Basic information
- CAS
2398-96-1- Standard SMILES
Cc1cccc(N(C)C(=S)Oc2ccc3ccccc3c2)c1- InChIKey
FUSNMLFNXJSCDI-UHFFFAOYSA-N- Molecular formula
- C19H17NOS
- Average molar mass
- 307.4 g/mol
- Monoisotopic mass
- 307.10308516
Overview
Crystals or white powder. (NTP, 1992)
Names & identifiers
- Preferred name
- Tolnaftate
- IUPAC
- O-naphthalen-2-yl N-methyl-N-(3-methylphenyl)carbamothioate
- English name
- Tolnaftate
- Molecular formula
- C19H17NOS
- Molecular weight
- 307.41
Names & synonyms
Show more names
Database identifiers
- CAS
2398-96-1- PubChem CID
- 5510
- DTXSID
DTXSID3042477- ChEMBL
CHEMBL83668- ChEBI
CHEBI:9620- UNII
- 06KB629TKV
- EC Number
- 219-266-6
- Nikkaji
- J4.423G
Properties
Computed structural properties
- XLogP
- 5.5
- Topological polar surface area
- 44.6 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 3
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 386
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals
Melting Point
230.9 to 232.7 °F (NTP, 1992)
111 °C
Physical Description
Crystals or white powder. (NTP, 1992)
Solid
Collision Cross Section
185.4 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID3042477]
173.6 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
163.3 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 110.5 · 110.5-111.5°C
- Boiling point
- 453.4 · 453.4±38.0 °C(Predicted)
- Density
- 1.1328 · 1.1328 (rough estimate)
- refractive index
- 1.697 · 1.6970 (estimate)
- storage temp.
- 2 · Sealed in dry,2-8°C
- solubility
- 50 mg/ml · Soluble in chloroform at 50 mg/ml. Sparingly soluble in ethanol or methanol
- form
- powder
- pka
- -0.35 · -0.35±0.50(Predicted)
- color
- white to off-white
- Water Solubility
- 0.1 g/100 · <0.1 g/100 mL at 22 ºC
- λmax
- 258 nm · 258nm(MeOH)(lit.)
- Merck
- 14 · 14,9519
- Major Application
- pharmaceutical (small molecule)
- Cosmetics Ingredients Functions
- ANTIMICROBIAL
- 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
- InChIKey
- FUSNMLFNXJSCDI-UHFFFAOYSA-N
- SMILES
- CN(C(=S)Oc1ccc2ccccc2c1)c3cccc(C)c3
- LogP
- 5.142 · 5.142 (est)
- EWG's Food Scores
- 1 · 1-4
- FDA UNII
- 6 KB629TKV · 06KB629TKV
- ATC code
- 1 AE18 · D01AE18
- NIST Chemistry Reference
- Tolnaftate(2398-96-1)
- EPA Substance Registry System
- Tolnaftate (2398-96-1)
- UNSPSC Code
- 51302004 · 51302004
- NACRES
- 85 · NA.85
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
- Precautionary statements
- 261 · P261-P305+P351+P338
- WGK Germany
- 2 · 2
- RTECS
- 8891300 · FD8891300
- TSCA
- TSCA listed
- HazardClass
- IRRITANT
- HS Code
- 2930206050 · 2930206050
- Storage Class
- 11 · 11 - Combustible Solids
- Toxicity
- 50 in · LD50 in mice, rats (g/kg): >10, >6 orally; >6, >4 s.c. (Hashimoto)
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 40.4% (38 of 94) of reports.
Warning
H319 (56.4%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
P264+P265, P273, P280, P305+P351+P338, P337+P317, P391, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 94 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Reactivity Profile
TOLNAFTATE is a thiocarbamate. Flammable gases are generated by the combination of thiocarbamates and dithiocarbamates with aldehydes, nitrides, and hydrides. Thiocarbamates and dithiocarbamates are incompatible with acids, peroxides, and acid halides.
Safety & protection
First Aid
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.
Nonfire Spill Response
SMALL SPILLS AND LEAKAGE: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.
Personal Protective Equipment (PPE)
RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)
Toxicology
Safety data
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- FD8891300
- hs_code
- 2930206050
- Toxicity
- LD50 in mice, rats (g/kg): >10, >6 orally; >6, >4 s.c. (Hashimoto)
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_class
- IRRITANT
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Pharmacology
ATC Code
D - Dermatologicals
QD - Dermatologicals
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.
FDA Pharmacological Classification
TOLNAFTATE
Azole Antifungal [EPC]; Azoles [CS]
ANTIFUNGAL POWDER SPRAY
Azoles [CS]; Azole Antifungal [EPC]
Uses & manufacturing
Applications
DescriptionTolnaftate is a thiocarbamate antifungal agent. It is active against clinical isolates of the dermatophytes T. rubrum, T. mentagraphytes, T. verrucosum, E. floccosum, and M. canis (MIC50s = 50, 100, 6, 50, and 50 ng/ml, respectively), as well as 18 additional yeast and filamentous fungi species (MIC = 0.003-0.8 μg/ml)., Tolnaftate also reduces aflatoxin production in A. parasiticus in a concentration-dependent manner. It inhibits squalene epoxidase with an IC50 value of 12.5 μg/ml in a cell-free assay.
UsesTolnaftate 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.
Usesantifungal for cutaneous infections. Tolnaftate (Aftate, Tinactin, etc.) is an odorless and nonstaining synthetic antifungal agent whose exact mechanism of action is unknown. It is effective against dermatophytes and P. orbiculare and Pityrosporum ovale. It is ineffective against C. albicans and bacteria.
UsesTolnaftate is used to study the mechanism of ergosterol (sterol) biosynthesis at the rate-limiting step of squalene epoxidase inhibition. Tolnaftate is clinically used to treat cutaneous infections such as athletes foot, jock itch, and ringworm1. It also has been used as a comparator compound for antifungal efficiency studies.
Upstream & downstream products
Upstream raw materials
Suppliers100 total
Additional notes
DefinitionChEBI: A monothiocarbamic ester that is the methyl(3-tolyl)carbamothioate ester of 2-naphthol. A synthetic anti-fungal agent used to treat jock itch, athlete's foot and ringworm.
Related reactions
No reaction records under the current filter.
Compound notes
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