Details of the Drug

General Information of Drug (ID: DMVRYT2)

• Drug Name: NABILONE
• Synonyms: Nabilone; Nabilona; Nabilonum; Cesamet; 51022-71-0; CHEMBL947; GECBBEABIDMGGL-RTBURBONSA-N; Nabilonum [Latin]; Nabilona [Spanish]; Nabilone [USAN:INN:BAN]; DEA No. 7379; Nabilon; CPD 109514; CPD-109514; 9H-Dibenzo(b,d)pyran-9-one, 3-(1,1-dimethylheptyl)-6,6a,7,8,10,10a-hexahydro-1-hydroxy-6,6-dimethyl-, (6aR,10aR)-rel-; 9H-Dibenzo[b,d]pyran-9-one, 3-(1,1-dimethylheptyl)-6,6a,7,8,10,10a-hexahydro-1-hydroxy-6,6-dimethyl-, (6aR,10aR)-rel-

Indication

Disease Entry	ICD 11	Status	REF
Insomnia	7A00-7A0Z	Approved	[1]

• Drug Type: Small molecular drug
• #Ro5 Violations (Lipinski): 1:
  Molecular Weight (mw); 372.5
  Logarithm of the Partition Coefficient (xlogp); 6.4
  Rotatable Bond Count (rotbonds); 6
  Hydrogen Bond Donor Count (hbonddonor); 1
  Hydrogen Bond Acceptor Count (hbondacc); 3
• ADMET Property:
  Half-life: The concentration or amount of drug in body reduced by one-half in 35 hours [2]
  Metabolism: The drug is metabolized via the hepatic []
  Vd: The volume of distribution (Vd) of drug is 12.5 L/kg []
• Chemical Identifiers:
  Formula: C24H36O3
  IUPAC Name: (6aR,10aR)-1-hydroxy-6,6-dimethyl-3-(2-methyloctan-2-yl)-7,8,10,10a-tetrahydro-6aH-benzo[c]chromen-9-one
  Canonical SMILES: CCCCCCC(C)(C)C1=CC(=C2[C@@H]3CC(=O)CC[C@H]3C(OC2=C1)(C)C)O
  InChI: InChI=1S/C24H36O3/c1-6-7-8-9-12-23(2,3)16-13-20(26)22-18-15-17(25)10-11-19(18)24(4,5)27-21(22)14-16/h13-14,18-19,26H,6-12,15H2,1-5H3/t18-,19-/m1/s1
  InChIKey: GECBBEABIDMGGL-RTBURBONSA-N
• Cross-matching ID:
  PubChem CID: 5284592
  CAS Number: 51022-71-0
  DrugBank ID: DB00486
  TTD ID: D0L7AS
  ACDINA ID: D01264

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Cannabinoid receptor 1 (CB1)	TT6OEDT	CNR1_HUMAN	Inhibitor	[3]
Cannabinoid receptor 2 (CB2)	TTMSFAW	CNR2_HUMAN	Inhibitor	[3]

Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Cannabinoid receptor 2 (CNR2)	OTYP9P43	CNR2_HUMAN	Protein Interaction/Cellular Processes	[4]

Molecular Expression Atlas of This Drug

• The Studied Disease: Insomnia
• ICD Disease Classification: 7A00-7A0Z

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Cannabinoid receptor 1 (CB1)	DTT	CNR1	5.59E-02	-0.22	-0.45
Cannabinoid receptor 1 (CB1)	DTT	CNR1	7.68E-01	-0.06	-0.46

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from NABILONE (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Olopatadine	DMKMWQG	Moderate	Additive CNS depression effects by the combination of Nabilone and Olopatadine.	Conjunctiva disorder [9A60]	[5]
Ethanol	DMDRQZU	Moderate	Additive CNS depression effects by the combination of Nabilone and Ethanol.	Cystitis [GC00]	[5]
Esketamine	DMVU687	Moderate	Additive CNS depression effects by the combination of Nabilone and Esketamine.	Depression [6A70-6A7Z]	[6]
Allopregnanolone	DMNLHAC	Moderate	Additive CNS depression effects by the combination of Nabilone and Allopregnanolone.	Mental/behavioural/neurodevelopmental disorder [6E20-6E8Z]	[7]
Lasmiditan	DMXLVDT	Moderate	Additive CNS depression effects by the combination of Nabilone and Lasmiditan.	Migraine [8A80]	[8]
Thalidomide	DM70BU5	Moderate	Additive CNS depression effects by the combination of Nabilone and Thalidomide.	Multiple myeloma [2A83]	[5]
Levomethadyl Acetate	DM06HG5	Major	Additive CNS depression effects by the combination of Nabilone and Levomethadyl Acetate.	Opioid use disorder [6C43]	[9]
Apraclonidine	DMO4PVE	Moderate	Additive CNS depression effects by the combination of Nabilone and Apraclonidine.	Optic nerve disorder [9C40]	[10]
Dextropropoxyphene	DM23HCX	Major	Additive CNS depression effects by the combination of Nabilone and Dextropropoxyphene.	Pain [MG30-MG3Z]	[11]
Buprenorphine	DMPRI8G	Major	Additive CNS depression effects by the combination of Nabilone and Buprenorphine.	Pain [MG30-MG3Z]	[12]
Biperiden	DME78OA	Moderate	Additive CNS depression effects by the combination of Nabilone and Biperiden.	Parkinsonism [8A00]	[13]
Tizanidine	DMR2IQ4	Moderate	Additive CNS depression effects by the combination of Nabilone and Tizanidine.	Tonus and reflex abnormality [MB47]	[14]

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
D&C red no. 28	E00491	6097185	Colorant
Food blue 1 aluminum lake	E00512	11979396	Colorant
Gelatin	E00630	Not Available	Other agent
Povidone	E00667	Not Available	Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
Pregelatinized starch	E00674	Not Available	Binding agent; Diluent; Disintegrant

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Nabilone 1mg capsule	1mg	Capsule	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

• [1] Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
• [2] Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
• [3] Novel 1',1'-chain substituted hexahydrocannabinols: 9-hydroxy-3-(1-hexyl-cyclobut-1-yl)-hexahydrocannabinol (AM2389) a highly potent cannabinoid r... J Med Chem. 2010 Oct 14;53(19):6996-7010.
• [4] Cloning and pharmacological characterization of the dog cannabinoid CB?receptor. Eur J Pharmacol. 2011 Nov 1;669(1-3):24-31. doi: 10.1016/j.ejphar.2011.08.002. Epub 2011 Aug 19.
• [5] Warrington SJ, Ankier SI, Turner P "Evaluation of possible interactions between ethanol and trazodone or amitriptyline." Neuropsychobiology 15 (1986): 31-7. [PMID: 3725002]
• [6] Cerner Multum, Inc. "Australian Product Information.".
• [7] Product Information. Zulresso (brexanolone). Sage Therapeutics, Inc., Cambridge, MA.
• [8] Product Information. Reyvow (lasmiditan). Lilly, Eli and Company, Indianapolis, IN.
• [9] Product Information. Addyi (flibanserin). Sprout Pharmaceuticals, Raleigh, NC.
• [10] Product Information. Alphagan (brimonidine ophthalmic). Allergan Inc, Irvine, CA.
• [11] Hansen BS, Dam M, Brandt J, et al "Influence of dextropropoxyphene on steady state serum levels and protein binding of three anti-epileptic drugs in man." Acta Neurol Scand 61 (1980): 357-67. [PMID: 6998251]
• [12] Sekar M, Mimpriss TJ "Buprenorphine, benzodiazepines and prolonged respiratory depression." Anaesthesia 42 (1987): 567-8. [PMID: 3592200]
• [13] Product Information. Artane (trihexyphenidyl). Lederle Laboratories, Wayne, NJ.
• [14] Product Information. Zanaflex (tizanidine). Acorda Therapeutics, Hawthorne, NY.