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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL1023
CHEMBL1023
Compound Name BEXAROTENE
ChEMBL Synonyms TARGRETIN | LG100069 | BEXAROTENE | LG-100069 | LGD1069 | LGD-1069 | Targretine
Max Phase 4 (Approved)
Trade Names TARGRETIN | BEXAROTENE | Targretine
Molecular Formula C24H28O2

Additional synonyms for CHEMBL1023 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES Cc1cc2c(cc1C(=C)c3ccc(cc3)C(=O)O)C(C)(C)CCC2(C)C
Standard InChI InChI=1S/C24H28O2/c1-15-13-20-21(24(5,6)12-11-23(20,3)4)14-1 ...
Download InChI
Standard InChI Key NAVMQTYZDKMPEU-UHFFFAOYSA-N

Sources

  • British National Formulary
  • Gene Expression Atlas Compounds
  • Orange Book
  • PubChem BioAssays
  • Sanger Institute Genomics of Drug Sensitivity in Cancer
  • Scientific Literature
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL1023

Molecule Features

CHEMBL1023 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:N First In Class:N Chirality:Achiral Molecule Prodrug:N Oral:Y Parenteral:N Topical:Y Black Box:Y Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Retinoid X receptor agonist Retinoid X receptor FDA

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Lymphoma, T-Cell, CutaneousD016410EFO:0002913Cutaneous T-cell lymphoma4ClinicalTrials
DailyMed
Pituitary ACTH HypersecretionD047748EFO:1001110pituitary-dependent Cushing's disease1ClinicalTrials
Psychotic DisordersD011618EFO:0005411schizoaffective disorder3ClinicalTrials
Sezary SyndromeD012751EFO:1000785Sezary's disease2ClinicalTrials
Breast NeoplasmsD001943EFO:0000305breast carcinoma2ClinicalTrials
Carcinoma, Non-Small-Cell LungD002289EFO:0003060non-small cell lung carcinoma3ClinicalTrials
PsoriasisD011565EFO:0000676psoriasis2ClinicalTrials
SchizophreniaD012559EFO:0000692schizophrenia3ClinicalTrials
Alzheimer DiseaseD000544EFO:0000249Alzheimers disease2ClinicalTrials
Leukemia, Myeloid, AcuteD015470EFO:0000222acute myeloid leukemia2ClinicalTrials
LymphomaD008223EFO:0000574lymphoma3ClinicalTrials
Thyroid NeoplasmsD013964EFO:0002892thyroid carcinoma0ClinicalTrials
Lung NeoplasmsD008175EFO:0001071lung carcinoma2ClinicalTrials
Lymphoma, Large-Cell, AnaplasticD017728EFO:0003032anaplastic large cell lymphoma3ClinicalTrials
Mycosis FungoidesD009182EFO:1001051mycosis fungoides3ClinicalTrials
Alopecia AreataD000506EFO:0004192alopecia areata2ClinicalTrials
ParapsoriasisD010267EFO:1000747parapsoriasis2ClinicalTrials
Multiple MyelomaD009101EFO:0001378multiple myeloma1ClinicalTrials
NeoplasmsD009369EFO:0000616neoplasm4ATC
ClinicalTrials

Clinical Data

ClinicalTrials.gov BEXAROTENE
The Cochrane Collaboration BEXAROTENE

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 CHEMBL1023. 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
CHEMBL2003 Retinoic acid receptor gamma Homo sapiens 1.000
CHEMBL2004 Retinoid X receptor gamma Homo sapiens 1.000
CHEMBL2008 Retinoic acid receptor beta Homo sapiens 1.000
CHEMBL2061 Retinoid X receptor alpha Homo sapiens 1.000
CHEMBL1870 Retinoid X receptor beta Homo sapiens 1.000
CHEMBL4047 Retinoid X receptor beta Mus musculus 1.000
CHEMBL4402 Retinoid X receptor gamma Mus musculus 1.000
CHEMBL2055 Retinoic acid receptor alpha Homo sapiens 1.000
CHEMBL1792 Somatostatin receptor 5 Homo sapiens 0.281



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL2003 Retinoic acid receptor gamma Homo sapiens 1.000
CHEMBL2004 Retinoid X receptor gamma Homo sapiens 1.000
CHEMBL2008 Retinoic acid receptor beta Homo sapiens 1.000
CHEMBL2061 Retinoid X receptor alpha Homo sapiens 1.000
CHEMBL1870 Retinoid X receptor beta Homo sapiens 1.000
CHEMBL2055 Retinoic acid receptor alpha Homo sapiens 1.000
CHEMBL4047 Retinoid X receptor beta Mus musculus 1.000
CHEMBL4402 Retinoid X receptor gamma Mus musculus 1.000
CHEMBL5398 Hepatocyte nuclear factor 4-alpha Homo sapiens 1.000
CHEMBL3180 Carboxylesterase 2 Homo sapiens 0.408

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
348.5 348.2089 6.1 3 37.3 ACID


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
1 1 1 2 1 1


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
4.08 - 6.9 3.97 2 26 0.73

Structural Alerts

There are 1 structural alerts for CHEMBL1023. To view alerts please click here.

Compound Cross References

ATC L - ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
L01 - ANTINEOPLASTIC AGENTS
L01X - OTHER ANTINEOPLASTIC AGENTS
L01XX - Other antineoplastic agents
L01XX25 - bexarotene

ChemSpider ChemSpider:NAVMQTYZDKMPEU-UHFFFAOYSA-N
DailyMed bexarotene
PubChem SID: 124893633 SID: 144206219 SID: 144212724 SID: 170465308 SID: 50125754
Wikipedia Bexarotene

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL1023



ACToR 153559-49-0
Atlas targretin
BindingDB 50032675
ChEBI 50859
ChemicalBook CB6506670
DrugBank DB00307
DrugCentral 361
eMolecules 2794932
EPA CompTox Dashboard DTXSID1040619
FDA SRS A61RXM4375
Guide to Pharmacology 2807
Human Metabolome Database HMDB0014452
IBM Patent System 5380D89B79B7C5473549C6944AA3B5CD
LINCS LSM-45378
Mcule MCULE-3783114634
MolPort MolPort-003-845-030
Nikkaji J612.549B
PDBe 9RA
PharmGKB PA164752250
PubChem 82146
PubChem: Drugs of the Future 87550948
PubChem: Thomson Pharma 14876119
Selleck bexarotene
SureChEMBL SCHEMBL9025
ZINC ZINC000001539579

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