Thymol

Identification

Name
Thymol
Accession Number
DB02513  (EXPT01913)
Type
Small Molecule
Groups
Approved
Description

A phenol obtained from thyme oil or other volatile oils. It is used as a stabilizer in pharmaceutic preparations. It has been used for its antiseptic, antibacterial, and antifungal actions, and was formerly used as a vermifuge. (Dorland, 28th ed)

Structure
Thumb
Synonyms
  • 2-isopropyl-5-methylphenol
  • 5-Methyl-2-(1-Methylethyl)Phenol
  • IPMP
External IDs
FEMA NO. 3066 / NSC-11215 / NSC-47821 / NSC-49142
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Acne Vanish Synergy for treatment of AcnesOil.7 g/50gTopicalPhytopia Co., Ltd.2016-02-29Not applicableUs
Acute Bronchitis SynergyOil1.5 g/50gTopicalPhytopia Co., Ltd.2016-02-29Not applicableUs
Benefect Natural Hand SanitizerSpray.06 mL/120mLTopicalSensible Life Products2010-03-01Not applicableUs
Benefect Natural Hand SanitizerLiquid.5 mL/LTopicalSensible Life Products2010-03-01Not applicableUs
Chronic Bronchitis SynergyOil.5 g/50gTopicalPhytopia Co., Ltd.2016-02-29Not applicableUs
Cleanwell Natural Antibacterial Foaming LavenderSoap.0004 kg/kgTopicalClean Well, Llc2007-11-012019-05-29Us
CleanWell Natural Antibacterial Foaming Orange VanillaSoap.0004 1/kgTopicalClean Well, Llc2007-11-012019-05-29Us
CleanWell Natural Antibacterial Foaming Spearmint LimeSoap.0004 kg/kgTopicalClean Well, Llc2007-11-012019-05-29Us
CleanWell Natural Orange Vanilla Hand SanitizerSpray.0005 kg/kgTopicalClean Well, Llc2007-11-01Not applicableUs
CleanWell Natural Orange Vanilla Hand Sanitizing WipesCloth.0005 kg/kgTopicalClean Well, Llc2010-06-15Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Advanced AntisepticThymol (.064 mL/100L) + Eucalyptol (.042 mL/100L) + Menthol (.042 mL/100L) + Methyl salicylate (.06 mL/100L)MouthwashOralWakfern Food Corporation2010-11-24Not applicableUs
Advanced AntisepticThymol (.064 kg/100L) + Eucalyptol (.092 kg/100L) + Menthol (.042 kg/100L) + Methyl salicylate (.06 kg/100L)MouthwashOralDemoulas Supermarkets, Inc.2010-07-22Not applicableUs
Advanced Antiseptic CitrusThymol (.042 mL/100L) + Eucalyptol (.092 mL/100L) + Menthol (.042 mL/100L) + Methyl salicylate (.06 mL/100L)MouthwashOralH.E.B.2010-10-15Not applicableUs
Advanced Antiseptic CitrusThymol (.042 mL/100L) + Eucalyptol (.092 mL/100L) + Menthol (.042 mL/100L) + Methyl salicylate (.06 mL/100L)MouthwashOralDrug Mart1991-06-15Not applicableUs
Advanced CitrusThymol (.064 kg/100L) + Eucalyptol (.092 kg/100L) + Menthol (.042 kg/100L) + Methyl salicylate (.06 kg/100L)MouthwashOralWalmart Stores2010-07-22Not applicableUs
Advanced Citrus AntisepticThymol (.064 mL/100L) + Eucalyptol (.092 mL/100L) + Menthol (.042 mL/100L) + Methyl salicylate (.06 mL/100L)MouthwashOralPublix Supermarkets, Inc.2001-05-03Not applicableUs
Amber Mouth RinseThymol (.64 mg/mL) + Eucalyptol (.92 mg/mL) + Menthol (.42 mg/mL) + Methyl salicylate (.6 mg/mL)LiquidOralFilo America2013-07-30Not applicableUs
Amber Mouth Wash - LiqThymol (0.064 %) + Eucalyptol (0.092 %) + Menthol (0.042 %)LiquidDentalPerrigo International1996-10-091999-08-06Canada
Amber Mouthwash - LiqThymol (0.064 %) + Eucalyptol (0.092 %) + Menthol (0.042 %)LiquidDentalPerrigo International1996-06-301999-08-06Canada
Anitseptic Mouth RinseThymol (.64 mg/mL) + Eucalyptol (.92 mg/mL) + Menthol (.42 mg/mL) + Methyl salicylate (.6 mg/mL)MouthwashOralPharmacy Vlaue Alliance Llc2003-08-19Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Antiseptic RinseThymol (.064 kg/100L) + Eucalyptol (.092 kg/100L) + Menthol (.042 kg/100L) + Methyl salicylate (.06 kg/100L)MouthwashOralMeijer2006-08-08Not applicableUs
Categories
UNII
3J50XA376E
CAS number
89-83-8
Weight
Average: 150.2176
Monoisotopic: 150.10446507
Chemical Formula
C10H14O
InChI Key
MGSRCZKZVOBKFT-UHFFFAOYSA-N
InChI
InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)6-10(9)11/h4-7,11H,1-3H3
IUPAC Name
5-methyl-2-(propan-2-yl)phenol
SMILES
CC(C)C1=CC=C(C)C=C1O

Pharmacology

Indication
Not Available
Associated Conditions
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
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
DrugInteractionDrug group
AgmatineThe therapeutic efficacy of Thymol can be increased when used in combination with Agmatine.Experimental, Investigational
AmiodaroneThe therapeutic efficacy of Thymol can be increased when used in combination with Amiodarone.Approved, Investigational
AmlodipineThe therapeutic efficacy of Thymol can be increased when used in combination with Amlodipine.Approved
Amphotericin BThe therapeutic efficacy of Amphotericin B can be decreased when used in combination with Thymol.Approved, Investigational
AmrinoneThe therapeutic efficacy of Thymol can be increased when used in combination with Amrinone.Approved
AranidipineThe therapeutic efficacy of Thymol can be increased when used in combination with Aranidipine.Approved, Investigational
AzelnidipineThe therapeutic efficacy of Thymol can be increased when used in combination with Azelnidipine.Approved, Investigational
AzimilideThe therapeutic efficacy of Thymol can be increased when used in combination with Azimilide.Investigational
BarnidipineThe therapeutic efficacy of Thymol can be increased when used in combination with Barnidipine.Approved
BencyclaneThe therapeutic efficacy of Thymol can be increased when used in combination with Bencyclane.Experimental
BenidipineThe therapeutic efficacy of Thymol can be increased when used in combination with Benidipine.Approved, Investigational
BepridilThe therapeutic efficacy of Thymol can be increased when used in combination with Bepridil.Approved, Withdrawn
BioallethrinThe therapeutic efficacy of Thymol can be increased when used in combination with Bioallethrin.Approved, Experimental
BuspironeThe metabolism of Buspirone can be decreased when combined with Thymol.Approved, Investigational
BusulfanThe serum concentration of Busulfan can be increased when it is combined with Thymol.Approved, Investigational
CarboxyamidotriazoleThe therapeutic efficacy of Thymol can be increased when used in combination with Carboxyamidotriazole.Investigational
CaroverineThe therapeutic efficacy of Thymol can be increased when used in combination with Caroverine.Experimental
CilnidipineThe therapeutic efficacy of Thymol can be increased when used in combination with Cilnidipine.Approved, Investigational
CinnarizineThe therapeutic efficacy of Thymol can be increased when used in combination with Cinnarizine.Approved, Investigational
CisaprideThe serum concentration of Cisapride can be increased when it is combined with Thymol.Approved, Investigational, Withdrawn
ClevidipineThe therapeutic efficacy of Thymol can be increased when used in combination with Clevidipine.Approved, Investigational
CyclandelateThe therapeutic efficacy of Thymol can be increased when used in combination with Cyclandelate.Approved
CyclosporineThe metabolism of Cyclosporine can be decreased when combined with Thymol.Approved, Investigational, Vet Approved
DarodipineThe therapeutic efficacy of Thymol can be increased when used in combination with Darodipine.Experimental
DidanosineDidanosine can cause a decrease in the absorption of Thymol resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
DiltiazemThe therapeutic efficacy of Thymol can be increased when used in combination with Diltiazem.Approved, Investigational
DocetaxelThe metabolism of Docetaxel can be decreased when combined with Thymol.Approved, Investigational
DofetilideThe serum concentration of Dofetilide can be increased when it is combined with Thymol.Approved, Investigational
DotarizineThe therapeutic efficacy of Thymol can be increased when used in combination with Dotarizine.Investigational
EfonidipineThe therapeutic efficacy of Thymol can be increased when used in combination with Efonidipine.Approved, Investigational
EperisoneThe therapeutic efficacy of Thymol can be increased when used in combination with Eperisone.Approved, Investigational
EthosuximideThe therapeutic efficacy of Thymol can be increased when used in combination with Ethosuximide.Approved
EtravirineThe serum concentration of Etravirine can be increased when it is combined with Thymol.Approved
FelodipineThe therapeutic efficacy of Thymol can be increased when used in combination with Felodipine.Approved, Investigational
FendilineThe therapeutic efficacy of Thymol can be increased when used in combination with Fendiline.Withdrawn
Fish oilThe therapeutic efficacy of Thymol can be increased when used in combination with Fish oil.Approved, Nutraceutical
FlunarizineThe therapeutic efficacy of Thymol can be increased when used in combination with Flunarizine.Approved
FluspirileneThe therapeutic efficacy of Thymol can be increased when used in combination with Fluspirilene.Approved, Investigational
FosphenytoinThe serum concentration of Thymol can be decreased when it is combined with Fosphenytoin.Approved, Investigational
GabapentinThe therapeutic efficacy of Thymol can be increased when used in combination with Gabapentin.Approved, Investigational
GallopamilThe therapeutic efficacy of Thymol can be increased when used in combination with Gallopamil.Investigational
IsradipineThe therapeutic efficacy of Thymol can be increased when used in combination with Isradipine.Approved, Investigational
LacidipineThe therapeutic efficacy of Thymol can be increased when used in combination with Lacidipine.Approved, Investigational
LamotrigineThe therapeutic efficacy of Thymol can be increased when used in combination with Lamotrigine.Approved, Investigational
LercanidipineThe therapeutic efficacy of Thymol can be increased when used in combination with Lercanidipine.Approved, Investigational
LevetiracetamThe therapeutic efficacy of Thymol can be increased when used in combination with Levetiracetam.Approved, Investigational
LidoflazineThe therapeutic efficacy of Thymol can be increased when used in combination with Lidoflazine.Experimental
LoperamideThe therapeutic efficacy of Thymol can be increased when used in combination with Loperamide.Approved
LosartanThe metabolism of Losartan can be decreased when combined with Thymol.Approved
Magnesium sulfateThe therapeutic efficacy of Thymol can be increased when used in combination with Magnesium sulfate.Approved, Investigational, Vet Approved
ManidipineThe therapeutic efficacy of Thymol can be increased when used in combination with Manidipine.Approved, Investigational
MentholThe therapeutic efficacy of Thymol can be increased when used in combination with Menthol.Approved
MethsuximideThe therapeutic efficacy of Thymol can be increased when used in combination with Methsuximide.Approved
MibefradilThe therapeutic efficacy of Thymol can be increased when used in combination with Mibefradil.Investigational, Withdrawn
NaftopidilThe therapeutic efficacy of Thymol can be increased when used in combination with Naftopidil.Investigational
NicardipineThe therapeutic efficacy of Thymol can be increased when used in combination with Nicardipine.Approved, Investigational
NifedipineThe therapeutic efficacy of Thymol can be increased when used in combination with Nifedipine.Approved
NiguldipineThe therapeutic efficacy of Thymol can be increased when used in combination with Niguldipine.Experimental
NiludipineThe therapeutic efficacy of Thymol can be increased when used in combination with Niludipine.Experimental
NilvadipineThe therapeutic efficacy of Thymol can be increased when used in combination with Nilvadipine.Approved, Investigational
NimesulideThe therapeutic efficacy of Thymol can be increased when used in combination with Nimesulide.Approved, Investigational, Withdrawn
NimodipineThe therapeutic efficacy of Thymol can be increased when used in combination with Nimodipine.Approved, Investigational
NisoldipineThe therapeutic efficacy of Thymol can be increased when used in combination with Nisoldipine.Approved
NitrendipineThe therapeutic efficacy of Thymol can be increased when used in combination with Nitrendipine.Approved, Investigational
NylidrinThe therapeutic efficacy of Thymol can be increased when used in combination with Nylidrin.Approved
OtiloniumThe therapeutic efficacy of Thymol can be increased when used in combination with Otilonium.Experimental, Investigational
PhenytoinThe serum concentration of Phenytoin can be increased when it is combined with Thymol.Approved, Vet Approved
PinaveriumThe therapeutic efficacy of Thymol can be increased when used in combination with Pinaverium.Approved
PrenylamineThe therapeutic efficacy of Thymol can be increased when used in combination with Prenylamine.Withdrawn
ProgesteroneThe absorption of Progesterone can be decreased when combined with Thymol.Approved, Vet Approved
QuinidineThe serum concentration of Quinidine can be increased when it is combined with Thymol.Approved, Investigational
RanolazineThe serum concentration of Ranolazine can be increased when it is combined with Thymol.Approved, Investigational
RifabutinThe serum concentration of Rifabutin can be increased when it is combined with Thymol.Approved, Investigational
RifampicinThe serum concentration of Rifampicin can be increased when it is combined with Thymol.Approved
RifapentineThe serum concentration of Rifapentine can be increased when it is combined with Thymol.Approved, Investigational
RifaximinThe serum concentration of Rifaximin can be increased when it is combined with Thymol.Approved, Investigational
SeletracetamThe therapeutic efficacy of Thymol can be increased when used in combination with Seletracetam.Investigational
SolifenacinThe metabolism of Solifenacin can be decreased when combined with Thymol.Approved
SucralfateSucralfate can cause a decrease in the absorption of Thymol resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
SunitinibThe metabolism of Sunitinib can be decreased when combined with Thymol.Approved, Investigational
TacrolimusThe metabolism of Tacrolimus can be decreased when combined with Thymol.Approved, Investigational
TerodilineThe therapeutic efficacy of Thymol can be increased when used in combination with Terodiline.Experimental
TetrahydropalmatineThe therapeutic efficacy of Thymol can be increased when used in combination with Tetrahydropalmatine.Investigational
Tolfenamic AcidThe therapeutic efficacy of Thymol can be increased when used in combination with Tolfenamic Acid.Approved, Investigational
TranilastThe therapeutic efficacy of Thymol can be increased when used in combination with Tranilast.Approved, Investigational
TrimebutineThe therapeutic efficacy of Thymol can be increased when used in combination with Trimebutine.Approved
TrimethadioneThe therapeutic efficacy of Thymol can be increased when used in combination with Trimethadione.Approved
VerapamilThe therapeutic efficacy of Thymol can be increased when used in combination with Verapamil.Approved
VinpocetineThe therapeutic efficacy of Thymol can be increased when used in combination with Vinpocetine.Investigational
WIN 55212-2The therapeutic efficacy of Thymol can be increased when used in combination with WIN 55212-2.Experimental
ZiconotideThe therapeutic efficacy of Thymol can be increased when used in combination with Ziconotide.Approved
ZolpidemThe serum concentration of Zolpidem can be increased when it is combined with Thymol.Approved
ZonisamideThe therapeutic efficacy of Thymol can be increased when used in combination with Zonisamide.Approved, Investigational
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0001878
KEGG Drug
D01039
KEGG Compound
C09908
PubChem Compound
6989
PubChem Substance
46504674
ChemSpider
21105998
BindingDB
50240432
ChEBI
27607
ChEMBL
CHEMBL29411
IUPHAR
2499
Guide to Pharmacology
GtP Drug Page
HET
IPB
Wikipedia
Thymol
PDB Entries
1e06

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedPreventionNeonatal Infections1
4CompletedTreatmentAggressive Periodontitis1
Not AvailableRecruitingTreatmentPeriodontitis / Type 2 Diabetes Mellitus1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
OilTopical.7 g/50g
OilTopical1.5 g/50g
LiquidDental
RinseOral
MouthwashBuccal
LiquidTopical.5 mL/L
SprayTopical.06 mL/120mL
LotionTopical
SprayTopical
PowderTopical
OintmentTopical
OilTopical.5 g/50g
SoapTopical.0004 1/kg
SprayTopical.0005 kg/kg
ClothTopical.0005 kg/kg
MouthwashBuccal; Oral
SoapTopical.0004 kg/kg
LiquidOral
OilTopical1.7 g/50g
GelTopical
MouthwashDental; Oral
MouthwashOral
JellyNasal
LiquidTopical
SoapTopical.0024 kg/kg
LozengeOral
PlasterTopical
PatchCutaneous; Topical; Transdermal
MouthwashDental
LiquidRespiratory (inhalation)
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)51.5 °CPhysProp
boiling point (°C)232.5 °CPhysProp
water solubility900 mg/L (at 20 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP3.30HANSCH,C ET AL. (1995)
pKa10.6 (at 20 °C)SERJEANT,EP & DEMPSEY,B (1979)
Predicted Properties
PropertyValueSource
Water Solubility0.643 mg/mLALOGPS
logP3.16ALOGPS
logP3.43ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)10.59ChemAxon
pKa (Strongest Basic)-5.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.27 m3·mol-1ChemAxon
Polarizability17.84 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9955
Blood Brain Barrier+0.9381
Caco-2 permeable+0.9153
P-glycoprotein substrateNon-substrate0.722
P-glycoprotein inhibitor INon-inhibitor0.9343
P-glycoprotein inhibitor IINon-inhibitor0.9883
Renal organic cation transporterNon-inhibitor0.9036
CYP450 2C9 substrateNon-substrate0.7352
CYP450 2D6 substrateSubstrate0.7838
CYP450 3A4 substrateNon-substrate0.5667
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9368
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.9196
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7429
Ames testNon AMES toxic0.9282
CarcinogenicityNon-carcinogens0.7195
BiodegradationNot ready biodegradable0.7808
Rat acute toxicity2.2996 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8987
hERG inhibition (predictor II)Non-inhibitor0.9087
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
GC-MS Spectrum - EI-BGC-MSsplash10-000i-0900000000-333dc57384e65e3b4cfa
GC-MS Spectrum - EI-BGC-MSsplash10-000i-1900000000-3679938a5ea114a30e48
GC-MS Spectrum - EI-BGC-MSsplash10-000i-3900000000-8ce5865e48dad7250d5e
GC-MS Spectrum - EI-BGC-MSsplash10-0udi-0109030000-5562c203cb318f30321b
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0a4i-2492200000-85342d698be72263a95f
Mass Spectrum (Electron Ionization)MSsplash10-000i-4900000000-73edaa628c1f5f2e1bd9
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-01p9-9700000000-e1a28495617d7b014e5c
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-014i-9300000000-baeee6cdcafaadeebdec
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-015c-9100000000-e1efa41eaf818832448a
MS/MS Spectrum - EI-B (SHIMADZU LKB-9000B) , PositiveLC-MS/MSsplash10-000i-0900000000-333dc57384e65e3b4cfa
MS/MS Spectrum - EI-B (HITACHI RMU-6L) , PositiveLC-MS/MSsplash10-000i-1900000000-3679938a5ea114a30e48
MS/MS Spectrum - EI-B (HITACHI M-80B) , PositiveLC-MS/MSsplash10-000i-3900000000-f72f603d97f0f7081b8d
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
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Prenol lipids
Sub Class
Monoterpenoids
Direct Parent
Aromatic monoterpenoids
Alternative Parents
Monocyclic monoterpenoids / Phenylpropanes / Cumenes / Meta cresols / Toluenes / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Organooxygen compounds / Hydrocarbon derivatives
Substituents
P-cymene / Aromatic monoterpenoid / Monocyclic monoterpenoid / Cumene / Phenylpropane / M-cresol / 1-hydroxy-4-unsubstituted benzenoid / 1-hydroxy-2-unsubstituted benzenoid / Phenol / Toluene
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
phenols, monoterpenoid (CHEBI:27607) / Menthane monoterpenoids, Cyclic monoterpenes (C09908) / Menthane monoterpenoids (LMPR0102090029)

Drug created on June 13, 2005 07:24 / Updated on June 02, 2018 07:04