METHYL-[3-METHYLPHENYL]-CARBAMOTHIOIC ACID O-2-NAPHTHYL ESTER
tolnaftate
CAS: 2398-96-1
Molecular Formula: C19H17NOS
METHYL-[3-METHYLPHENYL]-CARBAMOTHIOIC ACID O-2-NAPHTHYL ESTER - Names and Identifiers
| Name | tolnaftate |
| Synonyms | Aftate TOLAFTATE tolnaftate Chinofungin O-2-naphthyl N,3-dimethyl(thiocarbanilate) 2-naphthyl n-methyl-n-(3-tolyl)thionocarbamate O-naphthalen-2-yl methyl(3-methylphenyl)carbamothioate Carbanilic acid, m,N-dimethylthio-, O-2-naphthyl ester Carbanilic acid, N,m-dimethylthio-, O-2-naphthyl ester METHYL 3-TOLYLTHIOCARBAMIC ACID O-NAPHTHALEN-2-YL ESTER O-Naphthalen-2-yl N-methyl-N-(3-methylphenyl)thiocarbamate METHYL-[3-METHYLPHENYL]-CARBAMOTHIOIC ACID O-2-NAPHTHYL ESTER Carbamothioic acid, methyl(3-methylphenyl)-, O-2-naphthalenyl ester |
| CAS | 2398-96-1 |
| EINECS | 219-266-6 |
| InChI | InChI=1/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 |
METHYL-[3-METHYLPHENYL]-CARBAMOTHIOIC ACID O-2-NAPHTHYL ESTER - Physico-chemical Properties
| Molecular Formula | C19H17NOS |
| Molar Mass | 307.41 |
| Density | 1.1328 (rough estimate) |
| Melting Point | 110.5-111.5°C |
| Boling Point | 453.4±38.0 °C(Predicted) |
| Flash Point | 228°C |
| Water Solubility | <0.1 g/100 mL at 22 ºC |
| Solubility | DMSO 62 mg/mL Water <1 mg/mL Ethanol <1 mg/mL |
| Vapor Presure | 2.08E-08mmHg at 25°C |
| Appearance | White powder |
| Color | white to off-white |
| Maximum wavelength(λmax) | ['258nm(MeOH)(lit.)'] |
| Merck | 14,9519 |
| pKa | -0.35±0.50(Predicted) |
| Storage Condition | Sealed in dry,2-8°C |
| Sensitive | Sensitive to heat |
| Refractive Index | 1.6970 (estimate) |
| MDL | MFCD00056611 |
| In vitro study | Tolnaftate (NP-27) 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. Tolnaftate (NP-27) inhibited sterol biosynthesis, At 100 microM, tolnaftate caused up to a 30% release of intracellular [14C]aminoisobutyric acid. |
METHYL-[3-METHYLPHENYL]-CARBAMOTHIOIC ACID O-2-NAPHTHYL ESTER - Risk and Safety
| WGK Germany | 2 |
| RTECS | FD8891300 |
| TSCA | Yes |
| HS Code | 2930206050 |
| Hazard Class | IRRITANT |
| Toxicity | LD50 in mice, rats (g/kg): >10, >6 orally; >6, >4 s.c. (Hashimoto) |
METHYL-[3-METHYLPHENYL]-CARBAMOTHIOIC ACID O-2-NAPHTHYL ESTER - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| pharmacological effects | tolnaphthyl ester is the earliest listed thiocarbamate antifungal drug. It can inhibit the squalene cyclooxygenase in the fungal ergosterol synthesis pathway, causing the synthesis of ergosterol to be blocked. Ergosterol is an important component in fungal cell membranes and is essential for the growth and survival of fungi. It is believed that tolnaphthyl ester has only antibacterial activity. |
| indications | used for tinea manus, pedis, tinea corporis, tinea cruris, etc. |
| use | local antifungal drugs for superficial skin fungal infections, including tinea corporis, tinea cruris, tinea manus, pedis and tinea versicolor. But it is not effective for fungal infections of hair and finger (toe) nails. |
| Biological activity | Tolnaftate is a synthetic thiocarbamate used as an antifungal agent. |
| target | Antifungal. |
Last Update：2024-04-09 02:00:07
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View History
METHYL-[3-METHYLPHENYL]-CARBAMOTHIOIC ACID O-2-NAPHTHYL ESTER
C.I. PIGMENT RED 48)
TOSLAB 847197
(3,4-Epoxycyclohexyl)methyl Acrylate (stabilized with HQ)
假荜茇酰胺B
N6-[(2E)-1-氧代-2-丁烯-1-基]-L-赖氨酸
C.I. PIGMENT RED 48)
TOSLAB 847197
(3,4-Epoxycyclohexyl)methyl Acrylate (stabilized with HQ)
假荜茇酰胺B
N6-[(2E)-1-氧代-2-丁烯-1-基]-L-赖氨酸