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Record Information
Version3.6
Creation Date2012-09-06 15:16:49 UTC
Update Date2016-02-11 01:29:16 UTC
HMDB IDHMDB14629
Secondary Accession NumbersNone
Metabolite Identification
Common NameNabilone
DescriptionNabilone is a synthetic cannabinoid with therapeutic use as an antiemetic and as an adjunct analgesic for neuropathic pain. It is a synthetic cannabinoid, which mimics the main ingredient of marijuana (THC) but it has more predictable side effects and causes no or minimal euphoria. Nabilone is not derived from the cannabis plant as is dronabinol. In Canada, the United States, the United Kingdom and Mexico, nabilone is marketed as Cesamet. It was approved in 1985 by the United States FDA for treatment of chemotherapy-induced nausea and vomiting that has not responded to conventional antiemetics. Though it was approved by the FDA in 1985, the drug only began marketing in the United States in 2006. It is also approved for use in treatment of anorexia and weight loss in patients with AIDS. Although it doesn't have the official indication (except in Mexico), nabilone is widely used as an adjunct therapy for chronic pain management. Numerous trials and case studies have demonstrate various benefits for condition such as fibromyalgia and multiple scerosis. Nabilone is a racemate consisting of the (S,S) and the (R,R) isomers ('trans').
Structure
Thumb
Synonyms
ValueSource
CesametKegg
Chemical FormulaC24H36O3
Average Molecular Weight372.5408
Monoisotopic Molecular Weight372.266445018
IUPAC Name(6aR,10aR)-1-hydroxy-6,6-dimethyl-3-(2-methyloctan-2-yl)-6H,6aH,7H,8H,9H,10H,10aH-benzo[c]isochromen-9-one
Traditional Namenabilone
CAS Registry Number51022-71-0
SMILES
[H][C@@]12CC(=O)CC[C@@]1([H])C(C)(C)OC1=CC(=CC(O)=C21)C(C)(C)CCCCCC
InChI Identifier
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
InChI KeyInChIKey=GECBBEABIDMGGL-RTBURBONSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as naphthopyranones. These are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassNaphthopyrans
Sub ClassNaphthopyranones
Direct ParentNaphthopyranones
Alternative Parents
Substituents
  • Naphthopyranone
  • 2,2-dimethyl-1-benzopyran
  • 1-benzopyran
  • Benzopyran
  • Chromane
  • Cyclohexanone
  • Alkyl aryl ether
  • Benzenoid
  • Cyclic ketone
  • Ketone
  • Oxacycle
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Anti-anxiety Agents
  • Antiemetics
Application
  • Pharmaceutical
Cellular locations
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility4.93e-04 g/LNot Available
LogP6.8Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000493 mg/mLALOGPS
logP7.5ALOGPS
logP6.36ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)9.33ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity110.2 m3·mol-1ChemAxon
Polarizability44.91 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00486
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00486
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00486
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4447641
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNabilone
NuGOwiki LinkHMDB14629
Metagene LinkHMDB14629
METLIN IDNot Available
PubChem Compound5284592
PDB IDNot Available
ChEBI ID189797
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Herman TS, Einhorn LH, Jones SE, Nagy C, Chester AB, Dean JC, Furnas B, Williams SD, Leigh SA, Dorr RT, Moon TE: Superiority of nabilone over prochlorperazine as an antiemetic in patients receiving cancer chemotherapy. N Engl J Med. 1979 Jun 7;300(23):1295-7. [375088 ]
  2. Cunningham D, Bradley CJ, Forrest GJ, Hutcheon AW, Adams L, Sneddon M, Harding M, Kerr DJ, Soukop M, Kaye SB: A randomized trial of oral nabilone and prochlorperazine compared to intravenous metoclopramide and dexamethasone in the treatment of nausea and vomiting induced by chemotherapy regimens containing cisplatin or cisplatin analogues. Eur J Cancer Clin Oncol. 1988 Apr;24(4):685-9. [2838294 ]
  3. Niiranen A, Mattson K: Antiemetic efficacy of nabilone and dexamethasone: a randomized study of patients with lung cancer receiving chemotherapy. Am J Clin Oncol. 1987 Aug;10(4):325-9. [3039831 ]
  4. Einhorn LH, Nagy C, Furnas B, Williams SD: Nabilone: an effective antiemetic in patients receiving cancer chemotherapy. J Clin Pharmacol. 1981 Aug-Sep;21(8-9 Suppl):64S-69S. [6271844 ]

Enzymes

General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Involved in cannabinoid-induced CNS effects. Acts by inhibiting adenylate cyclase. Could be a receptor for anandamide. Inhibits L-type Ca(2+) channel current. Isoform 2 and isoform 3 have altered ligand binding
Gene Name:
CNR1
Uniprot ID:
P21554
Molecular weight:
52857.4
References
  1. Davis M, Maida V, Daeninck P, Pergolizzi J: The emerging role of cannabinoid neuromodulators in symptom management. Support Care Cancer. 2007 Jan;15(1):63-71. Epub 2006 Dec 1. [17139494 ]
  2. Darmani NA: The cannabinoid CB1 receptor antagonist SR 141716A reverses the antiemetic and motor depressant actions of WIN 55, 212-2. Eur J Pharmacol. 2001 Oct 26;430(1):49-58. [11698062 ]
  3. Hirst RA, Almond SL, Lambert DG: Characterisation of the rat cerebella CB1 receptor using SR141716A, a central cannabinoid receptor antagonist. Neurosci Lett. 1996 Dec 13;220(2):101-4. [8981483 ]
  4. Pertwee RG: Cannabis and cannabinoids: pharmacology and rationale for clinical use. Forsch Komplementarmed. 1999 Oct;6 Suppl 3:12-5. [10575283 ]
  5. Pertwee RG, Fernando SR: Evidence for the presence of cannabinoid CB1 receptors in mouse urinary bladder. Br J Pharmacol. 1996 Aug;118(8):2053-8. [8864542 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]