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

Stem definitionDrug idCAS RN
cannabinoid receptors agonists 4109 1972-08-3

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • tetrahydrocannabinol
  • THC
  • dronabinol
  • marinol
A psychoactive compound extracted from the resin of Cannabis sativa (marihuana, hashish). The isomer delta-9-tetrahydrocannabinol (THC) is considered the most active form, producing characteristic mood and perceptual changes associated with this compound.
  • Molecular weight: 314.47
  • Formula: C21H30O2
  • CLOGP: 7.24
  • LIPINSKI: 1
  • HAC: 2
  • HDO: 1
  • TPSA: 29.46
  • ALOGS: -5.08
  • ROTB: 4

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

None

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 0.50 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.91 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
Vd (Volume of distribution) 8.90 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 3.20 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.05 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 33 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
May 31, 1985 FDA ABBVIE

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
Decreased appetite 71.24 15.83 105 5915 193731 46486311
Nausea 39.79 15.83 184 5836 687270 45992772
Dehydration 38.99 15.83 72 5948 159468 46520574
Failure to thrive 37.64 15.83 18 6002 6646 46673396
Disease progression 37.15 15.83 52 5968 91248 46588794
Vomiting 32.07 15.83 129 5891 452665 46227377
Defaecation disorder 24.37 15.83 6 6014 291 46679751
Death 22.42 15.83 94 5926 335454 46344588
Toxicity to various agents 21.49 15.83 68 5952 211698 46468344
Rheumatoid arthritis 21.04 15.83 3 6017 240212 46439830
Diarrhoea 18.97 15.83 130 5890 559472 46120570
Hypophagia 18.82 15.83 21 5999 29285 46650757
Flatulence 17.37 15.83 20 6000 28858 46651184
Drug hypersensitivity 17.31 15.83 5 6015 243820 46436222
Sepsis 16.94 15.83 47 5973 135967 46544075
Constipation 16.82 15.83 55 5965 174042 46506000
Weight decreased 16.40 15.83 62 5958 210787 46469255

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
Toxicity to various agents 110.03 16.09 167 6746 177016 29768549
Hangover 68.01 16.09 20 6893 1058 29944507
Nausea 54.65 16.09 171 6742 296786 29648779
Brain oedema 50.62 16.09 33 6880 12365 29933200
Decreased appetite 48.79 16.09 107 6806 149803 29795762
Drug abuse 46.00 16.09 74 6839 81998 29863567
Failure to thrive 36.75 16.09 23 6890 8031 29937534
Dehydration 35.50 16.09 84 6829 123455 29822110
Vomiting 30.98 16.09 116 6797 219702 29725863
Drug screen positive 29.12 16.09 16 6897 4391 29941174
Rebound effect 26.98 16.09 11 6902 1550 29944015
Pulmonary oedema 26.46 16.09 41 6872 43934 29901631
Muscle mass 26.25 16.09 7 6906 258 29945307
Weight decreased 25.85 16.09 85 6828 150836 29794729
Accidental overdose 25.54 16.09 26 6887 18249 29927316
Aggression 24.46 16.09 36 6877 36871 29908694
Testicular atrophy 21.46 16.09 7 6906 523 29945042
Paradoxical drug reaction 21.36 16.09 11 6902 2651 29942914
Neonatal infection 21.13 16.09 6 6907 280 29945285
Fatigue 20.43 16.09 135 6778 320538 29625027
Drug withdrawal syndrome 20.39 16.09 24 6889 19785 29925780
Neuromuscular blockade 19.71 16.09 5 6908 151 29945414
Withdrawal syndrome 19.47 16.09 18 6895 11232 29934333
Sleep disorder 19.37 16.09 26 6887 24453 29921112
Myocardial fibrosis 19.34 16.09 7 6906 714 29944851
Paranoia 19.00 16.09 17 6896 10171 29935394
Seizure 18.22 16.09 57 6856 98418 29847147
Substance abuse 17.79 16.09 14 6899 7026 29938539
Mucosal infection 17.53 16.09 5 6908 237 29945328
Drug screen negative 17.10 16.09 5 6908 259 29945306
Cardiac death 16.90 16.09 7 6906 1026 29944539

Pharmacologic Action:

SourceCodeDescription
ATC A04AD10 ALIMENTARY TRACT AND METABOLISM
ANTIEMETICS AND ANTINAUSEANTS
ANTIEMETICS AND ANTINAUSEANTS
Other antiemetics
FDA CS M0003267 Cannabinoids
FDA EPC N0000175782 Cannabinoid
MeSH PA D000700 Analgesics
MeSH PA D018712 Analgesics, Non-Narcotic
MeSH PA D063386 Cannabinoid Receptor Agonists
MeSH PA D063385 Cannabinoid Receptor Modulators
MeSH PA D002491 Central Nervous System Agents
MeSH PA D006213 Hallucinogens
MeSH PA D006728 Hormones
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D011619 Psychotropic Drugs
MeSH PA D018689 Sensory System Agents
CHEBI has role CHEBI:25212 metabolites
CHEBI has role CHEBI:35499 psychedelics
CHEBI has role CHEBI:53000 epitope function
CHEBI has role CHEBI:67072 cannabinoid receptor agonists

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Chemotherapy-induced nausea and vomiting indication 236084000
Anorexia from HIV indication
Tachyarrhythmia contraindication 6285003
Alcoholism contraindication 7200002
Bipolar disorder contraindication 13746004 DOID:3312
Lowered convulsive threshold contraindication 19260006
Depressive disorder contraindication 35489007
Hypertensive disorder contraindication 38341003 DOID:10763
Low blood pressure contraindication 45007003
Schizophrenia contraindication 58214004 DOID:5419
Substance abuse contraindication 66214007
Epilepsy contraindication 84757009 DOID:1826
Syncope contraindication 271594007
Breastfeeding (mother) contraindication 413712001

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 10.15 acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Cannabinoid receptor 1 GPCR AGONIST Ki 8.54 CHEMBL CHEMBL
G-protein coupled receptor 55 GPCR IC50 4.85 CHEMBL
Cannabinoid receptor 2 GPCR Ki 8.48 CHEMBL
Cannabinoid receptor GPCR Ki 7.39 CHEMBL
N-arachidonyl glycine receptor GPCR EC50 6.02 CHEMBL
Glycine receptor subunit alpha-2 Ion channel ALLOSTERIC MODULATOR EC50 6 IUPHAR
Glycine receptor subunit alpha-3 Ion channel ALLOSTERIC MODULATOR EC50 5.30 IUPHAR
Glycine receptor subunit alpha-1 Ion channel EC50 5.89 CHEMBL
Transient receptor potential cation channel subfamily A member 1 Ion channel ACTIVATOR EC50 4.90 IUPHAR
Cannabinoid receptor 1 GPCR Ki 7.40 CHEMBL
Cannabinoid receptor 1 GPCR Ki 7.43 CHEMBL
Cannabinoid receptor 2 GPCR Ki 8.04 CHEMBL
Cannabinoid receptor GPCR Ki 7.34 CHEMBL
Transient receptor potential cation channel subfamily V member 2 Unclassified ACTIVATOR EC50 4.85 IUPHAR

External reference:

IDSource
4018511 VUID
N0000146833 NUI
D00306 KEGG_DRUG
4018511 VANDF
C0039663 UMLSCUI
CHEBI:66964 CHEBI
TCI PDB_CHEM_ID
CHEMBL465 ChEMBL_ID
DB00470 DRUGBANK_ID
D013759 MESH_DESCRIPTOR_UI
16078 PUBCHEM_CID
5547 INN_ID
7J8897W37S UNII
10402 RXNORM
138250 MMSL
1589 MMSL
4645 MMSL
d00866 MMSL
001685 NDDF
010757 NDDF
108415005 SNOMEDCT_US
386846008 SNOMEDCT_US
72024007 SNOMEDCT_US
96225007 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Dronabinol HUMAN PRESCRIPTION DRUG LABEL 1 0527-1450 CAPSULE 2.50 mg ORAL ANDA 26 sections
Dronabinol HUMAN PRESCRIPTION DRUG LABEL 1 0527-1451 CAPSULE 5 mg ORAL ANDA 26 sections
Dronabinol HUMAN PRESCRIPTION DRUG LABEL 1 0527-1452 CAPSULE 10 mg ORAL ANDA 26 sections
DRONULLBINOL HUMAN PRESCRIPTION DRUG LABEL 1 0904-6745 CAPSULE 2.50 mg ORAL ANDA 31 sections
DRONULLBINOL HUMAN PRESCRIPTION DRUG LABEL 1 0904-6746 CAPSULE 5 mg ORAL ANDA 31 sections
Dronabinol HUMAN PRESCRIPTION DRUG LABEL 1 0904-7144 CAPSULE 2.50 mg ORAL NDA 29 sections
Dronabinol HUMAN PRESCRIPTION DRUG LABEL 1 0904-7145 CAPSULE 5 mg ORAL NDA 29 sections
Dronabinol HUMAN PRESCRIPTION DRUG LABEL 1 17478-761 CAPSULE 2.50 mg ORAL ANDA 32 sections
Dronabinol HUMAN PRESCRIPTION DRUG LABEL 1 17478-762 CAPSULE 5 mg ORAL ANDA 32 sections
Dronabinol HUMAN PRESCRIPTION DRUG LABEL 1 17478-763 CAPSULE 10 mg ORAL ANDA 32 sections
SYNDROS HUMAN PRESCRIPTION DRUG LABEL 1 20482-335 SOLUTION 5 mg ORAL NDA 32 sections
DRONULLBINOL HUMAN PRESCRIPTION DRUG LABEL 1 31722-960 CAPSULE 2.50 mg ORAL ANDA 19 sections
DRONULLBINOL HUMAN PRESCRIPTION DRUG LABEL 1 31722-961 CAPSULE 5 mg ORAL ANDA 19 sections
DRONULLBINOL HUMAN PRESCRIPTION DRUG LABEL 1 31722-962 CAPSULE 10 mg ORAL ANDA 19 sections
DRONULLBINOL HUMAN PRESCRIPTION DRUG LABEL 1 42291-449 CAPSULE 2.50 mg ORAL ANDA 19 sections
DRONULLBINOL HUMAN PRESCRIPTION DRUG LABEL 1 42291-450 CAPSULE 5 mg ORAL ANDA 19 sections
DRONULLBINOL HUMAN PRESCRIPTION DRUG LABEL 1 42291-451 CAPSULE 10 mg ORAL ANDA 19 sections
DRONULLBINOL HUMAN PRESCRIPTION DRUG LABEL 1 42858-867 CAPSULE 2.50 mg ORAL ANDA 31 sections
DRONULLBINOL HUMAN PRESCRIPTION DRUG LABEL 1 42858-868 CAPSULE 5 mg ORAL ANDA 31 sections
DRONULLBINOL HUMAN PRESCRIPTION DRUG LABEL 1 42858-869 CAPSULE 10 mg ORAL ANDA 31 sections
Dronabinol HUMAN PRESCRIPTION DRUG LABEL 1 49884-867 CAPSULE 2.50 mg ORAL ANDA 23 sections
Dronabinol HUMAN PRESCRIPTION DRUG LABEL 1 49884-868 CAPSULE 5 mg ORAL ANDA 23 sections
Dronabinol HUMAN PRESCRIPTION DRUG LABEL 1 49884-869 CAPSULE 10 mg ORAL ANDA 23 sections
Marinol Human Prescription Drug Label 1 53097-568 CAPSULE 2.50 mg ORAL NDA 29 sections
Marinol Human Prescription Drug Label 1 53097-569 CAPSULE 5 mg ORAL NDA 29 sections
Marinol Human Prescription Drug Label 1 53097-570 CAPSULE 10 mg ORAL NDA 29 sections
MARINOL Human Prescription Drug Label 1 53097-571 CAPSULE 2.50 mg ORAL NDA 29 sections
MARINOL Human Prescription Drug Label 1 53097-572 CAPSULE 5 mg ORAL NDA 29 sections
MARINOL Human Prescription Drug Label 1 53097-573 CAPSULE 10 mg ORAL NDA 29 sections
Dronabinol HUMAN PRESCRIPTION DRUG LABEL 1 54868-5929 CAPSULE 5 mg ORAL ANDA 22 sections