Delving into the Latest Updates on Bifonazole with Synapse

Overview

Basic Info

Drug Type

Small molecule drug

Synonyms

(+-)-1-(p,alpha-Diphenylbenzyl)imidazole, 1-((4-Biphenylyl)phenylmethyl)-1H-imidazole, 1-(alpha-(4-Biphenylyl)benzyl)imidazole

+ [22]

Target

fungal CYP51A1

Action

inhibitors

Mechanism

fungal CYP51A1 inhibitors(Fungal CYP51A1 inhibitors)

Therapeutic Areas

Infectious DiseasesSkin and Musculoskeletal Diseases

Active Indication

CandidiasisTineaTinea Pedis+ [2]

Inactive Indication

Onychomycosis

Originator Organization

Bayer Yakuhin Ltd.

Active Organization

Bayer Yakuhin Ltd.

Inactive Organization

Bayer AG

Drug Highest PhaseApproved

First Approval Date

Japan (08 May 2009),

CandidiasisTinea PedisTinea Versicolor+ [1]

Regulation-

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Structure/Sequence

Molecular FormulaC22H18N2

InChIKeyOCAPBUJLXMYKEJ-UHFFFAOYSA-N

CAS Registry60628-96-8

AbstractSterols are produced via complex, multistep biosynthetic pathways involving similar enzymatic conversions in plants, animals, and fungi, yielding a variety of sterol metabolites with slightly different chemical properties to exert diverse and specific functions. A tremendously diverse landscape of sterols, and sterol-derived compounds can be found across the plant kingdom, determining a wide spectrum of functions. Resolving the underlying biosynthetic pathways is thus instrumental to understanding the function and use of these molecules. In only a few plants, sterol biosynthesis has been studied using mutants. In non-model species, a pharmacological approach is required. However, this relies on only a few inhibitors. Here, we investigated a collection of inhibitors of mammalian cholesterol biosynthesis to identify new inhibitors of plant sterol biosynthesis. We showed that imidazole-type fungicides, bifonazole, clotrimazole, and econazole, inhibited the obtusifoliol 14α-demethylase CYP51 in plants. Moreover, we found that the selective estrogen receptor modulator, clomiphene, inhibited sterol biosynthesis in part by inhibiting the plant-specific cyclopropyl-cycloisomerase CPI1. These results demonstrate that rescreening of inhibitors of animal sterol biosynthesis is an easy approach for identifying novel inhibitors of plant sterol biosynthesis. The molecules used in this study expand the range of inhibitors for studying and manipulating sterol biosynthesis in the plant kingdom.

05 Feb 2025·Journal of the American Chemical Society

Standardized Approach for Diversification of Complex Small Molecules via Aryl Thianthrenium Salts

Article

Author: Williams, Simon R. ; Xie, Yuanhao ; Ahmadli, Dilgam ; Jaeckh, Simon ; Müller, Sven ; Iosub, Andrei V. ; Ritter, Tobias ; Smejkal, Tomas

Thianthrenation is a useful strategy for the late-stage diversification of complex small molecules owing to the positional selectivity and the synthetic versatility of thianthrenium salts as electrophilic linchpins. However, substrate-dependent identification of suitable reaction conditions for thianthrenation can be difficult. Reported reaction conditions for the functionalization of thianthrenium salts vary significantly and, in some instances, lack robustness and practicality. Herein, we report a generalized approach for the preparation of thianthrenium salts and two reaction manifolds for practical, robust, and parallel diversification of thianthrenium salts.

27 Jan 2025·Angewandte Chemie International Edition

Late‐Stage Diazoester Installation via Arylthianthrenium Salts

Article

Author: Ritter, Tobias ; Li, Le ; Müller, Sven ; Petzold, Roland

AbstractBy leveraging the fast oxidative addition of arylthianthrenium salts (aryl‐TT+) to palladium(0), a regioselective diazoester installation has been developed. This approach enables the introduction of a diazo moiety to densely functionalized arenes at a late stage. The installed diazo group is amenable to facile further derivatization.

100 Deals associated with Bifonazole

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External Link

KEGG	Wiki	ATC	Drug Bank
D01775	Bifonazole	D01AC10	DB04794

R&D Status

Approved

10 top approved records.

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Indication	Country/Location	Organization	Date
Candidiasis	Japan	Bayer Yakuhin Ltd.	08 May 2009
Tinea	Japan	Bayer Yakuhin Ltd.	08 May 2009
Tinea Pedis	Japan	Bayer Yakuhin Ltd.	08 May 2009
Tinea Versicolor	Japan	Bayer Yakuhin Ltd.	08 May 2009
Mycoses	-	-	-

Developing

10 top R&D records.

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Indication	Highest Phase	Country/Location	Organization	Date
Tinea Pedis	Phase 2	Germany	Bayer AG	01 Dec 2009
Onychomycosis	Phase 2	Germany	Bayer AG	01 Oct 2008
Onychomycosis	Phase 2	Czechia	Bayer AG	01 Oct 2008
Onychomycosis	Phase 2	Poland	Bayer AG	01 Oct 2008