1-{2-[(2-chlorothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl}-1H-imidazole

• ChemBase编号: 880
• 分子式: C16H13Cl3N2OS
• 平均质量: 387.71122
• 单一同位素质量: 385.98141709
• SMILES: Clc1c(C(OCc2ccsc2Cl)Cn2ccnc2)ccc(Cl)c1
• Canonical SMILES: Clc1ccc(c(c1)Cl)C(Cn1ccnc1)OCc1ccsc1Cl
• InChI: InChI=1S/C16H13Cl3N2OS/c17-12-1-2-13(14(18)7-12)15(8-21-5-4-20-10-21)22-9-11-3-6-23-16(11)19/h1-7,10,15H,8-9H2
• InChIKey: QXHHHPZILQDDPS-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 1-{2-[(2-chlorothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl}-1H-imidazole
• IUPAC传统名: trosid; tioconazole
• 商标名: Fungibacid; GyneCure; Gyno-trosyd; Monistat 1; Trosyd; Trosyd AF; Trosyd J; Trosyl; Tz-3; Vagistat; Vagistat-1; Zoniden
• 别名: (±)-Tioconazole; Fungibacid; Gyno-Trosyd; New Straitus U; Trosyd; Trosyl; Vagistat; Vagistat 1; Zoniden; Tioconazol [INN-Spanish]; Tioconazolum [INN-Latin]; Tioconazole; 1-[2-[(2-Chloro-3-thienyl)methoxy]-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole; Thioconazole; Tioconazole; 1-(2-((2-chlorothiophen-3-yl)methoxy)-2-(2,4-dichlorophenyl)-ethyl)imidazole

登记号

• CAS号: 65899-73-2
• EC号: 265-973-8
• MDL号: MFCD00057276
• PubChem SID: 46508604; 160964343
• PubChem CID: 5482

理论计算性质

JChem

• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): 4.7685566
• LogD (pH = 7.4): 5.2330527
• Log P: 5.298762
• 摩尔折射率: 94.5285 cm^3
• 极化性: 36.8694 Å^3
• 极化表面积: 27.05 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: 4.86
• LOG S: -4.37
• 溶解度: 1.65e-02 g/l

分子性质

理化性质

• 疏水性(logP): 4.4

安全信息

• 保存条件: -20°C
• RTECS编号: NI4480000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302-H413
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves

产品相关信息

• 纯度: ≥96.5% (HPLC); 96.5-103.5% (NT); 97%; 98%
• 成盐信息: Free Base
• Empirical Formula (Hill Notation): C16H13Cl3N2OS

详细说明

DrugBank - DB01007

• Drug Groups: approved
• Description: Tioconazole is an antifungal medication of the Imidazole class used to treat infections caused by a fungus or yeast. Tioconazole topical (skin) preparations are also available for ringworm, jock itch, athlete's foot, and tinea versicolor or "sun fungus". Tioconazole interacts with 14-alpha demethylase, a cytochrome P-450 enzyme that converts lanosterol to ergosterol, an essential component of the yeast membrane. In this way, tioconazole inhibits ergosterol synthesis, resulting in increased cellular permeability.
• Indication: For the local treatment of vulvovaginal candidiasis (moniliasis).
• Pharmacology: Tioconazole is a broad-spectrum imidazole antifungal agent that inhibits the growth of human pathogenic yeasts. Tioconazole exhibits fungicidal activity in vitro against Candida albicans, other species of the genus Candida, and against Torulopsis glabrata. Tioconazole prevents the growth and function of some fungal organisms by interfering with the production of substances needed to preserve the cell membrane. This drug is effective only for infections caused by fungal organisms. It will not work for bacterial or viral infections.
• Toxicity: Symptoms of overdose include erythema, stinging, blistering, peeling, edema, pruritus, urticaria, burning,; and general irritation of the skin, and cramps.
• Affected Organisms: Yeast and other fungi
• Biotransformation: Orally administered tioconazole is extensively metabolized. The major metabolites are glucuronide conjugates.
• Absorption: Systemic absorption following a single intravaginal application of tioconazole in nonpregnant patients is negligible.
• External Links: Wikipedia; RxList; Drugs.com

Selleck Chemicals - S1910

Research Area: Infection
Biological Activity:

Sigma Aldrich - 03907

Application
Tioconazole is an antifungal medication of the imidazole class used to treat infections caused by fungus and yeast. It is used to study the synergistic mechanisms of antifungals on Candida albicans 1 as well as significant drug-drug interactions in vivo2.
Biochem/physiol Actions
Tioconazole is an antifungal that is more active than fluconazole or voriconazole against Candida glabrata mutant strains.3 Its mechanism of action is through membrane disruption and loss of intracellular ATP.4

Toronto Research Chemicals - T444680

Tioconazole is an antifungal that is more active than Fluconazole (F421000) or Voriconazole (V760000) against Candida glabrata mutant strains. Antifungal (topical).

参考文献

• Jevons, S., et al.: Antimicrob. Agents Chemother., 15, 597 (1979)
• Clayton, Y.M., et al.: Clin. Exp. Dermatol., 7, 543 (1979)
• Marriott, M.S., et al.: Dermatologica, 166, 1 (1979)