You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameEucalyptol
Accession NumberDB03852  (EXPT00969)
TypeSmall Molecule
GroupsNutraceutical
Description

Eucalyptol is a natural organic compound which is a colorless liquid. It is a cyclic ether and a monoterpenoid. Eucalyptol is an ingredient in many brands of mouthwash and cough suppressant. It controls airway mucus hypersecretion and asthma via anti-inflammatory cytokine inhibition. Eucalyptol is an effective treatment for nonpurulent rhinosinusitis. Eucalyptol reduces inflammation and pain when applied topically. It kills leukaemia cells in vitro.

Structure
Thumb
Synonyms
SynonymLanguageCode
1,8-cineolNot AvailableNot Available
1,8-CineoleNot AvailableNot Available
1,8-epoxy-p-menthaneNot AvailableNot Available
1,8-oxido-p-menthaneNot AvailableNot Available
cajeputolNot AvailableNot Available
cineolNot AvailableNot Available
cineoleNot AvailableNot Available
CucalyptolNot AvailableNot Available
EucapurNot AvailableNot Available
ZineolNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Antiseptic Mouth Rinsemouthwash.092; .042; .06; .064 kg/100L; kg/100L; kg/100L; kg/100LoralWalgreens Co.2007-03-30Not AvailableUs
Antisepticmouthwash.042; .042; .06; .064 kg/100L; kg/100L; kg/100L; kg/100LoralVi Jon, Inc1988-07-20Not AvailableUs
Antiseptic Mouth Rinsemouthwash.092; .042; .06; .064 kg/100L; kg/100L; kg/100L; kg/100LoralVi Jon1989-07-15Not AvailableUs
Antiseptic Mouth Rinsemouthwash.092; .042; .06; .064 kg/100L; kg/100L; kg/100L; kg/100LoralVi Jon2009-08-15Not AvailableUs
Antiseptic Mouth Rinsemouthwash.092; .042; .06; .064 kg/100L; kg/100L; kg/100L; kg/100LoralVi Jon2001-01-04Not AvailableUs
Antiseptic Mouth Rinsemouthwash.092; .042; .06; .064 kg/100L; kg/100L; kg/100L; kg/100LoralRite Aid1997-08-01Not AvailableUs
Oral Care Antisepticmouthwash.092; .042; .06; .064 mL/100L; mL/100L; mL/100L; mL/100LoralRite Aid1990-10-15Not AvailableUs
Antiseptic Mouth Rinsemouthwash.092; .042; .06; .064 kg/100L; kg/100L; kg/100L; kg/100LoralTOPCO ASSOCIATES, LLC1995-07-07Not AvailableUs
Original Antisepticmouthwash.092; .042; .06; .064 kg/100L; kg/100L; kg/100L; kg/100LoralTOPCO ASSOCIATES, LLC1990-07-15Not AvailableUs
Antiseptic Mouth Rinsemouthwash.092; .042; .06; .064 kg/100L; kg/100L; kg/100L; kg/100LoralCardinal Health1990-08-13Not AvailableUs
Advanced Antisepticmouthwash.042; .042; .06; .064 mL/100L; mL/100L; mL/100L; mL/100LoralWakefern Food Corporation2010-11-24Not AvailableUs
Antiseptic Mouth Rinsemouthwash.092; .042; .06; .064 kg/100L; kg/100L; kg/100L; kg/100LoralWakefern Food Corporation1990-08-13Not AvailableUs
Antiseptic Mouth Rinsemouthwash.092; .042; .06; .064 kg/100L; kg/100L; kg/100L; kg/100LoralMeijer Distribution, Inc1996-12-23Not AvailableUs
Antiseptic Mouth Rinsemouthwash.092; .042; .06; .064 kg/100L; kg/100L; kg/100L; kg/100LoralMeijer Distribution, Inc.1990-07-15Not AvailableUs
Antiseptic Mouth Rinsemouthwash.092; .042; .06; .064 kg/100L; kg/100L; kg/100L; kg/100LoralAmerican Sales Company2010-08-02Not AvailableUs
Antiseptic Mouth Rinsemouthwash.092; .042; .06; .064 kg/100L; kg/100L; kg/100L; kg/100LoralAmerican Sales Company1989-03-13Not AvailableUs
Antiseptic Mouth Rinsemouthwash.092; .042; .06; .064 kg/100L; kg/100L; kg/100L; kg/100LoralHy Vee, Inc.2001-05-23Not AvailableUs
Antiseptic Mouth Rinsemouthwash.092; .042; .06; .064 kg/100L; kg/100L; kg/100L; kg/100LoralHy Vee, Inc2010-07-22Not AvailableUs
Advanced Citrusmouthwash.092; .042; .06; .064 kg/100L; kg/100L; kg/100L; kg/100LoralWal Mart Stores, Inc2010-07-22Not AvailableUs
Antisepticrinse.092; .042; .06; .064 kg/100L; kg/100L; kg/100L; kg/100LoralWal Mart Stores, Inc.1992-07-27Not AvailableUs
Antiseptic Mouth Rinsemouthwash.092; .042; .06; .064 kg/100L; kg/100L; kg/100L; kg/100LoralMc Kesson1995-08-25Not AvailableUs
Antiseptic Mouth Rinsemouthwash.092; .042; .06; .064 kg/100L; kg/100L; kg/100L; kg/100LoralKmart Corporation2001-03-29Not AvailableUs
Antiseptic Mouth Rinsemouthwash.092; .042; .06; .064 kg/100L; kg/100L; kg/100L; kg/100LoralKmart Corporation1989-07-15Not AvailableUs
Antiseptic Mouth Rinsemouthwash.092; .042; .06; .064 kg/100L; kg/100L; kg/100L; kg/100LoralOnpoint, Inc2009-07-27Not AvailableUs
Antispetic Mouth Rinsemouthwash.092; .042; .06; .064 kg/100L; kg/100L; kg/100L; kg/100LoralOnpoint, Inc2010-07-16Not AvailableUs
Antisepticmouthwash.092; .042; .06; .064 mL/100L; mL/100L; mL/100L; mL/100LoralOnpoint, Inc2010-10-19Not AvailableUs
Mouth Rinsemouthwash.092; .042; .06; .064 kg/100L; kg/100L; kg/100L; kg/100LoralOnpoint, Inc2009-07-27Not AvailableUs
Antiseptic Mouth Rinsemouthwash.092; .042; .06; .064 kg/100L; kg/100L; kg/100L; kg/100LoralDemoulas Super Markets2007-03-30Not AvailableUs
Advanced Antisepticmouthwash.092; .042; .06; .064 kg/100L; kg/100L; kg/100L; kg/100LoralDemoulas Super Markets, Inc2010-07-22Not AvailableUs
Antisepticmouthwash.092; .042; .06; .064 mL/100L; mL/100L; mL/100L; mL/100LoralExchange Select2010-10-18Not AvailableUs
Antiseptic Mouth Rinsemouthwash.092; .042; .06; .064 kg/100L; kg/100L; kg/100L; kg/100LoralWestern Family Foods, Inc.1995-11-14Not AvailableUs
Tartar Controlmouthwash.092; .042; .06; .064 mL/100L; mL/100L; mL/100L; mL/100LoralWestern Family2010-09-23Not AvailableUs
Antiseptic Mouth Rinsemouthwash.092; .042; .06; .064 kg/100L; kg/100L; kg/100L; kg/100LoralWestern Family Foods, Inc.1996-06-14Not AvailableUs
Antiseptic Mouth Rinsemouthwash.092; .042; .06; .064 kg/100L; kg/100L; kg/100L; kg/100LoralDZA Brands, LLC2001-06-29Not AvailableUs
Antisepticrinse.092; .042; .06; .064 kg/100L; kg/100L; kg/100L; kg/100LoralDZA Brands, LLC2008-02-05Not AvailableUs
Mouth Rinsemouthwash.092; .042; .06; .064 kg/100L; kg/100L; kg/100L; kg/100LoralDOLGENCORP,LLC2001-01-11Not AvailableUs
Antiseptic Mouth Rinsemouthwash.092; .042; .06; .064 kg/100L; kg/100L; kg/100L; kg/100LoralCVS Pharmacy, Inc1995-08-09Not AvailableUs
Antiseptic Mouth Rinsemouthwash.092; .042; .06; .064 kg/100L; kg/100L; kg/100L; kg/100LoralChain Drug Consortium, L Lc2003-08-19Not AvailableUs
International Brands
NameCompany
SoledumNot Available
Brand mixtures
Brand NameIngredients
ArthriflexEucalyptol + Menthol
Balminil Suppositories AdultsDibunate Sodium + Eucalyptol + Menthol + Niaouli Oil
Balminil Suppositories ChildrenDibunate Sodium + Eucalyptol + Menthol + Niaouli Oil
Balminil Suppositories InfantsDibunate Sodium + Eucalyptol + Menthol + Niaouli Oil
Cal Mo Dol OntCamphor + Eucalyptol + Menthol + Methyl Salicylate + Oil of Turpentine + Peppermint Oil
CarboseptolEucalyptol + Menthol + Methyl Salicylate + Thymol + Zinc Oxide
Coolmint Antiseptic MouthwasEucalyptol + Menthol + Thymol
Demo Cineol AdulteCamphor + Eucalyptol + Guaiacol
Democineol Sup BebeCamphor + Eucalyptol + Guaiacol
Democineol Sup EnfantsCamphor + Eucalyptol + Guaiacol
Formule 12Eucalyptol + Menthol
Fresh Taste Antiseptic MouthwashEucalyptol + Menthol + Thymol
Glenalgesic ForteCamphor + Eucalyptol + Menthol + Methyl Salicylate
Inarub CrmEucalyptol + Menthol + Methyl Salicylate
Larynsol LozBenzoic Acid + Chlorobutanol + Eucalyptol
Listerine Antiseptic MouthwashEucalyptol + Menthol + Thymol
Listerine Antiseptic Mouthwash with FluorideEucalyptol + Menthol + Sodium Fluoride + Thymol
Listerine Antiseptic Tartar Control MouthwashEucalyptol + Menthol + Thymol + Zinc Chloride
Majorana Comp GelatumBeechwood Creosote + Calendula + Citric Acid + Echinacea Angustifolia + Eucalyptol + Lactic Acid + Origanum Majorana + Silver + Thuja Occidentalis + Tiger Lily
Mielocol SyrupAralia Racemosa + Eucalyptol + Guaifenesin + Honey + Poplar Bud + Sanguinaria Canadensis + White Pine + Wild Cherry
Naturub OntEucalyptol + Menthol + Methyl Salicylate
Original Antiseptic MouthwashEucalyptol + Menthol + Thymol
OrthorubEucalyptol + Menthol + Methyl Salicylate
Physio-RubEucalyptol + Menthol + Methyl Salicylate
Physiorub PlusEucalyptol + Menthol + Methyl Salicylate
Pin Blanc Compose SyrEucalyptol + Honey + White Pine
Plantago BalmCamphor + Drosera Rotundifolia + Eucalyptol + Plantago Major + Resina Laricis + Tussilago Petasites
Rhino-VaccinCamphor + Chlorobutanol + Eucalyptol + L-Ephedrine Hydrochloride + Menthol
Star-Vi-DolAmmonium Chloride + Eucalyptol + Menthol + Myroxylon Balsamum + White Pine + Wild Cherry
Thermo Rub OntEucalyptol + Menthol + Methyl Salicylate
Valda PastillesEucalyptol + Guaiacol + Menthol + Terpin Hydrate + Thymol
Vitarub OntEucalyptol + Menthol + Methyl Salicylate
SaltsNot Available
Categories
CAS number470-82-6
WeightAverage: 154.2493
Monoisotopic: 154.135765198
Chemical FormulaC10H18O
InChI KeyWEEGYLXZBRQIMU-WAAGHKOSSA-N
InChI
InChI=1S/C10H18O/c1-9(2)8-4-6-10(3,11-9)7-5-8/h8H,4-7H2,1-3H3/t8-,10+
IUPAC Name
(1s,4s)-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octane
SMILES
C[C@@]12CC[C@@H](CC1)C(C)(C)O2
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassOxanes
SubclassNot Available
Direct parentOxanes
Alternative parentsPolyamines; Ethers
Substituentspolyamine; ether
Classification descriptionThis compound belongs to the oxanes. These are compounds containing an oxane(tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms.
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityOral, rat LD50: 2480 mg/kg
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.988
Blood Brain Barrier + 0.9842
Caco-2 permeable + 0.7609
P-glycoprotein substrate Substrate 0.5435
P-glycoprotein inhibitor I Non-inhibitor 0.6374
P-glycoprotein inhibitor II Non-inhibitor 0.6455
Renal organic cation transporter Non-inhibitor 0.7847
CYP450 2C9 substrate Non-substrate 0.8132
CYP450 2D6 substrate Non-substrate 0.7839
CYP450 3A4 substrate Substrate 0.5962
CYP450 1A2 substrate Non-inhibitor 0.7719
CYP450 2C9 substrate Non-inhibitor 0.7571
CYP450 2D6 substrate Non-inhibitor 0.95
CYP450 2C19 substrate Non-inhibitor 0.658
CYP450 3A4 substrate Non-inhibitor 0.9395
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9399
Ames test Non AMES toxic 0.9574
Carcinogenicity Non-carcinogens 0.7856
Biodegradation Not ready biodegradable 0.8549
Rat acute toxicity 1.8144 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.8743
hERG inhibition (predictor II) Non-inhibitor 0.7089
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Mouthwashoral.042; .042; .06; .064 kg/100L; kg/100L; kg/100L; kg/100L
Mouthwashoral.042; .042; .06; .064 mL/100L; mL/100L; mL/100L; mL/100L
Mouthwashoral.092; .042; .06; .064 kg/100L; kg/100L; kg/100L; kg/100L
Mouthwashoral.092; .042; .06; .064 mL/100L; mL/100L; mL/100L; mL/100L
Rinseoral.092; .042; .06; .064 kg/100L; kg/100L; kg/100L; kg/100L
PricesNot Available
PatentsNot Available
Properties
Stateliquid
Experimental Properties
PropertyValueSource
melting point1.5 °CPhysProp
boiling point176.4 °CPhysProp
water solubility3500 mg/L (at 21 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP2.74GRIFFIN,S ET AL. (1999)
Predicted Properties
PropertyValueSource
Water Solubility0.0225ALOGPS
logP3.36ALOGPS
logP2.35ChemAxon
logS-3.8ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area9.23 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity45.86 m3·mol-1ChemAxon
Polarizability18.54 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra1D NMR
References
Synthesis ReferenceNot Available
General Reference
  1. Bastos VP, Gomes AS, Lima FJ, Brito TS, Soares PM, Pinho JP, Silva CS, Santos AA, Souza MH, Magalhaes PJ: Inhaled 1,8-Cineole Reduces Inflammatory Parameters in Airways of Ovalbumin-Challenged Guinea Pigs. Basic Clin Pharmacol Toxicol. 2010 Aug 16. Pubmed
External Links
ResourceLink
KEGG DrugD04115
KEGG CompoundC09844
ChEBI27961
ChEMBL
PharmGKBPA449555
IUPHAR2464
Guide to Pharmacology2464
HETCNL
WikipediaEucalyptol
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSshow(74.3 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:22