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

Mechanism

SQLE inhibitors(Squalene monooxygenase inhibitors)

Therapeutic Areas

Infectious DiseasesSkin and Musculoskeletal Diseases

Active Indication

Skin Diseases, InfectiousTinea corporistinea cruris+ [2]

Inactive Indication

Dermatitis, PhotoallergicDermatitis, Phototoxic

Originator Organization

Kaken Pharmaceutical Co., Ltd.

Active Organization

Hisamitsu Pharmaceutical Co., Inc.

Kaken Pharmaceutical Co., Ltd.

Sichuan Medshine Pharmaceutical Co.

+ [2]

Inactive Organization

Bayer AGMylan Pharmaceuticals, Inc.

Drug Highest PhaseApproved

First Approval Date

JP (21 Jan 1992),

Tinea corporistinea crurisTinea Pedis+ [1]

Regulation-

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Structure

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

United Laboratories, Inc.

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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107

Literatures (Medical) associated with Butenafine Hydrochloride

01 Jan 2024·European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences

Novel nanomicelle butenafine formulation for ocular drug delivery against fungal keratitis: In Vitro and In Vivo study

Article

Author: Yang, Jingjing ; Li, Jingguo ; Lu, Ping ; Zhang, Junjie ; Zhou, Tianyang ; Liang, Zhen ; Song, Fei ; Zhang, Zhen

Fungal keratitis (FK) is a serious infectious corneal disease that leads to blindness. Butenafine (BTF) is an allylamine drug with high antifungal activity, but its poor water solubility and low bioavailability limit its clinical application in ophthalmology. To increase its aqueous solubility and corneal permeability, butenafine was encapsulated in d-ɑ-tocopheryl polyethylene glycol succinate (TPGS) polymeric nanomicelles to improve the bioavailability of the drug for the treatment of FK. Butenafine was successfully fabricated into nanomicelles with a high EE of 96.34 ± 1.65 % and DL of 6.71 ± 0.099 %. The BTF-NM showed an average particle size of 13.12 ± 0.24 nm, a zeta potential of -0.56 ± 0.44 mV and a narrow PDI of 0.12 ± 0.02 with a nearly spherical shape. The characterization results of FTIR, XRD and DSC indicated that BTF was encapsulated in the TPGS nanomicelles. The BTF-NM formulation also showed high storage stability, and the in vitro drug release study showed typical biphasic-release characteristics. In addition, the BTF-NM formulation displayed good cellular tolerance and excellent ocular tolerance in rabbits. Significantly elevated in vitro antifungal activity was also observed in the BTF-NM formulation, and remarkable improvements regarding in vivo corneal permeation were observed compared with the BTF suspension formulation. Finally, the in vivo antifungal activity studies indicated that the BTF-NM formulation had a good therapeutic effect on FK and had similar efficacy to that of commercial natamycin suspension eye drops. These results suggest that the BTF-NM ophthalmic formulation could be a promising ocular drug delivery system for the treatment of FK.

08 Dec 2023·ACS infectious diseases

Combined Structure- and Ligand-Based Approach for the Identification of Inhibitors of AcrAB-TolC in Escherichia coli

Article

Author: Semple, Susan J ; Sykes, Matthew J ; Pisoni, Lily A ; Liu, Sida ; Venter, Henrietta

The inhibition of efflux pumps is a promising approach to combating multidrug-resistant bacteria. We have developed a combined structure- and ligand-based model, using OpenEye software, for the identification of inhibitors of AcrB, the inner membrane protein component of the AcrAB-TolC efflux pump in Escherichia coli. From a database of 1391 FDA-approved drugs, 23 compounds were selected to test for efflux inhibition in E. coli. Seven compounds, including ivacaftor (25), butenafine (19), naftifine (27), pimozide (30), thioridazine (35), trifluoperazine (37), and meloxicam (26), enhanced the activity of at least one antimicrobial substrate and inhibited the efflux pump-mediated removal of the substrate Nile Red from cells. Ivacaftor (25) inhibited efflux dose dependently, had no effect on an E. coli strain with genomic deletion of the gene encoding AcrB, and did not damage the bacterial outer membrane. In the presence of a sub-minimum inhibitory concentration (MIC) of the outer membrane permeabilizer colistin, ivacaftor at 1 μg/mL reduced the MICs of erythromycin and minocycline by 4- to 8-fold. The identification of seven potential AcrB inhibitors shows the merits of a combined structure- and ligand-based approach to virtual screening.

01 Oct 2023·Mycopathologia

Iranian National Survey on Tinea Capitis: Antifungal Susceptibility Profile, Epidemiological Characteristics, and Report of Two Strains with a Novel Mutation in SQLE Gene with Homology Modeling

Article

Author: Zaedi, Arezoo ; Kiasat, Neda ; Taghizadeh-Armaki, Mojtaba ; Shokohi, Tahereh ; Kharazi, Mahboobeh ; Hedayati, Mohammad Taghi ; Babaei, Maryam ; Ghasemi, Zeinab ; Khojasteh, Shaghayegh ; Keikha, Naser ; Aghili, Seyed Reza ; Abastabar, Mahdi ; Mohammadi, Rasoul ; Khodadadi, Hossein ; Haghani, Iman ; Reazaei-Matehkolaei, Ali ; Valadan, Reza ; Hesari, Kambiz Kamyab ; Azish, Maryam ; Zarrinfar, Hossein ; Javidnia, Javad

BACKGROUND:

The data on the epidemiological and antifungal susceptibility profile of tinea capitis (TC) in Iran has not been updated in recent decades. This report presents the Iranian epidemiological and drug susceptibility data regarding the distribution of dermatophytes species isolated by six national mycology centers for a period of one year (2020-2021).

MATERIAL AND METHODS:

A total of 2100 clinical samples from individuals suspeted to TC were subjected to mycological analysis of direct microscopy and culture. For definite species identification, the culture isolates were additionally subjected to PCR-RFLP and PCR-sequencing of the ITS ribosomal DNA (ITS-rDNA) region. Antifungal susceptibility profiles for eight common antifungal drugs were determined by CLSI M38-A3 guidelines. The SQLE gene was partially amplified and sequenced in two terbinafine-resistant and two susceptible T. mentagrophytes isolates to elucidate probable substitutions involved in resistance.

RESULTS:

TC (n = 94) was diagnosed in 75 children (79.8%) and 19 adults (20.2%) by direct microscopy and culture. Frequency of TC was significantly more among males (66 males = 70.2% vs 28 females = 29.8%). The prevalent age group affected was 5-9 years (39.36%). Thirty-two (34.04%) T. mentagrophytes, 27 (28.7%) T. tonsurans, 14 (14.9%) M. canis, 13 (13.8%) T. violaceum, 5 (5.32%) T. indotineae, 2 (2.1%) T. benhamiae, and 1 (1.1%) T. schoenleinii were identified as the causative agents. MIC values of isolates showed susceptibility to all antifungal agents, except for fluconazole and griseofulvin with GM MIC of 11.91 μg/ml and 2.01 μg/ml, respectively. Terbinafine exhibited more activity against isolates, with GM MIC 0.084 μg/ml followed by ketoconazole (0.100 μg/ml), econazole (0.107 μg/ml), itraconazole (0.133 μg/ml), butenafine (0.142 μg/ml), and miconazole (0.325 μg/ml). Two resistant T. mentagrophytes isolates harbored missense mutations in SQLE gene, corresponding to amino acid substitution F397L. Remarkably, one unique mutation, C1255T, in the SQLE sequence of two terbinafine-susceptible T. mentagrophytes strains leading to a change of leucine at the 419th position to phenylalanine (L419F) was detected.

CONCLUSIONS:

T. mentagrophytes, T. tonsurans, and M. canis remained the main agents of TC in Iran, however less known species such as T. indotinea and T. benhamiae are emerging as new ones. Terbinafine could still be the appropriate choice for the treatment of diverse forms of TC.

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	CN	Sichuan Medshine Pharmaceutical Co.	14 Jan 2002
Tinea corporis	JP	Hisamitsu Pharmaceutical Co., Inc.	21 Jan 1992
Tinea corporis	JP	Kaken Pharmaceutical Co., Ltd.	21 Jan 1992
tinea cruris	JP	Kaken Pharmaceutical Co., Ltd.	21 Jan 1992
tinea cruris	JP	Hisamitsu Pharmaceutical Co., Inc.	21 Jan 1992
Tinea Pedis	JP	Hisamitsu Pharmaceutical Co., Inc.	21 Jan 1992
Tinea Pedis	JP	Kaken Pharmaceutical Co., Ltd.	21 Jan 1992
Tinea Versicolor	JP	Hisamitsu Pharmaceutical Co., Inc.	21 Jan 1992
Tinea Versicolor	JP	Kaken Pharmaceutical Co., Ltd.	21 Jan 1992

Developing

10 top R&D records.

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Indication	Highest Phase	Country/Location	Organization	Date
Dermatitis, Phototoxic	Phase 3	US	Bayer AG	24 Jun 2013
Dermatitis, Photoallergic	Phase 3	US	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 1% (BAY1896425) - Challenge Phase	dvfzlcubtr(skkupuimcq) = dvlargkaft zoejtvzkix (fdmxbdajqj, uwmnxxqvgh - xwzdkhpslv) View more	-	16 Nov 2020
NCT04531540 (CTgov)	Phase 3	Hypersensitivity \| Central Sensitizations \| Skin Diseases	225	Butenafine HCl 1% (BAY1896425)	wzeoarmmrt(rdhhodtegf) = bzwpgsfrwb xqhulszrxa (jrpnjwrwqn, sxvxgbqaeq - mcseubqocu) View more	-	25 Sep 2020
NCT04531813 (CTgov)	Phase 3	Hypersensitivity \| Skin Diseases	32	Negative Control+Butenafine HCl 1% (BAY1896425)	xihnupvlco(wgranpkrbd) = heazfayyyh lszjxbrmpe (ewyhvaqdyd, gtvcyoytle - stnogksbyl) View more	-	25 Sep 2020
NCT04531527 (CTgov)	Phase 3	Dermatitis, Phototoxic \| Hypersensitivity	32	Butenafine HCl 1% (BAY1896425)	axkhpfosuv(mixlajlpol) = srcnkrzhup bfzamdnohd (bvtfppwplt, ufpxxcudlo - ibqcwzfmcp) View more	-	21 Sep 2020
NCT00835510 (CTgov)	Phase 1	Tinea Pedis	548	Butenafine cream 1% manufactured by Taro (Butenafine Cream 1% (Taro))	iaxnncpgnx(iumharhwco) = voakdnbrav xfizdgqgan (wmvuhnxqrg, zarjpbhgmo - toquzkhxzf) View more	-	06 Oct 2009
NCT00835510 (CTgov)	Phase 1	Tinea Pedis	548	Lotrimin Ultra (butenafine) 1% (Lotrimin Ultra (Butenafine) 1%)	iaxnncpgnx(iumharhwco) = fknborqppl xfizdgqgan (wmvuhnxqrg, vzcfttzqdj - byssexqxej) View more	-	06 Oct 2009