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Details

Stereochemistry ACHIRAL
Molecular Formula C23H27N
Molecular Weight 317.4672
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BUTENAFINE

SMILES

CN(CC1=CC=C(C=C1)C(C)(C)C)CC2=CC=CC3=CC=CC=C23

InChI

InChIKey=ABJKWBDEJIDSJZ-UHFFFAOYSA-N
InChI=1S/C23H27N/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

HIDE SMILES / InChI
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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
MENTAX

Approved Use

MENTAX-TC Cream, 1%, is indicated for the topical treatment of tinea (pityriasis) versicolor due to Malassezia furfur (formerly Pityrosporum orbiculare).

Launch Date

1996
Primary
Butenafine

Approved Use

OTC labeling: Topical treatment of tinea pedis (athlete's foot), tinea cruris (jock itch), and tinea corporis (ringworm)

Launch Date

1996
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse 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
PubMed

PubMed

TitleDatePubMed
Butenafine.
1998 Mar
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
Comparison of in vitro antifungal activities of topical antimycotics launched in 1990s in Japan.
2001 Aug
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
Six novel antimycotics.
2002
A Japanese case of tinea corporis caused by Arthroderma benhamiae.
2002 Apr
Butenafine: an update of its use in superficial mycoses.
2002 Sep
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
An unprecedented rearrangement in collision-induced mass spectrometric fragmentation of protonated benzylamines.
2006 Sep
Fungal toenail infections.
2008 Dec 15
In vitro antifungal activities of luliconazole, a new topical imidazole.
2009
[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
Patents

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
Butenafine HCl shows minimum inhibitory concentrations ranging from 0.03–1.0 ug/mL against 30 isolates representing different dermatophyte species.
Name Type Language
BUTENAFINE
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
BUTENAFINE [MI]
Common Name English
Butenafine [WHO-DD]
Common Name English
BUTENAFINE [VANDF]
Common Name English
butenafine [INN]
Common Name English
Classification Tree Code System Code
NDF-RT N0000007566
Created by admin on Fri Dec 15 15:45:42 GMT 2023 , Edited by admin on Fri Dec 15 15:45:42 GMT 2023
WHO-ATC D01AE23
Created by admin on Fri Dec 15 15:45:42 GMT 2023 , Edited by admin on Fri Dec 15 15:45:42 GMT 2023
NDF-RT N0000175875
Created by admin on Fri Dec 15 15:45:42 GMT 2023 , Edited by admin on Fri Dec 15 15:45:42 GMT 2023
NDF-RT N0000007566
Created by admin on Fri Dec 15 15:45:42 GMT 2023 , Edited by admin on Fri Dec 15 15:45:42 GMT 2023
NCI_THESAURUS C514
Created by admin on Fri Dec 15 15:45:42 GMT 2023 , Edited by admin on Fri Dec 15 15:45:42 GMT 2023
WHO-VATC QD01AE23
Created by admin on Fri Dec 15 15:45:42 GMT 2023 , Edited by admin on Fri Dec 15 15:45:42 GMT 2023
Code System Code Type Description
CAS
101828-21-1
Created by admin on Fri Dec 15 15:45:42 GMT 2023 , Edited by admin on Fri Dec 15 15:45:42 GMT 2023
PRIMARY
DRUG CENTRAL
444
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PRIMARY
MESH
C067594
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PRIMARY
DAILYMED
91Y494NL0X
Created by admin on Fri Dec 15 15:45:42 GMT 2023 , Edited by admin on Fri Dec 15 15:45:42 GMT 2023
PRIMARY
WIKIPEDIA
BUTENAFINE
Created by admin on Fri Dec 15 15:45:42 GMT 2023 , Edited by admin on Fri Dec 15 15:45:42 GMT 2023
PRIMARY
EVMPD
SUB06012MIG
Created by admin on Fri Dec 15 15:45:42 GMT 2023 , Edited by admin on Fri Dec 15 15:45:42 GMT 2023
PRIMARY
EPA CompTox
DTXSID7040657
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PRIMARY
MERCK INDEX
m2791
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PRIMARY Merck Index
INN
6550
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PRIMARY
CHEBI
3238
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PRIMARY
LACTMED
Butenafine
Created by admin on Fri Dec 15 15:45:42 GMT 2023 , Edited by admin on Fri Dec 15 15:45:42 GMT 2023
PRIMARY
PUBCHEM
2484
Created by admin on Fri Dec 15 15:45:42 GMT 2023 , Edited by admin on Fri Dec 15 15:45:42 GMT 2023
PRIMARY
NCI_THESAURUS
C72959
Created by admin on Fri Dec 15 15:45:42 GMT 2023 , Edited by admin on Fri Dec 15 15:45:42 GMT 2023
PRIMARY
DRUG BANK
DB01091
Created by admin on Fri Dec 15 15:45:42 GMT 2023 , Edited by admin on Fri Dec 15 15:45:42 GMT 2023
PRIMARY
RXCUI
47461
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PRIMARY RxNorm
SMS_ID
100000088608
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PRIMARY
ChEMBL
CHEMBL990
Created by admin on Fri Dec 15 15:45:42 GMT 2023 , Edited by admin on Fri Dec 15 15:45:42 GMT 2023
PRIMARY
FDA UNII
91Y494NL0X
Created by admin on Fri Dec 15 15:45:42 GMT 2023 , Edited by admin on Fri Dec 15 15:45:42 GMT 2023
PRIMARY