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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 SYNDROS | DRONABINOL | DELTA-9-TETRAHYDROCANNABINOL | MARINOL | DELTA-9-THC
Max Phase 4 (Approved)
Trade Names DRONABINOL | SYNDROS | 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
Alcohol DrinkingD000428EFO:0004329alcohol drinking2ClinicalTrials
Bipolar DisorderD001714EFO:0000289bipolar disorder1ClinicalTrials
AlcoholismD000437EFO:0003829alcohol dependence1ClinicalTrials
Amyotrophic Lateral SclerosisD000690EFO:0000253amyotrophic lateral sclerosis2ClinicalTrials
NauseaD009325EFO:0006911Chemotherapy-induced nausea and vomiting4ClinicalTrials
Alzheimer DiseaseD000544EFO:0000249Alzheimers disease2ClinicalTrials
Multiple SclerosisD009103EFO:0003885multiple sclerosis1ClinicalTrials
Opioid-Related DisordersD009293EFO:0005611opioid dependence2ClinicalTrials
Irritable Bowel SyndromeD043183EFO:0000555irritable bowel syndrome2ClinicalTrials
Marijuana AbuseD002189EFO:0004218marijuana dependence2ClinicalTrials
Migraine with AuraD020325EFO:0005295migraine with aura2ClinicalTrials
Migraine without AuraD020326EFO:0005296migraine without aura2ClinicalTrials
Sleep Apnea, ObstructiveD020181EFO:0003918obstructive sleep apnea2ClinicalTrials
Anorexia NervosaD000856EFO:0004215anorexia nervosa3ClinicalTrials
HIV InfectionsD015658EFO:0000764HIV infection1ClinicalTrials
Stress Disorders, Post-TraumaticD013313EFO:0001358post-traumatic stress disorder2ClinicalTrials
Substance-Related DisordersD019966EFO:0003890drug dependence1ClinicalTrials
DementiaD003704HP:0000726dementia2ClinicalTrials
NauseaD009325HP:0002018Nausea4ATC
PainD010146EFO:0003843pain2ClinicalTrials
TorticollisD0141032ClinicalTrials
SchizophreniaD012559EFO:0000692schizophrenia1ClinicalTrials
Tourette SyndromeD005879EFO:0004895Tourette syndrome3ClinicalTrials

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
CHEMBL5373 Cannabinoid CB2 receptor Mus musculus 1.000
CHEMBL3571 Cannabinoid CB1 receptor Rattus norvegicus 1.000
CHEMBL218 Cannabinoid CB1 receptor Homo sapiens 1.000
CHEMBL253 Cannabinoid CB2 receptor Homo sapiens 1.000
CHEMBL3037 Cannabinoid CB1 receptor Mus musculus 1.000
CHEMBL5160 Transient receptor potential cation channel subfamily A member 1 Rattus norvegicus 0.999
CHEMBL3998 Dopamine D2 receptor Bos taurus 0.701
CHEMBL242 Estrogen receptor beta Homo sapiens 0.620
CHEMBL3318 Tyrosinase Agaricus bisporus 0.422
CHEMBL3251 Nuclear factor NF-kappa-B p105 subunit Homo sapiens 0.246



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL5373 Cannabinoid CB2 receptor Mus musculus 1.000
CHEMBL3571 Cannabinoid CB1 receptor Rattus norvegicus 1.000
CHEMBL253 Cannabinoid CB2 receptor Homo sapiens 1.000
CHEMBL218 Cannabinoid CB1 receptor Homo sapiens 1.000
CHEMBL3037 Cannabinoid CB1 receptor Mus musculus 1.000
CHEMBL5160 Transient receptor potential cation channel subfamily A member 1 Rattus norvegicus 0.998
CHEMBL3318 Tyrosinase Agaricus bisporus 0.906
CHEMBL3775 Dual specificity phosphatase Cdc25A Homo sapiens 0.696
CHEMBL3251 Nuclear factor NF-kappa-B p105 subunit Homo sapiens 0.595
CHEMBL4804 Dual specificity phosphatase Cdc25B Homo sapiens 0.464
CHEMBL206 Estrogen receptor alpha Homo sapiens 0.406
CHEMBL3998 Dopamine D2 receptor Bos taurus 0.221
CHEMBL242 Estrogen receptor beta Homo sapiens 0.203
CHEMBL1978 Cytochrome P450 19A1 Homo sapiens 0.201

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
314.5 314.2246 5.74 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 0.57

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 60994
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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