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Purity: ≥98%
Tolnaftate (formerly NP-27; trade names: Tinactin, Tinaderm, Aftate) is a synthetic thiocarbamate used as an anti-fungal agent that may be sold as an OTC drug. It can be administered as a cream, powder, spray, and liquid aerosol. Tolnaftate is used to treat fungal conditions such as jock itch, athlete's foot and ringworm.
| ln Vitro |
In fungal cells and cell extracts, tolnaftate (NP-27) inhibits the formation of sterols, leading to a buildup of squalene. The direct suppression of Candida albicans' microsomal squalene epoxidase [1] verified this mechanism of action. Tolnaftate (NP-27) inhibits the formation of sterols and releases up to 30% of intracellular [14C]aminoisobutyric acid at a dose of 100 µM [2].
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| Toxicity/Toxicokinetics |
Effects During Pregnancy and Lactation
◉ Summary of Use during Lactation Topical tolnaftate has not been studied during breastfeeding and no data are available on the extent of its absorption after topical application. Because it is probably poorly absorbed after topical application, it is considered a low risk to the nursing infant. Avoid application to the nipple area and ensure that the infant's skin does not come into direct contact with the areas of skin that have been treated. Only water-miscible cream, gel or liquid products should be applied to the breast because ointments may expose the infant to high levels of mineral paraffins via licking.[1] ◉ Effects in Breastfed Infants Relevant published information was not found as of the revision date. ◉ Effects on Lactation and Breastmilk Relevant published information was not found as of the revision date. |
| References |
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| Additional Infomation |
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 is functionally related to 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. See also: TOLNAFTATE; Triclosan (component of). Drug 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. 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. Pharmacodynamics Tolnaftate is a synthetic over-the-counter anti-fungal agent. |
| Molecular Formula |
C19H17NOS
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|---|---|
| Molecular Weight |
307.41
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| Exact Mass |
307.103
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| CAS # |
2398-96-1
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| Related CAS # |
Tolnaftate-d7;1329835-64-4
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| PubChem CID |
5510
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| Appearance |
White to off-white solid powder
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| Density |
1.2±0.1 g/cm3
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| Boiling Point |
453.4±38.0 °C at 760 mmHg
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| Melting Point |
110.5-111.5ºC
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| Flash Point |
228.0±26.8 °C
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| Vapour Pressure |
0.0±1.1 mmHg at 25°C
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| Index of Refraction |
1.697
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| LogP |
5.15
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
22
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| Complexity |
386
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
FUSNMLFNXJSCDI-UHFFFAOYSA-N
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| InChi Code |
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
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| Chemical Name |
O-naphthalen-2-yl N-methyl-N-(3-methylphenyl)carbamothioate
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| Synonyms |
Tinactin, Tinaderm, Aftate; NP-27, NP 27, NP27
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~50 mg/mL (~162.65 mM)
H2O : < 0.1 mg/mL |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 3.25 mg/mL (10.57 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 32.5 mg/mL clear DMSO stock solution to 400 μL of PEG300 and mix evenly; then add 50 μL of Tween-80 to the above solution and mix evenly; then add 450 μL of normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 3.25 mg/mL (10.57 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 32.5 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 3.25 mg/mL (10.57 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.2530 mL | 16.2649 mL | 32.5298 mL | |
| 5 mM | 0.6506 mL | 3.2530 mL | 6.5060 mL | |
| 10 mM | 0.3253 mL | 1.6265 mL | 3.2530 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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