5-tetrahydropyridin-3-yl)-2,3-dihydro-1H-isoindol-1-one, CC5013, IMiD3 cpd, lenalidomidum, RefChem:5941, L04AX04, NSC703813, 691-297-1, Lenalidomide (CC-5013), MFCD07772307, 3-(7-amino-3-oxo-1H-isoindol-2-yl)piperidine-2,6-dione, CC 5013, Lenadoamide, C13H13N3O3, Revlimid (TN), 3-(4-amino-1,3-dihydro-1-oxo-2h-isoindol-2-yl)-2,6-piperidinedione, s1029, NCGC00167491-01, Lenalidomide [USAN], 3-(4-Amino-1-oxo-1,3-dihydro-isoindol-2-yl)-piperidine-2,6-dione, CAS-191732-72-6, Lenalidomide?, UNII-F0P408N6V4, Lenalidomide [USAN:INN:BAN], Revimid;, ENMD 0997, ENMD-0997, HSDB 8220, IMID-5013, CDC-5013, ALBB-015321, Lenalidomide (Standard), LENALIDOMIDE [MI], LENALIDOMIDE [INN], LENALIDOMIDE [JAN], CHEMBL848, Revlimid (TN) (Celgene), LENALIDOMIDE [VANDF], SCHEMBL32978, LENALIDOMIDE [MART.], MLS003899194, LENALIDOMIDE [WHO-DD], GTPL7331, Lenalidomide (JAN/USAN/INN), orb1307920, LENALIDOMIDE [EMA EPAR], 3-(4-amino-1-oxo-isoindolin-2-yl)piperidine-2,6-dione, SCHEMBL26646478, SCHEMBL29414335, BDBM65454, HY-A0003R, Lenalidomide - Bio-X trade mark, 3-(7-Amino-3-oxo-1H-isoindol-2-yl)-piperidine-2,6-dione, HMS3654G07, HMS3674C05, HMS5079I05, LENALIDOMIDE [ORANGE BOOK], CIA27191, HY-A0003, MSK10368, Revlimid, Lenalidomide, CC-5013, Tox21_112492, AC-914, EBC-11297, NSC747972, STK639603, 2,6-Piperidinedione, 3-(4-amino-1,3-dihydro-1-oxo-2H- isoindol-2-yl)-, AKOS005146276, AKOS005174869, Tox21_112492_1, CCG-264781, CS-0125, DB00480, FL24864, KS-1207, NSC 747972, SB66166, NCGC00167491-02, NCGC00167491-03, NCGC00167491-04, NCGC01443006-01, BL164614, BP-27972, SMR002529986, SY047646, NS00003666, SW218084-2, D04687, EN300-118706, AB01273975-01, AB01273975-02, AB01273975_03, F078933, Q425681, SR-01000883999, SR-01000883999-1, 1-Oxo-4-amino-2-(2,6-dioxopiperidin-3-yl)isoindole, BRD-A17883755-001-06-1, 3-(4-Amino-1-oxo-2-isoindolinyl)piperidine-2,6-dione, Z1515385074, 2, 3-(4-amino-1,3-dihydro-1-oxo-2H-isoindol-2-yl)-, 3-(4-amino-1-oxo-1,3-dihydro-2H-isoindol-2-yl)-2,6-dioxopiperidine
Theoretical properties:
molecular_formula: C13H13N3O3
molecular_weight: 259.26 g/mol
exact_mass: 259.09569129 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 1
heavy_atom_count: 19
topological_polar_surface_area: 92.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Off-white to pale-yellow solid powder
color: Off-white to pale-yellow solid powder
solubility: 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.
Descriptions:
pubchem: Lenalidomide is 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. It has a role as an antineoplastic agent, an angiogenesis inhibitor and an immunomodulator. It is a member of isoindoles, an aromatic amine, a dicarboximide and a member of piperidones.
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-α.
chembl: LENALIDOMIDE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: 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.
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.
Lenalidomide belongs to a class of drugs known as immunomodulatory imide drugs (IMiDs) or Cereblon E3 ligase modulators, which includes thalidomide and its analogs. In lymphocytes, these drugs target an E3 ubiquitin ligase and change its specificity to include new targets. This results in the rapid degradation of several disease-related proteins including IKZF1, IKZF3, and CSNK1A1.
Lenalidomide was approved for medical use in the United States in 2005. It is on the World Health Organization's List of Essential Medicines.