Identification

Name
Eugenol
Accession Number
DB09086
Type
Small Molecule
Groups
Approved
Description

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.

Structure
Thumb
Synonyms
Not Available
External IDs
FEMA NO. 2467 / NSC-209525 / NSC-8895
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Baby Orajel Naturals Remedy for Teething Pain ReliefGel12 mg/1gTopicalChurch & Dwight Company, Inc.2010-12-152012-04-24Us
DenTek EugenolLiquid850 mg/1mLDentalTeam Technologies, Inc2015-07-01Not applicableUs
DenTek EugenolLiquid850 mg/1mLDentalDenTek Oral Care, Inc.2015-07-01Not applicableUs
EugenolLiquid850 mg/1mLOralPolysciences, Inc2015-01-30Not applicableUs
EugenolLiquid100 %DentalGermiphene Corporation1972-12-312005-12-31Canada
Eugenol Toothache MedicationLiquid850 mg/1mLDentalDenTek Oral Care, Inc.2015-07-012017-08-31Us
Eugenol Toothache MedicationLiquid850 mg/1mLDentalTeam Technologies, Inc2015-07-01Not applicableUs
Nuby Teething GelGel8 mg/1gTopicalTalbot’s Pharmaceuticals Family Products, LLC.2017-06-22Not applicableUs
Nuby Teething GelGel8 mg/1gTopicalEuropharma Concepts Limited2017-06-28Not applicableUs
Nuby Teething GelGel8 mg/1gTopicalNingbo Longwell Baby Products Co Ltd2017-06-23Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Dry Socket PasteEugenol (4.16 %) + Acetylsalicylic acid (8.33 %) + Chlorobutanol (1.5 %)PasteDentalSultan Healthcare1985-12-312004-08-06Canada
Jiffy Toothache DropsEugenol (9 %) + Benzocaine (5 %)LiquidDentalBlock Drug Company (Canada) Ltd.1979-12-312001-03-14Canada
T.R.U.E. Test Thin-Layer Rapid Use Patch TestEugenol (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) + P-Tert-Butylphenol-Formaldehyde Resin (Low Molecular Weight) (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)KitSmartPractice Denmark ApS2012-03-01Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Dry SocketEugenol (0.0416 g/1g) + Guaiacol (0.0416 g/1g)PasteDentalDentsply Llc, Professional Division, Trading As "Sultan Healthcare"1900-01-01Not applicableUs
Categories
UNII
3T8H1794QW
CAS number
97-53-0
Weight
Average: 164.2011
Monoisotopic: 164.083729628
Chemical Formula
C10H12O2
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

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.

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.

TargetActionsOrganism
UEstrogen receptor alphaNot AvailableHuman
UEstrogen receptor betaNot AvailableHuman
UAndrogen receptor
antagonist
Human
UTransient receptor potential cation channel subfamily V member 3Not AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  1. 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. [PubMed:27355133]
  2. 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. [PubMed:21547684]
  3. 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. [PubMed:22775297]
External Links
Human Metabolome Database
HMDB0005809
KEGG Compound
C10453
PubChem Compound
3314
PubChem Substance
310265013
ChemSpider
13876103
BindingDB
50164168
ChEBI
4917
ChEMBL
CHEMBL42710
HET
EOL
Drugs.com
Drugs.com Drug Page
Wikipedia
Eugenol
PDB Entries
3s0e
FDA label
Download (1.32 MB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
GelTopical12 mg/1g
PasteDental
LiquidDental100 %
LiquidOral850 mg/1mL
LiquidDental
GelTopical13 mg/1g
GelTopical8 mg/1g
LiquidTopical850 mg/1mL
Kit
LiquidDental850 mg/1mL
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.44 mg/mLALOGPS
logP2.66ALOGPS
logP2.61ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)9.94ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity48.79 m3·mol-1ChemAxon
Polarizability17.9 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0ik9-5900000000-3d3a9e4f250074741003
GC-MS Spectrum - EI-BGC-MSsplash10-03di-2900000000-395df8510f0db4933abe
GC-MS Spectrum - EI-BGC-MSsplash10-03di-6900000000-1afdd3b83f6832b11f70
GC-MS Spectrum - EI-BGC-MSsplash10-03di-4900000000-1d96ae8b031e47e13112
GC-MS Spectrum - EI-BGC-MSsplash10-0ik9-6900000000-def0c646d72c040b58da
GC-MS Spectrum - EI-BGC-MSsplash10-03di-0900000000-dfa64951eb648f5c9df1
Mass Spectrum (Electron Ionization)MSsplash10-0il0-6900000000-ff0dc492bab70317bb2a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0900000000-9d2a857e8a482a061127
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-2900000000-9c846765367542bf4db1
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0fr6-9500000000-98fcaf3ccca850c34bd3
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0900000000-835320dc79855273af7f
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0900000000-3a70eb9601589d9108a1
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-052e-4900000000-1c4834945c53d64bab3b
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-014i-0900000000-4541582e8f6395e2fa87
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0900000000-84f950d2fc0742e324d5
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0ab9-0900000000-4c037643a10913a70f5e
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-0900000000-83f8f32dfd9b94fb1d24
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-2900000000-c65a2dab49b8ebb431da
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-001i-0900000000-65a67ccd1df0d2f1796f
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable

Taxonomy

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
Methoxyphenol / Phenoxy compound / Methoxybenzene / Phenol ether / Anisole / 1-hydroxy-2-unsubstituted benzenoid / Alkyl aryl ether / Monocyclic benzene moiety / Ether / Organic oxygen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
phenols, phenylpropanoid, monomethoxybenzene (CHEBI:4917) / Monolignols (C10453) / a monoterpenol, a phenol (CPD-6481)

Targets

Kind
Protein
Organism
Human
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
  1. 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. [PubMed:12495555]
Kind
Protein
Organism
Human
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
  1. 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. [PubMed:12495555]
Kind
Protein
Organism
Human
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
  1. 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. [PubMed:20226658]
Kind
Protein
Organism
Human
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
  1. 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. [PubMed:21593771]

Drug created on September 15, 2015 14:13 / Updated on October 01, 2018 14:46