Eucalyptol

Identification

Summary

Eucalyptol is a common ingredient in mouthwash and cosmetics derived naturally from the eucalyptus plant that is frequently used to to improve symptoms of airway mucus hypersecretion.

Brand Names
Listerine Antiseptic
Generic Name
Eucalyptol
DrugBank Accession Number
DB03852
Background

Eucalyptol is naturally produced cyclic ether and 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.

Type
Small Molecule
Groups
Experimental, Nutraceutical
Structure
Thumb
Weight
Average: 154.2493
Monoisotopic: 154.135765198
Chemical Formula
C10H18O
Synonyms
  • 1,8-cineol
  • 1,8-Cineole
  • 1,8-epoxy-p-menthane
  • 1,8-oxido-p-menthane
  • Cajeputol
  • Cineole
  • Eucalyptol
  • Zineol

Pharmacology

Indication

Not Available

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Hover over products below to view reaction partners

Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Medicalerrors
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Toxicity

Oral, rat LD50: 2480 mg/kg

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Products

Products
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Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Rosatra Synergy for treatment of Acne RosaceaOil0.7 g/50gTopicalPhytopia Co., Ltd.2016-02-29Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Advanced AntisepticEucalyptol (.042 mL/100L) + Levomenthol (.042 mL/100L) + Methyl salicylate (.060 mL/100L) + Thymol (.064 mL/100L)MouthwashOralWakfern Food Corporation2010-11-24Not applicableUS flag
Advanced AntisepticEucalyptol (.092 kg/100L) + Levomenthol (.042 kg/100L) + Methyl salicylate (.060 kg/100L) + Thymol (.064 kg/100L)MouthwashOralDemoulas Supermarkets, Inc.2010-07-22Not applicableUS flag
Advanced Antiseptic CitrusEucalyptol (.092 mL/100L) + Levomenthol (.042 mL/100L) + Methyl salicylate (.060 mL/100L) + Thymol (.042 mL/100L)MouthwashOralH.E.B.2010-10-15Not applicableUS flag
Advanced Antiseptic CitrusEucalyptol (.092 mL/100L) + Levomenthol (.042 mL/100L) + Methyl salicylate (.060 mL/100L) + Thymol (.042 mL/100L)MouthwashOralDrug Mart1991-06-15Not applicableUS flag
Advanced CitrusEucalyptol (.092 kg/100L) + Levomenthol (.042 kg/100L) + Methyl salicylate (.060 kg/100L) + Thymol (.064 kg/100L)MouthwashOralWalmart Stores2010-07-22Not applicableUS flag
Advanced Citrus AntisepticEucalyptol (.092 mL/100L) + Levomenthol (.042 mL/100L) + Methyl salicylate (.060 mL/100L) + Thymol (.064 mL/100L)MouthwashOralPublix Supermarkets, Inc.2001-05-03Not applicableUS flag
Alsirub OntEucalyptol (2.5 %) + Levomenthol (4 %) + Methyl salicylate (7.5 %)OintmentTopicalAlsi Cie Ltee1977-12-312003-05-21Canada flag
Amber Mouth RinseEucalyptol (0.92 mg/1mL) + Levomenthol (0.42 mg/1mL) + Methyl salicylate (0.6 mg/1mL) + Thymol (0.64 mg/1mL)LiquidOralFilo America2013-07-30Not applicableUS flag
Amber Mouth Wash - LiqEucalyptol (0.092 %) + Levomenthol (0.042 %) + Thymol (0.064 %)LiquidDentalPerrigo International1996-10-091999-08-06Canada flag
Amber Mouthwash - LiqEucalyptol (0.092 %) + Levomenthol (0.042 %) + Thymol (0.064 %)LiquidDentalPerrigo International1996-06-301999-08-06Canada flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Antiseptic RinseEucalyptol (.092 kg/100L) + Levomenthol (.042 kg/100L) + Methyl salicylate (.060 kg/100L) + Thymol (.064 kg/100L)MouthwashOralMeijer2006-08-08Not applicableUS flag

Categories

ATC Codes
R05CA13 — Cineole
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as 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.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Oxanes
Sub Class
Not Available
Direct Parent
Oxanes
Alternative Parents
Oxacyclic compounds / Dialkyl ethers / Hydrocarbon derivatives
Substituents
Aliphatic heteropolycyclic compound / Dialkyl ether / Ether / Hydrocarbon derivative / Organic oxygen compound / Organooxygen compound / Oxacycle / Oxane
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
cineole (CHEBI:27961)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
RV6J6604TK
CAS number
470-82-6
InChI Key
WEEGYLXZBRQIMU-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

References

General References
  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. 2011 Jan;108(1):34-9. doi: 10.1111/j.1742-7843.2010.00622.x. Epub 2010 Aug 16. [Article]
KEGG Drug
D04115
KEGG Compound
C09844
PubChem Compound
2758
PubChem Substance
46506161
ChemSpider
21111689
RxNav
21116
ChEBI
27961
ChEMBL
CHEMBL1231862
PharmGKB
PA449555
Guide to Pharmacology
GtP Drug Page
PDBe Ligand
CNL
Wikipedia
Eucalyptol
PDB Entries
1t2b / 3be0 / 4fmx / 4fyz / 4l6g / 4l77 / 4lht
MSDS
Download (74.3 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3Unknown StatusTreatmentCoughing1
Not AvailableNot Yet RecruitingNot AvailableBronchitis / Rhinosinusitis Acute / Rhinosinusitis Chronic1
Not AvailableUnknown StatusTreatmentPeriodontitis / Type 2 Diabetes Mellitus1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
OintmentNasal
LiquidDental
RinseOral
MouthwashOral
MouthwashBuccal
LotionTopical
SprayTopical
PowderTopical
SolutionRespiratory (inhalation)
LiquidTopical
CreamTopical
MouthwashBuccal; Oral
LiquidIntramuscular
SuppositoryRectal
Capsule
OintmentTopical
GelTopical
LozengeOral
SolutionTopical
MouthwashDental; Oral
SprayOral
LiquidOral
EmulsionTopical
OilTopical0.7 g/50g
CapsuleOral
OilTopical
MouthwashDental
Capsule, gelatin coatedOral
LiquidRespiratory (inhalation)
SolutionOral
Prices
Not Available
Patents
Not Available

Properties

State
Liquid
Experimental Properties
PropertyValueSource
melting point (°C)1.5 °CPhysProp
boiling point (°C)176.4 °CPhysProp
water solubility3500 mg/L (at 21 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP2.74GRIFFIN,S ET AL. (1999)
Predicted Properties
PropertyValueSource
Water Solubility0.0225 mg/mLALOGPS
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
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.988
Blood Brain Barrier+0.9842
Caco-2 permeable+0.7609
P-glycoprotein substrateSubstrate0.5435
P-glycoprotein inhibitor INon-inhibitor0.6374
P-glycoprotein inhibitor IINon-inhibitor0.6455
Renal organic cation transporterNon-inhibitor0.7847
CYP450 2C9 substrateNon-substrate0.8132
CYP450 2D6 substrateNon-substrate0.7839
CYP450 3A4 substrateSubstrate0.5962
CYP450 1A2 substrateNon-inhibitor0.7719
CYP450 2C9 inhibitorNon-inhibitor0.7571
CYP450 2D6 inhibitorNon-inhibitor0.95
CYP450 2C19 inhibitorNon-inhibitor0.658
CYP450 3A4 inhibitorNon-inhibitor0.9395
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9399
Ames testNon AMES toxic0.9574
CarcinogenicityNon-carcinogens0.7856
BiodegradationNot ready biodegradable0.8549
Rat acute toxicity1.8144 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8743
hERG inhibition (predictor II)Non-inhibitor0.7089
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-0536-9200000000-aa52695ff4a2c1313e0b
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable

Drug created on June 13, 2005 13:24 / Updated on February 21, 2021 18:51