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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL468
CHEMBL468
Compound Name THALIDOMIDE
ChEMBL Synonyms THALIDOMIDE | TALIDEX | K-17 | THALIDOMIDE | THALOMID
Max Phase 4 (Approved)
Trade Names THALOMID | TALIDEX
Molecular Formula C13H10N2O4

Additional synonyms for CHEMBL468 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES O=C1CCC(N2C(=O)c3ccccc3C2=O)C(=O)N1
Standard InChI InChI=1S/C13H10N2O4/c16-10-6-5-9(11(17)14-10)15-12(18)7-3-1- ...
Download InChI
Standard InChI Key UEJJHQNACJXSKW-UHFFFAOYSA-N

Sources

  • AstraZeneca Deposited Data
  • British National Formulary
  • DrugMatrix
  • Gene Expression Atlas Compounds
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL468

Molecule Features

CHEMBL468 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Racemic Mixture Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:Y Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
CRL4(CRBN) E3 ubiquitin ligase inhibitor CRL4(CRBN) E3 ubiquitin ligase PubMed PubMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Carcinoma, HepatocellularD006528EFO:0000182hepatocellular carcinoma3ClinicalTrials
Esophageal NeoplasmsD004938EFO:0002916esophageal carcinoma2ClinicalTrials
GliomaD005910EFO:0005543glioma2ClinicalTrials
Hepatitis CD006526EFO:0003047hepatitis C infection2ClinicalTrials
Lymphoma, Non-HodgkinD008228EFO:0005952non-Hodgkins lymphoma2ClinicalTrials
MedulloblastomaD008527EFO:0002939medulloblastoma2ClinicalTrials
MelanomaD008545EFO:0000389cutaneous melanoma2ClinicalTrials
Spondylitis, AnkylosingD013167EFO:0003898ankylosing spondylitis2ClinicalTrials
Acquired Immunodeficiency SyndromeD000163EFO:0000765AIDS2ClinicalTrials
Alzheimer DiseaseD000544EFO:0000249Alzheimers disease2ClinicalTrials
AmyloidosisD000686Orphanet:314701Primary systemic amyloidosis2ClinicalTrials
CarcinomaD002277EFO:0000313carcinoma2ClinicalTrials
Colorectal NeoplasmsD015179EFO:0000365colorectal adenocarcinoma3ClinicalTrials
GliomaD005910EFO:0000326central nervous system cancer2ClinicalTrials
Head and Neck NeoplasmsD006258EFO:0006859head and neck malignant neoplasia2ClinicalTrials
Leukemia, Lymphocytic, Chronic, B-CellD015451EFO:0000095chronic lymphocytic leukemia2ClinicalTrials
Myelodysplastic SyndromesD009190EFO:0000198myelodysplastic syndrome3ClinicalTrials
Pancreatic NeoplasmsD010190EFO:0002618pancreatic carcinoma2ClinicalTrials
Pancreatitis, ChronicD050500EFO:0000342chronic pancreatitis2ClinicalTrials
Vascular MalformationsD054079EFO:0006888vascular malformation3ClinicalTrials
Colorectal NeoplasmsD015179EFO:0004142colorectal neoplasm3ClinicalTrials
CoughD003371HP:0012735Cough3ClinicalTrials
MelanomaD008545EFO:0000756melanoma2ClinicalTrials
Neuroendocrine TumorsD018358EFO:1001901neuroendocrine neoplasm2ClinicalTrials
PainD010146EFO:0003843pain2ClinicalTrials
Primary MyelofibrosisD055728EFO:0002430primary myelofibrosis2ClinicalTrials
PsoriasisD011565EFO:0000676psoriasis2ClinicalTrials
Purpura, Thrombocytopenic, IdiopathicD016553EFO:0007160autoimmune thrombocytopenic purpura2ClinicalTrials
Scleroderma, SystemicD012595EFO:0000717systemic scleroderma1ClinicalTrials
Brain Stem NeoplasmsD020295EFO:1001767brain stem neoplasm2ClinicalTrials
Breast NeoplasmsD001943EFO:0000305breast carcinoma2ClinicalTrials
Castleman DiseaseD005871EFO:1001332Giant Lymph Node Hyperplasia2ClinicalTrials
Cholangitis, SclerosingD015209EFO:0004268sclerosing cholangitis2ClinicalTrials
HIV InfectionsD015658EFO:0000764HIV infection2ClinicalTrials
HIV Wasting SyndromeD019247EFO:0007312HIV wasting syndrome2ClinicalTrials
Lymphoma, Large B-Cell, DiffuseD016403EFO:0000403diffuse large B-cell lymphoma3ClinicalTrials
Neuroendocrine TumorsD018358EFO:1000045pancreatic neuroendocrine tumor2ClinicalTrials
Ovarian NeoplasmsD010051EFO:0001075ovarian carcinoma2ClinicalTrials
Prostatic NeoplasmsD011471EFO:0000673prostate adenocarcinoma3ClinicalTrials
SarcomaD012509EFO:0000691sarcoma2ClinicalTrials
Waldenstrom MacroglobulinemiaD008258EFO:0002616macroglobulinemia2ClinicalTrials
AmyloidosisD000686EFO:1001875amyloidosis2ClinicalTrials
Colitis, UlcerativeD003093EFO:0000729ulcerative colitis3ClinicalTrials
EpilepsyD004827EFO:0000474epilepsy1ClinicalTrials
Leukemia, LymphoidD007945EFO:0004289lymphoid leukemia2ClinicalTrials
Multiple MyelomaD009101EFO:0001378multiple myeloma3ClinicalTrials
NeoplasmsD009369EFO:0000616neoplasm3ClinicalTrials
Amyloidosis, FamilialD028226Orphanet:85443AL amyloidosis3ClinicalTrials
Carcinoma, Non-Small-Cell LungD002289EFO:0003060non-small cell lung carcinoma2ClinicalTrials
Carcinoma, Renal CellD002292EFO:0000681renal cell carcinoma3ClinicalTrials
Crohn DiseaseD003424EFO:0000384Crohn's disease3ClinicalTrials
EndometriosisD004715EFO:0001065endometriosis1ClinicalTrials
Lung NeoplasmsD008175EFO:0001071lung carcinoma3ClinicalTrials
Lymphoma, FollicularD008224EFO:0000096neoplasm of mature B-cells2ClinicalTrials
Carcinoma, Renal CellD002292EFO:0002890renal carcinoma3ClinicalTrials
Colonic NeoplasmsD003110EFO:1001950colon carcinoma2ClinicalTrials
GlioblastomaD005909EFO:0000519glioblastoma multiforme2ClinicalTrials
Hodgkin DiseaseD006689EFO:0000183Hodgkins lymphoma2ClinicalTrials
Idiopathic Pulmonary FibrosisD054990EFO:0000768idiopathic pulmonary fibrosis3ClinicalTrials
Immune System DiseasesD007154EFO:0000540immune system disease4ATC
LeukemiaD007938EFO:0000565leukemia2ClinicalTrials
Lupus Erythematosus, SystemicD008180EFO:0002690systemic lupus erythematosus2ClinicalTrials
LymphomaD008223EFO:0000574lymphoma3ClinicalTrials
Amyotrophic Lateral SclerosisD000690EFO:0000253amyotrophic lateral sclerosis2ClinicalTrials
Colorectal NeoplasmsD015179EFO:1001951colorectal carcinoma3ClinicalTrials
Kidney NeoplasmsD007680EFO:0003865kidney neoplasm2ClinicalTrials
Lymphoma, B-Cell, Marginal ZoneD018442EFO:0000191MALT lymphoma2ClinicalTrials
NeoplasmsD009369EFO:0000311cancer3ClinicalTrials
Prostatic NeoplasmsD011471EFO:0001663prostate carcinoma3ClinicalTrials
SarcoidosisD012507Orphanet:797Sarcoidosis3ClinicalTrials
ThalassemiaD013789EFO:1001996Thalassemia2ClinicalTrials

Clinical Data

ClinicalTrials.gov THALIDOMIDE
The Cochrane Collaboration THALIDOMIDE

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL468. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL217 Dopamine D2 receptor Homo sapiens 0.278

10uM


ChEMBL_ID Target Name Organism Score
CHEMBL219 Dopamine D4 receptor Homo sapiens 0.238
CHEMBL217 Dopamine D2 receptor Homo sapiens 0.235

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
258.2 258.0641 0.09 1 83.55 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
4 1 0 6 1 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
10.7 - .33 .33 1 19 0.72

Structural Alerts

There are 3 structural alerts for CHEMBL468. To view alerts please click here.

Compound Cross References

ATC L - ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
L04 - IMMUNOSUPPRESSANTS
L04A - IMMUNOSUPPRESSANTS
L04AX - Other immunosuppressants
L04AX02 - thalidomide

ChemSpider ChemSpider:UEJJHQNACJXSKW-UHFFFAOYSA-N
DailyMed thalidomide
PubChem SID: 111716 SID: 11532929 SID: 124881523 SID: 144210897 SID: 170465323 SID: 174007312 SID: 26747126 SID: 26751823 SID: 50104514 SID: 90341724
Wikipedia Thalidomide

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL468



ACToR 841-67-8 50-35-1 731-40-8 2614-06-4 14088-68-7
Atlas thalidomide
BindingDB 50070114
Brenda 160374
ChEBI 74947
DrugBank DB01041
DrugCentral 2616
eMolecules 594669
EPA CompTox Dashboard DTXSID9022524
Guide to Pharmacology 7327
Human Metabolome Database HMDB0015175
IBM Patent System DB7696934EECEC8F4E85C723E18A1E3E
KEGG Ligand C07910
LINCS LSM-1914
Mcule MCULE-6327754946
MolPort MolPort-003-665-582
NIH Clinical Collection SAM002564245
Nikkaji J4.101G
PharmGKB PA451644
PubChem 5426
PubChem: Drugs of the Future 12013404
PubChem: Thomson Pharma 14798889
Selleck Thalidomide
SureChEMBL SCHEMBL7581

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/UEJJHQNACJXSKW-UHFFFAOYSA-N spacer
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