| Size | Price | Stock | Qty |
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| 250mg |
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| 500mg |
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| 1g |
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| 10g | |||
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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: Systemic absorption rate after topical application is 2%–6%. Plasma concentrations in most subjects are below the detection limit (<0.5 ng/mL) [4]
Metabolized by CYP450 to inactive metabolites. Excreted mainly in urine (75%) and feces (22%) [4] Absorption, distribution and excretion> In healthy subjects, absorption is as high as 4.2% after a single topical application of 1% 3H-labeled naftifine gel. Naftifine and/or its metabolites are excreted in urine and feces, with a half-life of approximately 2–3 days. Biological half-life Approximately 2–3 days after topical administration. |
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| Toxicity/Toxicokinetics |
Topical application: Low systemic exposure; adverse reactions (5.3% vs. 3.5% excipients) include burning, itching and irritation [3]
No significant hepatotoxicity or nephrotoxicity has been reported in clinical studies [4] Use during pregnancy and lactation ◉ Overview of use during lactation The use of topical naftifine during lactation has not been studied. The risk to nursing infants is low because only 4% to 6% is absorbed after topical application. [1] Avoid application to the nipple area and ensure that the infant’s skin does not come into direct contact with the treated area. Only water-soluble creams, gels or liquid products should be applied to the breast, as ointments may expose the infant to high concentrations of mineral oil through licking. [2] ◉ Effects on breastfed infants No relevant published information was found as of the revision date. ◉ Effects on lactation and breast milk No relevant published information was found as of the revision date. |
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| References | ||
| Additional Infomation |
Naftifine hydrochloride is an allylamine antifungal drug in the form of a hydrochloride salt. Naftifine hydrochloride is the hydrochloride form of naftifine, an allylamine derivative with broad-spectrum antifungal activity. Although the exact mechanism of action of naftifine hydrochloride is not well understood, it appears to selectively inhibit squalene 2,3-cyclooxygenase, thereby inhibiting the biosynthesis of sterols. This leads to a decrease in sterol content, especially ergosterol, which is the main membrane sterol in fungi, and results in a corresponding accumulation of squalene in fungal cells. Naftifine hydrochloride has both bactericidal and bacteriostatic effects on yeast, depending on the concentration and the species of microorganism involved. See also: Naftifine (containing the active moiety). Topical application: Low systemic exposure; adverse events (5.3% vs. 3.5% in the excipient group) included burning, itching, and irritation [3]. No significant hepatotoxicity or nephrotoxicity has been reported in clinical studies [4].
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| 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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