<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-22 05:52:22 UTC</creation_date>
  <update_date>2026-08-18 23:27:02 UTC</update_date>
  <accession/>
  <common_name>Lenalidomide</common_name>
  <class>SmallMolecule</class>
  <description>Lenalidomide (C13H13N3O3) is an organic compound with an average molecular weight of 259.26 g/mol. Lenalidomide belongs to the isoindolines, a subclass of isoindoles and derivatives within the organic compounds. It functions as a drug (PMC4695140) and an anti-inflammatory agent (PMC3732931). The compound acts as an antagonist, inhibitor, or negative modulator of Protein cereblon (CRBN), Tumor necrosis factor ligand superfamily member 11 (TNFSF11), Prostaglandin G/H synthase 2 (PTGS2), Cadherin-5 (CDH5), and one other protein. Oral exposure is a recorded route for this compound, which is found in sources including healthcare, pharmaceuticals and veterinary products (immunosuppressants), household cleaning and consumer products (non electric simulated smoking devices), food, food processing and cookware (preparation of wine or sparkling wine), and electrical and electronic equipment (antennas, electric hearing aids).

Lenalidomide is used in the treatment of anemia (PMC3977019, PMC4706836), B-cell lymphoma (PMC11743790), acute myeloid leukemia (PMC3128214), neuropathy (PMC7109734), and multiple myeloma (PMC10022849, PMC10040899, PMC10184122, PMC10216254, PMC10649824, PMC11172882, PMC11201495, PMC11219377). It has therapeutic effects on fatigue (PMC4408989) and multiple myeloma (PMC3496085, PMC4889030, PMC5217191, PMC5930136, PMC6410697, PMC7368820). Associated health effects include fatigue (PMC11219377, PMC12405678, PMC3674591, PMC3699390, PMC5215577, PMC6290473, PMC8171498, PMC8212249), neutropenia (PMC10230432, PMC10651865, PMC11219377, PMC11404760, PMC12052864, PMC12399965, PMC12405678, PMC12553274, PMC12801173), thrombocytopenia (PMC10651865, PMC12052864, PMC2361627, PMC3670754, PMC3674591, PMC3699390, PMC4232868, PMC4559079), diarrhea (PMC10828760, PMC12405678, PMC12801173, PMC4559079, PMC4753325, PMC6290473, PMC7271593), and thrombosis (PMC10519171, PMC10651865, PMC12946163, PMC13187128, PMC3674591, PMC4753325). Other associations include rash (PMC10230432, PMC10519171, PMC12405678, PMC4436674, PMC5215577, PMC6290473, PMC8171498, PMC8212249), pneumonia (PMC3227886, PMC3699390, PMC5679834, PMC8212249), hypokalemia (PMC5930136, PMC6290473, PMC8212249), bleeding (PMC10230432), neuropathy (PMC11219377), neuropathic pain (PMC4559079), confusion (PMC5930136), hypertension (PMC12946163), congestive heart failure (PMC12946163), cough (PMC8171498), bronchitis (PMC8171498), and renal failure (PMC11554676). The compound is elevated in the blood during renal insufficiency (PMC3673285).</description>
  <categories/>
  <types>
    <type>Human Neurotoxin</type>
  </types>
  <synonyms>
    <synonym>Lenalidomid</synonym>
  </synonyms>
  <chemical_formula>C13H13N3O3</chemical_formula>
  <average_molecular_weight>259.2606</average_molecular_weight>
  <monisotopic_moleculate_weight>259.095691297</monisotopic_moleculate_weight>
  <iupac_name>3-(4-amino-1-oxo-2,3-dihydro-1H-isoindol-2-yl)piperidine-2,6-dione</iupac_name>
  <traditional_iupac>lenalidomide</traditional_iupac>
  <cas_registry_number>191732-72-6</cas_registry_number>
  <smiles>NC1=CC=CC2=C1CN(C1CCC(=O)NC1=O)C2=O</smiles>
  <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)</inchi>
  <inchikey>GOTYRUGSSMKFNF-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Isoindoles and derivatives</class>
    <sub_class>Isoindolines</sub_class>
    <direct_parent>Isoindolones</direct_parent>
    <alternate_parents>
      <alternative_parent>Alpha amino acids and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Benzenoids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Delta lactams</alternative_parent>
      <alternative_parent>Dicarboximides</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Isoindoles</alternative_parent>
      <alternative_parent>N-unsubstituted carboxylic acid imides</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Piperidinediones</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Tertiary carboxylic acid amides</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid imide</substituent>
      <substituent>Carboxylic acid imide, n-unsubstituted</substituent>
      <substituent>Delta-lactam</substituent>
      <substituent>Dicarboximide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Isoindole</substituent>
      <substituent>Isoindolone</substituent>
      <substituent>Lactam</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Piperidine</substituent>
      <substituent>Piperidinedione</substituent>
      <substituent>Piperidinone</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Tertiary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>aromatic amine</descriptor>
      <descriptor>dicarboximide</descriptor>
      <descriptor>isoindoles</descriptor>
      <descriptor>piperidones</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Lenalidomide Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0142934</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lenalidomide Predicted Metabolism Pathway</name>
      <smpdb_id>SMP0174656</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>-0.71</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.43</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.05</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>2.33e+00 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>11.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>2.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-(4-amino-1-oxo-2,3-dihydro-1H-isoindol-2-yl)piperidine-2,6-dione</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>259.2606</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>259.095691297</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=CC=CC2=C1CN(C1CCC(=O)NC1=O)C2=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C13H13N3O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>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)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>GOTYRUGSSMKFNF-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>92.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>68.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>25.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <route_of_exposure/>
  <mechanism_of_toxicity/>
  <metabolism/>
  <toxicity/>
  <lethaldose/>
  <carcinogenicity/>
  <use_source/>
  <min_risk_level/>
  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f727a9b0200&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB00480</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>216326</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>187515</chemspider_id>
  <kegg_id/>
  <uniprot_id/>
  <omim_id/>
  <chebi_id/>
  <biocyc_id/>
  <ctd_id/>
  <stitch_id/>
  <actor_id/>
  <pdb_id/>
  <wikipidia/>
  <general_references/>
  <targets>
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</compound>
