cannabidiol Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
5288 13956-29-1

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • cannabidiol
  • GWP42003-P
  • epidiolex
The precise mechanisms by which cannabidiol exerts its anticonvulsant effect in humans are unknown. Cannabidiol does not appear to exert its anticonvulsant effects through interaction with cannabinoid receptors.
  • Molecular weight: 314.47
  • Formula: C21H30O2
  • CLOGP:
  • LIPINSKI: None
  • HAC: 2
  • HDO: 2
  • TPSA: 40.46
  • ALOGS:
  • ROTB: 6

Drug dosage:

DoseUnitRoute
0.70 g O

ADMET properties:

PropertyValueReference
Vd (Volume of distribution) 6.69 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 13.55 mL/min/kg Lombardo F, Berellini G, Obach RS
t_half (Half-life) 23.82 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Sept. 19, 2019 EMA GW Pharma (International) B.V.
June 25, 2018 FDA GW RESEARCH LTD

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Device related thrombosis 110.67 22.31 25 4345 1327 53343369
Drug resistance 70.93 22.31 34 4336 19928 53324768
Blood pressure diastolic decreased 67.03 22.31 31 4339 16772 53327924
Multiple-drug resistance 62.48 22.31 19 4351 3216 53341480
Large intestine polyp 59.28 22.31 23 4347 8074 53336622
Nail disorder 58.40 22.31 24 4346 9781 53334915
Body temperature decreased 43.43 22.31 23 4347 16604 53328092
Heart rate irregular 41.70 22.31 24 4346 20360 53324336
Tonic convulsion 40.73 22.31 11 4359 1220 53343476
Skin exfoliation 37.99 22.31 28 4342 36055 53308641
Blood pressure systolic increased 36.36 22.31 27 4343 35150 53309546
Urine leukocyte esterase positive 35.18 22.31 12 4358 2924 53341772
Hip fracture 34.50 22.31 24 4346 28233 53316463
Therapeutic product effective for unapproved indication 34.09 22.31 6 4364 86 53344610
Diarrhoea 33.04 22.31 119 4251 625427 52719269
Drug interaction 31.75 22.31 61 4309 219268 53125428
Drug level increased 31.34 22.31 20 4350 20401 53324295
Urine abnormality 29.17 22.31 13 4357 6447 53338249
Therapeutic product ineffective for unapproved indication 29.15 22.31 6 4364 204 53344492
Breast cancer metastatic 28.58 22.31 17 4353 15311 53329385
Infusion site scar 28.43 22.31 6 4364 231 53344465
Tri-iodothyronine free decreased 27.51 22.31 6 4364 270 53344426
Metastases to bone 27.37 22.31 18 4352 19310 53325386
Productive cough 27.00 22.31 28 4342 56701 53287995
Metastases to liver 25.63 22.31 18 4352 21478 53323218
Seizure 25.14 22.31 41 4329 129468 53215228
Cystic fibrosis 24.69 22.31 10 4360 3921 53340775
Creatinine urine decreased 23.65 22.31 5 4365 194 53344502

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Seizure 81.33 27.41 59 1865 103795 32407807
Drug interaction 65.57 27.41 72 1852 218113 32293489
Behaviour disorder 57.63 27.41 17 1907 3607 32507995
Social avoidant behaviour 38.02 27.41 12 1912 3187 32508415
Alcohol intolerance 33.02 27.41 7 1917 384 32511218
Prescription drug used without a prescription 29.16 27.41 8 1916 1307 32510295
Hyperacusis 28.29 27.41 7 1917 764 32510838
Off label use 28.00 27.41 58 1866 306262 32205340

Pharmacologic Action:

SourceCodeDescription
ATC N03AX24 NERVOUS SYSTEM
ANTIEPILEPTICS
ANTIEPILEPTICS
Other antiepileptics
FDA CS M0003267 Cannabinoids
MeSH PA D000927 Anticonvulsants
MeSH PA D002491 Central Nervous System Agents
FDA MoA N0000182138 Cytochrome P450 1A2 Inhibitors
FDA MoA N0000182139 Cytochrome P450 2B6 Inhibitors
FDA MoA N0000182140 Cytochrome P450 2C19 Inhibitors
FDA MoA N0000185504 Cytochrome P450 2C9 Inhibitors
FDA MoA N0000187062 Cytochrome P450 2C8 Inhibitors
FDA MoA N0000187064 Cytochrome P450 2B6 Inducers
FDA MoA N0000191273 UGT2B7 Inhibitors
FDA MoA N0000191278 UGT1A9 Inhibitors
CHEBI has role CHEBI:76924 plant metabolites

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Lennox-Gastaut syndrome indication 230418006
Severe myoclonic epilepsy in infancy indication 230437002

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 9.34 acidic
pKa2 11.34 acidic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
100MG/ML EPIDIOLEX GW RES LTD N210365 Sept. 28, 2018 RX SOLUTION ORAL 11154516 June 17, 2034 USE FOR THE TREATMENT OF SEIZURES ASSOCIATED WITH DRAVET SYNDROME
100MG/ML EPIDIOLEX GW RES LTD N210365 Sept. 28, 2018 RX SOLUTION ORAL 11154516 June 17, 2034 USE FOR THE TREATMENT OF SEIZURES ASSOCIATED WITH LENNOX-GASTAUT SYNDROME
100MG/ML EPIDIOLEX GW RES LTD N210365 Sept. 28, 2018 RX SOLUTION ORAL 10092525 June 17, 2035 USE FOR THE TREATMENT OF DROP SEIZURES IN PATIENTS WITH DRAVET SYNDROME
100MG/ML EPIDIOLEX GW RES LTD N210365 Sept. 28, 2018 RX SOLUTION ORAL 10111840 June 17, 2035 USE FOR THE TREATMENT OF ATONIC SEIZURES IN PATIENTS WITH DRAVET SYNDROME
100MG/ML EPIDIOLEX GW RES LTD N210365 Sept. 28, 2018 RX SOLUTION ORAL 10111840 June 17, 2035 USE FOR THE TREATMENT OF ATONIC SEIZURES IN PATIENTS WITH LENNOX-GASTAUT SYNDROME
100MG/ML EPIDIOLEX GW RES LTD N210365 Sept. 28, 2018 RX SOLUTION ORAL 10137095 June 17, 2035 USE FOR THE TREATMENT OF DROP SEIZURES IN PATIENTS WITH LENNOX-GASTAUT SYNDROME
100MG/ML EPIDIOLEX GW RES LTD N210365 Sept. 28, 2018 RX SOLUTION ORAL 10137095 June 17, 2035 USE IN COMBINATION WITH CLOBAZAM FOR TREATMENT OF DROP SEIZURES IN PATIENTS WITH LENNOX GASTAUT SYNDROME
100MG/ML EPIDIOLEX GW RES LTD N210365 Sept. 28, 2018 RX SOLUTION ORAL 10603288 June 17, 2035 USE FOR REDUCING CONVULSIVE SEIZURE FREQUENCY IN PATIENTS WITH DRAVET SYNDROME
100MG/ML EPIDIOLEX GW RES LTD N210365 Sept. 28, 2018 RX SOLUTION ORAL 10603288 June 17, 2035 USE FOR REDUCING CONVULSIVE SEIZURE FREQUENCY IN PATIENTS WITH LENNOX GASTAUT SYNDROME
100MG/ML EPIDIOLEX GW RES LTD N210365 Sept. 28, 2018 RX SOLUTION ORAL 10603288 June 17, 2035 USE FOR THE TREATMENT OF SEIZURES IN PATIENTS WITH DRAVET SYNDROME
100MG/ML EPIDIOLEX GW RES LTD N210365 Sept. 28, 2018 RX SOLUTION ORAL 10603288 June 17, 2035 USE FOR THE TREATMENT OF SEIZURES IN PATIENTS WITH LENNOX-GASTAUT SYNDROME
100MG/ML EPIDIOLEX GW RES LTD N210365 Sept. 28, 2018 RX SOLUTION ORAL 10709671 June 17, 2035 USE FOR THE TREATMENT OF FOCAL SEIZURES IN PATIENTS WITH DRAVET SYNDROME
100MG/ML EPIDIOLEX GW RES LTD N210365 Sept. 28, 2018 RX SOLUTION ORAL 10709674 June 17, 2035 USE FOR THE TREATMENT OF SEIZURES IN PATIENTS WITH DRAVET SYNDROME
100MG/ML EPIDIOLEX GW RES LTD N210365 Sept. 28, 2018 RX SOLUTION ORAL 10709674 June 17, 2035 USE FOR THE TREATMENT OF SEIZURES IN PATIENTS WITH LENNOX-GASTAUT SYNDROME
100MG/ML EPIDIOLEX GW RES LTD N210365 Sept. 28, 2018 RX SOLUTION ORAL 10849860 June 17, 2035 USE FOR THE TREATMENT OF DROP SEIZURES IN PATIENTS WITH DRAVET SYNDROME
100MG/ML EPIDIOLEX GW RES LTD N210365 Sept. 28, 2018 RX SOLUTION ORAL 10849860 June 17, 2035 USE FOR THE TREATMENT OF DROP SEIZURES IN PATIENTS WITH LENNOX-GASTAUT SYNDROME
100MG/ML EPIDIOLEX GW RES LTD N210365 Sept. 28, 2018 RX SOLUTION ORAL 10966939 June 17, 2035 USE FOR THE TREATMENT OF SEIZURES IN PATIENTS WITH DRAVET SYNDROME
100MG/ML EPIDIOLEX GW RES LTD N210365 Sept. 28, 2018 RX SOLUTION ORAL 10966939 June 17, 2035 USE FOR THE TREATMENT OF SEIZURES IN PATIENTS WITH LENNOX-GASTAUT SYNDROME
100MG/ML EPIDIOLEX GW RES LTD N210365 Sept. 28, 2018 RX SOLUTION ORAL 9949937 June 17, 2035 USE IN COMBINATION WITH CLOBAZAM FOR THE TREATMENT OF SEIZURES IN PATIENTS WITH DRAVET SYNDROME
100MG/ML EPIDIOLEX GW RES LTD N210365 Sept. 28, 2018 RX SOLUTION ORAL 9956183 June 17, 2035 USE IN COMBINATION WITH CLOBAZAM FOR THE TREATMENT OF SEIZURES IN PATIENTS WITH DRAVET SYNDROME WHO HAVE BEEN PREVIOUSLY TREATED WITH CLOBAZAM
100MG/ML EPIDIOLEX GW RES LTD N210365 Sept. 28, 2018 RX SOLUTION ORAL 9956183 June 17, 2035 USE IN COMBINATION WITH CLOBAZAM FOR THE TREATMENT OF SEIZURES IN PATIENTS WITH LENNOX GASTAUT SYNDROME WHO HAVE BEEN PREVIOUSLY TREATED WITH CLOBAZAM
100MG/ML EPIDIOLEX GW RES LTD N210365 Sept. 28, 2018 RX SOLUTION ORAL 9956184 June 17, 2035 USE IN COMBINATION WITH CLOBAZAM FOR TREATMENT OF SEIZURES IN PATIENTS WITH LENNOX GASTAUT SYNDROME
100MG/ML EPIDIOLEX GW RES LTD N210365 Sept. 28, 2018 RX SOLUTION ORAL 9956185 June 17, 2035 USE FOR THE TREATMENT OF CONVULSIVE SEIZURES IN PATIENTS WITH DRAVET SYNDROME
100MG/ML EPIDIOLEX GW RES LTD N210365 Sept. 28, 2018 RX SOLUTION ORAL 9956186 June 17, 2035 USE FOR THE TREATMENT OF CONVULSIVE SEIZURES IN PATIENTS WITH LENNOX GASTAUT SYNDROME
100MG/ML EPIDIOLEX GW RES LTD N210365 Sept. 28, 2018 RX SOLUTION ORAL 10918608 Oct. 14, 2035 USE FOR REDUCING SEIZURE FREQUENCY IN PATIENTS WITH TUBEROUS SCLEROSIS COMPLEX
100MG/ML EPIDIOLEX GW RES LTD N210365 Sept. 28, 2018 RX SOLUTION ORAL 10918608 Oct. 14, 2035 USE FOR THE TREATMENT OF GENERALIZED SEIZURES OR FOCAL SEIZURES WITH IMPAIRMENT IN PATIENTS WITH TUBEROUS SCLEROSIS COMPLEX
100MG/ML EPIDIOLEX GW RES LTD N210365 Sept. 28, 2018 RX SOLUTION ORAL 10918608 Oct. 14, 2035 USE FOR THE TREATMENT OF SEIZURES IN PATIENTS WITH TUBEROUS SCLEROSIS COMPLEX
100MG/ML EPIDIOLEX GW RES LTD N210365 Sept. 28, 2018 RX SOLUTION ORAL 11065209 Oct. 14, 2035 USE FOR THE TREATMENT OF SEIZURES IN PATIENTS WITH TUBEROUS SCLEROSIS COMPLEX
100MG/ML EPIDIOLEX GW RES LTD N210365 Sept. 28, 2018 RX SOLUTION ORAL 11096905 Oct. 14, 2035 USE FOR THE TREATMENT OF SEIZURES IN PATIENTS WITH DRAVET SYNDROME
100MG/ML EPIDIOLEX GW RES LTD N210365 Sept. 28, 2018 RX SOLUTION ORAL 11096905 Oct. 14, 2035 USE FOR THE TREATMENT OF SEIZURES IN PATIENTS WITH LENNOX-GASTAUT SYNDROME
100MG/ML EPIDIOLEX GW RES LTD N210365 Sept. 28, 2018 RX SOLUTION ORAL 11207292 April 26, 2039 USE FOR THE TREATMENT OF SEIZURES ASSOCIATED WITH DRAVET SYNDROME
100MG/ML EPIDIOLEX GW RES LTD N210365 Sept. 28, 2018 RX SOLUTION ORAL 11207292 April 26, 2039 USE FOR THE TREATMENT OF SEIZURES ASSOCIATED WITH LENNOX-GASTAUT SYNDROME
100MG/ML EPIDIOLEX GW RES LTD N210365 Sept. 28, 2018 RX SOLUTION ORAL 11207292 April 26, 2039 USE FOR THE TREATMENT OF SEIZURES ASSOCIATED WITH TUBEROUS SCLEROSIS COMPLEX
100MG/ML EPIDIOLEX GW RES LTD N210365 Sept. 28, 2018 RX SOLUTION ORAL 11160795 March 1, 2041 USE FOR THE TREATMENT OF SEIZURES ASSOCIATED WITH TUBEROUS SCLEROSIS COMPLEX IN PATIENTS TAKING EVEROLIMUS

Orange Book exclusivity data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
100MG/ML EPIDIOLEX GW RES LTD N210365 Sept. 28, 2018 RX SOLUTION ORAL July 31, 2023 NEW PATIENT POPULATION
100MG/ML EPIDIOLEX GW RES LTD N210365 Sept. 28, 2018 RX SOLUTION ORAL Sept. 28, 2023 NEW CHEMICAL ENTITY
100MG/ML EPIDIOLEX GW RES LTD N210365 Sept. 28, 2018 RX SOLUTION ORAL Sept. 28, 2025 INDICATED FOR THE TREATMENT OF SEIZURES ASSOCIATED WITH LENNOX-GASTAUT SYNDROME (LGS) OR DRAVET SYNDROME (DS) IN PATIENTS 2 YEARS OF AGE AND OLDER
100MG/ML EPIDIOLEX GW RES LTD N210365 Sept. 28, 2018 RX SOLUTION ORAL July 31, 2027 TREATMENT OF SEIZURES ASSOCIATED WITH LENNOX-GASTAUT SYNDROME (LGS) OR DRAVET SYNDROME (DS) IN PATIENTS BETWEEN 1 AND 2 YEARS OF AGE
100MG/ML EPIDIOLEX GW RES LTD N210365 Sept. 28, 2018 RX SOLUTION ORAL July 31, 2027 TREATMENT OF SEIZURES ASSOCIATED WITH TUBEROUS SCLEROSIS COMPLEX (TSC) IN PATIENTS 1 YEAR OF AGE AND OLDER

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Transient receptor potential cation channel subfamily V member 1 Ion channel INHIBITOR UNKNOWN SCIENTIFIC LITERATURE
G-protein coupled receptor 55 GPCR ANTAGONIST EC50 6.35 CHEMBL SCIENTIFIC LITERATURE
N-arachidonyl glycine receptor GPCR AGONIST EC50 4.29 IUPHAR
Cannabinoid receptor 1 GPCR Ki 5.62 CHEMBL
Transient receptor potential cation channel subfamily V member 2 Ion channel ACTIVATOR EC50 4.50 IUPHAR
Cannabinoid receptor 2 GPCR Ki 5.54 CHEMBL
Cannabinoid receptor 1 GPCR Ki 5.90 CHEMBL
Cannabinoid receptor 2 GPCR Ki 6.64 CHEMBL
Transient receptor potential cation channel subfamily V member 2 Ion channel ACTIVATOR EC50 5.43 IUPHAR
Fatty-acid amide hydrolase 1 Enzyme IC50 4.27 CHEMBL

External reference:

IDSource
19GBJ60SN5 UNII
4036658 VANDF
C0006863 UMLSCUI
CHEBI:69478 CHEBI
P0T PDB_CHEM_ID
CHEMBL190461 ChEMBL_ID
644019 PUBCHEM_CID
DB09061 DRUGBANK_ID
D002185 MESH_DESCRIPTOR_UI
D10915 KEGG_DRUG
4150 IUPHAR_LIGAND_ID
10423 INN_ID
2045371 RXNORM
010751 NDDF
771981005 SNOMEDCT_US
96223000 SNOMEDCT_US
20468 MMSL
291103 MMSL
d08919 MMSL

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Epidiolex HUMAN PRESCRIPTION DRUG LABEL 1 70127-100 SOLUTION 100 mg ORAL NDA 31 sections
NanoCDB HUMAN OTC DRUG LABEL 1 70658-122 SOLUTION/ DROPS 1.94 g BUCCAL Export only 8 sections
leafPro CBDmed Oil FS QP 3% HUMAN OTC DRUG LABEL 1 73674-001 OIL 3 g ORAL unapproved drug other 15 sections
leafPro CBDmed Oil FS QP 5% HUMAN OTC DRUG LABEL 1 73674-002 OIL 5 g ORAL unapproved drug other 15 sections
leafPro CBDmed Oil FS QP 20% HUMAN OTC DRUG LABEL 1 73674-005 OIL 20 g ORAL unapproved drug other 15 sections
leafPro CBDmed Oil T-FS QD 3% HUMAN OTC DRUG LABEL 1 73674-020 OIL 3 g ORAL unapproved drug other 15 sections
leafPro CBDmed Oil T-FS QD 5% HUMAN OTC DRUG LABEL 1 73674-021 OIL 5 g ORAL unapproved drug other 15 sections
leafPro CBDmed Oil T-FS QD 20% HUMAN OTC DRUG LABEL 1 73674-024 OIL 20 g ORAL unapproved drug other 15 sections
leafPro CBDmed Softgels FS QP 20 HUMAN OTC DRUG LABEL 1 73674-052 CAPSULE, LIQUID FILLED 20 mg ORAL unapproved drug other 15 sections
leafPro CBDmed Softgels T-FS QD 20 HUMAN OTC DRUG LABEL 1 73674-061 CAPSULE, LIQUID FILLED 20 mg ORAL unapproved drug other 15 sections
Kaydia Patch HUMAN OTC DRUG LABEL 3 75140-002 PATCH 0.15 g TOPICAL unapproved drug other 8 sections