Tolnaftate

Identification

Summary

Tolnaftate is an antifungal agent used to treat various skin infections caused by fungi.

Brand Names
Absorbine Jr Antifungal, Clarus, Fungi-nail, Fungoid-D, Pitrex, Sanafitil Antifungal, Tinactin, Tineacide Antifungal, Ting
Generic Name
Tolnaftate
DrugBank Accession Number
DB00525
Background

Tolnaftate is a synthetic over-the-counter anti-fungal agent. It may come as a cream, powder, spray, or liquid aerosol, and is used to treat jock itch, athlete's foot and ringworm. It is sold under several brand names, most notably Tinactin and Odor Eaters.

Type
Small Molecule
Groups
Approved, Investigational, Vet approved
Structure
Thumb
Weight
Average: 307.409
Monoisotopic: 307.103084861
Chemical Formula
C19H17NOS
Synonyms
  • 2-Naphthyl N-methyl-N-(3-tolyl)thionocarbamate
  • m,N-Dimethylthiocarbanilic acid O-2-naphthyl ester
  • Methyl (3-methylphenyl)carbamothioic acid O-2-naphthalenyl ester
  • N-methyl-N-(3-methylphenyl)-1-(naphthalen-2-yloxy)methanethioamide
  • O-2-Naphthyl m,N-dimethylthiocarbanilate
  • Tolnaftate
  • Tolnaftato
  • Tolnaftatum
  • Tolnaphthate

Pharmacology

Indication

Tolnaftate topical is used to treat skin infections such as athlete's foot, jock itch, and ringworm infections. Tolnaftate is also used, along with other antifungals, to treat infections of the nails, scalp, palms, and soles of the feet. The powder and powder aerosol may be used to prevent athlete's foot.

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Tolnaftate is a synthetic over-the-counter anti-fungal agent.

Mechanism of action

Tolnaftate is a topical fungicide. Though its exact mechanism unknown, it is believed to prevent ergosterol biosynthesis by inhibiting squalene epoxidase. It has also been reported to distort the hyphae and to stunt mycelial growth in susceptible organisms.

TargetActionsOrganism
ASqualene monooxygenase
inhibitor
Yeast
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
Adverseeffects
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Toxicity

Oral rat LD50: 891 mg/kg. Inhalation rat LC50: > 900 mg/m3/1hr. Irritation: skin rabbit: 500 mg/24H mild. Eye rabbit: 100 mg severe. Investigated a mutagen and reproductive effector.

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.
No interactions found.
Food Interactions
No interactions found.

Products

Products2
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dosage, form, labeller, route of administration, and marketing period.
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International/Other Brands
Aftate / Dr. Scholl's athlete's foot spray / Genaspor / Lamisil AF / NP-27 / Odor Eaters / Pitrex / Separin / Tinaderm
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Absorbine Antifungal Powder 1%Powder1 %TopicalW.F. Young, Inc.1992-12-311997-07-28Canada flag
Absorbine Jr Antifungal LiquidLiquid10 mg / mLTopicalClarion Brands, Llc1999-08-18Not applicableCanada flag
Aftate Athlete Foot CreamCream1 g/100gTopicalSabel Med Llc2016-12-01Not applicableUS flag
Anti-FungalPowder1 g/100gTopicalRugby2011-11-01Not applicableUS flag
Anti-FungalPowder.45 g/45gTopicalRij Pharmaceutical Corporation1999-03-16Not applicableUS flag
AntifungalSolution1 mg/100mLTopicalPerrigo New York Inc.2005-12-062013-08-09US flag
AntifungalCream1 g/100gTopicalRite Aid2005-07-232015-10-20US flag
AntifungalCream1 g/100gTopicalChain Drug Marketing Association Inc.2020-08-14Not applicableUS flag
AntifungalCream10 mg/1gTopicalUnifirst First Aid Corporation2002-06-302018-07-09US flag
AntifungalSolution1 mg/100mLTopicalPerrigo New York Inc.2011-08-172013-08-17US flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Absorbine Jr Antifungal LiqTolnaftate (1 g / 100 mL) + Levomenthol (200 mg / 100 mL)LiquidTopicalClarion Brands, Llc1994-12-31Not applicableCanada flag
COSMOS FUNGIL CREAMTolnaftate (1 %) + Chlorhexidine acetate (0.2 %)CreamTopicalDuopharma Marketing Sdn. Bhd.2020-09-08Not applicableMalaysia flag
ELAN-FORTE CREAMTolnaftate (1 %) + Chlorhexidine hydrochloride (0.2 %)CreamTopicalY.S.P. INDUSTRIES (M) SDN BHD2020-09-08Not applicableMalaysia flag
HeeltasticTolnaftate (1 g/100g) + Dimethicone (1 g/100g)StickTopicalNeutraderm, Inc.2009-06-302009-07-22US flag
HEXIDERM CREAMTolnaftate (1 %) + Chlorhexidine hydrochloride (0.1 %)CreamTopicalPRIME PHARMACEUTICAL SDN. BHD.2020-09-08Not applicableMalaysia flag
MiconatateTolnaftate (0.3 g/30mL) + Miconazole nitrate (2 g/85g)TopicalPureTek Corporation2021-09-02Not applicableUS flag
Nail MDTolnaftate (100 mg/1mg) + Triclosan (20 mg/1mg)SprayTopicalOmg Medical Group, Llc2013-02-14Not applicableUS flag
Natouch Antifungal Antiseptic WipesTolnaftate (2 g/200mL) + Ethanol (140 mL/200mL)ClothTopicalNatouch LLC2020-07-01Not applicableUS flag
PERMUT®Tolnaftate (1 mg) + Betamethasone valerate (0.05 mg) + Clioquinol (1 mg) + Gentamicin sulfate (0.1 mg)CreamTopicalEUROFARMA COLOMBIA S.A.S2019-10-15Not applicableColombia flag
ครีม โทนาฟ -บีTolnaftate (1 G/100G) + Betamethasone (0.1 G/100G)Creamบริษัท แสงไทยกำปะนี จำกัด1988-04-03Not applicableThailand flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Clear 50 Nail GelTolnaftate (1 g/100mL)GelTopicalSSG Ventures Inc2019-10-07Not applicableUS flag
Terbinafine HCl Chlortimazole and TolnaftateTolnaftate (1 g/100mL) + Clotrimazole (1 g/100mL) + Terbinafine hydrochloride (1 g/100mL)SolutionTopicalDr Marc's Manufacturing And Sales2018-01-302018-04-17US flag

Categories

ATC Codes
D01AE18 — Tolnaftate
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as naphthalenes. These are compounds containing a naphthalene moiety, which consists of two fused benzene rings.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Naphthalenes
Sub Class
Not Available
Direct Parent
Naphthalenes
Alternative Parents
Toluenes / Thiocarbamic acid esters / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Hydrocarbon derivatives
Substituents
Aromatic homopolycyclic compound / Hydrocarbon derivative / Monocyclic benzene moiety / Naphthalene / Organic nitrogen compound / Organic oxygen compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound / Organosulfur compound
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
monothiocarbamic ester (CHEBI:9620)
Affected organisms
  • Yeast and other fungi

Chemical Identifiers

UNII
06KB629TKV
CAS number
2398-96-1
InChI Key
FUSNMLFNXJSCDI-UHFFFAOYSA-N
InChI
InChI=1S/C19H17NOS/c1-14-6-5-9-17(12-14)20(2)19(22)21-18-11-10-15-7-3-4-8-16(15)13-18/h3-13H,1-2H3
IUPAC Name
N-methyl-N-(3-methylphenyl)-1-(naphthalen-2-yloxy)methanethioamide
SMILES
CN(C(=S)OC1=CC2=CC=CC=C2C=C1)C1=CC=CC(C)=C1

References

Synthesis Reference

Chris E. Platt, "Topical preparation of tolnaftate and hydrocortisone to treat fungal infections of the skin." U.S. Patent US5496812, issued November, 1989.

US5496812
General References
  1. Barrett-Bee K, Dixon G: Ergosterol biosynthesis inhibition: a target for antifungal agents. Acta Biochim Pol. 1995;42(4):465-79. [Article]
  2. Ryder NS, Frank I, Dupont MC: Ergosterol biosynthesis inhibition by the thiocarbamate antifungal agents tolnaftate and tolciclate. Antimicrob Agents Chemother. 1986 May;29(5):858-60. [Article]
Human Metabolome Database
HMDB0005005
KEGG Drug
D00381
PubChem Compound
5510
PubChem Substance
46505456
ChemSpider
5309
BindingDB
39349
RxNav
10637
ChEBI
9620
ChEMBL
CHEMBL83668
ZINC
ZINC000000057522
Therapeutic Targets Database
DAP001237
PharmGKB
PA164752438
Drugs.com
Drugs.com Drug Page
Wikipedia
Tolnaftate
MSDS
Download (73.2 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentDermatitis, Dermatitis Atopic1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Chain Drug
  • Medisca Inc.
  • Perrigo Co.
  • S&P Healthcare
  • Stiefel Labs
Dosage Forms
FormRouteStrength
LiquidTopical
LiquidTopical10 mg / mL
PowderTopical.45 g/45g
SprayTopical1 % w/w
TinctureTopical1 % w/w
SprayTopical1 %
CreamTopical0.01 mg/10g
AerosolTopical1 g/100g
CreamTopical1 g/1g
LiquidTopical1 %
SolutionTopical1.0 mL/100mL
SolutionTopical1 mg/100mL
CreamTopical.56 g/56.69g
PowderTopical1 %
SolutionTopical1 g/100mL
GelTopical1 g/100mL
LiquidTopical0.04 g/4g
Solution / dropsTopical10 mg/1mL
CreamTopical
SoapTopical1 g/100g
OintmentTopical
SolutionTopical10 mg/1mL
OilTopical0.14 g/14g
OilTopical0.3 g/28g
LotionTopical0.3 g/28g
Aerosol; powderTopical1 % w/w
Aerosol, powderTopical10 mg/1g
SprayTopical1 g/150g
CreamTopical1 %
Aerosol, foamTopical1 % w/w
PowderTopical1 % w/w
SolutionTopical1 % w/w
SolutionTopical1 g/100g
GelTopical1 g/100g
LiquidTopical10 g/1000g
LiquidTopical8.65 mg/1mL
GelTopical1 %
Aerosol, foamTopical10 mg/1mL
SprayTopical10 mg/1mL
LiquidTopical1 g/100mL
LotionTopical2.8 g/28g
SprayTopical10 mg/1g
StickTopical
Aerosol, powderTopical0.1 g/10g
CreamTopical0.1 g/10g
KitTopical10 mg/1g
LiquidTopical1 mL/100mL
Aerosol, sprayTopical10 mg/1g
PowderTopical10 mg/1g
Aerosol, sprayTopical1.3 g/57g
PowderTopical1.04 g
CreamTopical0.59 g/59g
CreamTopical0.01 g/1g
LiquidTopical1.0 g/100mL
OilTopical0.01 mg/1mL
LotionTopical1 % w/v
LotionTopical100 g/1g
SprayTopical
ClothTopical
GelTopical10 mg/1g
AerosolTopical1 % w/w
LiquidTopical1 mg/100mL
KitTopical1 g/100mL
SprayTopical1 g/100g
OintmentTopical1 g/100g
SolutionTopical1 % w/v
SolutionTopical1 %
OintmentTopical10 mg/1g
SprayTopical0.068 % w/w
LotionTopical10 mg/1mL
ClothTopical1 g/100g
SwabTopical1 %
SolutionTopical
Aerosol, powderTopical
AerosolTopical1 %
CreamTopical10 mg / g
PowderTopical10 mg / g
AerosolTopical.72 mg / g
SprayTopical
CreamTopical
LotionTopical
PowderTopical
PowderTopical1 g
SolutionTopical1 g
CreamTopical1 g
CreamTopical1 % w/w
SolutionTopical
LiquidTopical140 mg/15mL
Aerosol, sprayTopical1.28 g/128g
CreamTopical.2 mg/20mg
Aerosol, powderTopical1 g/100g
Aerosol, powderTopical1.1 g/113.3g
Aerosol, powderTopical1.3 g/113g
Aerosol, powderTopical1.3 g/130g
Aerosol, sprayTopical0.13 g/130g
Aerosol, sprayTopical0.15 g/150g
Aerosol, sprayTopical1.13 g/113g
Aerosol, sprayTopical1.3 g/130g
Aerosol, sprayTopical1.3 g/113g
Aerosol, sprayTopical1.5 g/150g
Aerosol, sprayTopical1.5 g/150.2g
Aerosol, sprayTopical150 g/150g
CreamTopical0.15 g/15g
CreamTopical1 g/100g
CreamTopical10 mg/1g
LiquidTopical0.3 g/30mL
PowderTopical1 g/100g
SprayTopical1.3 g/130g
SprayTopical1.5 g/150g
CreamTopical1.0 %
LiquidTopical10 mg/1g
LiquidTopical10 mg/1mL
Cream
CreamTopical1 %w/w
CreamTopical2 %w/w
OintmentTopical
OintmentTopical1 %w/w
Prices
Unit descriptionCostUnit
Zeasorb-AF 2% Powder 70 gm Can14.99USD can
Zeasorb Powder 70.9 gm Can12.99USD can
Tolnaftate powder4.77USD g
Zeasorb-af 2% lotion0.19USD g
Zeasorb powder0.05USD g
Tinactin 1% aerosol0.04USD ml
Athlete's foot 1% liquid spray0.03USD g
Pv antifungal 1% spray liquid0.02USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)111 °CPhysProp
water solubility7.02e-05 mg/mL at 25 °CMEYLAN,WM et al. (1996)
logP5.1Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000546 mg/mLALOGPS
logP4.87ALOGPS
logP5.75ChemAxon
logS-5.8ALOGPS
pKa (Strongest Basic)0.075ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.47 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity94.92 m3·mol-1ChemAxon
Polarizability34.22 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9904
Blood Brain Barrier+0.9689
Caco-2 permeable+0.6348
P-glycoprotein substrateNon-substrate0.8667
P-glycoprotein inhibitor INon-inhibitor0.5537
P-glycoprotein inhibitor IINon-inhibitor0.857
Renal organic cation transporterNon-inhibitor0.8281
CYP450 2C9 substrateNon-substrate0.7363
CYP450 2D6 substrateNon-substrate0.6071
CYP450 3A4 substrateSubstrate0.6401
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorInhibitor0.8948
CYP450 2D6 inhibitorNon-inhibitor0.923
CYP450 2C19 inhibitorInhibitor0.8994
CYP450 3A4 inhibitorInhibitor0.7959
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9229
Ames testAMES toxic0.8449
CarcinogenicityNon-carcinogens0.7425
BiodegradationNot ready biodegradable1.0
Rat acute toxicity1.7405 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8836
hERG inhibition (predictor II)Non-inhibitor0.5943
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (8.78 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-052b-0905000000-19e117da217d372632e2
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-00kb-0900000000-a065921efa544c82d972
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-0006-9600000000-19faf0e6dcd285dad8d1
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
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0002-0900000000-c4dd1b126170bea2c620
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0002-0900000000-b026e71179265a982a40
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00di-0900000000-a17707ff263e82d6e00e
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00di-3900000000-d0563822804c2844660b
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-006x-9700000000-a217b6444068e1406235
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00kf-9200000000-dc89d8219d5ce2567f3c
MS/MS Spectrum - , positiveLC-MS/MSsplash10-01ot-0901000000-c6fc83b073e80d5851f5
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Targets

Drugtargets2
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Kind
Protein
Organism
Yeast
Pharmacological action
Yes
Actions
Inhibitor
General Function
Squalene monooxygenase activity
Specific Function
Catalyzes the first oxygenation step in sterol biosynthesis and is suggested to be one of the rate-limiting enzymes in this pathway.
Gene Name
ERG1
Uniprot ID
Q92206
Uniprot Name
Squalene monooxygenase
Molecular Weight
55297.635 Da
References
  1. Barrett-Bee K, Dixon G: Ergosterol biosynthesis inhibition: a target for antifungal agents. Acta Biochim Pol. 1995;42(4):465-79. [Article]
  2. Ryder NS, Frank I, Dupont MC: Ergosterol biosynthesis inhibition by the thiocarbamate antifungal agents tolnaftate and tolciclate. Antimicrob Agents Chemother. 1986 May;29(5):858-60. [Article]
  3. Georgopapadakou NH, Bertasso A: Effects of squalene epoxidase inhibitors on Candida albicans. Antimicrob Agents Chemother. 1992 Aug;36(8):1779-81. [Article]

Drug created on June 13, 2005 13:24 / Updated on October 20, 2021 19:48