| Size | Price | Stock | Qty |
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| 250mg |
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| 500mg |
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| 1g |
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Purity: ≥98%
Naftifine HCl (AW-105843; SN 105843) is an allylamine-based, synthetic, and broad spectrum antifungal drug for the topical treatment of tinea pedis, tinea cruris, and tinea corporis, probably involves selectively blocking sterol biosynthesis via inhibition of the squalene 2,3-epoxidase enzyme. Naftifine exhibits an interesting in vitro spectrum of activity against dermatophytes (38 strains; minimal inhibitory concentration (MIC) range 0.1 to 0.2 mg/mL), aspergilli (6 strains; MIC range, 0.8 to 12.5 mg/mL), Sporothrix schenckii (2 strains; MICs, 0.8 and 1.5 mg/mL), and yeasts of the genus Candida (77 strains; MIC range, 1.5 to greater than 100 mg/mL).
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.| Targets |
Inhibits sterol biosynthesis by targeting squalene epoxidase, leading to ergosterol depletion and accumulation of squalene in fungal cells [2]
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| ln Vitro |
In vitro activity: Naftifine exhibits an interesting in vitro spectrum of activity against dermatophytes (38 strains; minimal inhibitory concentration (MIC) range 0.1 to 0.2 mg/mL), aspergilli (6 strains; MIC range, 0.8 to 12.5 mg/mL), Sporothrix schenckii (2 strains; MICs, 0.8 and 1.5 mg/mL), and yeasts of the genus Candida (77 strains; MIC range, 1.5 to greater than 100 mg/mL). The MIC of naftifine for C. albicans Δ63 is 100 mg/L in Sabouraud medium (initial pH 6.5). Naftifine (50 mg/L) gives greater than 99% inhibition of sterol biosynthesis both in whole cells and in cell extracts of C. albicans. The primary action of naftifine appears to be the blocking of fungal squalene epoxidation.
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] |
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| ln Vivo |
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| 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]
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| 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] |
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| 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.
Results: 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.[3]
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| ADME/Pharmacokinetics |
Human skin penetration: 2–6% systemic absorption after topical application. Plasma levels undetectable (<0.5 ng/mL) in most subjects [4]
Metabolized via CYP450 to inactive metabolites. Excreted primarily in urine (75%) and feces (22%) [4] 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. |
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| Toxicity/Toxicokinetics |
Topical use: Low systemic exposure; adverse events (5.3% vs. 3.5% vehicle) included burning, pruritus, and irritation [3]
No significant hepatotoxicity or nephrotoxicity reported in clinical studies [4] 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. |
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| References | ||
| Additional Infomation |
Naftifine hydrochloride is a hydrochloride and an allylamine antifungal drug.
Naftifine Hydrochloride is the hydrochloride salt form of naftifine, an allylamine derivate with synthetic broad-spectrum antifungal activity. Although the exact mechanism through which naftifine hydrochloride exerts its effect is unknown, it appears to selectively inhibit the enzyme squalene 2,3-epoxidase, thereby inhibiting the biosynthesis of sterol. This results in a decreased amount of sterols, especially ergosterol which is the primary fungal membrane sterol, and a corresponding accumulation of squalene in fungal cells. Naftifine hydrochloride can be fungicidal as well as fungistatic to yeasts depending on the concentration and the organisms involved. See also: Naftifine (has active moiety). Topical use: Low systemic exposure; adverse events (5.3% vs. 3.5% vehicle) included burning, pruritus, and irritation [3] No significant hepatotoxicity or nephrotoxicity reported in clinical studies [4] |
| Molecular Formula |
C21H21N.HCL
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| Molecular Weight |
323.86
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| Exact Mass |
323.144
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| Elemental Analysis |
C, 77.88; H, 6.85; Cl, 10.95; N, 4.32
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| CAS # |
65473-14-5
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| Related CAS # |
Naftifine-d3 hydrochloride;1246833-81-7; 65473-14-5 (HCl); 65472-88-0
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| PubChem CID |
5281098
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| Appearance |
White to off-white solid powder
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| Boiling Point |
440.1ºC at 760 mmHg
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| Melting Point |
172-175ºC
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| Flash Point |
194.4ºC
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| LogP |
5.787
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
1
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| Rotatable Bond Count |
5
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| Heavy Atom Count |
23
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| Complexity |
342
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CN(C/C=C/C1=CC=CC=C1)CC2=CC=CC3=CC=CC=C23.Cl
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| InChi Key |
PGYDRGZVXVVZQC-LLVKDONJSA-N
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| InChi Code |
InChI=1S/C15H19N5/c1-11(15(2,3)4)19-14(18-10-17)20-13-7-5-12(9-16)6-8-13/h5-8,11H,1-4H3,(H2,18,19,20)/t11-/m1/s1
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| Chemical Name |
(E)-N-methyl-N-(naphthalen-1-ylmethyl)-3-phenylprop-2-en-1-amine hydrochloride
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| Synonyms |
SN 105843; SN105843; NAFTIFINE HYDROCHLORIDE; 65473-14-5; Naftifine HCl; Naftin; Exoderil; AW 105-843; NAFT900; NSC-760068; SN-105843;AW 105843; AW105843; AW-105843; AW 105-843; Naftifine hydrochloride; Naftin
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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 Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| 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 : ~100 mg/mL (~308.78 mM )
Ethanol : 8~25 mg/mL (~77.19 mM ) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.72 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 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL 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: ≥ 2.5 mg/mL (7.72 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 25.0 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: ≥ 2.5 mg/mL (7.72 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. Solubility in Formulation 4: ≥ 2.5 mg/mL (7.72 mM) (saturation unknown) in 10% EtOH + 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 25.0 mg/mL clear EtOH 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 5: ≥ 2.5 mg/mL (7.72 mM) (saturation unknown) in 10% EtOH + 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 25.0 mg/mL clear EtOH 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. Solubility in Formulation 6: 10% DMSO+40% PEG300+5% Tween-80+45% Saline: ≥ 2.5 mg/mL (7.72 mM) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.0878 mL | 15.4388 mL | 30.8775 mL | |
| 5 mM | 0.6176 mL | 3.0878 mL | 6.1755 mL | |
| 10 mM | 0.3088 mL | 1.5439 mL | 3.0878 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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