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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 DELTA-9-TETRAHYDROCANNABINOL | DRONABINOL | MARINOL | 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

Alternate Forms of Compound in ChEMBL


CHEMBL465

Molecule Features

CHEMBL465 compound icon
Drug Type:Natural Product 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
ALCOHOLISMD000437EFO:0003829ALCOHOL DEPENDENCE1
ANOREXIA NERVOSAD000856EFO:0004215ANOREXIA NERVOSA3
DIGESTIVE SYSTEM DISEASESD004066EFO:0000405DIGESTIVE SYSTEM DISEASE4
IRRITABLE BOWEL SYNDROMED043183EFO:0000555IRRITABLE BOWEL SYNDROME2
MARIJUANA ABUSED002189EFO:0004218MARIJUANA DEPENDENCE2
NAUSEAD009325EFO:0006911CHEMOTHERAPY-INDUCED NAUSEA AND VOMITING4
NAUSEAD009325HP:0002018NAUSEA4
PAIND010146EFO:0003843PAIN4
SCHIZOPHRENIAD012559EFO:0000692SCHIZOPHRENIA1
SLEEP APNEA, OBSTRUCTIVED020181EFO:0003918OBSTRUCTIVE SLEEP APNEA2
SUBSTANCE-RELATED DISORDERSD019966EFO:0003890DRUG DEPENDENCE1

Clinical Data

Number of clinical trials registered at clinicaltrials.gov
Number of reviews at The Cochrane Collaboration
Number of entries at British National Formulary

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
CHEMBL5373 Cannabinoid CB2 receptor Mus musculus 1.000
CHEMBL3571 Cannabinoid CB1 receptor Rattus norvegicus 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 0.994
CHEMBL3998 Dopamine D2 receptor Bos taurus 0.476
CHEMBL2008 Retinoic acid receptor beta Homo sapiens 0.457
CHEMBL4666 Steroidogenic factor 1 Homo sapiens 0.210



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL253 Cannabinoid CB2 receptor Homo sapiens 1.000
CHEMBL5373 Cannabinoid CB2 receptor Mus musculus 1.000
CHEMBL3571 Cannabinoid CB1 receptor Rattus norvegicus 1.000
CHEMBL218 Cannabinoid CB1 receptor Homo sapiens 1.000
CHEMBL5160 Transient receptor potential cation channel subfamily A member 1 Rattus norvegicus 0.999
CHEMBL3037 Cannabinoid CB1 receptor Mus musculus 0.926
CHEMBL2008 Retinoic acid receptor beta Homo sapiens 0.919
CHEMBL3318 Tyrosinase Agaricus bisporus 0.827
CHEMBL3251 Nuclear factor NF-kappa-B p105 subunit Homo sapiens 0.432
CHEMBL4666 Steroidogenic factor 1 Homo sapiens 0.427
CHEMBL5845 Glycine receptor subunit alpha-1 Homo sapiens 0.411

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
ChEBI 66964
DrugBank DB00470
eMolecules 27524156 594744
EPA CompTox Dashboard DTXSID6021327
FDA SRS 7J8897W37S
Guide to Pharmacology 2424
Human Metabolome Database HMDB14613
IBM Patent System 70DF85191FFCEF8AD9F57A6A76728800
KEGG Ligand C06972
Nikkaji J882F
PDBe TCI
PubChem 16078
PubChem: Drugs of the Future 12013925
PubChem: Thomson Pharma 14899056 14776764
SureChEMBL SCHEMBL4609
ZINC ZINC01530625

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