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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
Structure for Eucalyptol (DB03852)
- 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
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Prophylaxis of Gingivitis ••• ••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism ATransient receptor potential cation channel subfamily M member 8 activatorHumans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- 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
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Germ Free ARIA Liquid 1.2 g/100mL Topical Omega Vision Co., Ltd. 2022-09-24 Not applicable US 
Rosatra Synergy for treatment of Acne Rosacea Oil 0.7 g/50g Topical Phytopia Co., Ltd. 2016-02-29 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image 365 Whole Foods Market Anticavity/Antigingivitis Mouthwash Eucalyptol (0.92 mg/1mL) + Menthol (0.42 mg/1mL) + Methyl salicylate (0.6 mg/1mL) + Sodium fluoride (0.1 mg/1mL) + Thymol (0.64 mg/1mL) Mouthwash Dental Whole Foods Market, Inc. 2022-01-31 Not applicable US 365 Whole Foods Market Antigingivitis Mouthwash Eucalyptol (0.92 mg/1mL) + Menthol (0.42 mg/1mL) + Methyl salicylate (0.6 mg/1mL) + Thymol (0.64 mg/1mL) Mouthwash Dental Whole Foods Market, Inc. 2022-01-31 Not applicable US Advanced Antiseptic Eucalyptol (.042 mL/100L) + Menthol (.042 mL/100L) + Methyl salicylate (.060 mL/100L) + Thymol (.064 mL/100L) Mouthwash Oral Wakefern Food Corporation 2010-11-24 Not applicable US Advanced Antiseptic Eucalyptol (.092 kg/100L) + Menthol (.042 kg/100L) + Methyl salicylate (.060 kg/100L) + Thymol (.064 kg/100L) Mouthwash Oral Demoulas Super Markets, Inc 2010-07-22 Not applicable US Advanced Antiseptic Citrus Eucalyptol (.092 mL/100L) + Menthol (.042 mL/100L) + Methyl salicylate (.060 mL/100L) + Thymol (.042 mL/100L) Mouthwash Oral H E B 2010-10-15 Not applicable US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Antiseptic Rinse Eucalyptol (.092 kg/100L) + Menthol (.042 kg/100L) + Methyl salicylate (.060 kg/100L) + Thymol (.064 kg/100L) Mouthwash Oral Meijer 2006-08-08 Not applicable US Germ Free ARIA Eucalyptol (1.2 g/100mL) Liquid Topical Omega Vision Co., Ltd. 2022-09-24 Not applicable US
Categories
- ATC Codes
- R05CA13 — Cineole
- Drug Categories
- Agrochemicals
- Alcohols
- Anti-Infective Agents
- Antitussive Agents
- Central Nervous System Agents
- Compounds used in a research, industrial, or household setting
- Cosmetics
- Cough and Cold Preparations
- Cyclohexanes
- Cyclohexanols
- Cycloparaffins
- Diet, Food, and Nutrition
- Expectorants
- Fatty Alcohols
- Flavoring Agents
- Food
- Food Additives
- Food Ingredients
- Hexanols
- Insect Repellents
- Lipids
- Monoterpenes
- Mouthwashes
- Pesticides
- Pharmaceutic Aids
- Pharmaceutical Preparations
- Physiological Phenomena
- Protective Agents
- Respiratory System Agents
- Solvents
- Terpenes
- Toxic Actions
- 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
- 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]
- External Links
- KEGG Drug
- D04115
- KEGG Compound
- C09844
- PubChem Compound
- 2758
- PubChem Substance
- 46506161
- ChemSpider
- 21111689
- 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
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data4 Completed Prevention Healthy Volunteers (HV) 1 somestatus stop reason just information to hide 3 Unknown Status Treatment Cough 1 somestatus stop reason just information to hide 2 Recruiting Prevention Gonorrhea 1 somestatus stop reason just information to hide Not Available Completed Not Available Acute rhino-sinusitis / Bronchitis / Chronic Sinusitis 1 somestatus stop reason just information to hide Not Available Recruiting Not Available Community Acquired Pneumonia (CAP) 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Ointment Nasal Liquid Dental Mouthwash Oral Mouthwash Buccal Lotion Topical Spray Topical Powder Topical Solution Respiratory (inhalation) Liquid Topical Cream Topical Mouthwash Buccal; Oral Liquid Intramuscular Suppository Rectal Capsule Gel Topical Liquid Topical 1.2 g/100mL Ointment Topical Rinse Oral Lozenge Oral Solution Topical Mouthwash Dental; Oral Spray Oral Liquid Oral Emulsion Topical Oil Topical 0.7 g/50g Capsule Oral Oil Topical Mouthwash Dental Capsule, gelatin coated Oral Liquid Respiratory (inhalation) Solution Oral - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Liquid
- Experimental Properties
Property Value Source melting point (°C) 1.5 °C PhysProp boiling point (°C) 176.4 °C PhysProp water solubility 3500 mg/L (at 21 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) logP 2.74 GRIFFIN,S ET AL. (1999) - Predicted Properties
Property Value Source Water Solubility 0.0225 mg/mL ALOGPS logP 3.36 ALOGPS logP 2.35 Chemaxon logS -3.8 ALOGPS pKa (Strongest Basic) -4.2 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 9.23 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 45.86 m3·mol-1 Chemaxon Polarizability 18.54 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - 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 inhibitor Non-inhibitor 0.7571 CYP450 2D6 inhibitor Non-inhibitor 0.95 CYP450 2C19 inhibitor Non-inhibitor 0.658 CYP450 3A4 inhibitor 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 138.77718 predictedDeepCCS 1.0 (2019) [M+H]+ 133.3374801 predictedDarkChem Lite v0.1.0 [M+H]+ 141.17274 predictedDeepCCS 1.0 (2019) [M+Na]+ 133.1899801 predictedDarkChem Lite v0.1.0 [M+Na]+ 147.40157 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Activator
- General Function
- Receptor-activated non-selective cation channel involved in detection of sensations such as coolness, by being activated by cold temperature below 25 degrees Celsius. Activated by icilin, eucalyptol, menthol, cold and modulation of intracellular pH. Involved in menthol sensation. Permeable for monovalent cations sodium, potassium, and cesium and divalent cation calcium. Temperature sensing is tightly linked to voltage-dependent gating. Activated upon depolarization, changes in temperature resulting in graded shifts of its voltage-dependent activation curves. The chemical agonist menthol functions as a gating modifier, shifting activation curves towards physiological membrane potentials. Temperature sensitivity arises from a tenfold difference in the activation energies associated with voltage-dependent opening and closing. In prostate cancer cells, shows strong inward rectification and high calcium selectivity in contrast to its behavior in normal cells which is characterized by outward rectification and poor cationic selectivity. Plays a role in prostate cancer cell migration (PubMed:25559186). Isoform 2 and isoform 3 negatively regulate menthol- and cold-induced channel activity by stabilizing the closed state of the channel
- Specific Function
- Calcium channel activity
- Gene Name
- TRPM8
- Uniprot ID
- Q7Z2W7
- Uniprot Name
- Transient receptor potential cation channel subfamily M member 8
- Molecular Weight
- 127684.035 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Drug created at June 13, 2005 13:24 / Updated at August 26, 2024 19:21