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Namespace Prefixes

PrefixIRI
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Statements

Subject Item
n2:DB01091
rdf:type
n3:Drug
n3:description
Butenafine hydrochloride is a synthetic benzylamine antifungal agent. Butenafine works by inhibiting the synthesis of sterols by inhibiting squalene epoxidase, an enzyme responsible for the creation of sterols needed in fungal cell membranes.
n3:dosage
n29:271B64B2-363D-11E5-9242-09173F13E4C5
n3:generalReferences
# McNeely W, Spencer CM: Butenafine. Drugs. 1998 Mar;55(3):405-12; discussion 413. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/9530545 # Singal A: Butenafine and superficial mycoses: current status. Expert Opin Drug Metab Toxicol. 2008 Jul;4(7):999-1005. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/18624686 # Gupta AK: Butenafine: an update of its use in superficial mycoses. Skin Therapy Lett. 2002 Sep;7(7):1-2, 5. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/12432425 # Mingeot-Leclercq MP, Gallet X, Flore C, Van Bambeke F, Peuvot J, Brasseur R: Experimental and conformational analyses of interactions between butenafine and lipids. Antimicrob Agents Chemother. 2001 Dec;45(12):3347-54. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/11709307 # Syed TA, Maibach HI: Butenafine hydrochloride: for the treatment of interdigital tinea pedis. Expert Opin Pharmacother. 2000 Mar;1(3):467-73. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/11249531 # Reyes BA, Beutner KR, Cullen SI, Rosen T, Shupack JL, Weinstein MB: Butenafine, a fungicidal benzylamine derivative, used once daily for the treatment of interdigital tinea pedis. Int J Dermatol. 1998 Jun;37(6):450-3. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/9646136 # Iwatani W, Arika T, Yamaguchi H: Two mechanisms of butenafine action in Candida albicans. Antimicrob Agents Chemother. 1993 Apr;37(4):785-8. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/8494375
n3:group
approved
n3:halfLife
Following topical application, a biphasic decline of plasma butenafine concentrations was observed with the half-lives estimated to be 35 hours initial and over 150 hours terminal.
n3:indication
For the topical treatment of the following dermatologic infections: tinea (pityriasis) versicolor due to <i>M. furfur</i>, interdigital tinea pedis (athlete&rsquo;s foot), tinea corporis (ringworm) and tinea cruris (jock itch) due to <i>E. floccosum</i>, <i>T. mentagrophytes</i>, <i>T. rubrum</i>, and <i>T. tonsurans</i>.
owl:sameAs
n26:DB01091 n28:DB01091
dcterms:title
Butenafine
adms:identifier
n8:C08067 n9:0378-6151-46 n10:DB01091 n14:3238 n15:2390 n16:46506191 n19:2484 n21:PA164745478 n23:Butenafine
n3:mechanismOfAction
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.
n3:packager
n20:271B64AC-363D-11E5-9242-09173F13E4C5 n20:271B64AD-363D-11E5-9242-09173F13E4C5 n20:271B64AB-363D-11E5-9242-09173F13E4C5
n3:patent
n22:5021458
n3:synonym
Butenafine 4-Tert-butylbenzyl(methyl)(1-naphthalenemethyl)amine (4-Tert-butyl-benzyl)-methyl-naphthalen-1-ylmethyl-amine (4-Tert-butylphenyl)-N-methyl-N-(naphthalen-1-ylmethyl)methanamine Butenafinum N-(P-Tert-butylbenzyl)-N-methyl-1-naphthalenemethylamine Butenafina
n3:salt
n3:synthesisReference
"DrugSyn.org":http://www.drugsyn.org/Butenafine.htm
n12:hasConcept
n13:M0185247
foaf:page
n18:butenafine-cream.html n27:butenafine.htm
n3:IUPAC-Name
n4:271B64B7-363D-11E5-9242-09173F13E4C5
n3:InChI
n4:271B64BD-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n4:271B64BC-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n4:271B64B9-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n4:271B64BA-363D-11E5-9242-09173F13E4C5
n3:SMILES
n4:271B64BB-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n4:271B64B5-363D-11E5-9242-09173F13E4C5 n4:271B64CC-363D-11E5-9242-09173F13E4C5
n3:logP
n4:271B64B3-363D-11E5-9242-09173F13E4C5 n4:271B64B6-363D-11E5-9242-09173F13E4C5 n4:271B64CD-363D-11E5-9242-09173F13E4C5
n3:logS
n4:271B64B4-363D-11E5-9242-09173F13E4C5
n5:hasATCCode
n6:D01AE23
n3:H-Bond-Acceptor-Count
n4:271B64C3-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n4:271B64C4-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n4:271B64BE-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n4:271B64BF-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n4:271B64C1-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n4:271B64C0-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n4:271B64C2-363D-11E5-9242-09173F13E4C5
n3:absorption
The total amount absorbed through the skin into the systemic circulation has not been quantified.
n3:affectedOrganism
Fungi
n3:casRegistryNumber
101828-21-1
n3:category
n3:containedIn
n24:271B64B0-363D-11E5-9242-09173F13E4C5 n24:271B64B1-363D-11E5-9242-09173F13E4C5 n24:271B64AE-363D-11E5-9242-09173F13E4C5 n24:271B64AF-363D-11E5-9242-09173F13E4C5
n3:Bioavailability
n4:271B64C8-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n4:271B64CA-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n4:271B64CB-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n4:271B64C7-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n4:271B64C6-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n4:271B64C9-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n4:271B64B8-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n4:271B64C5-363D-11E5-9242-09173F13E4C5