Delving into the Latest Updates on Butenafine Hydrochloride with Synapse

Overview

Basic Info

Drug Type

Small molecule drug

Synonyms

(4-tert-Butyl-benzyl)-methyl-naphthalen-1-ylmethyl-amine, (4-tert-butylphenyl)-N-methyl-N-(naphthalen-1-ylmethyl)methanamine, 4-tert-butylbenzyl(methyl)(1-naphthalenemethyl)amine

+ [30]

Target

SQLE

Action

inhibitors

Mechanism

SQLE inhibitors(Squalene monooxygenase inhibitors)

Therapeutic Areas

Infectious DiseasesSkin and Musculoskeletal Diseases

Active Indication

Skin Diseases, InfectiousTinea corporistinea cruris+ [2]

Inactive Indication

Allergic skin reactionDermatitis, PhotoallergicDermatitis, Phototoxic

Originator Organization

Kaken Pharmaceutical Co., Ltd.

Active Organization

Kaken Pharmaceutical Co., Ltd.

Hisamitsu Pharmaceutical Co., Inc.

Sichuan Medshine Pharmaceutical Co.

+ [2]

Inactive Organization

Bayer AGNORVIUM BIOSCIENCE

Drug Highest PhaseApproved

First Approval Date

Japan (21 Jan 1992),

Tinea corporistinea crurisTinea Pedis+ [1]

Regulation-

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Structure/Sequence

Molecular FormulaC23H28ClN

InChIKeyLJBSAUIFGPSHCN-UHFFFAOYSA-N

CAS Registry101827-46-7

Tinea pedis or athlete's foot is the most common fungal infection worldwide, caused by infection of the feet with dermatophytes such as Trichophyton rubrum, Trichophyton interdigitale (formerly Trichophyton mentagrophytes), and Epidermophyton floccosum. Diagnosis of tinea pedia involves clinical symptoms as well as microscopic examination. Topical therapies are usually applied once or twice daily for as long as 4 weeks, posing a challenge to compliance. The current study aims to test a formulation of the single-dose 1% terbinafine hydrochloride, as well as a single-dose 1% butenafine hydrochloride, versus a vehicle control in adult Filipino patients with athlete's foot. This study will benefit the Filipino community by helping us determine which anti-fungal cream is most effective for athlete's foot.

Start Date02 Jan 2019

Sponsor / Collaborator-

NCT04531540

/ CompletedPhase 3

HT201321- Repeated Insult Patch Test With Modified Challenge

In this study researcher want to learn more about possible skin reactions such after repeated application of an antifungal cream containing Trolamine. They are especially interested in skin irritations or allergic skin reactions. The study plans to enroll about 225 female or male participants with the age 18 - 79 years. The antifungal test cream will be applied on the back between the shoulder blades of the participants and covered by a special dressing patch. This will be repeated 3 times a week for the first 3 weeks of this study applying the cream on the same area of the back. At each visit the skin will be investigated for redness, dryness and other reactions. After a rest period of two weeks the test cream will be applied on the same skin area as before and on a second new skin area nearby. After 2 and 4 days the two skin areas will again be investigated for redness, dryness and other reactions.

Start Date09 Sep 2013

Sponsor / Collaborator

Bayer AG

NCT04531527

/ CompletedPhase 3

HT201308- Human Phototoxicity Test

In this study researchers want to gather information about the potential of Antifungal Cream V61-044 containing Trolamine to produce a phototoxic reaction on the skin. A phototoxic reaction is an irritant reaction of the skin to ultra violet light. In order to find this out the study drug will be applied to the skin of healthy human subjects. By using a solar simulator to generate a UV spectrum similar to that of sunlight the potential of the study drug to produce a superficial reddening of the skin will be measured.

Start Date24 Jun 2013

Sponsor / Collaborator

Bayer AG

100 Clinical Results associated with Butenafine Hydrochloride

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100 Translational Medicine associated with Butenafine Hydrochloride

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100 Patents (Medical) associated with Butenafine Hydrochloride

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259

Literatures (Medical) associated with Butenafine Hydrochloride

01 Jan 2025·GENE

Evidence for high-risk pollutants and emerging microbial contaminants at two major bathing ghats of the river Ganga using high-resolution mass spectrometry and metagenomics

Article

Author: Pandey, Parul ; Kumar Tripathi, Anil ; Narain Singh, Durgesh ; Shankar Singh, Vijay

An efficient wastewater treatment plant is imperative to limit the entry of emerging pollutants (EPs) and emerging microbial contaminants (EMCs) in the river ecosystem. The detection of emerging EPs in aquatic environments is challenging due to complex sample preparation methods, and the need for sophisticated accurate analytical tools. In Varanasi (India), the river Ganga holds immense significance as a holy river but is consistently polluted with municipal (MWW) and hospital wastewater (HWW). We developed an efficient method for untargeted detection of EPs in the water samples using High-resolution mass spectrometry (HRMS), and identified 577 and 670 chemicals (or chemical components) in the water samples from two major bathing ghats, Assi Ghat (AG) and Dashashwamedh Ghat (DG), respectively. The presence of EPs of different categories viz chemicals from research labs, diagnostic labs, lifestyle and industrial chemicals, toxins, flavor and food additives indicated the unsafe disposal of MWW and HWW or inefficient wastewater treatment plants (WWTPs). Besides, shotgun metagenomic analysis depicted the presence of bacteria associated with MWW viz Cloacibacterium normanse, Sphaerotilus natans (sewage fungi), E. coli, and Prevotella. Also, the presence of human pathogens Arcobacter, Polynucleobacter, Pseudomonas, Klebsiella, Aeromonas, Acinetobacter, Vibrio, and Campylobacter suggests the discharge of HWW. EPs are linked to the development, and transmission of antimicrobial resistance (AMR). Occurrence of antibiotic resistance genes (ARGs), plasmid-borne β-lactamases, aminoglycoside transferases, and ARGs associated with integrons, transposons and plasmids viz mcr-3 gene that confer resistance to colistin, the last resort of antibiotics confirmed the presence of emerging microbial contaminants. Subsequent genome reconstruction studies showed the presence of uncultivable ARB and transmission of ARGs through horizontal gene transfer. This study can be used to monitor the health of aquatic bodies as well as the efficiency of WWTPs and raise an urgent need for efficient WWTPs to safeguard the river, Ganga.

01 Dec 2024·FUNDAMENTAL & CLINICAL PHARMACOLOGY

Nociceptive TRP channels function as molecular target for several antifungal drugs

Article

Author: Takahashi, Kenji ; Ohta, Toshio ; Okabe, Shota ; Hashimoto, Miho

Abstract:

Background/objectives:

Topically applied antifungal agents can induce adverse effects, such as pain and irritation. The transient receptor potential (TRP) channels—TRPA1 and TRPV1—mainly expressed in sensory neurons, act as sensors for detecting irritants. This study aims to evaluate the involvement of nociceptive channels in topical antifungal‐induced pain and irritation. We tested nine topical antifungals belonging five classes: isoconazole, econazole, miconazole, clotrimazole, and ketoconazole as imidazoles; liranaftate as a thiocarbamate; terbinafine as an allylamine; amorolfine as a morpholine; and butenafine as a benzylamine.

Methods:

Intracellular calcium concentrations ([Ca2+]i) and membrane currents in response to antifungals were measured to estimate channel activity using heterologously expressing cells and isolated mouse sensory neurons.

Results:

In mouse TRPA1‐expressing cells, all the tested drugs induced an increase in [Ca2+]i, which was abrogated or reduced by a TRPA1 blocker. Although many drugs evoked the TRPA1‐nonspecific [Ca2+]i response at high concentrations, responses to clotrimazole, ketoconazole, and liranaftate were TRPA1 specific and elicited current responses in TRPA1‐expressing cells. In mouse TRPV1‐expressing cells, clotrimazole and ketoconazole elicited [Ca2+]i and current responses. In mouse sensory neurons, liranaftate‐induced increase in [Ca2+]i was abrogated by a TRPA1 blocker and Trpa1 deletion. Responses to ketoconazole were inhibited by TRPA1 and TRPV1 blockers and by the genetic deletion of either channel.

Conclusion:

These results suggest that topical antifungal‐induced pain and irritation are attributable to the activation of nociceptive TRPA1 and/or TRPV1 channel/s. Consequently, caution should be exercised in the use of topical antifungals with symptoms of pain.

25 Nov 2024·JACS Au

CF₃-Cyclobutanes: Synthesis, Properties, and Evaluation as a Unique tert-Butyl Group Analogue

Article

Author: Trofymchuk, Serhii ; Ahunovych, Volodymyr ; Panasiuk, Yaroslav ; Kosach, Viktoriia ; Lesyk, Dmytro ; Shablykin, Oleh ; Bodenchuk, Iryna ; Boretskyi, Andrii ; Horbatok, Kateryna ; Razhyk, Bohdan ; Borysko, Petro ; Stanko, Oleh ; Mykhailiuk, Pavel K. ; Klipkov, Anton A. ; Kubyshkin, Vladimir ; Klymenko-Ulianov, Oleksii ; Tarasenko, Karen ; Al-Maali, Galeb ; Bugera, Maksym

Isosteric replacement of functional groups is an emerging strategy for optimizing bioactive molecules in drug discovery. tert-Butyl group is a particularly important moiety, yet its isosteric replacement with 1-trifluoromethyl-cyclobutyl group has been rather neglected. To enable the advance of this molecular fragment in drug discovery programs, we report the synthesis of over 30 small-molecule building blocks featuring the trifluoromethyl-cyclobutyl fragment, achieved by reacting sulfur tetrafluoride with cyclobutylcarboxylic acids on a gram-to-multigram scale. Furthermore, we characterized the structural properties of this group through X-ray analysis, studied its effect on acid-base transitions, and evaluated its Hammett parameters. Finally, we evaluated the replacement of tert-butyl with 1-trifluoromethyl-cyclobutyl in several bioactive compounds that represent commercial drugs and agrochemicals. Our findings indicate that while the trifluoromethyl-cyclobutyl group exhibited slightly larger steric size and moderately increased lipophilicity, it preserved the original mode of bioactivity in the examined cases and, in some cases, enhanced resistance to metabolic clearance.

100 Deals associated with Butenafine Hydrochloride

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External Link

KEGG	Wiki	ATC	Drug Bank
D01093	Butenafine Hydrochloride	D01AE23	DB01091

R&D Status

Approved

10 top approved records.

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Indication	Country/Location	Organization	Date
Skin Diseases, Infectious	China	Sichuan Medshine Pharmaceutical Co.	14 Jan 2002
Tinea corporis	Japan	Kaken Pharmaceutical Co., Ltd.	21 Jan 1992
Tinea corporis	Japan	Hisamitsu Pharmaceutical Co., Inc.	21 Jan 1992
tinea cruris	Japan	Kaken Pharmaceutical Co., Ltd.	21 Jan 1992
tinea cruris	Japan	Hisamitsu Pharmaceutical Co., Inc.	21 Jan 1992
Tinea Pedis	Japan	Hisamitsu Pharmaceutical Co., Inc.	21 Jan 1992
Tinea Pedis	Japan	Kaken Pharmaceutical Co., Ltd.	21 Jan 1992
Tinea Versicolor	Japan	Hisamitsu Pharmaceutical Co., Inc.	21 Jan 1992
Tinea Versicolor	Japan	Kaken Pharmaceutical Co., Ltd.	21 Jan 1992

Developing

10 top R&D records.

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Indication	Highest Phase	Country/Location	Organization	Date
Pruritus	Phase 3	United States	Bayer AG	09 Sep 2013
Dermatitis, Phototoxic	Phase 3	United States	Bayer AG	24 Jun 2013
Allergic skin reaction	Phase 3	United States	Bayer AG	10 Jun 2013
Dermatitis, Photoallergic	Phase 3	United States	Bayer AG	10 Jun 2013
Mycoses	Phase 3	United States	Bayer AG	10 Jun 2013

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Clinical Result

Indication

Phase

Evaluation

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Study	Phase	Population	Analyzed Enrollment	Group	Results	Evaluation	Publication Date


NCT04532164 (CTgov)	Phase 3	Mycoses \| Allergic skin reaction \| Dermatitis, Photoallergic	137	Butenafine HCl	dleraiogsh(rdetpmylsi) = lktwgvhxbf gowkjdobry (xmekjkgcsz, qyapqhkptp - upgqkkugfj) View more	-	16 Nov 2020
NCT04531540 (CTgov)	Phase 3	Pruritus \| Hypersensitivity	225	Butenafine HCl 1% (BAY1896425)	zclouncvzp = etrgsjckhm deixkpmxni (rjwqgobxnd, qjrvmkyfuj - omkurxsrle) View more	-	25 Sep 2020
NCT04531527 (CTgov)	Phase 3	Dermatitis, Phototoxic	32	Butenafine HCl	gjveybgrmr = xcgqhigpcy hwvrlhhbyl (hgwazcgnym, qznndrmuti - rymhweksqc) View more	-	21 Sep 2020
NCT00835510 (CTgov)	Phase 1	Tinea Pedis	548	Butenafine cream 1% manufactured by Taro (Butenafine Cream 1% (Taro))	bwmofsaowf = eedrtcysgb otobfvgnoc (wxhrjmoary, ifpgpxhtbe - ogozentamb) View more	-	06 Oct 2009
NCT00835510 (CTgov)	Phase 1	Tinea Pedis	548	Lotrimin Ultra (butenafine) 1% (Lotrimin Ultra (Butenafine) 1%)	bwmofsaowf = pmgroxttra otobfvgnoc (wxhrjmoary, ysozpendsp - kqzneaunjj) View more	-	06 Oct 2009