Thalidomide (CED0001765)

Record Information
Version1.0
Creation Date2009-07-30 17:59:11 UTC
Update Date2026-05-14 16:56:32 UTC
Accession NumberCHEM002534
Identification
Common NameThalidomide
ClassSmall Molecule
Description
Thalidomide belongs to the isoindolines, a subclass of isoindoles and derivatives within the organic compounds. This exogenous solid has the formula C13H10N2O4 and an average molecular weight of 258.23 g/mol. It functions as a drug (PMC10316824, PMC7186126), inhibitor (PMC13125077), and agonist (PMC5776038). Its recorded biological roles and applications include use as an immunosuppressive agent, anti-inflammatory agent (PMC10316824), anti-inflammatory drug, antineoplastic agent, angiogenesis inhibitor, leprostatic drug, teratogenic agent, sedative, antiemetic, and anticonvulsant. It is administered via the oral exposure route and is found in healthcare, pharmaceuticals, and veterinary products as an immunosuppressant, as well as in various electrical equipment, household cleaning and consumer products, and food processing sources. The compound targets several proteins, including Protein cereblon (CRBN), Tumor necrosis factor (TNF), Nuclear factor NF-kappa-B p105 subunit (NFKB1), Prostaglandin G/H synthase 2 (PTGS2), Hepatocyte nuclear factor 4-alpha (HNF4A), Nuclear receptor subfamily 1 group I member 2 (NR1I2), and is a binder of Fibroblast growth factor receptor 2 (FGFR2). In patients with erythema nodosum leprosum (ENL), its immunologic effects may relate to the down-modulation of selected cell surface adhesion molecules and the suppression of excessive tumor necrosis factor-alpha (TNF-a) production. Thalidomide is used as a treatment for cancer (PMC10216254, PMC4084783), multiple myeloma (PMC10216254, PMC10316824, PMC11158875, PMC11201495, PMC11637717, PMC12650601, PMC12923561, PMC13187128, PMC1779467, PMC2330021), angiosarcoma (PMC3715084, PMC5102718), rheumatoid arthritis (PMC1010320, PMC7298168), cutaneous lupus erythematosus (PMC9724583), pulmonary fibrosis (PMC9724583), gastrointestinal bleeding (PMC4986528, PMC6360670), pancytopenia (PMC4718299), vomiting (PMC8546762, PMC9903622), and bleeding (PMC12863811, PMC2776553, PMC5370822). It has therapeutic effects on inflammation (PMC6415974, PMC9724583), dilated cardiomyopathy (PMC4380242), pulmonary fibrosis (PMC5677010), rheumatoid arthritis (PMC4408009), gastrointestinal bleeding (PMC4250877), and multiple myeloma (PMC4084783, PMC4889030, PMC7298168). Associated health effects include neuropathy (PMC3674591, PMC4382664, PMC6081177, PMC7271593, PMC9387014, PMC9530276), drowsiness (PMC12863811, PMC9530276), fatigue (PMC3134146, PMC5370822, PMC6415974), rash (PMC3134146, PMC6212999), Stevens-Johnson syndrome (PMC3134146), neutropenia (PMC4439262, PMC5927128), edema (PMC4436674), increased headache (PMC5927128), and prostate cancer (PMC4439262).
Contaminant Type
  • Amide
  • Amine
  • Angiogenesis Inhibitor
  • Drug
  • Ester
  • Human Neurotoxin
  • Immunosuppressive Agent
  • Leprostatic Agent
  • Metabolite
  • Organic Compound
  • Synthetic Compound
  • Teratogen
Chemical Structure
Synonyms
ValueSource
ThalomidKegg
ThaledKegg
alpha-PhthalimidoglutarimideHMDB
N-Phthalimidoglutamic acid imideHMDB
N-PhthaloylglutamimideHMDB
N-Phthalylglutamic acid imideHMDB
Thalidomine usp26HMDB
SedovalHMDB
Celgene brand OF thalidomideHMDB
ThalidomideMeSH
Chemical FormulaC13H10N2O4
Average Molecular Mass258.230 g/mol
Monoisotopic Mass258.064 g/mol
CAS Registry Number50-35-1
IUPAC Name2-(2,6-dioxopiperidin-3-yl)-2,3-dihydro-1H-isoindole-1,3-dione
Traditional Namethalidomide
SMILESO=C1N(C2CCC(=O)NC2=O)C(=O)C2=CC=CC=C12
InChI IdentifierInChI=1S/C13H10N2O4/c16-10-6-5-9(11(17)14-10)15-12(18)7-3-1-2-4-8(7)13(15)19/h1-4,9H,5-6H2,(H,14,16,17)
InChI KeyUEJJHQNACJXSKW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phthalimides. These are aromatic heterocyclic compounds containing a 1,3-dioxoisoindoline moiety. They are imide derivatives of phthalic anhydrides.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIsoindoles and derivatives
Sub ClassIsoindolines
Direct ParentPhthalimides
Alternative Parents
Substituents
  • Phthalimide
  • Alpha-amino acid or derivatives
  • Isoindole
  • Piperidinedione
  • Delta-lactam
  • Piperidinone
  • Benzenoid
  • Piperidine
  • Carboxylic acid imide, n-substituted
  • Carboxylic acid imide
  • Dicarboximide
  • Carboxylic acid imide, n-unsubstituted
  • Lactam
  • Carboxylic acid derivative
  • Azacycle
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
Applications
Biological Roles
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateSolid
AppearanceThalidomide is an off-white to white, odorless, crystalline powder.
Experimental Properties
PropertyValue
Melting Point270°C
Boiling PointNot Available
Solubility545 mg/L (at 25°C)
Predicted Properties
PropertyValueSource
Water Solubility2.55 g/LALOGPS
logP0.42ALOGPS
logP0.016ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)11.59ChemAxon
pKa (Strongest Basic)-6.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area83.55 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity64.32 m³·mol⁻¹ChemAxon
Polarizability24.42 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-05d0-4950000000-f29254c7cc48a749c100Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-1940000000-f6d6997d1eaa7a83ec1bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0930000000-e92e8e23d5db87f50f53Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0019-2900000000-ecfd1b7ec17b857ea977Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0930000000-e92e8e23d5db87f50f53Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-1940000000-f6d6997d1eaa7a83ec1bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0019-2900000000-ecfd1b7ec17b857ea977Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0aou-3910000000-91636cf8948ff2a1ec8cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0aou-4900000000-0354536dffa9acdee12dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-066u-6900000000-ea3e7b4b381e65a7c9a4Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0aou-4900000000-c5062441ebfb6523331bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0bvl-2970000000-1e251d07e623c9fbe2a2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0aou-3910000000-19940b0b041ba51e96e0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a6r-0190000000-a818a5ae6100d0f996baNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0090000000-42e8be928c8508c213f2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0bvl-2970000000-fcf57e68d7f7156f09d4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0090000000-094c39302b7589d69293Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4r-0590000000-a8eb9abb005e68bb1fdfNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000f-9800000000-e219527727ba0e4f62ddNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0190000000-88a6f8cb2bfe0f1b603fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0bti-1790000000-bdf020cb11e65e0077f7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01oy-9700000000-ce19845489ffe3fdb389Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0bta-0960000000-38a7ecf36472375bfe14Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4j-1590000000-40230dba1a083dee9f10Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0005-4900000000-b49c37804603e0525f05Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052b-0960000000-d36ac6ec3b1b89dff27dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0690000000-80f3bc65113a7e246892Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0bu0-2910000000-f5c7d25ac889c736f325Not AvailableView Spectrum
MSMS Spectrumsplash10-0wba-4900000000-77362eaf27267f59650dNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityIn patients with erythema nodosum leprosum (ENL) the mechanism of action is not fully understood. Available data from in vitro studies and preliminary clinical trials suggest that the immunologic effects of this compound can vary substantially under different conditions, but may be related to suppression of excessive tumor necrosis factor-alpha (TNF-a) production and down-modulation of selected cell surface adhesion molecules involved in leukocyte migration. For example, administration of thalidomide has been reported to decrease circulating levels of TNF-a in patients with ENL, however, it has also been shown to increase plasma TNF-a levels in HIV-seropositive patients. As a cancer treatment, the drug may act as a VEGF inhibitor. The R-configuration and the S-configuration are more toxic individually than the racemic mixture. The LD50 could not be established in mice for racemic thalidomide, whereas LD50 values for the R and S configurations are reported to be 0.4 to 0.7 g/kg and 0.5 to 1.5 g/kg, respectively.
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Minimum Risk LevelNot Available
SymptomsThalidomide is associated with drowsiness/somnolence, peripheral neuropathy, dizziness/orthostatic hypotension, neutro-penia, and HIV viral load increase.
TreatmentPrecipitation of acyclovir in renal tubules may occur when the solubility (2.5 mg/mL) is exceeded in the intratubular fluid. In the event of acute renal failure and anuria, the patient may benefit from hemodialysis until renal function is restored. (2)
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
8760.0Log mg/kg[4900:16000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
inflammationhas_therapeutic_effect_onNot AvailablePMC6415974 , PMC9724583
inflammationassociated_withincreasePMC5605327
canceris_treatment_forNot AvailablePMC10216254 , PMC4084783
drowsinessassociated_withNot AvailablePMC12863811 , PMC12863811 , PMC9530276
dizzinessassociated_withNot AvailablePMC13125077 , PMC4436674
anemiahas_therapeutic_effect_onNot AvailablePMC4979191
anemiais_treatment_forNot AvailablePMC5370822
insomniahas_therapeutic_effect_onNot AvailablePMC7271593
fatigueassociated_withNot AvailablePMC3134146 , PMC5370822 , PMC6415974
multiple myelomais_treatment_forNot AvailablePMC10216254 , PMC10316824 , PMC11158875 , PMC11201495 , PMC11637717 , PMC12650601 , PMC12923561 , PMC13187128 , PMC1779467 , PMC2330021
multiple myelomahas_therapeutic_effect_onNot AvailablePMC4084783 , PMC4084783 , PMC4889030 , PMC7298168
diabetes mellitusassociated_withincreasePMC7432171
rheumatoid arthritisis_treatment_forNot AvailablePMC1010320 , PMC7298168
rheumatoid arthritishas_therapeutic_effect_onNot AvailablePMC4408009
diarrheais_treatment_forNot AvailablePMC13125077
diarrheahas_therapeutic_effect_onNot AvailablePMC13125077
diarrheaassociated_withincreasePMC4753325
neutropeniaassociated_withNot AvailablePMC4439262 , PMC5927128
neuropathic painis_treatment_forNot AvailablePMC2959022
feverhas_therapeutic_effect_onNot AvailablePMC13389440
feveris_treatment_forNot AvailablePMC13389440
bleedingis_treatment_forNot AvailablePMC12863811 , PMC2776553 , PMC5370822
bleedinghas_therapeutic_effect_onNot AvailablePMC12863811 , PMC12863811
painhas_therapeutic_effect_onNot AvailablePMC7271593
headacheassociated_withincreasePMC5927128
Prostate cancerassociated_withNot AvailablePMC4439262
Prostate canceris_treatment_forNot AvailablePMC6415974 , PMC6415974
melanomais_treatment_forNot AvailablePMC6415974
depressionassociated_withincreasePMC7432171
abdominal painhas_therapeutic_effect_onNot AvailablePMC13389440
abdominal painis_treatment_forNot AvailablePMC13389440
abdominal painassociated_withNot AvailablePMC12517424
psoriasisis_treatment_forNot AvailablePMC7834521
COVID-19is_treatment_forNot AvailablePMC7834521 , PMC7834521 , PMC7834521 , PMC7834521
COVID-19has_therapeutic_effect_onNot AvailablePMC7834521
angiosarcomais_treatment_forNot AvailablePMC3715084 , PMC5102718
nauseaassociated_withincreasePMC4753325
nauseais_treatment_forNot AvailablePMC8546762
vomitingis_treatment_forNot AvailablePMC8546762 , PMC9903622
vomitingassociated_withincreasePMC4753325
heart failureassociated_withNot AvailablePMC12863811 , PMC12863811
edemaassociated_withNot AvailablePMC4436674
rashassociated_withNot AvailablePMC3134146 , PMC6212999
pneumoniaassociated_withNot AvailablePMC4753325
renal cell carcinomais_treatment_forNot AvailablePMC6415974
neuropathyassociated_withNot AvailablePMC3674591 , PMC3674591 , PMC4382664 , PMC6081177 , PMC7271593 , PMC9387014 , PMC9530276
thrombosisassociated_withNot AvailablePMC12863811 , PMC4382664 , PMC4753325
thrombosisassociated_withincreasePMC4753325
gastrointestinal bleedingis_treatment_forNot AvailablePMC4986528 , PMC6360670
gastrointestinal bleedinghas_therapeutic_effect_onNot AvailablePMC4250877
pulmonary fibrosishas_therapeutic_effect_onNot AvailablePMC5677010 , PMC5677010
pulmonary fibrosisis_treatment_forNot AvailablePMC9724583
epilepsyis_treatment_forNot AvailablePMC6212999
acute myeloid leukemiais_treatment_forNot AvailablePMC6415974
Endometriosisis_treatment_forNot AvailablePMC10316824
Endometriosishas_therapeutic_effect_onNot AvailablePMC10316824
ovarian dysfunctionassociated_withNot AvailablePMC12517424
pancreatic cancerhas_therapeutic_effect_onNot AvailablePMC10316824
inflammatory bowel diseaseis_treatment_forNot AvailablePMC13389440
dilated cardiomyopathyhas_therapeutic_effect_onNot AvailablePMC4380242
bradycardiaassociated_withNot AvailablePMC3820489
cutaneous lupus erythematosusis_treatment_forNot AvailablePMC9724583
cutaneous lupus erythematosushas_therapeutic_effect_onNot AvailablePMC3674591
pancytopeniais_treatment_forNot AvailablePMC4718299
Stevens-Johnson syndromeassociated_withNot AvailablePMC3134146
graft-versus-host diseaseis_treatment_forNot AvailablePMC6415974
polyneuropathyassociated_withNot AvailablePMC12517424 , PMC12517424 , PMC3674591
Silicosisis_treatment_forNot AvailablePMC9724583
Telangiectasisassociated_withNot AvailablePMC4986528
arthropathyassociated_withincreasePMC7432171
plasma cell leukemiais_treatment_forNot AvailablePMC6223128 , PMC9387011
mantle cell lymphomais_treatment_forNot AvailablePMC4439262
mantle cell lymphomahas_therapeutic_effect_onNot AvailablePMC4725701
myelodysplastic syndromehas_therapeutic_effect_onNot AvailablePMC3496085
systemic lupus erythematosusis_treatment_forNot AvailablePMC7834521
erythema nodosumis_treatment_forNot AvailablePMC9903622
syndactylyassociated_withNot AvailablePMC5362654
myelofibrosisis_treatment_forNot AvailablePMC2361627
leprosyis_treatment_forNot AvailablePMC10216254 , PMC5350610 , PMC7479632
rosaceahas_therapeutic_effect_onNot AvailablePMC9724583
pyoderma gangrenosumis_treatment_forNot AvailablePMC9724583
amenorrheaassociated_withNot AvailablePMC9530276
POEMS syndromehas_therapeutic_effect_onNot AvailablePMC6928515
PFAPA syndromeis_treatment_forNot AvailablePMC9530276
multicentric Castleman diseaseis_treatment_forNot AvailablePMC7816226
lichen planusis_treatment_forNot AvailablePMC7816226
prostate adenocarcinomais_treatment_forNot AvailablePMC6415974
sensory peripheral neuropathyassociated_withNot AvailablePMC6415974
mucocutaneous leishmaniasisis_treatment_forNot AvailablePMC6904840 , PMC6904840
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
233BrushesPersonal care & cosmeticsNot Available
362ImmunosuppressantsHealthcare, pharmaceuticals & veterinary productsNot Available
498LaddersBuilding & ConstructionNot Available
500Stairs And RampsBuilding & ConstructionNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
507Auxiliary DevicesElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
520Emergency Protective DevicesElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
525Line Transmission SystemsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
538Thin Magnetic FilmsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
551Processing FishFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
564Soap DispensersHousehold cleaning & consumer productsNot Available
566Tobacco PipesHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
584BuoysMarine, shipping & aquacultureNot Available
589Life BuoysMarine, shipping & aquacultureNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
630ToysRecreation & sports surfacesNot Available
632ApparelTextiles, leather & furnishingsNot Available
640Embroidering And TuftingTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
647Multicolour DyeingTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
653SewingTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
2 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Cytochrome P450 2C19 structureClick to view 3D structureCytochrome P450 2C19P33261HumansPredicted (SEA)739.49
Cytochrome P450 1A2 structureClick to view 3D structureCytochrome P450 1A2P05177HumansPredicted (SEA)859.3
Cyclin-dependent kinase 2 structureClick to view 3D structureCyclin-dependent kinase 2P24941HumansPredicted (SEA)1298.14
Interleukin-1 receptor-associated kinase 4 structureClick to view 3D structureInterleukin-1 receptor-associated kinase 4Q9NWZ3HumansPredicted (SEA)1065.37
Casein kinase I isoform alpha structureClick to view 3D structureCasein kinase I isoform alphaP48729HumansPredicted (SEA)1250.96
Interleukin-1 receptor-associated kinase 1 structureClick to view 3D structureInterleukin-1 receptor-associated kinase 1P51617HumansPredicted (SEA)1041.78
Amine oxidase [flavin-containing] A structureClick to view 3D structureAmine oxidase [flavin-containing] AP21397HumansPredicted (SEA)379.126
Cytochrome P450 2D6 structureClick to view 3D structureCytochrome P450 2D6P10635HumansPredicted (SEA)2123.88
Indoleamine 2,3-dioxygenase 1 structureClick to view 3D structureIndoleamine 2,3-dioxygenase 1P14902HumansPredicted (SEA)75.8251
Protein cereblon structureClick to view 3D structureProtein cereblonQ96SW2HumansPredicted (SEA)0.0778492
Tumor necrosis factor structureClick to view 3D structureTumor necrosis factorP01375HumansPredicted (SEA)0.0778492
Click to view 3D structureZinc finger protein AiolosQ9UKT9HumansPredicted (SEA)0.0778492
Interleukin-1 beta structureClick to view 3D structureInterleukin-1 betaP01584HumansPredicted (SEA)0.0778492
Click to view 3D structureGlyceraldehyde-3-phosphate dehydrogenase, cytosolicQ01558Leishmania mexicanaPredicted (SEA)0.0778492
Click to view 3D structureCereblon isoform 4A4TVL0Magnetospirillum gryphiswaldensePredicted (SEA)0.0778492
Zinc finger protein Helios structureClick to view 3D structureZinc finger protein HeliosQ9UKS7HumansPredicted (SEA)0.0778492
DNA-binding protein Ikaros structureClick to view 3D structureDNA-binding protein IkarosQ13422HumansPredicted (SEA)0.233548
Click to view 3D structureProtein Aster-AQ96CP6HumansPredicted (SEA)0.233548
Bromodomain-containing protein 4 structureClick to view 3D structureBromodomain-containing protein 4O60885HumansPredicted (SEA)72.2441
Click to view 3D structureProstaglandin G/H synthase 1P05979Ovis ariesPredicted (SEA)20.3965
Click to view 3D structureProstaglandin G/H synthase 2P79208Ovis ariesPredicted (SEA)10.8989
PCNA-associated factor structureClick to view 3D structurePCNA-associated factorQ15004HumansPredicted (SEA)4.67095
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansPredicted (SEA)1210.56
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)1640.67
Voltage-gated inwardly rectifying potassium channel KCNH2 structureClick to view 3D structureVoltage-gated inwardly rectifying potassium channel KCNH2Q12809HumansPredicted (SEA)1579.72
Prostaglandin G/H synthase 2 structureClick to view 3D structureProstaglandin G/H synthase 2P35354HumansKnownIn patients with erythema nodosum leprosum (ENL) the mechanism of action is not fully understood. Available data from in vitro studies and preliminary clinical trials suggest that the immunologic effects of this compound can vary substantially under different conditions, but may be related to suppression of excessive tumor necrosis factor-alpha (TNF-a) production and down-modulation of selected cell surface adhesion molecules involved in leukocyte migration. For example, administration of thalidomide has been reported to decrease circulating levels of TNF-a in patients with ENL, however, it has also been shown to increase plasma TNF-a levels in HIV-seropositive patients.
Tumor necrosis factor structureClick to view 3D structureTumor necrosis factorP01375HumansKnownIn patients with erythema nodosum leprosum (ENL) the mechanism of action is not fully understood. Available data from in vitro studies and preliminary clinical trials suggest that the immunologic effects of this compound can vary substantially under different conditions, but may be related to suppression of excessive tumor necrosis factor-alpha (TNF-a) production and down-modulation of selected cell surface adhesion molecules involved in leukocyte migration. For example, administration of thalidomide has been reported to decrease circulating levels of TNF-a in patients with ENL, however, it has also been shown to increase plasma TNF-a levels in HIV-seropositive patients.
Nuclear factor NF-kappa-B p105 subunit structureClick to view 3D structureNuclear factor NF-kappa-B p105 subunitP19838HumansKnownIn patients with erythema nodosum leprosum (ENL) the mechanism of action is not fully understood. Available data from in vitro studies and preliminary clinical trials suggest that the immunologic effects of this compound can vary substantially under different conditions, but may be related to suppression of excessive tumor necrosis factor-alpha (TNF-a) production and down-modulation of selected cell surface adhesion molecules involved in leukocyte migration. For example, administration of thalidomide has been reported to decrease circulating levels of TNF-a in patients with ENL, however, it has also been shown to increase plasma TNF-a levels in HIV-seropositive patients.
Fibroblast growth factor receptor 2 structureClick to view 3D structureFibroblast growth factor receptor 2P21802HumansKnownNot Available
Protein cereblon structureClick to view 3D structureProtein cereblonQ96SW2HumansKnownNot Available
Hepatocyte nuclear factor 4-alpha structureClick to view 3D structureHepatocyte nuclear factor 4-alphaP41235HumansKnownNot Available
Nuclear receptor subfamily 1 group I member 2 structureClick to view 3D structureNuclear receptor subfamily 1 group I member 2O75469HumansKnownNot Available
Concentrations
Not Available
External Links
DrugBank IDDB01041
HMDB IDHMDB0015175
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkThalidomide
Chemspider ID5233
ChEBI ID74947
PubChem Compound ID5426
Kegg Compound IDC07910
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Jamshed Shah, “Synthesis and anti-tumor activity of nitrogen substituted thalidomide analogs.” U.S. Patent US20030139451, issued July 24, 2003.

MSDSLink
General References