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
名称をさらに表示
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
- 形式電荷
- 0
- 複雑度
- 374
実験および物理化学的性質
LogP
6.6
6.6
Solubility
Slightly soluble (HCl salt)
7.56e-05 g/L
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)
- 水溶解度
- Water: Insoluble
- LogP
- 6.77 · 6.770 (est)
- CAS データベース
- 101828 · 101828-21-1(CAS DataBase Reference)
安全と法規制
毒性情報
Effects During Pregnancy and Lactation
◉ 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
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
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
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.
FDA Pharmacological Classification
91Y494NL0X
BUTENAFINE
Established Pharmacologic Class [EPC] - Benzylamine Antifungal
Chemical Structure [CS] - Benzylamines
Butenafine is a Benzylamine Antifungal.
応用分野
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.
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補足説明
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.
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関連ノート
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