Cannabidiol

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Cannabidiol
Accession Number
DB09061
Type
Small Molecule
Groups
Approved, Investigational
Description

Cannabidiol (CBD) is one of at least 85 active cannabinoids identified in cannabis. It is a major phytocannabinoid, accounting for up to 40% of the plant's extract. CBD is considered to have a wider scope of medical applications than tetrahydrocannabinol (THC). An orally-administered liquid containing CBD has received orphan drug status in the US, for use as a treatment for Dravet syndrome, under the brand name Epidiolex.

Structure
Thumb
Synonyms
  • (−)-trans-2-p-mentha-1,8-dien-3-yl-5-pentylresorcinol
  • (−)-trans-cannabidiol
  • (1'R,2'R)-5'-methyl-4-pentyl-2'-(prop-1-en-2-yl)-1',2',3',4'-tetrahydrobiphenyl-2,6-diol
  • CBD
  • Δ1(2)-trans-cannabidiol
External IDs
GWP-42003 / GWP-42003-P / GWP42003 / GWP42003-P
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
SativexCannabidiol (25 mg) + Dronabinol (27 mg)SprayBuccalGw Pharma Limited2005-06-22Not applicableCanada
Categories
UNII
19GBJ60SN5
CAS number
13956-29-1
Weight
Average: 314.469
Monoisotopic: 314.224580206
Chemical Formula
C21H30O2
InChI Key
QHMBSVQNZZTUGM-ZWKOTPCHSA-N
InChI
InChI=1S/C21H30O2/c1-5-6-7-8-16-12-19(22)21(20(23)13-16)18-11-15(4)9-10-17(18)14(2)3/h11-13,17-18,22-23H,2,5-10H2,1,3-4H3/t17-,18+/m0/s1
IUPAC Name
2-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]-5-pentylbenzene-1,3-diol
SMILES
CCCCCC1=CC(O)=C([[email protected]@H]2C=C(C)CC[[email protected]]2C(C)=C)C(O)=C1

Pharmacology

Indication

When used in combination with delta-9-tetrahydrocannabinol as the product Sativex, cannabidiol was given a standard marketing authorization (ie. a Notice of Compliance (NOC)) by Health Canada for the following indications: 1) as adjunctive treatment for symptomatic relief of spasticity in adult patients with multiple sclerosis (MS) who have not responded adequately to other therapy and who demonstrate meaningful improvement during an initial trial of therapy [1];

Due to the need for confirmatory studies to verify the clinical benefit coupled with the promising nature of the clinical evidence, Sativex was also given a Notice of Compliance with Conditions (NOC/c) by Health Canada for the following indications: 1) as adjunctive treatment for the symptomatic relief of neuropathic pain in adult patients with multiple sclerosis; 2) as adjunctive analgesic treatment in adult patients with advanced cancer who experience moderate to severe pain during the highest tolerated dose of strong opioid therapy for persistent background pain [1].

Structured Indications
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
CarbamazepineThe serum concentration of Cannabidiol can be decreased when it is combined with Carbamazepine.Approved, Investigational
EnzalutamideThe serum concentration of Cannabidiol can be decreased when it is combined with Enzalutamide.Approved
FosphenytoinThe serum concentration of Cannabidiol can be decreased when it is combined with Fosphenytoin.Approved
LumacaftorThe serum concentration of Cannabidiol can be decreased when it is combined with Lumacaftor.Approved
MitotaneThe serum concentration of Cannabidiol can be decreased when it is combined with Mitotane.Approved
NevirapineThe serum concentration of Cannabidiol can be decreased when it is combined with Nevirapine.Approved
PentobarbitalThe serum concentration of Cannabidiol can be decreased when it is combined with Pentobarbital.Approved, Vet Approved
PhenobarbitalThe serum concentration of Cannabidiol can be decreased when it is combined with Phenobarbital.Approved
PhenytoinThe serum concentration of Cannabidiol can be decreased when it is combined with Phenytoin.Approved, Vet Approved
PrimidoneThe serum concentration of Cannabidiol can be decreased when it is combined with Primidone.Approved, Vet Approved
RifabutinThe serum concentration of Cannabidiol can be decreased when it is combined with Rifabutin.Approved
RifampicinThe serum concentration of Cannabidiol can be decreased when it is combined with Rifampicin.Approved
RifapentineThe serum concentration of Cannabidiol can be decreased when it is combined with Rifapentine.Approved
St. John's WortThe serum concentration of Cannabidiol can be decreased when it is combined with St. John's Wort.Nutraceutical
Food Interactions
Not Available

References

Synthesis Reference
Not Available
General References
  1. Health Canada Product Label [Link]
External Links
KEGG Compound
C07578
ChemSpider
559095
BindingDB
50121429
ChEBI
69478
ChEMBL
CHEMBL190461
ATC Codes
Not Available
AHFS Codes
Not Available
PDB Entries
Not Available
FDA label
Not Available
MSDS
Not Available

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0Not Yet RecruitingBasic ScienceCannabis / Retinal Degenerations / Retinitis Pigmentosa (RP)1
0Not Yet RecruitingTreatmentChronic Pain, Widespread1
1Active Not RecruitingBasic ScienceHealthy Volunteers1
1Active Not RecruitingTreatmentEpilepsies1
1CompletedBasic ScienceEffects of Sativex on ECG1
1CompletedBasic ScienceEvaluation of Abuse Potential of Sativex1
1CompletedBasic ScienceEvaluation of Pharmacokinetics of Sativex in the Absence and Presence of a CYP2C19 Inhibitor / Evaluation of Pharmacokinetics of Sativex in the Absence and Presence of a Known Inducer of CYP3A4 / Evaluation of Pharmacokinetics of Sativex in the Absence and Presence of a Potent Inhibitor of CYP3A41
1CompletedBasic ScienceFood Effect1
1CompletedBasic ScienceHealthy Volunteers1
1CompletedBasic ScienceHealthy Volunteers / Modeling Psychosis1
1CompletedBasic SciencePain1
1CompletedOtherCannabis / Cannabis Abuse / Dependence / FMRI / Pharmacokinetics1
1CompletedOtherHealthy Volunteers1
1CompletedTreatmentHepatic Impairment1
1CompletedTreatmentLymphoma, Large B-Cell, Diffuse (DLBCL) / Multiple Myeloma (MM) / Non-Hodgkin's Lymphoma (NHL) / Other B-cell NHL Subtypes, Including WM / T-cell NHL / Waldenstrom's Macroglobulinemia (WM)1
1CompletedTreatmentOpiate Addiction1
1Enrolling by InvitationSupportive CarePain Management in Terminally Ill Patients Receiving Scheduled Opioid Therapy1
1Not Yet RecruitingBasic ScienceHealthy Volunteers / Modeling Psychosis1
1RecruitingTreatmentCannabis Use Disorders1
1RecruitingTreatmentEpilepsies / Seizures1
1RecruitingTreatmentFumarate Hydratase (FH)-Deficient Tumors / Lung Cancer Non-Small Cell Cancer (NSCLC) / Mesothelioma / Renal Cell Adenocarcinoma / Succinate Dehydrogenase (SDH)-Deficient Gastrointestinal Stromal Tumors (GIST) / Succinate Dehydrogenase (SDH)-Deficient Non-gastrointestinal Stromal Tumors / Triple-Negative Breast Cancer (TNBC) / Tumors Harboring Amplifications in the cMyc Gene / Tumors Harboring Isocitrate Dehydrogenase-1 (IDH1) and IDH2 Mutations / Tumors, Solid1
1RecruitingTreatmentSchizophrenic Disorders1
1TerminatedBasic ScienceTo Provide Further Information About the Potential Need for Sativex Dose Adjustments in Patient Populations1
1TerminatedTreatmentHead and Neck Squamous Cell Carcinoma (HNSCC)1
1WithdrawnBasic ScienceImpaired Renal Function / Kidney Diseases1
1WithdrawnTreatmentCancer, Advanced1
1, 2Active Not RecruitingTreatmentSturge-Weber Syndrome1
1, 2CompletedTreatmentCancers2
1, 2CompletedTreatmentCrohn's Disease (CD) / Ulcerative Colitis (UC)1
1, 2CompletedTreatmentSeizures1
1, 2RecruitingBasic SciencePain1
1, 2Unknown StatusPreventionGraft Versus Host Disease (GVHD)1
1, 2Unknown StatusTreatmentGraft Versus Host Disease (GVHD)1
2Active Not RecruitingTreatmentCannabis Use Disorders1
2Active Not RecruitingTreatmentInfantile Spasms (IS)1
2Active Not RecruitingTreatmentOpiate Addiction1
2CompletedSupportive CareCancers / Pain / Palliative Care1
2CompletedTreatmentCannabis Dependence1
2CompletedTreatmentDravet Syndrome / Epilepsies1
2CompletedTreatmentDyslipidemias / Type 2 Diabetes Mellitus1
2CompletedTreatmentEpilepsies2
2CompletedTreatmentFatty Liver1
2CompletedTreatmentHuntington's Disease (HD)1
2CompletedTreatmentOpiate Addiction1
2CompletedTreatmentPsychotic Disorder NOS / Schizophrenic Disorders1
2CompletedTreatmentSchizoaffective Disorders / Schizophrenic Disorders1
2CompletedTreatmentSchizophrenia-related Psychotic Disorder / Schizophrenic Disorders1
2CompletedTreatmentSchizophrenic Disorders1
2CompletedTreatmentUlcerative Colitis (UC)1
2Enrolling by InvitationTreatmentEpilepsies1
2Not Yet RecruitingBasic ScienceFeeling Anxious1
2Not Yet RecruitingPreventionGraft Versus Host Disease (GVHD)1
2Not Yet RecruitingTreatmentAcute-graft-versus-host Disease1
2Not Yet RecruitingTreatmentPrader-Willi Syndrome1
2RecruitingTreatmentDependence, Cocaine / Substance Use Disorder (SUD) / Withdrawal From Addictive Substance; Detoxification1
2RecruitingTreatmentEpilepsies1
2RecruitingTreatmentParkinson's Disease (PD)1
2RecruitingTreatmentPosttraumatic Stress Disorders1
2RecruitingTreatmentSchizoaffective Disorders / Schizophrenic Disorders1
2RecruitingTreatmentSchizophrenic Disorders2
2SuspendedPreventionAmphetamine Addiction1
2Unknown StatusTreatmentCannabis Use Disorders1
2Unknown StatusTreatmentDisseminated Sclerosis1
2Unknown StatusTreatmentTumors, Solid1
2, 3CompletedSupportive CareAmyotrophic Lateral Sclerosis (ALS) / Motor Neurone Disease1
2, 3Not Yet RecruitingBasic ScienceDisseminated Sclerosis1
2, 3RecruitingTreatmentFeeling Anxious / Postoperative pain / Prophylaxis against postoperative nausea and vomiting1
3Active Not RecruitingTreatmentSeizures1
3CompletedSupportive CareCancers / Pain1
3CompletedSupportive CareCancers / Pain / Palliative Care1
3CompletedSupportive CareDetrusor Overactivity / Disseminated Sclerosis1
3CompletedSupportive CareDiabetic Neuropathies / Pain1
3CompletedSupportive CareDisseminated Sclerosis / Spasticity3
3CompletedSupportive CarePain / Peripheral Neuropathy4
3CompletedTreatmentCancer, Advanced / Pain4
3CompletedTreatmentCerebral Palsy (CP)1
3CompletedTreatmentDisseminated Sclerosis5
3CompletedTreatmentDisseminated Sclerosis / Pain1
3CompletedTreatmentDisseminated Sclerosis / Pain, Neuropathic1
3CompletedTreatmentDisseminated Sclerosis / Pain / Spasticity1
3CompletedTreatmentDisseminated Sclerosis / Spasticity1
3CompletedTreatmentDravet Syndrome / Epilepsies1
3CompletedTreatmentEpilepsies / Lennox-Gastaut Syndrome (LGS)2
3CompletedTreatmentPain2
3CompletedTreatmentPain, Neuropathic1
3Enrolling by InvitationTreatmentDravet Syndrome / Epilepsies / Lennox-Gastaut Syndrome (LGS)1
3Enrolling by InvitationTreatmentSeizures / Seizures, Focal / Tuberous Sclerosis Complex (TSC)1
3Not Yet RecruitingTreatmentDravet Syndrome1
3Not Yet RecruitingTreatmentEpilepsies1
3Not Yet RecruitingTreatmentLennox-Gastaut Syndrome (LGS)1
3RecruitingTreatmentDravet Syndrome / Epilepsies1
3RecruitingTreatmentInfantile Spasms (IS)2
3RecruitingTreatmentPain1
3RecruitingTreatmentSeizures / Seizures, Focal / Tuberous Sclerosis Complex (TSC)1
3WithdrawnSupportive CareDisseminated Sclerosis / Spasticity1
4CompletedTreatmentDisseminated Sclerosis / Spasticity1
Not AvailableAvailableNot AvailableDrug Resistant Epilepsy1
Not AvailableAvailableNot AvailableEpilepsies3
Not AvailableAvailableNot AvailableRefractory Epilepsy1
Not AvailableCompletedNot AvailableFailed Back Surgery Syndrome1
Not AvailableCompletedBasic ScienceDrug Dependence1
Not AvailableCompletedBasic ScienceHealthy Humans1
Not AvailableCompletedBasic ScienceHealthy Volunteers1
Not AvailableCompletedBasic ScienceSensory Science1
Not AvailableCompletedTreatmentCannabis Dependence1
Not AvailableNo Longer AvailableNot AvailableRefractory Childhood Epilepsy1
Not AvailableNot Yet RecruitingBasic ScienceSchizophrenic Disorders1
Not AvailableRecruitingTreatmentRehabilitation1
Not AvailableUnknown StatusNot AvailableCancers / Diabetes / Disseminated Sclerosis / Pain, Neuropathic1
Not AvailableUnknown StatusBasic ScienceAttention Deficit Hyperactivity Disorder (ADHD)1
Not AvailableUnknown StatusBasic ScienceSmoking, Marijuana1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
SprayBuccal
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0126 mg/mLALOGPS
logP6.1ALOGPS
logP6.33ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)9.13ChemAxon
pKa (Strongest Basic)-5.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity98.53 m3·mol-1ChemAxon
Polarizability38.35 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Prenol lipids
Sub Class
Monoterpenoids
Direct Parent
Aromatic monoterpenoids
Alternative Parents
Monocyclic monoterpenoids / Menthane monoterpenoids / Resorcinols / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Benzene and substituted derivatives / Cyclic alcohols and derivatives / Hydrocarbon derivatives
Substituents
P-menthane monoterpenoid / Monocyclic monoterpenoid / Aromatic monoterpenoid / Resorcinol / 1-hydroxy-4-unsubstituted benzenoid / 1-hydroxy-2-unsubstituted benzenoid / Phenol / Benzenoid / Monocyclic benzene moiety / Cyclic alcohol
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
organic molecular entity (CHEBI:69478 )

Drug created on May 11, 2015 15:59 / Updated on October 02, 2017 06:12