[(2E)-6,6-dimethylhept-2-en-4-yn-1-yl](methyl)(naphthalen-1-ylmethyl)amine hydrochloride

• ChemBase编号: 73056
• 分子式: C21H26ClN
• 平均质量: 327.89084
• 单一同位素质量: 327.17537752
• SMILES: c1cc2c(cc1)c(ccc2)CN(C/C=C/C#CC(C)(C)C)C.Cl
• Canonical SMILES: CN(Cc1cccc2c1cccc2)C/C=C/C#CC(C)(C)C.Cl
• InChI: InChI=1S/C21H25N.ClH/c1-21(2,3)15-8-5-9-16-22(4)17-19-13-10-12-18-11-6-7-14-20(18)19;/h5-7,9-14H,16-17H2,1-4H3;1H/b9-5+
• InChIKey: BWMISRWJRUSYEX-SZKNIZGXSA-N

名称和登记号

名称

• IUPAC标准名: [(2E)-6,6-dimethylhept-2-en-4-yn-1-yl](methyl)(naphthalen-1-ylmethyl)amine hydrochloride; (6,6-dimethylhept-2-en-4-yn-1-yl)(methyl)(naphthalen-1-ylmethyl)amine hydrochloride
• IUPAC传统名: terbinafine hydrochloride; lamisil hydrochloride
• 别名: trans-N-(6,6-Dimethyl-2-hepten-4-ylyl)-N-methyl-1-naphthylmethylamine 盐酸盐; Terbinafine 盐酸盐; Zabel; Corbinal; Zimig; Terbinafine hydrochloride; Lamisil; Sebifin; mycoCeaze; MycoVa; trans-N-(6,6-Dimethyl-2-hepten-4-ylyl)-N-methyl-1-naphthylmethylamine hydrochloride; Terbinafine hydrochloride; (E)-N,6,6-trimethyl-N-(naphthalen-1-ylmethyl)hept-2-en-4-yn-1-amine hydrochloride; Trebinafine hydrochloride; ({[(2E)-6,6-Dimethylhept-2-en-4-yn-1-yl](methyl)amino}methyl)naphthalene hydrochloride; N-[(2E)-6,6-Dimethyl-2-hepten-4-ynyl]-N-methyl-1-naphthalenemethanamine; trans-N-Methyl-N-(1-naphthylmethyl)-6,6-dimethylhept-2-en-4-ynyl-1-amine; Bramazil; Bramizil; Muzonal; Terbina; Terbine

登记号

• CAS号: 78628-80-5
• MDL号: MFCD00145430
• PubChem SID: 162037976
• PubChem CID: 5282481

理论计算性质

• 质子受体: 1
• 质子供体: 0
• LogD (pH = 5.5): 2.3570302
• LogD (pH = 7.4): 3.9767735
• Log P: 5.527483
• 摩尔折射率: 98.0752 cm^3
• 极化性: 38.508842 Å^3
• 极化表面积: 3.24 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: Methanol
• 外观: White Solid
• 熔点: 195-198°C

安全信息

• 保存条件: -20°C; -20°C Freezer
• 保存注意事项: Irritant
• RTECS编号: QJ8600100
• 欧盟危险性物质标志: 环境危害性(Nature polluting) (N); 刺激性(Irritant) (Xi)
• 联合国危险货物编号: 3077
• 德国WGK号: 3
• 联合国危险货物等级: 9
• 联合国危险货物包装类别(PG): 3
• 危险公开号: 36/37/38-50/53
• 安全公开号: 26-60-61
• GHS危险品标识: GHS07; GHS09
• GHS警示词: Warning
• GHS危险声明: H315-H319-H335-H410
• GHS警示性声明: P261-P273-P305 + P351 + P338-P501
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• RID/ADR: UN 3077 9/PG 3

产品相关信息

• 纯度: ≥98%
• 成盐信息: HCl; hydrochloride
• Empirical Formula (Hill Notation): C21H25N · HCl

详细说明

Selleck Chemicals - S2513

Research Area: Infection
Biological Activity:
Terbinafine hydrochloride (Lamisil) is a hydrochloride salt of terbinafine that is a synthetic allylamine antifungal and a squalene epoxidase inhibitor with an IC50 of 30 nM for Candida albicans. Terbinafine hydrochloride (Lamisil) is highly lipophilic in nature and tends to accumulate in skin, nails, and fatty tissues. Like other allylamines, terbinafine hydrochloride (Lamisil) inhibits ergosterol synthesis by inhibiting squalene epoxidase, an enzyme that is part of the fungal cell membrane synthesis pathway. Because terbinafine hydrochloride (Lamisil) prevents conversion of squalene to lanosterol, ergosterol cannot be synthesized. This is thought to change cell membrane permeability, causing fungal cell lysis. At 90-120 µM, terbinafine exhibits antitumor and antiangiogenic activity by inducing cell cycle arrest at the G0/G1 stage in COLO 205 tumor cells and human vascular endothelia cells. [1][2][3]

Selleck Chemicals - S2557

Research Area: Infection
Biological Activity:
Terbinafine hydrochloride (Lamisil) is a hydrochloride salt of terbinafine that is a synthetic allylamine antifungal and a squalene epoxidase inhibitor with an IC50 of 30 nM for Candida albicans. Terbinafine hydrochloride (Lamisil) is highly lipophilic in nature and tends to accumulate in skin, nails, and fatty tissues. Like other allylamines, terbinafine hydrochloride (Lamisil) inhibits ergosterol synthesis by inhibiting squalene epoxidase, an enzyme that is part of the fungal cell membrane synthesis pathway. Because terbinafine hydrochloride (Lamisil) prevents conversion of squalene to lanosterol, ergosterol cannot be synthesized. This is thought to change cell membrane permeability, causing fungal cell lysis. At 90-120 µM, terbinafine exhibits antitumor and antiangiogenic activity by inducing cell cycle arrest at the G0/G1 stage in COLO 205 tumor cells and human vascular endothelia cells. [1][2][3]

Sigma Aldrich - T8826

Biochem/physiol Actions
Mode of Action: Inhibits squalene epoxidase, preventing biosynthesis of ergosterol.Antimicrobial spectrum: Antifungal and antimycotic. Fungicidal against dermatopytes and some yeasts; fungistatic against Candida albicans.
Terbinafine inhibits squalene monooxygenase thereby blocking the biosynthesis of ergosterol, which is an essential component of fungal cell membranes. The inhibition of squalene monooxygenase also results in the accumulation of squalene. Terbinafine hydrochloride is highly lipophilic and tends to accumulate in skin, nails, and fatty tissues1. It is antifungal and antimycotic. It is fungicidal against dermatopytes and some yeasts and is fungistatic against Candida albicans.
General description
Allylamine derivative.
Application
Terbinafine hydrochloride is a synthetic allylamine antifungal. It is used to treat dermatophyte infections of the toenail/fingernail, ringworm and jock itch1. It is used in adsorption, partition and stability studies2,3.

Toronto Research Chemicals - T107500

An orally active, antimycotic allylamine related to Naftifine. A specfic inhibitor of squalene epoxidase, a key enzyme in fungal ergosterol biosynthesis. Antifungal.

参考文献

• Lee WS et al. Int J Cancer. 2003 Aug 10;106(1)
• Ho PY et al. Int J Cancer. 2004 Aug 10; 111(1):51-9.
• Petranyi, G., et al.: Science, 224, 1239 (1984)
• Ryder, N.S., et al.: Antimicrob. Agents Chemother., 27, 252 (1984)
• Evans, E.G.V., et al.: Br. Med. J., 318, 1031 (1984)