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

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
Toxicity to various agents 113.58 37.59 30 117 32724 2325214
Defaecation disorder 46.48 37.59 5 142 15 2357923
Vomiting 44.46 37.59 18 129 71584 2286354
Decreased appetite 43.36 37.59 14 133 28877 2329061
Nausea 39.76 37.59 19 128 112170 2245768
Overdose 39.67 37.59 12 135 19895 2338043

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 295.49 57.44 80 223 29061 1717417
Brain oedema 119.16 57.44 24 279 2172 1744306
Drug abuse 114.76 57.44 33 270 13656 1732822
Pulmonary oedema 107.83 57.44 27 276 6559 1739919
Hangover 102.37 57.44 15 288 195 1746283
Accidental overdose 82.78 57.44 20 283 4144 1742334
Nausea 78.69 57.44 35 268 51161 1695317
Aggression 78.65 57.44 22 281 8093 1738385
Sleep disorder 78.11 57.44 19 284 4044 1742434
Substance abuse 66.51 57.44 13 290 990 1745488
Drug dependence 66.14 57.44 16 287 3311 1743167
Overdose 63.00 57.44 22 281 16679 1729799
Rebound effect 62.13 57.44 10 293 246 1746232
Paranoia 61.84 57.44 14 289 2167 1744311
Drug withdrawal syndrome 61.25 57.44 16 287 4509 1741969
Fatigue 59.92 57.44 29 274 50752 1695726
Seizure 58.66 57.44 22 281 20419 1726059

Pharmacologic Action:

SourceCodeDescription
ATC A04AD10 ALIMENTARY TRACT AND METABOLISM
ANTIEMETICS AND ANTINAUSEANTS
ANTIEMETICS AND ANTINAUSEANTS
Other antiemetics
FDA EPC N0000175782 Cannabinoid
FDA Chemical/Ingredient N0000008010 Cannabinoids
MeSH PA D000700 Analgesics
MeSH PA D018712 Analgesics, Non-Narcotic
CHEBI has role CHEBI:35481 non-narcotic analgesic
CHEBI has role CHEBI:35499 hallucinogen
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

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

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Marinol HUMAN PRESCRIPTION DRUG LABEL 1 0051-0021 CAPSULE 2.50 mg ORAL NDA 18 sections
Marinol HUMAN PRESCRIPTION DRUG LABEL 1 0051-0022 CAPSULE 5 mg ORAL NDA 18 sections
Marinol HUMAN PRESCRIPTION DRUG LABEL 1 0051-0023 CAPSULE 10 mg ORAL NDA 18 sections
Dronabinol HUMAN PRESCRIPTION DRUG LABEL 1 0527-1450 CAPSULE 2.50 mg ORAL ANDA 18 sections
Dronabinol HUMAN PRESCRIPTION DRUG LABEL 1 0527-1451 CAPSULE 5 mg ORAL ANDA 18 sections
Dronabinol HUMAN PRESCRIPTION DRUG LABEL 1 0527-1452 CAPSULE 10 mg ORAL ANDA 18 sections
DRONABINOL HUMAN PRESCRIPTION DRUG LABEL 1 0904-6745 CAPSULE 2.50 mg ORAL ANDA 19 sections
DRONABINOL HUMAN PRESCRIPTION DRUG LABEL 1 0904-6746 CAPSULE 5 mg ORAL ANDA 19 sections
Dronabinol HUMAN PRESCRIPTION DRUG LABEL 1 17478-761 CAPSULE 2.50 mg ORAL ANDA 18 sections
Dronabinol HUMAN PRESCRIPTION DRUG LABEL 1 17478-762 CAPSULE 5 mg ORAL ANDA 18 sections
Dronabinol HUMAN PRESCRIPTION DRUG LABEL 1 17478-763 CAPSULE 10 mg ORAL ANDA 18 sections
SYNDROS HUMAN PRESCRIPTION DRUG LABEL 1 20482-335 SOLUTION 5 mg ORAL NDA 20 sections
DRONABINOL HUMAN PRESCRIPTION DRUG LABEL 1 31722-960 CAPSULE 2.50 mg ORAL ANDA 18 sections
DRONABINOL HUMAN PRESCRIPTION DRUG LABEL 1 31722-961 CAPSULE 5 mg ORAL ANDA 18 sections
DRONABINOL HUMAN PRESCRIPTION DRUG LABEL 1 31722-962 CAPSULE 10 mg ORAL ANDA 18 sections
DRONABINOL HUMAN PRESCRIPTION DRUG LABEL 1 42291-449 CAPSULE 2.50 mg ORAL ANDA 18 sections
DRONABINOL HUMAN PRESCRIPTION DRUG LABEL 1 42291-450 CAPSULE 5 mg ORAL ANDA 18 sections
DRONABINOL HUMAN PRESCRIPTION DRUG LABEL 1 42291-451 CAPSULE 10 mg ORAL ANDA 18 sections
DRONABINOL HUMAN PRESCRIPTION DRUG LABEL 1 42858-867 CAPSULE 2.50 mg ORAL ANDA 19 sections
DRONABINOL HUMAN PRESCRIPTION DRUG LABEL 1 42858-868 CAPSULE 5 mg ORAL ANDA 19 sections
DRONABINOL HUMAN PRESCRIPTION DRUG LABEL 1 42858-869 CAPSULE 10 mg ORAL ANDA 19 sections
Dronabinol HUMAN PRESCRIPTION DRUG LABEL 1 49884-867 CAPSULE 2.50 mg ORAL ANDA 13 sections
Dronabinol HUMAN PRESCRIPTION DRUG LABEL 1 49884-868 CAPSULE 5 mg ORAL ANDA 13 sections
Dronabinol HUMAN PRESCRIPTION DRUG LABEL 1 49884-869 CAPSULE 10 mg ORAL ANDA 13 sections
Marinol HUMAN PRESCRIPTION DRUG LABEL 1 53097-568 CAPSULE 2.50 mg ORAL NDA 18 sections
Marinol HUMAN PRESCRIPTION DRUG LABEL 1 53097-569 CAPSULE 5 mg ORAL NDA 18 sections
Marinol HUMAN PRESCRIPTION DRUG LABEL 1 53097-570 CAPSULE 10 mg ORAL NDA 18 sections
Dronabinol HUMAN PRESCRIPTION DRUG LABEL 1 54868-5929 CAPSULE 5 mg ORAL ANDA 13 sections
DRONABINOL HUMAN PRESCRIPTION DRUG LABEL 1 60687-375 CAPSULE 2.50 mg ORAL ANDA 19 sections
DRONABINOL HUMAN PRESCRIPTION DRUG LABEL 1 60687-386 CAPSULE 5 mg ORAL ANDA 19 sections