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, Sanafitil Antifungal, Silka Cream, 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
Structure for Tolnaftate (DB00525)
- 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.
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- Contraindications & Blackbox Warnings
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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.
Target Actions Organism ASqualene monooxygenase inhibitorYeast - 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
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
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.- 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
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Absorbine Antifungal Powder 1% Powder 1 % Topical W.F. Young, Inc. 1992-12-31 1997-07-28 Canada 
Absorbine Jr Antifungal Liquid Liquid 10 mg / mL Topical Clarion Brands, Llc 1999-08-18 Not applicable Canada Aftate Athlete Foot Cream Cream 1 g/100g Topical Sabel Med Llc 2016-12-01 Not applicable US 
Anti-Fungal Powder .45 g/45g Topical Rij Pharmaceutical Corporation 1999-03-16 Not applicable US Anti-Fungal Powder 1 g/100g Topical RUGBY LABORATORIES 2011-11-01 2023-02-01 US Anti-Fungal Liquid Maximum Strength Liquid 10 mg/1mL Topical Better Living Brands 2023-06-06 Not applicable US Antifungal Solution 1 mg/100mL Topical Perrigo New York Inc. 2005-12-06 2013-08-09 US Antifungal Cream 1 g/100g Topical Chain Drug Marketing Association Inc. 2020-08-14 Not applicable US Antifungal Cream 10 mg/1g Topical Moore Medical LLC 2012-07-16 2019-11-07 US Antifungal Cream 1 g/100g Topical Rite Aid 2005-07-23 2015-10-20 US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Absorbine Jr Antifungal Liq Tolnaftate (1 g / 100 mL) + Levomenthol (200 mg / 100 mL) Liquid Topical Clarion Brands, Llc 1994-12-31 Not applicable Canada COSMOS FUNGIL CREAM Tolnaftate (1 %) + Chlorhexidine acetate (0.2 %) Cream Topical Duopharma Marketing Sdn. Bhd. 2020-09-08 Not applicable Malaysia 
ELAN-FORTE CREAM Tolnaftate (1 %) + Chlorhexidine hydrochloride (0.2 %) Cream Topical Y.S.P. INDUSTRIES (M) SDN BHD 2020-09-08 Not applicable Malaysia Heeltastic Tolnaftate (1 g/100g) + Dimethicone (1 g/100g) Stick Topical Neutraderm, Inc. 2009-06-30 2009-07-22 US HEXIDERM CREAM Tolnaftate (1 %) + Chlorhexidine hydrochloride (0.1 %) Cream Topical PRIME PHARMACEUTICAL SDN. BHD. 2020-09-08 Not applicable Malaysia Miconatate Tolnaftate (0.3 g/30mL) + Miconazole nitrate (2 g/85g) Kit; Liquid; Powder Topical PureTek Corporation 2021-09-02 Not applicable US Nail MD Tolnaftate (100 mg/1mg) + Triclosan (20 mg/1mg) Spray Topical Omg Medical Group, Llc 2013-02-14 Not applicable US Natouch Antifungal Antiseptic Wipes Tolnaftate (2 g/200mL) + Ethanol (140 mL/200mL) Cloth Topical Natouch LLC 2020-07-01 Not applicable US PERMUT® Tolnaftate (1 mg) + Betamethasone valerate (0.05 mg) + Clioquinol (1 mg) + Gentamicin sulfate (0.1 mg) Cream Topical EUROFARMA COLOMBIA S.A.S. 2019-10-15 Not applicable Colombia 
ครีม โทนาฟ -บี Tolnaftate (1 G/100G) + Betamethasone (0.1 G/100G) Cream บริษัท แสงไทยกำปะนี จำกัด 1988-04-03 Not applicable Thailand 
- Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Clear 50 Nail Gel Tolnaftate (1 g/100mL) Gel Topical SSG Ventures Inc 2019-10-07 Not applicable US Terbinafine HCl Chlortimazole and Tolnaftate Tolnaftate (1 g/100mL) + Clotrimazole (1 g/100mL) + Terbinafine hydrochloride (1 g/100mL) Solution Topical Dr Marc's Manufacturing And Sales 2018-01-30 2018-04-17 US
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
- Barrett-Bee K, Dixon G: Ergosterol biosynthesis inhibition: a target for antifungal agents. Acta Biochim Pol. 1995;42(4):465-79. [Article]
- 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]
- External Links
- Human Metabolome Database
- HMDB0005005
- KEGG Drug
- D00381
- PubChem Compound
- 5510
- PubChem Substance
- 46505456
- ChemSpider
- 5309
- BindingDB
- 39349
- 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
Phase Status Purpose Conditions Count 3 Completed Treatment Atopic Dermatitis 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Chain Drug
- Medisca Inc.
- Perrigo Co.
- S&P Healthcare
- Stiefel Labs
- Dosage Forms
Form Route Strength Liquid Topical Powder Topical .45 g/45g Tincture Topical 1 % w/w Gel Topical 1 % Cream Topical 0.01 mg/10g Aerosol Topical 1 g/100g Cream Topical 1 g/1g Liquid Topical 1 % Solution Topical 1.0 mL/100mL Solution Topical 1 mg/100mL Cream Topical .56 g/56.69g Solution Topical 1 g/100mL Gel Topical 1 g/100mL Liquid Topical 0.04 g/4g Solution / drops Topical 10 mg/1mL Cream Topical Soap Topical 1 g/100g Ointment Topical Solution Topical 10 mg/1mL Oil Topical 0.14 g/14g Oil Topical 0.3 g/28g Lotion Topical 0.3 g/28g Aerosol; powder Topical 1 % w/w Swab Topical 10 g/1000g Aerosol, powder Topical 10 mg/1g Spray Topical 1 g/150g Aerosol, foam Topical 1 % w/w Powder Topical 1 % w/w Spray Topical 1 % w/w Solution Topical 1 % w/w Solution Topical 1 g/100g Gel Topical 1 g/100g Liquid Topical 10 g/1000g Liquid Topical 8.65 mg/1mL Aerosol, foam Topical 10 mg/1mL Spray Topical 10 mg/1mL Liquid Topical 1 g/100mL Lotion Topical 2.8 g/28g Spray Topical 10 mg/1g Stick Topical Aerosol, powder Topical 0.1 g/10g Cream Topical 0.1 g/10g Kit Topical 10 mg/1g Liquid Topical 1 mL/100mL Aerosol, spray Topical 10 mg/1g Powder Topical 10 mg/1g Aerosol, spray Topical 1.3 g/57g Powder Topical 1.04 g Kit; liquid; powder Topical Ointment Topical 1 % Cream Topical 0.59 g/59g Cream Topical 0.01 g/1g Liquid Topical 1.0 g/100mL Oil Topical 0.01 mg/1mL Lotion Topical 1 % w/v Lotion Topical 100 g/1g Spray Topical Cloth Topical Cloth Topical 2 g/200mL Gel Topical 10 mg/1g Aerosol Topical 1 % w/w Liquid Topical 1 mg/100mL Kit Topical 1 g/100mL Spray Topical 1 g/100g Ointment Topical 1 g/100g Solution Topical 1 % w/v Solution Topical 1 % Ointment Topical 10 mg/1g Aerosol, spray Topical 0.01 g/1g Spray Topical 0.068 % w/w Lotion Topical 10 mg/1mL Cloth Topical 1 g/100g Swab Topical 1 % Solution Topical Aerosol, powder Topical 1 % Cream Topical 10 mg / g Powder Topical 10 mg / g Aerosol Topical .72 mg / g Aerosol Topical 1 % Spray Topical 1 % Liquid Topical 10 mg / mL Cream Topical Lotion Topical Powder Topical Powder Topical 1 g Cream Topical 1 g Solution Topical 1 g Cream Topical 1 % w/w Solution Topical Liquid Topical 140 mg/15mL Aerosol, spray Topical 1.28 g/128g Cream Topical .2 mg/20mg Aerosol, powder Topical 1 g/100g Aerosol, powder Topical 1.1 g/113.3g Aerosol, powder Topical 1.3 g/113g Aerosol, powder Topical 1.3 g/130g Aerosol, spray Topical 0.13 g/130g Aerosol, spray Topical 0.15 g/150g Aerosol, spray Topical 1.13 g/113g Aerosol, spray Topical 1.3 g/130g Aerosol, spray Topical 1.3 g/113g Aerosol, spray Topical 1.5 g/150g Aerosol, spray Topical 1.5 g/150.2g Aerosol, spray Topical 150 g/150g Cream Topical 0.15 g/15g Cream Topical 1 g/100g Cream Topical 10 mg/1g Liquid Topical 0.3 g/30mL Powder Topical 1 g/100g Spray Topical 1.3 g/130g Spray Topical 1.5 g/150g Cream Topical 1.0 % Cream Topical 1 % Liquid Topical 10 mg/1g Aerosol, spray Topical 1 g/100g Liquid Topical 10 mg/1mL Powder Topical 1 % Cream Cream Topical 1 %w/w Cream Topical 2 %w/w Ointment Topical Ointment Topical 1 %w/w - Prices
Unit description Cost Unit Zeasorb-AF 2% Powder 70 gm Can 14.99USD can Zeasorb Powder 70.9 gm Can 12.99USD can Tolnaftate powder 4.77USD g Zeasorb-af 2% lotion 0.19USD g Zeasorb powder 0.05USD g Tinactin 1% aerosol 0.04USD ml Athlete's foot 1% liquid spray 0.03USD g Pv antifungal 1% spray liquid 0.02USD g DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 111 °C PhysProp water solubility 7.02e-05 mg/mL at 25 °C MEYLAN,WM et al. (1996) logP 5.1 Not Available - Predicted Properties
Property Value Source Water Solubility 0.000546 mg/mL ALOGPS logP 4.87 ALOGPS logP 5.75 Chemaxon logS -5.8 ALOGPS pKa (Strongest Basic) 0.075 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 12.47 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 94.92 m3·mol-1 Chemaxon Polarizability 34.22 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9904 Blood Brain Barrier + 0.9689 Caco-2 permeable + 0.6348 P-glycoprotein substrate Non-substrate 0.8667 P-glycoprotein inhibitor I Non-inhibitor 0.5537 P-glycoprotein inhibitor II Non-inhibitor 0.857 Renal organic cation transporter Non-inhibitor 0.8281 CYP450 2C9 substrate Non-substrate 0.7363 CYP450 2D6 substrate Non-substrate 0.6071 CYP450 3A4 substrate Substrate 0.6401 CYP450 1A2 substrate Inhibitor 0.9107 CYP450 2C9 inhibitor Inhibitor 0.8948 CYP450 2D6 inhibitor Non-inhibitor 0.923 CYP450 2C19 inhibitor Inhibitor 0.8994 CYP450 3A4 inhibitor Inhibitor 0.7959 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.9229 Ames test AMES toxic 0.8449 Carcinogenicity Non-carcinogens 0.7425 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 1.7405 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8836 hERG inhibition (predictor II) Non-inhibitor 0.5943
Spectra
- Mass Spec (NIST)
- Download (8.78 KB)
- Spectra
Targets
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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
- Barrett-Bee K, Dixon G: Ergosterol biosynthesis inhibition: a target for antifungal agents. Acta Biochim Pol. 1995;42(4):465-79. [Article]
- 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]
- Georgopapadakou NH, Bertasso A: Effects of squalene epoxidase inhibitors on Candida albicans. Antimicrob Agents Chemother. 1992 Aug;36(8):1779-81. [Article]
Drug created at June 13, 2005 13:24 / Updated at September 28, 2023 01:14