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Sulconazole Nitrate, formerly known as Sulconazole and RS-44872, is an imidazole class of antifungal agent used to treat fungal skin infections.
Physicochemical Properties
| Molecular Formula | C18H15N2SCL3 |
| Molecular Weight | 397.7491 |
| Exact Mass | 396.002 |
| CAS # | 61318-90-9 |
| Related CAS # | Sulconazole mononitrate;61318-91-0 |
| PubChem CID | 5318 |
| Appearance | Typically exists as solid at room temperature |
| Density | 1.34 g/cm3 |
| Boiling Point | 558.2ºC at 760 mmHg |
| Melting Point | 130ºC |
| Flash Point | 291.4ºC |
| LogP | 6.518 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 6 |
| Heavy Atom Count | 24 |
| Complexity | 379 |
| Defined Atom Stereocenter Count | 0 |
| InChi Key | AFNXATANNDIXLG-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C18H15Cl3N2S/c19-14-3-1-13(2-4-14)11-24-18(10-23-8-7-22-12-23)16-6-5-15(20)9-17(16)21/h1-9,12,18H,10-11H2 |
| Chemical Name | 1-[2-[(4-chlorophenyl)methylsulfanyl]-2-(2,4-dichlorophenyl)ethyl]imidazole |
| 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) |
Biological Activity
| ADME/Pharmacokinetics |
Absorption, Distribution and Excretion A study done on healthy subjects given sulconazole 1% cream over a seven-day period, showed that the total percutaneous absorption of sulconazole after topical administration was 8.71-11.3% of the dose. Another study also done on healthy volunteers given 1 g of sulconazole 1% cream, estimated that about 12% of the dose was absorbed through the skin. In general, topical imidazoles are poorly absorbed (<15%); however, sulconazole may have higher levels of absorption compared to others. About 6.70% of the dose was recovered in urine, and 2.01% in feces over a 7 day collection period. Radioactivity could be detected in both urine and feces at 7 days potentially due to a reservoir effect. |
| Toxicity/Toxicokinetics |
Effects During Pregnancy and Lactation ◉ Summary of Use during Lactation Topical sulconazole has not been studied during breastfeeding. About 11% of a dose is absorbed after topical application. It is considered a low risk to the nursing infant;[1] however, other antifungal agents with less absorption may be preferred, especially while nursing a newborn or preterm infant. 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 or gel 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 |
[1]. Disruption of the NF-κB/IL-8 Signaling Axis by Sulconazole Inhibits Human Breast Cancer Stem Cell Formation. Cells. 2019;8(9):1007. |
| Additional Infomation |
1-{2-[(4-chlorobenzyl)sulfanyl]-2-(2,4-dichlorophenyl)ethyl}-1H-imidazole is a member of the class of imidazoles that is 1-ethyl-1H-imidazole in which one of the hydrogens of the methyl group is replaced by a (4-chlorobenzyl)sulfanediyl group while a second is replaced by a 2,4-dichlorophenyl group. It is a member of imidazoles, an organic sulfide, a dichlorobenzene and a member of monochlorobenzenes. Sulconazole, brand name Exelderm, is a broad-spectrum anti-fungal agent available as a topical cream and solution. Sulconazole nitrate, the active ingredient, is an imidazole derivative that inhibits the growth of common pathogenic dermatophytes, making it an effective treatment for tinea cruris and tinea corporis infections. Sulconazole appears to be effective and well-tolerated in the treatment of superficial fungal infections. Sulconazole is an Azole Antifungal. Sulconazole is a topical imidazole derivative with broad-spectrum antifungal and antibacterial activity. Sulconazole is excreted in both the feces and urine. See also: Sulconazole Nitrate (has salt form). Drug Indication Sulconazole solution 1.0% is indicated for the treatment of tinea cruris and tinea corporis caused by _Trichophyton rubrum_, _Trichophyton mentagrophytes_, _Epidermophyton floccosum_, and _Microsporum canis_; and for the treatment of tinea versicolor. Effectiveness has not been proven in tinea pedis (athlete’s foot). Mechanism of Action The mechanism of action of sulconazole is not well established; however, it is thought to be similar to other imidazole derivatives. The function of imidazoles can be attributed to their structural resemblance to purines essential to metabolism. Imidazoles inhibit lanosterol 14-alpha demethylase, a cytochrome P-450-dependent enzyme in fungi responsible for converting lanosterol to ergosterol. Since ergosterol is required to maintain the integrity of the fungi membrane, the inhibition of lanosterol 14-alpha demethylase leads to increased fungal cellular permeability. Therefore, the use of an imidazole such as sulconazole inhibits fungal growth. Pharmacodynamics Sulconazole is a broad-spectrum antifungal that inhibits the growth of dermatophytes, yeasts and other filamentous and dimorphic fungi. The relative inhibition factor (RIF), a measurement that represents a fixed portion of the antigungal dose-response curve, can be determined to measure the inhibitory activity of antifungal drugs. Against pathogenic yeasts such as dermatophytes and Aspergilli, sulconazole had similar RIF values compared to other imidazoles. In _in vitro_ conditions, the fungicidal potency of sulconazole depends on its concentration and the growth phase of the inoculum cells. Sulconazole has also shown antibacterial properties _in vitro_, with inhibitory concentrations (MICs) under 12.5 mg/L against several _Staphylococcus_ species, as well as _Streptococcus faecalis_ and several Gram-positive anaerobes. |
Solubility Data
| 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 (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *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). 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)] *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. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL 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). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.5141 mL | 12.5707 mL | 25.1414 mL | |
| 5 mM | 0.5028 mL | 2.5141 mL | 5.0283 mL | |
| 10 mM | 0.2514 mL | 1.2571 mL | 2.5141 mL |