| Identification | Back Directory | [Name]
SULCONAZOLE | [CAS]
61318-90-9 | [Synonyms]
Sulconazol
SULCONAZOLE
SULCONAZOLE USP/EP/BP
1-(2-((4-Chlorobenzyl)
-2-(2,4-dichlorophenyl)
Uniconazole sulfur nitrate
Sulconazole (base and/or unspecified salts)
1-(2-((4-Chlorobenzyl)thio)-2-(2,4-dichlorophenyl)ethyl)-1H-iMidazole
1-{2-[(4-chlorobenzyl)sulfanyl]-2-(2,4-dichlorophenyl)ethyl}-1H-imidazole
1-[2-[(4-chlorophenyl)methylthio]-2-(2，4-dichlorophenyl)ethyl]-Lh-imidade
1H-Imidazole, 1-[2-[[(4-chlorophenyl)methyl]thio]-2-(2,4-dichlorophenyl)ethyl]- (9CI)
1H-Imidazole, 1-[2-[[(4-chlorophenyl)methyl]thio]-2-(2,4-dichlorophenyl)ethyl]-, (+-)- | [Molecular Formula]
C18H15Cl3N2S | [MDL Number]
MFCD00865585 | [MOL File]
61318-90-9.mol | [Molecular Weight]
397.75 |
| Hazard Information | Back Directory | [Chemical Properties]
Crystalline, melting point 130-131.5°C.
Sulconazole Nitrate: C????H????C????N??S??HNO??. [61318-91-0]. White crystals or crystalline powder, odorless or with a slight odor. Freely soluble in dimethylformamide, soluble in methanol, slightly soluble in glacial acetic acid, poorly soluble in ethanol, acetone, or chloroform, and practically insoluble in water. Melting point 130.5-132°C (acetone). | [Uses]
Sulconazole (Exelderm) is a synthetic, sulfur-substituted imidazole that is structurally related to the other imidazole antifungals (ketoconazole, econazole, and miconazole). It is postulated to inhibit 14-α-demethylase for decreased ergosterol synthesis, increased cell membrane permeability, and resultant cell death. It is active against most dermatophytes, yeast, and P. orbiculare. It also displays activity against some aerobic and anaerobic gram-positive bacteria. Sulconazole is a mild inducer of the cytochrome P-450 microsomal enzymes CYP1A1 and CYP2B1 and could theoretically induce the metabolism of other drugs. | [Definition]
ChEBI: 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. | [Indications]
Sulconazole (Exelderm) is a synthetic, sulfur-substituted imidazole that is
structurally related to the other imidazole antifungals (ketoconazole, econazole,
and miconazole). It is postulated to inhibit 14-α-demethylase for
decreased ergosterol synthesis, increased cell membrane permeability, and
resultant cell death. It is active against most dermatophytes, yeast, and
P. orbiculare. It also displays activity against some aerobic and anaerobic
gram-positive bacteria. Sulconazole is a mild inducer of the cytochrome P-450
microsomal enzymes CYP1A1 and CYP2B1 and could theoretically induce
the metabolism of other drugs. | [Side effects]
Local irritations and allergic reactions may occur in rare cases and are mainly due to the galenic formulation. | [Synthesis]
Sulconazole, 1-[2,4-dichloro-|?-[(4-chlorobenzyl)thio]phenethyl]-imidazole
(35.2.9), is an analog of exonazole. It differs in the replacement of the etheral oxygen
bridge (which connects the 4-chlorobenzyl part of the molecule with phenethylimidazole)
for a thioether bond. The corresponding changes in the synthesis of this drug are the
replacement of the hydroxyl group in 1-(2,4-dichlorophenyl)-2-(1-imidazolyl)-ethanol
(35.2.6) with a chlorine atom using thionyl chloride, followed by a reaction of the resulting chloride with 4-chlorobenzylmercaptane to make sulconazole.
| [Solubility in organics]
1 part in 3,333 (water), 1 part in 100 (ethanol), 1 part in 130 (acetone), 1 part in 333 (chloroform), 1 part in 2000 (dioxan), 1 part in 71 (methanol), 1 part in 286(chloromethane), 1 part in 10 (pyridine), 1 part in 2000 (toluene). |
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