ブテナフィン

Butenafine

HCID 2484CAS 101828-21-1

基本情報

標準SMILES
CN(Cc1ccc(C(C)(C)C)cc1)Cc1cccc2ccccc12
InChIKey
ABJKWBDEJIDSJZ-UHFFFAOYSA-N
分子式
C23H27N
平均分子量
317.5 g/mol
単同位体質量
317.21434987

名称と識別子

優先名称
Butenafine
IUPAC
1-(4-tert-butylphenyl)-N-methyl-N-(naphthalen-1-ylmethyl)methanamine
現地名
ブテナフィン
英語名
Butenafine
分子式
C23H27N
分子量
317.47

名称と別名

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
名称をさらに表示
ブテナフィン4-(tert-ブチル)-N-メチル-N-(1-ナフチルメチル)ベンゼンメタンアミン4-tert-ブチルベンジルメチル1-ナフチルメチルアミン(4-tert-ブチルベンジル)(メチル)(1-ナフチルメチル)アミンN-(4-tert-ブチルベンジル)-N-メチル-1-ナフタレンメタンアミンN-4-三級ブチルベンジル-N-メチル-1-ナフタレンメチルアミン4-tert-ブチル-N-メチル-N-[(ナフタレン-1-イル)メチル]アニリン1-[[(4-tert-ブチルフェニル)(メチル)アミノ]メチル]ナフタレン[(4-tert-ブチルフェニル)メチル](メチル)[(ナフタレン-1-イル)メチル]アミン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

データベース識別子

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

物性

構造計算による物性

XLogP
6.3
極性表面積
3.2 Ų
水素結合供与体数
0
水素結合受容体数
1
回転可能結合数
5
重原子数
24

実験および物理化学的性質

LogP · 2 件

6.6

6.6

Solubility · 2 件

Slightly soluble (HCl salt)

7.56e-05 g/L

Physical DescriptionSolid

物理化学的性質

融点
200 · 200-202 °C
沸点
426.1 · 426.1±14.0 °C(Predicted)
比重(密度)
1.032 · 1.032±0.06 g/cm3(Predicted)
貯蔵温度
-20 °C · Store at -20°C
溶解性
63 mg/mL · DMSO: 63 mg/mL (198.44 mM);Ethanol: 63 mg/mL (198.44 mM)
酸解離定数(Pka)
7.87 · 7.87±0.50(Predicted)

安全と法規制

毒性情報

Effects During Pregnancy and Lactation · 1 件

◉ 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.

化学と産業

薬理情報

ATC Code · 2 件

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 件

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 件

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 件

91Y494NL0X

BUTENAFINE

Established Pharmacologic Class [EPC] - Benzylamine Antifungal

Chemical Structure [CS] - Benzylamines

Butenafine is a Benzylamine Antifungal.

応用分野 · 1 件

使用Butenafine (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.

サプライヤー50 社

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]
補足説明 · 1 件

定義ChEBI: 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.

関連反応

3 件

関連ノート

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