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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).
Physicochemical Properties
| Molecular Formula | C21H21N.HCL | |
| Molecular Weight | 323.86 | |
| Exact Mass | 323.144 | |
| Elemental Analysis | C, 77.88; H, 6.85; Cl, 10.95; N, 4.32 | |
| CAS # | 65473-14-5 | |
| Related CAS # | Naftifine-d3 hydrochloride;1246833-81-7 | |
| PubChem CID | 5281098 | |
| Appearance | White to off-white solid powder | |
| Boiling Point | 440.1ºC at 760 mmHg | |
| Melting Point | 172-175ºC | |
| Flash Point | 194.4ºC | |
| LogP | 5.787 | |
| Hydrogen Bond Donor Count | 1 | |
| Hydrogen Bond Acceptor Count | 1 | |
| Rotatable Bond Count | 5 | |
| Heavy Atom Count | 23 | |
| Complexity | 342 | |
| Defined Atom Stereocenter Count | 0 | |
| 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 | |
| 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 | |
| Chemical Name | (E)-N-methyl-N-(naphthalen-1-ylmethyl)-3-phenylprop-2-en-1-amine hydrochloride | |
| Synonyms |
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| 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 Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
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| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
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| ln Vivo |
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| Animal Protocol |
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| References |
[1]. In vitro activity of naftifine, a new antifungal agent. Antimicrob Agents Chemother, 1981. 19(3): p. 386-9. [2]. Ryder, N.S., G. Seidl, and P.F. Troke, Effect of the antimycotic drug naftifine on growth of and sterol biosynthesis in Candida albicans. Antimicrob Agents Chemother, 1984. 25(4): p. 483-7. [3]. A double-blind, randomized, vehicle-controlled study evaluating the efficacy and safety of naftifine 2% cream in tinea cruris. J Drugs Dermatol, 2011. 10(10): p. 1142-7. [4]. Gupta, A.K., J.E. Ryder, and E.A. Cooper, Naftifine: a review. J Cutan Med Surg, 2008. 12(2): p. 51-8. |
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| 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). |
Solubility Data
| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~308.78 mM ) Ethanol : 8~25 mg/mL (~77.19 mM ) |
| 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. 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. 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 corn oil and mix evenly. 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) (Please use freshly prepared in vivo formulations for optimal results.) |
| 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 |