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Econazole Sulfosalicylate

Econazole Sulfosalicylate is an antifungal agent applied topically or intravaginally. Econazole, an imidazole derivative, is indicated in the treatment of skin infections such as dermatophytosis, superficial candidasis, and tinea versicolor, and of infections of the nails. Econazole is also used as a topical antimycotic in veterinary medicine.

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CAT No: 10-101-116

CAS No: 27220-47-9 (net), 118308-71-7 (sulfosalicylate)

Synonyms/Alias: 1-[2-[(4-Chlorophenyl)methoxy]-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole sulfosalicylate; SQ-13050 sulfosalicylate; 1-[2,4-Dichloro-β-(4-chlorobenzyloxy)phenethyl]-imidazole sulfosalicylate

Chemical Name: 1-[2-[(4-chlorophenyl)methoxy]-2-(2,4-dichlorophenyl)ethyl]imidazole;2-hydroxy-5-sulfobenzoic acid

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M.F/FormulaC18H15Cl3N2O.C7H6O6S
M.W/Mr.599.87
Labeling TargetLanosterol 14-alpha demethylase
Nuclear receptor subfamily 1 group I member 2
ApplicationFor the treatment of skin infections such as dermatophytosis, superficial candidasis, and tinea versicolor, and of infections of the nails.
ActivityAntagonist
Areas of InterestInfection
Veterinary medicine
Source#Synthetic
OrganismHuman
InChIInChI=1S/C18H15Cl3N2O.C7H6O6S/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;8-6-2-1-4(14(11,12)13)3-5(6)7(9)10/h1-9,12,18H,10-11H2;1-3,8H,(H,9,10)(H,11,12,13)
InChI KeyWJRNYYWHDHVDCF-UHFFFAOYSA-N
Canonical SMILESC1=CC(=CC=C1COC(CN2C=CN=C2)C3=C(C=C(C=C3)Cl)Cl)Cl.C1=CC(=C(C=C1S(=O)(=O)O)C(=O)O)O
References

The aim of this investigation was to compare the contact action of econazole sulfosalicylate (E-SSA) on mycetes (Candida albicans, Cryptococcus neoformans, Aspergillus fumigatus, Trichophyton rubrum, T. cutaneum, Pityrosporum sp.), Gram-positive bacteria (Staphylococcus aureus, Streptococcus faecalis) and Gram-negative bacteria (Escherichia coli, Citrobacter freundii) with that exerted by econazole nitrate (E-NIT). The results show E-SSA activity greater than E-NIT (in particular against mycetes and Gram-negative bacteria). The E-SSA contact activity trials illustrated certain properties of this imidazole sulfosolicylate such as: absence of latency time, antimicrobial activity proportional to its concentration, when a high concentration is used, given the limiting influence of pH and ionic strength of the medium. The higher E-SSA contact activity, in relation to E-NIT, can be correlated to its greater lipophylia considering also the lipophylic properties of SSA and the scarce dissociation of E-SSA.

Simonetti, N., Spignoli, G., D'Auria, F. D., & Strippoli, V. (1991). Antimicrobial Contact Activity of Econazole Sulfosalicylate. Journal of Chemotherapy, 3(2), 101-107.

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