Structure‐Activity Relationships of 2‐(1<i>H</i>‐Imidazol‐1‐yl)vinyl Ethers

Zirngibl, Ludwig; Fischer, J.; Jahn, Ullrich; Thiele, K.

doi:10.1111/j.1749-6632.1988.tb40389.x

Cited by 10 publications

(5 citation statements)

References 4 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Omoconazole has a high antifungal activity and a broad spectrum (Zirngibl et al, 1988). As part of our ongoing studies in this area, we report herein the crystal structure of the title compound.…”

Section: S1 Commentmentioning

confidence: 99%

See 1 more Smart Citation

1-(3-Bromopropoxy)-4-chlorobenzene

et al. 2008

View full text Add to dashboard Cite

show abstract

Section: S1 Commentmentioning

confidence: 99%

“…For general background, see: Zirngibl et al (1988). For related structures, see: Menini & Gusevskaya (2006); Baggaley & Watts (1982).…”

Section: Related Literaturementioning

confidence: 99%

1-(3-Bromopropoxy)-4-chlorobenzene

et al. 2008

View full text Add to dashboard Cite

show abstract

“…88 , 89 Siegfried (Pennsville, NJ) developed the antimycotic azole agent, omoconazole, from econazole. 90 Lastly, the FDA approved luliconazole to treat fungal infections in late 2013. Luliconazole displays broad-spectrum topical antifungal potency against the dermatophytes that cause 90% of onychomycosis.…”

Section: Cyp51: Target Of Antifungal Drugsmentioning

confidence: 99%

“…Discovery of clotrimazole by Bayer AG in the late 1960s led to the development of bifonazole, a halogen-free imidazole antifungal agent that is very lipophilic and has poor aqueous solubility . Bifonazole has broad-spectrum in vitro antifungal activity and is an effective and well-tolerated treatment for superficial fungal infections of the skin. , Siegfried (Pennsville, NJ) developed the antimycotic azole agent, omoconazole, from econazole . Lastly, the FDA approved luliconazole to treat fungal infections in late 2013.…”

Section: Cyp51: Target Of Antifungal Drugsmentioning

confidence: 99%

Drug Strategies Targeting CYP51 in Neglected Tropical Diseases

Choi

Podust²,

Roush

2014

Chem. Rev.

View full text Add to dashboard Cite

“…Omoconazole nitrate is used as a topical antifungal agent in Europe (Zirngibl et al 1988). To estimate the required concentration of omoconazole nitrate in the skin, we have studied the pharmacokinetics of the topically applied drug, and its therapeutic efficacy.…”

Section: Introductionmentioning

confidence: 99%

Study of the Effective Dose of a Topical Antifungal Agent, Omoconazole Nitrate, on the Basis of Percutaneous Pharmacokinetics in Guinea-pigs and Mice

Hashiguchi

Ryu

Itoyama

et al. 1997

Journal of Pharmacy and Pharmacology

View full text Add to dashboard Cite

The clinically useful optimum dose of omoconazole nitrate, a topical antifungal agent, has been examined by analysing the percutaneous pharmacokinetics of the drug to assess its pharmacological activity in an in-vivo study. Creams containing omoconazole nitrate were prepared on a pilot basis. The therapeutic effect of the omoconazole nitrate creams was examined in an in-vivo pharmacological dermatophytosis infection model in guinea-pigs. Creams containing 0.25% or higher concentrations of omoconazole nitrate resulted in significant inhibition compared with no treatment and with vehicle-treated controls. In the mycological examination no growth of dermatophytes was observed for creams containing 1% or higher concentrations. In an in-vitro hairless mouse skin-permeability test a non-linear least squares program based on a fast inverse Laplace transform algorithm was used to calculate the partition and diffusion parameters of omoconazole nitrate in the stratum corneum and viable epidermis. The time-course of drug concentrations in the skin of the guinea-pig, estimated on the basis of these parameters, led to predictions that percutaneous drug concentrations on the guinea-pig would require 10 or more days to reach equilibrium in the skin; that drug concentrations in the corneum-viable epidermis border, where dermatophytes are considered to grow, would exceed the minimum effective concentration when 0.1% higher concentration creams were used; and that for binding to keratin drug concentrations would reach the practical minimum effective concentration when creams containing 0.5% or more omoconazole nitrate were used. These results show that partition and diffusion parameters obtained from in-vitro skin permeation studies can be used to predict in-vivo percutaneous pharmacokinetics and to estimate therapeutically effective concentrations.

show abstract

Structure‐Activity Relationships of 2‐(1H‐Imidazol‐1‐yl)vinyl Ethers

Cited by 10 publications

References 4 publications

1-(3-Bromopropoxy)-4-chlorobenzene

1-(3-Bromopropoxy)-4-chlorobenzene

Drug Strategies Targeting CYP51 in Neglected Tropical Diseases

Study of the Effective Dose of a Topical Antifungal Agent, Omoconazole Nitrate, on the Basis of Percutaneous Pharmacokinetics in Guinea-pigs and Mice

Contact Info

Product

Resources

About