128326-82-9 Usage
Description
Eberconazole, also known as Ebernet, is a novel member of the azole class of antifungal agents. It is characterized by its ability to inhibit fungal lanosterol 14α-demethylase, which is crucial for the synthesis of ergosterol, an essential component of fungal cell membranes. Eberconazole exhibits potent in vitro activity against a broad spectrum of Candida species, dermatophytes, and Malassezia spp. yeasts, making it a promising candidate for the treatment of various cutaneous fungal infections.
Uses
Used in Pharmaceutical Industry:
Eberconazole is used as an antifungal agent for the topical treatment of cutaneous fungal infections, such as tinea corporis (ringworm of the body), tinea cruris (ringworm of the groin), and tinea pedis (athlete's foot). Its effectiveness against a wide range of Candida species, including Candida parapsilosis, Candida glabrata, Candida krusei, and fluconazole-resistant Candida albicans, makes it a valuable addition to the arsenal of antifungal medications.
In clinical studies, Eberconazole has demonstrated high cure rates when applied topically as a 1% or 2% cream, either once or twice daily for 6 weeks. The treatment resulted in cure rates ranging from 73.3–93.3% at the end of therapy and 66.7–100% six weeks post-therapy. Importantly, the topical application of Eberconazole does not result in detectable serum, urine, or fecal levels, which is a significant advantage in terms of safety and reduced systemic side effects.
Additionally, Eberconazole's effectiveness against some highly triazole-resistant yeasts, such as Candida glabrata and Candida krusei, highlights its potential utility in treating infections that are resistant to conventional antifungal treatments. This makes Eberconazole a valuable asset in the ongoing battle against the growing threat of antifungal resistance.
Originator
Chiesi Wassermann (Spain)
Synthesis
The synthesis of Eberconazole started with the Wittig reaction of the phosphonium
bromide 43 with the 3,5-dichlorobenzaldehyde to
give the olefin mixture 44. Hydrolysis of the ester followed
by hydrogenation gives acid 46, which was cyclized to tricyclized
ketone 47. Completion of the synthesis was accomplished
in three steps via reduction of the ketone 47 with
sodium borohydride, chlorination of resulting alcohol 48
with thionyl chloride and alkylation of the chloride 49 with
imidazole to give eberconazole (VII).
Check Digit Verification of cas no
The CAS Registry Mumber 128326-82-9 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,2,8,3,2 and 6 respectively; the second part has 2 digits, 8 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 128326-82:
(8*1)+(7*2)+(6*8)+(5*3)+(4*2)+(3*6)+(2*8)+(1*2)=129
129 % 10 = 9
So 128326-82-9 is a valid CAS Registry Number.
InChI:InChI=1/C18H14Cl2N2/c19-14-9-13-6-5-12-3-1-2-4-15(12)18(17(13)16(20)10-14)22-8-7-21-11-22/h1-4,7-11,18H,5-6H2
128326-82-9Relevant articles and documents
In vitro susceptibilities of clinical yeast isolates to the new antifungal eberconazole compared with their susceptibilities to clotrimazole and ketoconazole
Torres-Rodri?guez, Josep M.,Mendez, Rau?l,Lo?pez-Jodra, Olga,Morera, Yolanda,Espasa, Mateu,Jimenez, Teresa,Lagunas, Carme
, p. 1258 - 1259 (1999)
The antifungal activity of eberconazole, a new imidazole derivative, against 124 clinical isolates of Candida comprising eight different species and to 34 isolates of Cryptococcus neoformans was compared to those od clotrimazole and ketoconazole. MICs of eberconazole, determined by the National Committee for Clinical Laboratory Standards standardized microbroth method, were equal to or lower than those of other azoles, especially for Candida krusei and Candida glabrata, which are usually resistant to triazoles.
