| Size | Price | |
|---|---|---|
| 500mg | ||
| 1g | ||
| Other Sizes |
| Targets |
Inhibits sterol biosynthesis by targeting squalene epoxidase, leading to ergosterol depletion and accumulation of squalene in fungal cells [2]
|
|---|---|
| ln Vitro |
Exhibited broad-spectrum antifungal activity against dermatophytes (MIC range 0.001–0.1 µg/mL) and some yeasts (MIC 12.5–>100 µg/mL). Higher activity against molds than azoles [1]
Inhibited C. albicans growth dose-dependently (MIC ³25 µg/mL) and blocked sterol biosynthesis at 0.1–10 µg/mL, causing squalene accumulation and ergosterol depletion [2] |
| ln Vivo |
At week 4, 25 percent of naftifine-treated subjects achieved complete cure vs. three percent of vehicle subjects and 72 percent achieved mycological cure vs. 16 percent of vehicle treated subjects (one-sided, P<0.001). Treatment effectiveness was achieved in 60 percent of NAFT-2% subjects vs. 10 percent of vehicle subjects (one-sided, P<0.001). Clinical cure rate and clinical success rate were 33 percent and 84 percent in NAFT-2% subjects, respectively vs. 10 percent and 46 percent in vehicle subjects (both P is less than 0.001, 2-sided). Week 2 efficacy response rates in NAFT-2% subjects were all lower than at week 4 but were significantly higher than week 2 vehicle-treated counterparts (P<0.025). Treatment-related AE occurred in 11 subjects (7 NAFT-2%, 4 vehicle) during the study. The most common AE in both groups were contact dermatitis (2 NAFT-2%), pruritus (2 vehicle), and application site reaction (1 per group).
Conclusion: NAFT-2% applied once daily for two weeks (one-half the treatment duration for naftifine 1% cream) is efficacious and safe for the treatment of T. cruris.
|
| Enzyme Assay |
Sterol biosynthesis measured in C. albicans cultures incubated with radiolabeled [²H]acetate. Lipids extracted, saponified, and analyzed by TLC and radio-scanning. Naftifine (0.1–10 µg/mL) caused squalene accumulation and reduced ergosterol synthesis [2]
|
| Cell Assay |
Antifungal susceptibility testing using broth microdilution (Sabouraud dextrose broth) for dermatophytes/yeasts. Incubated at 30°C for 48h (yeasts) or 7d (dermatophytes). MIC defined as 80% growth inhibition [1]
C. albicans growth inhibition assessed via turbidimetry after 24h incubation with naftifine (0.1–100 µg/mL) in glucose-yeast extract broth [2] |
| Animal Protocol |
A total of 334 subjects with T. cruris were enrolled and randomly assigned to NAFT-2% (n=166) or vehicle (n=168), which was applied once daily for 14 days. Efficacy and safety were evaluated at week 2 (end of treatment) and week 4. Efficacy measures included complete cure, treatment effectiveness, mycological cure, clinical cure, and clinical success and were analyzed only in subjects with a positive potassium hydroxide (KOH) and dermatophyte culture at baseline (n=75, naftifine; n=71, vehicle). Safety was assessed by adverse events and changes from baseline in clinical status and laboratory studies.[3]
|
| ADME/Pharmacokinetics |
Absorption, Distribution and Excretion
Following single topical applications of 3H-labeled naftifine gel 1% to the skin of healthy subjects, up to 4.2% of the applied dose was absorbed. Naftifine and/or its metabolites are excreted via the urine and feces with a half-life of approximately two to three days. Biological Half-Life Approximately 2 to 3 days following topical administration. |
| Toxicity/Toxicokinetics |
Effects During Pregnancy and Lactation
◉ Summary of Use during Lactation Topical naftifine has not been studied during breastfeeding. Because only 4 to 6% is absorbed after topical application, it is considered a low risk to the nursing infant.[1] 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.[2] ◉ 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 | |
| Additional Infomation |
Naftifine is a tertiary amine in which the nitrogen is substituted by methyl, alpha-naphthylmethyl, and (1E)-cinnamyl groups. It is used (usually as its hydrochloride salt) for the treatment of fungal skin infections. It has a role as an EC 1.14.13.132 (squalene monooxygenase) inhibitor and a sterol biosynthesis inhibitor. It is a member of naphthalenes, a tertiary amine and an allylamine antifungal drug.
Naftifine is a synthetic, broad spectrum, antifungal agent and allylamine derivative for the topical treatment of tinea pedis, tinea cruris, and tinea corporis caused by the organisms Trichophyton rubrum, Trichophyton mentagrophytes, Trichophyton tonsurans and Epidermophyton floccosum. Naftifine is an Allylamine Antifungal. Naftifine is a topical, synthetic allylamine derivate similar to terbinafine with broad-spectrum antifungal activity. Naftifine can be fungicidal or fungistatic depending on the concentration and the organisms involved. See also: Naftifine Hydrochloride (has salt form). Drug Indication For the topical treatment of tinea pedis, tinea cruris, and tinea corporis caused by the organisms Trichophyton rubrum, Trichophyton mentagrophytes, Trichophyton tonsurans and Epidermophyton floccosum. Mechanism of Action Although the exact mechanism of action against fungi is not known, naftifine appears to interfere with sterol biosynthesis by inhibiting the enzyme squalene 2,3-epoxidase. This inhibition of enzyme activity results in decreased amounts of sterols, especially ergosterol, and a corresponding accumulation of squalene in the cells. Pharmacodynamics Naftifine is a synthetic, broad spectrum, antifungal agent and allylamine derivative. The following in vitro data are available, but their clinical significance is unknown. Naftifine has been shown to exhibit fungicidal activity in vitro against a broad spectrum of organisms including Trichophyton rubrum, Trichophyton mentagrophytes, Trichophyton tonsurans, Epidermophyton floccosum, and Microsporum canis, Microsporum audouini, and Microsporum gypseum; and fungistatic activity against Candida species including Candida albicans. However it is only used to treat the organisms listed in the indications. |
| Molecular Formula |
C21H21N
|
|---|---|
| Molecular Weight |
287.39814
|
| Exact Mass |
287.167
|
| CAS # |
65472-88-0
|
| Related CAS # |
Naftifine-d3 hydrochloride;1246833-81-7; 65473-14-5 (HCl); 65472-88-0
|
| PubChem CID |
47641
|
| Appearance |
Typically exists as solid at room temperature
|
| Density |
1.082 g/cm3
|
| Boiling Point |
440.1ºC at 760 mmHg
|
| Melting Point |
177 °C
|
| Flash Point |
194.4ºC
|
| LogP |
4.985
|
| Hydrogen Bond Donor Count |
0
|
| Hydrogen Bond Acceptor Count |
1
|
| Rotatable Bond Count |
5
|
| Heavy Atom Count |
22
|
| Complexity |
342
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
CN(C/C=C/C1=CC=CC=C1)CC2=CC=CC3=CC=CC=C32
|
| InChi Key |
OZGNYLLQHRPOBR-DHZHZOJOSA-N
|
| InChi Code |
InChI=1S/C21H21N/c1-22(16-8-11-18-9-3-2-4-10-18)17-20-14-7-13-19-12-5-6-15-21(19)20/h2-15H,16-17H2,1H3/b11-8+
|
| Chemical Name |
(E)-N-methyl-N-(naphthalen-1-ylmethyl)-3-phenylprop-2-en-1-amine
|
| Synonyms |
Naftifine; 65472-88-0; Naftifin; Naftifina; Naftifinum; Naft-500; 4FB1TON47A; CHEBI:7451;
|
| HS Tariff Code |
2934.99.9001
|
| 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)
|
| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
|
|---|---|
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.4795 mL | 17.3974 mL | 34.7947 mL | |
| 5 mM | 0.6959 mL | 3.4795 mL | 6.9589 mL | |
| 10 mM | 0.3479 mL | 1.7397 mL | 3.4795 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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