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 77.93 15.89 113 6465 214861 53127627
Nausea 47.55 15.89 201 6377 755890 52586598
Dehydration 44.92 15.89 77 6501 168333 53174155
Failure to thrive 40.65 15.89 19 6559 6973 53335515
Disease progression 35.97 15.89 53 6525 101867 53240621
Vomiting 35.74 15.89 138 6440 497001 52845487
Rheumatoid arthritis 28.20 15.89 3 6575 314528 53027960
Death 27.11 15.89 101 6477 357131 52985357
Toxicity to various agents 23.71 15.89 70 6508 219528 53122960
Defaecation disorder 21.21 15.89 6 6572 522 53341966
Diarrhoea 20.90 15.89 140 6438 625406 52717082
Sepsis 19.06 15.89 50 6528 146379 53196109
Hypophagia 18.59 15.89 21 6557 31041 53311447
Constipation 18.39 15.89 60 6518 198352 53144136
Malnutrition 18.37 15.89 15 6563 14856 53327632
Drug ineffective 18.14 15.89 47 6531 817198 52525290
Malignant neoplasm progression 18.10 15.89 32 6546 71509 53270979
Plasma cell myeloma 17.02 15.89 25 6553 47849 53294639
Flatulence 16.67 15.89 20 6558 31497 53310991
Weight decreased 16.60 15.89 65 6513 234883 53107605
Drug hypersensitivity 16.58 15.89 6 6572 265236 53077252

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 138.80 16.81 186 7245 177855 32328240
Drug abuse 88.40 16.81 100 7331 80143 32425952
Hangover 67.82 16.81 20 7411 1079 32505016
Aggression 55.51 16.81 56 7375 39333 32466762
Brain oedema 54.46 16.81 35 7396 12925 32493170
Nausea 53.03 16.81 177 7254 320672 32185423
Decreased appetite 47.70 16.81 110 7321 160703 32345392
Failure to thrive 38.48 16.81 24 7407 8411 32497684
Dehydration 37.96 16.81 88 7343 128870 32377225
Accidental overdose 31.92 16.81 30 7401 19309 32486786
Drug screen positive 29.85 16.81 16 7415 4225 32501870
Vomiting 28.71 16.81 118 7313 235439 32270656
Pulmonary oedema 27.96 16.81 43 7388 46224 32459871
Muscle mass 27.06 16.81 7 7424 231 32505864
Rebound effect 24.16 16.81 11 7420 2045 32504050
Weight decreased 23.66 16.81 87 7344 164731 32341364
Seizure 22.34 16.81 63 7368 103791 32402304
Substance abuse 22.24 16.81 16 7415 7091 32499004
Testicular atrophy 21.76 16.81 7 7424 505 32505590
Neonatal infection 21.14 16.81 6 7425 282 32505813
Sleep disorder 20.75 16.81 28 7403 26724 32479371
Paradoxical drug reaction 20.59 16.81 11 7420 2885 32503210
Dysarthria 20.26 16.81 31 7400 33170 32472925
Drug withdrawal syndrome 20.17 16.81 24 7407 20207 32485888
Myocardial fibrosis 19.20 16.81 7 7424 737 32505358
Drug dependence 18.86 16.81 25 7406 23459 32482636
Fatigue 18.48 16.81 140 7291 350561 32155534
Withdrawal syndrome 18.47 16.81 18 7413 12104 32493991
Paranoia 18.29 16.81 17 7414 10782 32495313
Neuromuscular blockade 18.26 16.81 5 7426 206 32505889
Mucosal infection 17.26 16.81 5 7426 253 32505842
Respiratory depression 17.17 16.81 18 7413 13193 32492902
Cardiac death 17.02 16.81 7 7424 1018 32505077
Drug screen negative 16.88 16.81 5 7426 274 32505821

Pharmacologic Action:

SourceCodeDescription
ATC A04AD10 ALIMENTARY TRACT AND METABOLISM
ANTIEMETICS AND ANTINAUSEANTS
ANTIEMETICS AND ANTINAUSEANTS
Other antiemetics
FDA CS M0003267 Cannabinoids
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
FDA EPC N0000175782 Cannabinoid
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
D(3) dopamine receptor GPCR EC50 7.99 CHEMBL
Glycine receptor subunit alpha-1 Ion channel EC50 5.89 CHEMBL
Glycine receptor subunit alpha-2 Ion channel ALLOSTERIC MODULATOR EC50 6 IUPHAR
Cannabinoid receptor 2 GPCR Ki 8.48 CHEMBL
Glycine receptor subunit alpha-3 Ion channel ALLOSTERIC MODULATOR EC50 5.30 IUPHAR
N-arachidonyl glycine receptor GPCR EC50 6.02 CHEMBL
Transient receptor potential cation channel subfamily A member 1 Ion channel ACTIVATOR EC50 4.90 IUPHAR
G-protein coupled receptor 55 GPCR IC50 4.85 CHEMBL
Cannabinoid receptor GPCR Ki 7.39 CHEMBL
Cannabinoid receptor 1 GPCR Ki 7.43 CHEMBL
Cannabinoid receptor 2 GPCR Ki 8.04 CHEMBL
Cannabinoid receptor 1 GPCR Ki 7.40 CHEMBL
Cannabinoid receptor GPCR Ki 7.34 CHEMBL
Transient receptor potential cation channel subfamily V member 2 Ion channel ACTIVATOR EC50 4.85 IUPHAR

External reference:

IDSource
4018511 VUID
N0000146833 NUI
D00306 KEGG_DRUG
4018511 VANDF
CHEBI:66964 CHEBI
TCI PDB_CHEM_ID
CHEMBL465 ChEMBL_ID
5547 INN_ID
DB00470 DRUGBANK_ID
7J8897W37S UNII
16078 PUBCHEM_CID
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
D013759 MESH_DESCRIPTOR_UI
C0039663 UMLSCUI

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
DRONABINOL HUMAN PRESCRIPTION DRUG LABEL 1 0527-4125 CAPSULE 2.50 mg ORAL ANDA 18 sections
DRONABINOL HUMAN PRESCRIPTION DRUG LABEL 1 0904-6745 CAPSULE 2.50 mg ORAL ANDA 31 sections
DRONABINOL 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
DRONABINOL HUMAN PRESCRIPTION DRUG LABEL 1 31722-960 CAPSULE 2.50 mg ORAL ANDA 19 sections
DRONABINOL HUMAN PRESCRIPTION DRUG LABEL 1 31722-961 CAPSULE 5 mg ORAL ANDA 19 sections
DRONABINOL HUMAN PRESCRIPTION DRUG LABEL 1 31722-962 CAPSULE 10 mg ORAL ANDA 19 sections
DRONABINOL HUMAN PRESCRIPTION DRUG LABEL 1 42291-449 CAPSULE 2.50 mg ORAL ANDA 19 sections
DRONABINOL HUMAN PRESCRIPTION DRUG LABEL 1 42291-450 CAPSULE 5 mg ORAL ANDA 19 sections
DRONABINOL HUMAN PRESCRIPTION DRUG LABEL 1 42291-451 CAPSULE 10 mg ORAL ANDA 19 sections
DRONABINOL HUMAN PRESCRIPTION DRUG LABEL 1 42858-867 CAPSULE 2.50 mg ORAL ANDA 31 sections
DRONABINOL HUMAN PRESCRIPTION DRUG LABEL 1 42858-868 CAPSULE 5 mg ORAL ANDA 31 sections
DRONABINOL 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