2-Naphthyl N-methyl-N-(3-tolyl)thiocarbamate
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2-Naphthyl N-methyl-N-(3-tolyl)thiocarbamate
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CAS No:
2398-96-1
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Formula:
C19H17NOS
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Chemical Name:
2-Naphthyl N-methyl-N-(3-tolyl)thiocarbamate
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Synonyms:
Carbamothioic acid,N-methyl-N-(3-methylphenyl)-,O-2-naphthalenyl ester;Carbanilic acid,m,N-dimethylthio-,O-2-naphthyl ester;Carbamothioic acid,methyl(3-methylphenyl)-,O-2-naphthalenyl ester;Naphthiomate T;O-2-Naphthyl m,N-dimethylthiocarbanilate;2-Naphthyl N-methyl-N-(3-tolyl)thionocarbamate;Tinactin;Tolnaftate;2-Naphthyl N-methyl-N-m-tolylthiocarbamate;2-Naphthyl N-methyl-N-(3-tolyl)thiocarbamate;Tonoftal;Dermoxin;Focusan;Pitrex;Sporiline;Tinaderm;Tolsanil;Tolnaphthate;Phytoderm;Timoped;Hi-Alarzin;Dr. Scholl's Athlete's Foot Spray;Dungistop;Tniaderm;Sch 10144;Tritin;Aftate;Chinofungin;NSC 233648;Tineacure;94256-64-1
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CAS No:
Description
Tolnaftate is a synthetic thiocarbamate used as an anti-fungal agent. Target: AntifungalTolnaftate blocked sterol biosynthesis in fungal cells and cell extracts, with accumulation of squalene. This point of action was confirmed by the direct inhibition of microsomal squalene epoxidase from Candida albicans [1]. Tolnaftate inhibited sterol biosynthesis, At 100 microM, tolnaftate caused up to a 30% release of intracellular [14C]aminoisobutyric acid [2].
Crystals or white powder. (NTP, 1992)|Solid
Crystals or white powder. (NTP, 1992)|Tolnaftate is 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. It has a role as an antifungal drug. It derives from a 2-naphthol.|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.|Tolnaftate is a thiocarbamate derivative with either fungicidal or fungistatic property. Tolnaftate is a selective, reversible and non-competitive inhibitor of membrane-bound squalene-2,3- epoxidase, an enzyme involved in the biosynthesis of ergosterol. Inhibition leads to the accumulation of squalene and a deficiency in ergosterol, an essential component of fungal cell walls, thereby increasing membrane permeability, disrupting cellular organization and causing cell death. In addition, this agent may also distort the hyphae and stunts mycelial growth in susceptible fungi.|A synthetic antifungal agent.
2-Naphthyl N-methyl-N-(3-tolyl)thiocarbamate Basic Attributes
307.41
307.41
219-266-6
06KB629TKV
757355|233648
DTXSID3042477
C47763
D - Dermatologicals
2930909090
Characteristics
44.6
5.5
white to off-white
1.2±0.1 g/cm3
111 °C
453.4°C at 760 mmHg
228.0±26.8 °C
1.697
H2O: <0.1 g/100 mL at 22 ºC;soluble in chloroform at 50 mg/ml. Sparingly soluble in ethanol or methanol
2-8°C
2.08E-08mmHg at 25°C
LD50 in mice, rats (g/kg): >10, >6 orally; >6, >4 s.c. (Hashimoto)
173.6 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]
Thio and dithiocarbamates slowly decompose in aqueous solution to form carbon disulfide and methylamine or other amines. Such decompositions are accelerated by acids. Insoluble in water.
Thiocarbamate Esters and Salts/Dithiocarbamate Esters and Salts
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 Information
IRRITANT
NONH for all modes of transport
2
FD8891300
P264, P273, P280, P305+P351+P338, P337+P313, P391, P501
H319
Flash point data on this chemical are not available, it is probably combustible. (NTP, 1992)
|Warning|H319 (92.31%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]|P264, P273, P280, P305+P351+P338, P337+P313, P391, and P501|Aggregated GHS information provided by 77 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
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. STORAGE PRECAUTIONS: You should store this material in a refrigerator. (NTP, 1992)
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)
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.
Drug Information
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.
Tolnaftate is a synthetic over-the-counter anti-fungal agent.
Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. (See all compounds classified as Antifungal Agents.)
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.
SYMPTOMS: In susceptible persons, this compound may cause sensitization or irritation. (NTP, 1992)
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. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)
Aftate
2-Naphthyl N-methyl-N-(3-tolyl)thiocarbamate Use and Manufacturing
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 po
Carbamothioic acid, N-methyl-N-(3-methylphenyl)-, O-2-naphthalenyl ester: ACTIVE
Animal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients
Computed Properties
Molecular Weight:307.4
XLogP3:5.5
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:307.10308534
Monoisotopic Mass:307.10308534
Topological Polar Surface Area:44.6
Heavy Atom Count:22
Complexity:386
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
synthetic thiocarbamate antifungal compound effective against fungal infections of the skin
Registered Holders
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Fermion Oy
Active
Finland
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SOUVIN PHARMACEUTICALS I PVT LTD
Inactive
United States
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PLANTEX LTD CHEMICAL AND PHARMACEUTICAL WORKS
Inactive
United States
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