Fenticonazole is an azole class of antifungal drug used locally as the nitrate form for the treatment of vulvovaginal candidiasis. It is a 14-α demethylase inhibitor and potentially a glucosamine-6-phosphate synthase inhibitor. It is active against a range of organisms including dermatophyte pathogens, Malassezia furfur, and Candida albicans. Application of fenticonazole nitrate 1 g intravaginal ovules on 2 alternate days is a suitable first-line treatment of vulvovaginitis with acceptable broad-spectrum efficacy against the most commonly involved pathogens and with a low rate of early relapse, reserving antibiotics for patients with treatment failure or relapse of infection .
Physicochemical Properties
| Molecular Formula | C24H20CL2N2OS.HNO3 | |
| Molecular Weight | 518.41 | |
| Exact Mass | 517.062 | |
| Elemental Analysis | C, 55.61; H, 4.08; Cl, 13.68; N, 8.11; O, 12.34; S, 6.18 | |
| CAS # | 73151-29-8 | |
| Related CAS # | 72479-26-6;73151-29-8 (nitrate); | |
| PubChem CID | 51754 | |
| Appearance | White to off-white solid powder | |
| Density | 1.26g/cm3 | |
| Boiling Point | 637.2ºC at 760 mmHg | |
| Melting Point | 135-137ºC | |
| Flash Point | 339.2ºC | |
| Index of Refraction | 1.632 | |
| LogP | 7.474 | |
| Hydrogen Bond Donor Count | 1 | |
| Hydrogen Bond Acceptor Count | 6 | |
| Rotatable Bond Count | 8 | |
| Heavy Atom Count | 34 | |
| Complexity | 524 | |
| Defined Atom Stereocenter Count | 0 | |
| SMILES | ClC1C([H])=C(C([H])=C([H])C=1C([H])(C([H])([H])N1C([H])=NC([H])=C1[H])OC([H])([H])C1C([H])=C([H])C(=C([H])C=1[H])SC1C([H])=C([H])C([H])=C([H])C=1[H])Cl.O([H])[N+](=O)[O-] |
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| InChi Key | MXQVMHNIUUXDQW-UHFFFAOYSA-O | |
| InChi Code | InChI=1S/C24H20Cl2N2OS.NO3/c25-19-8-11-22(23(26)14-19)24(15-28-13-12-27-17-28)29-16-18-6-9-21(10-7-18)30-20-4-2-1-3-5-20;2-1(3)4/h1-14,17,24H,15-16H2;/q;-1/p+1 | |
| Chemical Name | 1-(2-(2,4-dichlorophenyl)-2-((4-(phenylthio)benzyl)oxy)ethyl)-1H-imidazol-3-ium nitrate | |
| 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
| ln Vitro | Fenticonazole is an azole antifungal medication that is applied topically as a nitrate to treat vaginal candidiasis. Malassezia furfur, Candida albicans, and dermatophyte infections are only a few of the species it is effective against [2]. |
| References |
[1]. Ultra-deformable liposomes containing terpenes (terpesomes) loaded fenticonazole nitrate for treatment of vaginal candidiasis: Box-Behnken design optimization, comparative ex vivo and in vivo studies. Drug Deliv. 2020 Dec;27(1):1514-1523. [2]. Fenticonazole nitrate for treatment of vulvovaginitis: efficacy, safety, and tolerability of 1-gram ovules, administered as ultra-short 2-day regimen. J Chemother, 2004. 16(2): p. 179-86. |
| Additional Infomation | Fenticonazole nitrate is a racemate comprising equimolar amounts of (R)- and (S)-fenticonazole nitrate. Used for the treatment of vaginal candidiasis. It has a role as an antibacterial drug. It is a racemate, an imidazole antifungal drug and a conazole antifungal drug. It contains a (S)-fenticonazole nitrate and a (R)-fenticonazole nitrate. |
Solubility Data
| Solubility (In Vitro) |
DMSO : 100~104 mg/mL (192.90~ 200.61 mM ) Ethanol : ~2 mg/mL |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (4.82 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 (4.82 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 (4.82 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: 10% DMSO+40% PEG300+5% Tween-80+45% Saline: ≥ 2.5 mg/mL (4.82 mM) (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.9290 mL | 9.6449 mL | 19.2898 mL | |
| 5 mM | 0.3858 mL | 1.9290 mL | 3.8580 mL | |
| 10 mM | 0.1929 mL | 0.9645 mL | 1.9290 mL |