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 |
---|---|---|
Two mechanisms of butenafine action in Candida albicans. | 1993 Apr |
|
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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Experimental and conformational analyses of interactions between butenafine and lipids. | 2001 Dec |
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Efficacy and safety of butenafine in superficial dermatophytoses (tinea pedis, tinea cruris, tinea corporis). | 2001 May |
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Six novel antimycotics. | 2002 |
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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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Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
|
What is the best way to treat tinea cruris? | 2006 Mar |
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Update on terbinafine with a focus on dermatophytoses. | 2009 Apr 21 |
|
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