Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C35H39F2N7O4 |
Molecular Weight | 659.7255 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)N1CCN(C1=O)C2=CC=C(C=C2)N3CCN(CC3)C4=CC=C(OC[C@H]5OC[C@@](CN6C=NC=N6)(O5)C7=C(F)C=C(F)C=C7)C=C4
InChI
InChIKey=AEKNYBWUEYNWMJ-QWOOXDRHSA-N
InChI=1S/C35H39F2N7O4/c1-25(2)43-17-18-44(34(43)45)29-6-4-27(5-7-29)40-13-15-41(16-14-40)28-8-10-30(11-9-28)46-20-33-47-22-35(48-33,21-42-24-38-23-39-42)31-12-3-26(36)19-32(31)37/h3-12,19,23-25,33H,13-18,20-22H2,1-2H3/t33-,35+/m0/s1
Pramiconazole is a novel azole with potent antifungal activity against yeasts, dermatophytes and many other fungal species. It is a new addition to the family of triazole antifungal agents that act by inhibiting fungal cell membrane ergosterol synthesis, thereby leading to increased cell permeability and destruction. In preclinical studies, pramiconazole exhibited similar or superior antifungal activity to ketoconazole and itraconazole, and selectively inhibited ergosterol synthesis with a broad spectrum activity. Pramiconazole was absorbed rapidly and had a long half-life, allowing for once-daily dosing. In phase I and II clinical trials, pramiconazole reduced the growth of Candida albicans, Malassezia globosa, Microsporum canis, Trichophyton mentagrophytes and Trichophyton rubrum, and was generally well tolerated. Pramiconazole is a well-tolerated and effective treatment for pityriasis versicolor.
Originator
Approval Year
PubMed
Title | Date | PubMed |
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The novel azole R126638 is a selective inhibitor of ergosterol synthesis in Candida albicans, Trichophyton spp., and Microsporum canis. | 2004 Sep |
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Gateways to clinical trials. | 2006 Oct |
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Absence of an active metabolite for the triazole antifungal pramiconazole. | 2007 |
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The efficacy of oral treatment with pramiconazole in pityriasis versicolor: a phase II a trial. | 2007 Jun |
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Efficacy of a single oral dose of 200 mg pramiconazole in vulvovaginal yeast infections: an exploratory phase IIa trial. | 2008 |
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The efficacy of oral treatment with pramiconazole in tinea pedis and tinea cruris/corporis: two exploratory phase IIa trials. | 2008 Apr |
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Gateways to clinical trials. | 2008 May |
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Pramiconazole, a triazole compound for the treatment of fungal infections. | 2008 Sep |
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A double-blind, randomized, placebo-controlled, dose-finding study of oral pramiconazole in the treatment of pityriasis versicolor. | 2009 Dec |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19828211
200 or 400 mg taken once, and 200 mg taken once daily for 2 or 3 days
Route of Administration:
Oral
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C514
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DTXSID80944594
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C482452
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C72830
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CHEMBL175797
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4SYH0R661F
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PRAMICONAZOLE
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RR-98
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ACTIVE MOIETY