Identification
- Summary
Eugenol is a phenol used for the temporary relief of toothaches.
- Generic Name
- Eugenol
- DrugBank Accession Number
- DB09086
- Background
Eugenol is a naturally occurring phenolic molecule found in several plants such as cinnamon, clove, and bay leaves. It has been used as a topical antiseptic as a counter-irritant and in dental preparations with zinc oxide for root canal sealing and pain control. Although not currently available in any FDA-approved products (including OTC), eugenol has been found to have anti-inflammatory, neuroprotective, antipyretic, antioxidant, antifungal and analgesic properties. Its exact mechanism of action is unknown, however, it has been shown to interfere with action potential conduction. There are a number of unapproved OTC products available containing eugenol that advertise its use for the treatment of toothache.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Eugenol (DB09086)
- Weight
- Average: 164.2011
Monoisotopic: 164.083729628 - Chemical Formula
- C10H12O2
- Synonyms
- Eugenol
- External IDs
- FEMA NO. 2467
- NSC-209525
- NSC-8895
Pharmacology
- Indication
Eugenol is not currently available in any FDA-approved drug products. There are a number of unapproved OTC products that advertise it for the use of toothache. Eugenol is is also commonly used in combination with zinc oxide in dental procedures for the cementation of temporary prostheses and the temporary restoration of teeth and cavities.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Not Available
- Mechanism of action
The exact mechanism of action of eugenol is unknown. However, eugenol has been shown to interrupt action potentials, which may be involved in its anti-pain activity. Research has also shown eugenol to have anti-inflammatory, neuroprotective, antipyretic, antioxidant, antifungal and analgesic properties.
Target Actions Organism UEstrogen receptor alpha Not Available Humans UEstrogen receptor beta Not Available Humans UAndrogen receptor antagonistHumans UTransient receptor potential cation channel subfamily V member 3 Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- 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.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- 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
- No interactions found.
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 AnaDent Childrens Kanka Gel Gel 12 mg/1g Dental Belmora LLC 2022-11-08 Not applicable US 
Baby Orajel Naturals Remedy for Teething Pain Relief Gel 12 mg/1g Topical Church & Dwight Company, Inc. 2010-12-15 2012-04-24 US DenTek Eugenol Liquid 850 mg/1mL Dental DenTek Oral Care, Inc. 2015-07-01 Not applicable US DenTek Eugenol Liquid 850 mg/1mL Dental Team Technologies, Inc 2015-07-01 Not applicable US DenTek Eugenol Liquid 850 mg/1mL Dental IIMED MEDICAL MEXICANA S. DE R.L. DE C.V. 2022-10-10 Not applicable US DYNA-TDS Solution Dental DYNAPHARM (M) SDN BHD 2020-09-08 Not applicable Malaysia 
Eugenol Liquid 100 % Dental Germiphene Corporation 1972-12-31 2005-12-31 Canada 
Eugenol Liquid 850 mg/1mL Oral Polysciences, Inc 2015-01-30 2019-12-12 US Eugenol Toothache Medication Liquid 850 mg/1mL Dental Team Technologies, Inc 2015-07-01 Not applicable US Eugenol Toothache Medication Liquid 850 mg/1mL Dental DenTek Oral Care, Inc. 2015-07-01 2017-08-31 US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image AMMELTZ YOKO YOKO Massage Cream Eugenol (1.36 g/100g) + Levomenthol (5.44 g/100g) + Methyl salicylate (10.2 g/100g) Cream Topical KOBAYASHI Healthcare (Malaysia) Sdn. Bhd. 2020-09-08 Not applicable Malaysia BIO-MUSCLAX CREAM Eugenol (1.2 g/100g) + Levomenthol (5.5 g/100g) + Methyl salicylate (11 g/100g) Cream Topical Top Biopharma Sdn Bhd 2020-09-08 Not applicable Malaysia COUNTERPAIN ANALGESIC BALM Eugenol (1.36 %) + Levomenthol (5.44 %) + Methyl salicylate (10.2 %) Ointment Topical HOE PHARMACEUTICALS SDN. BHD. 2020-09-08 Not applicable Malaysia Dry Socket Paste Eugenol (4.16 %) + Acetylsalicylic acid (8.33 %) + Chlorobutanol (1.5 %) Paste Dental Sultan Healthcare 1985-12-31 2004-08-06 Canada FLANIL, CREAM Eugenol (1.36 % w/w) + Levomenthol (5.44 % w/w) + Methyl salicylate (10.2 % w/w) Cream Topical MEDISPEC (M) SDN.BHD 2020-09-08 Not applicable Malaysia Jiffy Toothache Drops Eugenol (9 %) + Benzocaine (5 %) Liquid Dental Block Drug Company (Canada) Ltd. 1979-12-31 2001-03-14 Canada Masabalm Eugenol (1.36 % w/w) + Levomenthol (5.44 % w/w) + Methyl salicylate (10.2 % w/w) Cream Topical Health Pharm Marketing Sdn Bhd 2020-09-08 Not applicable Malaysia NEOTICA CREME Eugenol (1.36 g/100g) + Camphor (1.8 g/100g) + Eucalyptus oil (1.8 g/100g) + Levomenthol (5.64 g/100g) + Methyl salicylate (12.5 g/100g) Cream Topical บริษัท ไทยนครพัฒนา จำกัด 2018-08-17 Not applicable Thailand 
PainONil Eugenol (20 mg/1g) + Camphor (80 mg/1g) + Eucalyptus oil (50 mg/1g) Ointment Topical PhytoBiologic Pharmaceutics LLC 2021-08-12 Not applicable US T.R.U.E. Test Thin-Layer Rapid Use Patch Test Eugenol (41 ug/48h) + 2,2'-Dibenzothiazyl disulfide (20 ug/48h) + 2-mercaptobenzothiazole (61 ug/48h) + 4-(Isopropylamino)diphenylamine (10 ug/48h) + Bacitracin (486 ug/48h) + Balsam of Peru (648 ug/48h) + Benzocaine (378 ug/48h) + Benzylparaben (162 ug/48h) + Bisphenol A diglycidyl ether (32 ug/48h) + Bromothalonil (4 ug/48h) + Bronopol (203 ug/48h) + Budesonide (0.8 ug/48h) + Butylparaben (162 ug/48h) + Chlorquinaldol (77 ug/48h) + Cinchocaine hydrochloride (66 ug/48h) + Cinnamaldehyde (41 ug/48h) + Cinnamyl alcohol (63 ug/48h) + Clioquinol (77 ug/48h) + Cobalt chloride hexahydrate (4 ug/48h) + Diazolidinylurea (446 ug/48h) + Potassium dichromate (15.7 ug/48h) + Dipentamethylenethiuram disulfide (5.5 ug/48h) + Diphenylguanidine (68 ug/48h) + Disperse Blue 106 (41 ug/48h) + Disulfiram (5.5 ug/48h) + Ditiocarb zinc (68 ug/48h) + Ethyl hydroxybenzoate (162 ug/48h) + Ethylenediamine (18 ug/48h) + Evernia prunastri (81 ug/48h) + Formaldehyde (146 ug/48h) + Geraniol (81 ug/48h) + Hydrocortisone butyrate (16 ug/48h) + Hydroxycitronellal (63 ug/48h) + Imidurea (486 ug/48h) + Isoeugenol (17 ug/48h) + Lanolin alcohols (810 ug/48h) + Methylchloroisothiazolinone (3 ug/48h) + Methylparaben (162 ug/48h) + Morpholinylmercaptobenzothiazole (20 ug/48h) + N,N'-diphenyl-1,4-phenylenediamine (25 ug/48h) + N-Cyclohexyl-N'-phenyl-1,4-phenylenediamine (25 ug/48h) + Neomycin sulfate (486 ug/48h) + Nickel sulfate hexahydrate (36 ug/48h) + Parthenolide (2 ug/48h) + Propylparaben (162 ug/48h) + Quaternium-15 (81 ug/48h) + Rosin (972 ug/48h) + Sodium aurotiosulfate (23 ug/48h) + Tetracaine hydrochloride (66 ug/48h) + Tetramethylthiuram monosulfide (5.5 ug/48h) + Thimerosal (6 ug/48h) + Thiohexam (20 ug/48h) + Thiram (5.5 ug/48h) + Tixocortol pivalate (2 ug/48h) + Zinc dibutyldithiocarbamate (68 ug/48h) + alpha-Amyl cinnamaldehyde (17 ug/48h) + p-Phenylenediamine (65 ug/48h) + p-tert-Butylphenol-formaldehyde resin (low molecular weight) (36 ug/48h) Kit Cutaneous SmartPractice Denmark ApS 2012-03-01 Not applicable US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Dry Socket Eugenol (0.0416 g/1g) + Guaiacol (0.0416 g/1g) Paste Dental Dentsply Llc, Professional Division, Trading As "Sultan Healthcare" 1963-01-01 Not applicable US
Categories
- Drug Categories
- Acids, Carbocyclic
- Alkenes
- Allyl Compounds
- Allylbenzene Derivatives
- Anti-Infective Agents
- Benzene Derivatives
- Caffeic Acids
- Cell-mediated Immunity
- Cinnamates
- Compounds used in a research, industrial, or household setting
- Hydrocarbons, Acyclic
- Increased Histamine Release
- Solvents
- Standardized Chemical Allergen
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as methoxyphenols. These are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Phenols
- Sub Class
- Methoxyphenols
- Direct Parent
- Methoxyphenols
- Alternative Parents
- Phenoxy compounds / Methoxybenzenes / Anisoles / Alkyl aryl ethers / 1-hydroxy-2-unsubstituted benzenoids / Hydrocarbon derivatives
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / Alkyl aryl ether / Anisole / Aromatic homomonocyclic compound / Ether / Hydrocarbon derivative / Methoxybenzene / Methoxyphenol / Monocyclic benzene moiety / Organic oxygen compound
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- phenols, phenylpropanoid, monomethoxybenzene (CHEBI:4917) / Monolignols (C10453) / a monoterpenol, a phenol (CPD-6481)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 3T8H1794QW
- CAS number
- 97-53-0
- InChI Key
- RRAFCDWBNXTKKO-UHFFFAOYSA-N
- InChI
- InChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H3
- IUPAC Name
- 2-methoxy-4-(prop-2-en-1-yl)phenol
- SMILES
- COC1=C(O)C=CC(CC=C)=C1
References
- General References
- Fonseca DV, Salgado PR, Aragao Neto Hde C, Golzio AM, Caldas Filho MR, Melo CG, Leite FC, Piuvezam MR, Pordeus LC, Barbosa Filho JM, Almeida RN: Ortho-eugenol exhibits anti-nociceptive and anti-inflammatory activities. Int Immunopharmacol. 2016 Sep;38:402-8. doi: 10.1016/j.intimp.2016.06.005. Epub 2016 Jun 27. [Article]
- Park SH, Sim YB, Lee JK, Kim SM, Kang YJ, Jung JS, Suh HW: The analgesic effects and mechanisms of orally administered eugenol. Arch Pharm Res. 2011 Mar;34(3):501-7. doi: 10.1007/s12272-011-0320-z. Epub 2011 May 6. [Article]
- Dal Bo W, Luiz AP, Martins DF, Mazzardo-Martins L, Santos AR: Eugenol reduces acute pain in mice by modulating the glutamatergic and tumor necrosis factor alpha (TNF-alpha) pathways. Fundam Clin Pharmacol. 2013 Oct;27(5):517-25. doi: 10.1111/j.1472-8206.2012.01052.x. Epub 2012 Jul 8. [Article]
- External Links
- Human Metabolome Database
- HMDB0005809
- KEGG Compound
- C10453
- PubChem Compound
- 3314
- PubChem Substance
- 310265013
- ChemSpider
- 13876103
- BindingDB
- 50164168
- 4186
- ChEBI
- 4917
- ChEMBL
- CHEMBL42710
- ZINC
- ZINC000000001411
- PDBe Ligand
- EOL
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Eugenol
- PDB Entries
- 3s0e / 7lid / 7ywu / 7ywv
- FDA label
- Download (1.32 MB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 0 Not Yet Recruiting Treatment Pulp Necroses 1 0 Recruiting Treatment Pulpitis dental 1 0 Unknown Status Supportive Care Gingival Pigmentation 1 Not Available Completed Not Available Inflammations, Endodontic / Operative Dentistry / Pulpitides / Toothache 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Gel Dental 12 mg/1g Gel Topical 12 mg/1g Gel Topical Paste Dental Solution Dental Liquid Dental 100 % Liquid Oral 850 mg/1mL Liquid Dental Solution / drops Dental 17 mg/1mL Cream Topical Gel Topical 13 mg/1g Gel Topical 8 mg/1g Liquid Topical 850 mg/1mL Kit Cutaneous Ointment Topical Liquid Dental 850 mg/1mL - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 1.44 mg/mL ALOGPS logP 2.66 ALOGPS logP 2.61 Chemaxon logS -2.1 ALOGPS pKa (Strongest Acidic) 9.94 Chemaxon pKa (Strongest Basic) -4.9 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 29.46 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 48.79 m3·mol-1 Chemaxon Polarizability 17.9 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Zinc ion binding
- Specific Function
- Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissu...
- Gene Name
- ESR1
- Uniprot ID
- P03372
- Uniprot Name
- Estrogen receptor
- Molecular Weight
- 66215.45 Da
References
- Howes MJ, Houghton PJ, Barlow DJ, Pocock VJ, Milligan SR: Assessment of estrogenic activity in some common essential oil constituents. J Pharm Pharmacol. 2002 Nov;54(11):1521-8. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Zinc ion binding
- Specific Function
- Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent m...
- Gene Name
- ESR2
- Uniprot ID
- Q92731
- Uniprot Name
- Estrogen receptor beta
- Molecular Weight
- 59215.765 Da
References
- Howes MJ, Houghton PJ, Barlow DJ, Pocock VJ, Milligan SR: Assessment of estrogenic activity in some common essential oil constituents. J Pharm Pharmacol. 2002 Nov;54(11):1521-8. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Zinc ion binding
- Specific Function
- Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription ...
- Gene Name
- AR
- Uniprot ID
- P10275
- Uniprot Name
- Androgen receptor
- Molecular Weight
- 98987.9 Da
References
- Ogawa Y, Akamatsu M, Hotta Y, Hosoda A, Tamura H: Effect of essential oils, such as raspberry ketone and its derivatives, on antiandrogenic activity based on in vitro reporter gene assay. Bioorg Med Chem Lett. 2010 Apr 1;20(7):2111-4. doi: 10.1016/j.bmcl.2010.02.059. Epub 2010 Feb 21. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Calcium channel activity
- Specific Function
- Putative receptor-activated non-selective calcium permeant cation channel. It is activated by innocuous (warm) temperatures and shows an increased response at noxious temperatures greater than 39 d...
- Gene Name
- TRPV3
- Uniprot ID
- Q8NET8
- Uniprot Name
- Transient receptor potential cation channel subfamily V member 3
- Molecular Weight
- 90635.115 Da
References
- Borbiro I, Lisztes E, Toth BI, Czifra G, Olah A, Szollosi AG, Szentandrassy N, Nanasi PP, Peter Z, Paus R, Kovacs L, Biro T: Activation of transient receptor potential vanilloid-3 inhibits human hair growth. J Invest Dermatol. 2011 Aug;131(8):1605-14. doi: 10.1038/jid.2011.122. Epub 2011 May 19. [Article]
Drug created at September 15, 2015 20:13 / Updated at February 21, 2021 18:52