Details
Stereochemistry | ACHIRAL |
Molecular Formula | C23H27N.ClH |
Molecular Weight | 353.928 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CN(CC1=CC=C(C=C1)C(C)(C)C)CC2=CC=CC3=CC=CC=C23
InChI
InChIKey=LJBSAUIFGPSHCN-UHFFFAOYSA-N
InChI=1S/C23H27N.ClH/c1-23(2,3)21-14-12-18(13-15-21)16-24(4)17-20-10-7-9-19-8-5-6-11-22(19)20;/h5-15H,16-17H2,1-4H3;1H
Butenafine is a synthetic antifungal agent that is structurally and pharmacologically related to allylamine antifungals. The exact mechanism of action has not been established, but it is suggested that butenafine's antifungal activity is exerted through the alteration of cellular membranes, which results in increased membrane permeability, and growth inhibition. Butenafine is mainly active against dermatophytes and has superior fungicidal activity against this group of fungi when compared to that of terbinafine, naftifine, tolnaftate, clotrimazole, and bifonazole. It is also active against Candida albicans and this activity is superior to that of terbinafine and naftifine. Butenafine also generates low MICs for Cryptococcus neoformans and Aspergillus spp. as well. Butenafine hydrochloride is marketed under the trade names Mentax, Butop (India) and is the active ingredient in Lotrimin Ultra. MENTAX Cream, 1%, is indicated for the topical treatment of tinea (pityriasis)
versicolor due to Malassezia furfur (formerly Pityrosporum orbiculare). Although the mechanism of action has not been fully established, it has been suggested that butenafine, like allylamines, interferes with sterol biosynthesis (especially ergosterol) by inhibiting squalene monooxygenase, an enzyme responsible for converting squalene to 2,3-oxydo squalene. As ergosterol is an essential component of the fungal cell membrane, inhibition of its synthesis results in increased cellular permeability causing leakage of cellular contents. Blockage of squalene monooxygenase also leads to a subsequent accumulation of squalene. When a high concentration of squalene is reached, it is thought to have an effect of directly kill fungal cells. Butenafine cream 1% is indicated in treatment of tinea
pedis, tinea corporis and tinea cruris. In tinea pedis it is
recommended twice daily for 7 days or once daily for
4 weeks. In tinea cruris and tinea corporis it is recommended
once daily for two weeks.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL366 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8494375 |
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Target ID: CHEMBL613162 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11516941 |
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Target ID: CHEMBL612926 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | MENTAX Approved UseMENTAX-TC Cream, 1%, is indicated for the topical treatment of tinea (pityriasis)
versicolor due to Malassezia furfur (formerly Pityrosporum orbiculare). Launch Date1996 |
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Sources: https://www.drugs.com/ppa/butenafine.html |
Primary | Butenafine Approved UseOTC labeling: Topical treatment of tinea pedis (athlete's foot), tinea cruris (jock itch), and tinea corporis (ringworm) Launch Date1996 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.4 ng/mL |
6 g 1 times / day multiple, topical dose: 6 g route of administration: Topical experiment type: MULTIPLE co-administered: |
BUTENAFINE blood | Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
5 ng/mL |
20 g 1 times / day multiple, topical dose: 20 g route of administration: Topical experiment type: MULTIPLE co-administered: |
BUTENAFINE blood | Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
23.9 ng × h/mL |
6 g 1 times / day multiple, topical dose: 6 g route of administration: Topical experiment type: MULTIPLE co-administered: |
BUTENAFINE blood | Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
87.8 ng × h/mL |
20 g 1 times / day multiple, topical dose: 20 g route of administration: Topical experiment type: MULTIPLE co-administered: |
BUTENAFINE blood | Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
35 h |
20 g 1 times / day multiple, topical dose: 20 g route of administration: Topical experiment type: MULTIPLE co-administered: |
BUTENAFINE blood | Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
1 % 1 times / day multiple, topical Recommended Dose: 1 %, 1 times / day Route: topical Route: multiple Dose: 1 %, 1 times / day Sources: Page: CL2001-01 |
unhealthy, 2-12 n = 100 Health Status: unhealthy Condition: Tinea corporis Age Group: 2-12 Sex: M+F Population Size: 100 Sources: Page: CL2001-01 |
Sources: Page: CL2001-01 |
PubMed
Title | Date | PubMed |
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[Synthesis and antifungal activity of butenafine hydrochloride (KP-363), a new benzylamine antifungal agent]. | 1991 Feb |
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Two mechanisms of butenafine action in Candida albicans. | 1993 Apr |
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Synthesis and structure-activity relationships of phenyl-substituted benzylamine antimycotics: a novel benzylbenzylamine antifungal agent for systemic treatment. | 1993 Jul 23 |
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Butenafine, a fungicidal benzylamine derivative, used once daily for the treatment of interdigital tinea pedis. | 1998 Jun |
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Butenafine. | 1998 Mar |
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Butenafine hydrochloride: for the treatment of interdigital tinea pedis. | 2000 Mar |
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Butenafine hydrochloride (Mentax) cream for the treatment of hyperkeratotic type tinea pedis and its transfer into the horny layer, with or without concomitant application of 20% urea ointment (Keratinamin). | 2001 |
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Comparison of in vitro antifungal activities of topical antimycotics launched in 1990s in Japan. | 2001 Aug |
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KP-103, a novel triazole derivative, is effective in preventing relapse and successfully treating experimental interdigital tinea pedis and tinea corporis in guinea pigs. | 2002 |
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Six novel antimycotics. | 2002 |
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A Japanese case of tinea corporis caused by Arthroderma benhamiae. | 2002 Apr |
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Butenafine: an update of its use in superficial mycoses. | 2002 Sep |
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Evaluation of in vitro activity of ciclopirox olamine, butenafine HCl and econazole nitrate against dermatophytes, yeasts and bacteria. | 2003 Sep |
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In vitro antifungal activity of ZJ-522, a new triazole restructured from fluconazole and butenafine, against clinically important fungi in comparison with fluconazole and butenafine. | 2005 Aug |
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Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
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An unprecedented rearrangement in collision-induced mass spectrometric fragmentation of protonated benzylamines. | 2006 Sep |
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Fungal toenail infections. | 2008 Dec 15 |
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Butenafine and superficial mycoses: current status. | 2008 Jul |
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Are placebo-controlled trials of creams for athlete's foot still justified? | 2008 Sep |
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In vitro antifungal activities of luliconazole, a new topical imidazole. | 2009 |
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Update on terbinafine with a focus on dermatophytoses. | 2009 Apr 21 |
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Simultaneous HPLC determination of butenafine hydrochloride and betamethasone in a cream formulation. | 2009 Sep |
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[Activity of butenafine against ocular pathogenic filamentous fungi in vitro]. | 2010 Jan |
|
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. | 2011 Jul 14 |
Sample Use Guides
Patients with tinea (pityriasis) versicolor should apply MENTAX-TC Cream, 1% (Butenafine), once daily for seven days. Sufficient MENTAX-TC Cream, 1%, should be applied to cover affected areas and
extending 4 inches (10.2 cm) onto normal skin immediately surrounding the affected area.
Route of Administration:
Topical
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12895182
Butenafine HCl shows minimum inhibitory concentrations ranging from 0.03–1.0 ug/mL against 30 isolates representing different dermatophyte species.
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C514
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ACTIVE MOIETY
SUBSTANCE RECORD