Sulconazole
Grundinformationen
- CAS
61318-90-9- Standard-SMILES
Clc1ccc(CSC(Cn2ccnc2)c2ccc(Cl)cc2Cl)cc1- InChIKey
AFNXATANNDIXLG-UHFFFAOYSA-N- Summenformel
- C18H15Cl3N2S
- Durchschnittliche Molmasse
- 397,7 g/mol
- Monoisotopische Masse
- 396,002153
Überblick
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 an organic sulfide, a dichlorobenzene, a member of imidazoles and a member of monochlorobenzenes.
Namen und Bezeichner
- Bevorzugter Name
- Sulconazole
- IUPAC
- 1-[2-[(4-chlorophenyl)methylsulfanyl]-2-(2,4-dichlorophenyl)ethyl]imidazole
- Englischer Name
- SULCONAZOLE
- Summenformel
- C18H15Cl3N2S
- Molmasse
- 397.75
Namen und Synonyme
sulconazole61318-90-9SulconazolSulconazolum1-[2-[(4-chlorophenyl)methylsulfanyl]-2-(2,4-dichlorophenyl)ethyl]imidazole5D9HAA5Q5SDTXSID8044129(+-)-1-(2,4-dichloro-beta-((p-chlorobenzyl)thio)phenethyl)imidazole1H-Imidazole, 1-(2-(((4-chlorophenyl)methyl)thio)-2-(2,4-dichlorophenyl)ethyl)-, (+-)-1-(2-(((4-CHLOROPHENYL)METHYL)THIO)-2-(2,4-DICHLOROPHENYL)ETHYL)-1H-IMIDAZOLE1-(2-((4-chlorophenyl)methylsulfanyl)-2-(2,4-dichlorophenyl)ethyl)imidazoleRefChem:56487
Weitere Namen anzeigen
SulconazleSULCONAZOLE USP/EP/BPSulconazle Impurity 31-(2-((4-Chlorobenzyl)-2-(2,4-dichlorophenyl)Uniconazole sulfur nitrateQuizalofop Impurity 8(Propaquizafop)Sulconazole (base and/or unspecified salts)
CHEBI:9325DTXCID6024129D01AC091-(beta-(4''-chlorobenzylthio)-2'4'-dichlorophenethyl)imidazole919-950-0Exelderm1-(2-((4-Chlorobenzyl)thio)-2-(2,4-dichlorophenyl)ethyl)-1H-imidazoleSulconazolum [INN-Latin]
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 6,1
- Polarare Oberfläche (TPSA)
- 43,1 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 2
- Frei drehbare Bindungen
- 6
- Schwere Atome
- 24
- Formalladung
- 0
- Komplexität
- 379
Experimentelle und physikochemische Eigenschaften
SolubilitySlightly soluble
Human DrugsBreast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antifungal Agents; Dermatologic Agents
Melting Point130ºC
Collision Cross Section183.06 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physikochemische Eigenschaften
- Siedepunkt
- 558.2 · 558.2±50.0 °C(Predicted)
- Dichte
- 1.34 · 1.34±0.1 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- pka
- 6.55 · 6.55±0.12(Predicted)
- CAS Datenbank
- 61318 · 61318-90-9
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Toxikologische Informationen
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Chemie und Industrie
Pharmakologische Informationen
ATC Code
D01AC09
D - Dermatologicals
QD - Dermatologicals
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.
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.
FDA Pharmacological Classification
5D9HAA5Q5S
SULCONAZOLE
Established Pharmacologic Class [EPC] - Azole Antifungal
Chemical Structure [CS] - Azoles
Sulconazole is an Azole Antifungal.
MeSH Pharmacological ClassificationSubstances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues.
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