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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL465
CHEMBL465
Compound Name DRONABINOL
ChEMBL Synonyms MARINOL | DRONABINOL | DELTA-9-TETRAHYDROCANNABINOL | DELTA-9-THC
Max Phase 4 (Approved)
Trade Names DRONABINOL | MARINOL
Molecular Formula C21H30O2

Additional synonyms for CHEMBL465 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CCCCCc1cc(O)c2[C@@H]3C=C(C)CC[C@H]3C(C)(C)Oc2c1
Standard InChI InChI=1S/C21H30O2/c1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10- ...
Download InChI
Standard InChI Key CYQFCXCEBYINGO-IAGOWNOFSA-N

Sources

  • 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


CHEMBL465

Molecule Features

CHEMBL465 compound icon
Drug Type:Natural Product-derived Rule of Five:N First In Class:N Chirality:Single Stereoisomer Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:N Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Cannabinoid CB1 receptor agonist Cannabinoid CB1 receptor DailyMed PubMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
SCHIZOPHRENIAD012559EFO:0000692SCHIZOPHRENIA1ClinicalTrials
ALZHEIMER DISEASED000544EFO:0000249ALZHEIMERS DISEASE2ClinicalTrials
MARIJUANA ABUSED002189EFO:0004218MARIJUANA DEPENDENCE2ClinicalTrials
SLEEP APNEA, OBSTRUCTIVED020181EFO:0003918OBSTRUCTIVE SLEEP APNEA2ClinicalTrials
ANOREXIA NERVOSAD000856EFO:0004215ANOREXIA NERVOSA3ClinicalTrials
IRRITABLE BOWEL SYNDROMED043183EFO:0000555IRRITABLE BOWEL SYNDROME2ClinicalTrials
NAUSEAD009325HP:0002018NAUSEA4ATC
SUBSTANCE-RELATED DISORDERSD019966EFO:0003890DRUG DEPENDENCE1ClinicalTrials
ALCOHOLISMD000437EFO:0003829ALCOHOL DEPENDENCE1ClinicalTrials
NAUSEAD009325EFO:0006911CHEMOTHERAPY-INDUCED NAUSEA AND VOMITING4ClinicalTrials

Clinical Data

ClinicalTrials.gov DRONABINOL
The Cochrane Collaboration DRONABINOL

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 CHEMBL465. 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
CHEMBL253 Cannabinoid CB2 receptor Homo sapiens 1.000
CHEMBL3571 Cannabinoid CB1 receptor Rattus norvegicus 1.000
CHEMBL5373 Cannabinoid CB2 receptor Mus musculus 1.000
CHEMBL218 Cannabinoid CB1 receptor Homo sapiens 1.000
CHEMBL5160 Transient receptor potential cation channel subfamily A member 1 Rattus norvegicus 1.000
CHEMBL3037 Cannabinoid CB1 receptor Mus musculus 0.992
CHEMBL3998 Dopamine D2 receptor Bos taurus 0.433



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL218 Cannabinoid CB1 receptor Homo sapiens 1.000
CHEMBL253 Cannabinoid CB2 receptor Homo sapiens 1.000
CHEMBL5373 Cannabinoid CB2 receptor Mus musculus 1.000
CHEMBL3571 Cannabinoid CB1 receptor Rattus norvegicus 1.000
CHEMBL5160 Transient receptor potential cation channel subfamily A member 1 Rattus norvegicus 0.998
CHEMBL3037 Cannabinoid CB1 receptor Mus musculus 0.904
CHEMBL3318 Tyrosinase Agaricus bisporus 0.782
CHEMBL2008 Retinoic acid receptor beta Homo sapiens 0.492
CHEMBL3251 Nuclear factor NF-kappa-B p105 subunit Homo sapiens 0.318
CHEMBL4666 Steroidogenic factor 1 Homo sapiens 0.253
CHEMBL3775 Dual specificity phosphatase Cdc25A Homo sapiens 0.233

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
314.5 314.2246 6.11 4 29.46 NEUTRAL


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


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
9.81 - 6.84 6.84 1 23 0.54

Structural Alerts

There are 2 structural alerts for CHEMBL465. To view alerts please click here.

Compound Cross References

ATC A - ALIMENTARY TRACT AND METABOLISM
A04 - ANTIEMETICS AND ANTINAUSEANTS
A04A - ANTIEMETICS AND ANTINAUSEANTS
A04AD - Other antiemetics
A04AD10 - dronabinol

ChemSpider ChemSpider:CYQFCXCEBYINGO-IAGOWNOFSA-N
DailyMed dronabinol
PubChem SID: 144206169
Wikipedia Tetrahydrocannabinol

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL465



ACToR 1363-19-5 6465-30-1 1972-08-3 308064-99-5
BindingDB 50007391
Brenda 135425
ChEBI 66964
DrugBank DB00470
DrugCentral 4109
eMolecules 27524156 594744
EPA CompTox Dashboard DTXSID6021327
FDA SRS 7J8897W37S
Guide to Pharmacology 2424
Human Metabolome Database HMDB0014613
IBM Patent System 70DF85191FFCEF8AD9F57A6A76728800
KEGG Ligand C06972
Metabolights MTBLC66964
Nikkaji J882F
PDBe TCI
PharmGKB PA449421
PubChem 16078
PubChem: Drugs of the Future 12013925
PubChem: Thomson Pharma 14899056 14776764
Rhea 66964
SureChEMBL SCHEMBL4609
ZINC ZINC000001530625

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