DRONABINOL

Search structure
Trade Names:
Synonyms:
Status: Approved (1985)
Entry Type: Small molecule
Molecule Category: UNKNOWN
ATC: A04AD10
UNII: 7J8897W37S

Structure
InChI Key CYQFCXCEBYINGO-IAGOWNOFSA-N
Smile CCCCCc1cc(O)c2c(c1)OC(C)(C)[C@@H]1CCC(C)=C[C@@H]21
InChI
InChI=1S/C21H30O2/c1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10-17(16)21(3,4)23-19(20)13-15/h11-13,16-17,22H,5-10H2,1-4H3/t16-,17-/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C21H30O2
Molecular Weight 314.47
AlogP 5.74
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 4.0
Polar Surface Area 29.46
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 23.0

Pharmacology

Action Mechanism of Action Reference
AGONIST Cannabinoid CB1 receptor agonist
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Hydrolase
- 11600 - - 31
Enzyme Oxidoreductase
- - - 14000 -
Enzyme
460 11600 - 14000 31
Ion channel Ligand-gated ion channel Glycine receptor
1300 - - - -
Ion channel Voltage-gated ion channel Transient receptor potential channel
230 160 - - -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Lipid-like ligand receptor (family A GPCR) Cannabinoid receptor
1.42-327 5.8-218 - 3.3-71.6 21
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Lipid-like ligand receptor (family A GPCR) Lysophosphatidylinositol receptor
14200 14200 - - -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Dopamine receptor
10.2 - - - -
Membrane receptor Family A G protein-coupled receptor
1.42-327 5.8-218 - 3.3-71.6 21
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group I Nuclear hormone receptor subfamily 1 group I member 2
12600-31600 - - - -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Nausea 4 D009325 ClinicalTrials
Osteoarthritis, Knee 3 D020370 ClinicalTrials
Anorexia Nervosa 3 D000856 ClinicalTrials
Dementia 2 D003704 ClinicalTrials
Marijuana Abuse 2 D002189 ClinicalTrials
Chronic Pain 2 D059350 ClinicalTrials
Arthritis, Psoriatic 2 D015535 ClinicalTrials
Torticollis 2 D014103 ClinicalTrials
Irritable Bowel Syndrome 2 D043183 ClinicalTrials
Sleep Apnea, Obstructive 2 D020181 ClinicalTrials
Pain 2 D010146 ClinicalTrials
HIV Infections 2 D015658 ClinicalTrials
Stress Disorders, Post-Traumatic 2 D013313 ClinicalTrials
Alcohol Drinking 2 D000428 ClinicalTrials
Tourette Syndrome 2 D005879 ClinicalTrials
Opioid-Related Disorders 2 D009293 ClinicalTrials
Neuralgia 2 D009437 ClinicalTrials
Amyotrophic Lateral Sclerosis 2 D000690 ClinicalTrials
Multiple Sclerosis 2 D009103 ClinicalTrials
Migraine with Aura 2 D020325 ClinicalTrials
Anemia, Sickle Cell 2 D000755 ClinicalTrials
Migraine without Aura 2 D020326 ClinicalTrials
Child Development Disorders, Pervasive 2 D002659 ClinicalTrials
Arthritis, Rheumatoid 2 D001172 ClinicalTrials
Trichotillomania 2 D014256 ClinicalTrials
Joint Diseases 1 D007592 ClinicalTrials
Substance-Related Disorders 1 D019966 ClinicalTrials
Mental Disorders 1 D001523 ClinicalTrials
Schizophrenia 1 D012559 ClinicalTrials
Diabetes Mellitus, Type 2 1 D003924 ClinicalTrials
Bipolar Disorder 1 D001714 ClinicalTrials
Cognitive Dysfunction 1 D060825 ClinicalTrials
Alcoholism 1 D000437 ClinicalTrials
Essential Tremor 1 D020329 ClinicalTrials

Related Entries

MCS

Scaffolds

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Gastrointestinal disorders
15.64
General disorders and administration site conditions
14.52
Nervous system disorders
11.0
Injury, poisoning and procedural complications
9.56
Psychiatric disorders
9.56
Investigations
5.6
Musculoskeletal and connective tissue disorders
4.71
Vascular disorders
4.27
Metabolism and nutrition disorders
4.11
Respiratory, thoracic and mediastinal disorders
4.05
Cardiac disorders
3.79

Cross References

Resources Reference
CAS NUMBER 1972-08-3
ChEBI 66964
ChEMBL CHEMBL465
DrugBank DB00470
DrugCentral 4109
EPA CompTox DTXSID6021327
FDA SRS 7J8897W37S
Human Metabolome Database HMDB14613
Guide to Pharmacology 2424
KEGG C06972
PDB TCI
PharmGKB PA449421
PubChem 16078
SureChEMBL SCHEMBL4609
ZINC ZINC000001530625
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