Butenafine

HCID 2484CAS 101828-21-1

Grundinformationen

Standard-SMILES
CN(Cc1ccc(C(C)(C)C)cc1)Cc1cccc2ccccc12
InChIKey
ABJKWBDEJIDSJZ-UHFFFAOYSA-N
Summenformel
C23H27N
Durchschnittliche Molmasse
317,5 g/mol
Monoisotopische Masse
317,21434987

Namen und Bezeichner

Bevorzugter Name
Butenafine
IUPAC
1-(4-tert-butylphenyl)-N-methyl-N-(naphthalen-1-ylmethyl)methanamine
Englischer Name
Butenafine
Summenformel
C23H27N
Molmasse
317.47

Namen und Synonyme

butenafine101828-21-1ButenafinaButenafinumN-(p-tert-Butylbenzyl)-N-methyl-1-naphthalenemethylamineDTXSID704065791Y494NL0X4-tert-butylbenzyl(methyl)(1-naphthalenemethyl)amineCHEBI:3238DTXCID5020657(4-tert-Butyl-benzyl)-methyl-naphthalen-1-ylmethyl-amine(4-tert-butylphenyl)-N-methyl-N-(naphthalen-1-ylmethyl)methanamine
Weitere Namen anzeigen
But·NafineButenafine USP/EP/BP4-tert-Butylbenzylmethyl 1-naphtylmethylamine(4-tert-butylbenzyl)-methyl-(1-naphthylmethyl)amineN-methyl-N-(4-methylbenzyl)-N-(1-naphthylmethyl)amineN-(4-tert-Butylbenzyl)-N-methyl-1-naphthalenemethanaminen-methyl-n-(naphthalen-1-ylmethyl)-1-(4-tert-butylphenyl)methanamine
((4-tert-butylphenyl)methyl)(methyl)(naphthalen-1-ylmethyl)amine[(4-tert-butylphenyl)methyl](methyl)(naphthalen-1-ylmethyl)amineRefChem:54581D01AE23Butenafine [INN]Butenafina [INN-Spanish]Butenafinum [INN-Latin]1-(4-tert-butylphenyl)-N-methyl-N-(naphthalen-1-ylmethyl)methanamine

Datenbank-Bezeichner

CAS
101828-21-1
PubChem CID
2484
DTXSID
DTXSID7040657
ChEMBL
CHEMBL990
ChEBI
CHEBI:3238
UNII
91Y494NL0X
Nikkaji
J276.436I

Eigenschaften

Berechnete Struktureigenschaften

XLogP
6,3
Polarare Oberfläche (TPSA)
3,2 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
1
Frei drehbare Bindungen
5
Schwere Atome
24

Experimentelle und physikochemische Eigenschaften

LogP · 2 Einträge

6.6

6.6

Solubility · 2 Einträge

Slightly soluble (HCl salt)

7.56e-05 g/L

Physical DescriptionSolid

Physikochemische Eigenschaften

Schmelzpunkt
200 · 200-202 °C
Siedepunkt
426.1 · 426.1±14.0 °C(Predicted)
Dichte
1.032 · 1.032±0.06 g/cm3(Predicted)
storage temp.
-20 °C · Store at -20°C
Löslichkeit
63 mg/mL · DMSO: 63 mg/mL (198.44 mM);Ethanol: 63 mg/mL (198.44 mM)
pka
7.87 · 7.87±0.50(Predicted)

Sicherheit und Regulatorisches

Toxikologische Informationen

Effects During Pregnancy and Lactation · 1 Eintrag

◉ Summary of Use during Lactation;Topical butenafine has not been studied during breastfeeding. Because it is poorly absorbed after topical application, it is not likely to reach the bloodstream of the infant or cause any adverse effects in breastfed infants. Ensure that the infant's skin does not come into direct contact with the areas of skin that have been treated. Only water-miscible cream or gel products should be applied to the breast because ointments may expose the infant to high levels of mineral paraffins via licking.;◉ Effects in Breastfed Infants;Relevant published information was not found as of the revision date.;◉ Effects on Lactation and Breastmilk;Relevant published information was not found as of the revision date.

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

D - Dermatologicals;D01 - Antifungals for dermatological use;D01A - Antifungals for topical use;D01AE - Other antifungals for topical use;D01AE23 - Butenafine

QD - Dermatologicals;QD01 - Antifungals for dermatological use;QD01A - Antifungals for topical use;QD01AE - Other antifungals for topical use;QD01AE23 - Butenafine

Pharmacodynamics · 1 Eintrag

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 <i>Candida albicans</i> and this activity is superior to that of terbinafine and naftifine. Butenafine also generates low MICs for <i>Cryptococcus neoformans</i> and <i>Aspergillus spp.</i> as well.

Mechanism of Action · 1 Eintrag

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.

Biological Half-LifeFollowing 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.
Metabolism/MetabolitesThe primary metabolite in urine was formed through hydroxylation at the terminal <i>t</i>-butyl side-chain.
FDA Pharmacological Classification · 5 Einträge

91Y494NL0X

BUTENAFINE

Established Pharmacologic Class [EPC] - Benzylamine Antifungal

Chemical Structure [CS] - Benzylamines

Butenafine is a Benzylamine Antifungal.

Anwendungen · 1 Eintrag

VerwendenButenafine (Mentax) is a synthetic benzylamine antifungal agent, related structurally and pharmacologically to terbinafine. It is thought to act by inhibiting the enzyme squalene 2,3-epoxidase, resulting in decreased ergosterol and corresponding increase in squalene, with subsequent cell membrane permeability alteration and cell death. It is active against dermatophytes, yeast, and Sporothrix.

Anbieter50 Anbieter

北京华美互利生物化工010-56205725 · [email protected]
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]
广州隽沐生物科技股份有限公司020-36607679; 13502246435 · [email protected]
陕西缔都化学有限公司029-029-81123119 17391733320 · [email protected]
LGM Pharma1-(800)-881-8210 · [email protected]
Ergänzende Hinweise · 1 Eintrag

DefinitionChEBI: Trimethylamine in which hydrogen atoms attached to different methyl groups are substituted by 1-naphthyl and 4-tert-butylphenyl groups. It is an inhibitor of squalene epoxidase, an enzyme responsible for the creation of sterols needed in funga cell membranes, and is used as its hydrochloride salt for treatment of dermatological fungal infections.

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