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チオコナゾール

Tioconazole

HCID 5482
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
65899-73-2
標準SMILES
Clc1ccc(C(Cn2ccnc2)OCc2ccsc2Cl)c(Cl)c1
InChIKey
QXHHHPZILQDDPS-UHFFFAOYSA-N
分子式
C16H13Cl3N2OS
平均分子量
387.7 g/mol
単同位体質量
385.98141708

概要

1-{2-[(2-chloro-3-thienyl)methoxy]-2-(2,4-dichlorophenyl)ethyl}imidazole is a member of the class of imidazoles that comprises 2-(2,4-dichlorophenyl)ethylimidazole carrying an additional (2-chloro-3-thienyl)methoxy substituent at position 2. It is a dichlorobenzene, a member of imidazoles, an ether and a member of thiophenes.

名称と識別子

優先名称
Tioconazole
IUPAC
1-[2-[(2-chlorothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl]imidazole
現地名
チオコナゾール
英語名
Vagistat
分子式
C16H13Cl3N2OS
分子量
387.71

名称と別名

tioconazole65899-73-2VagistatVagistat-1TrosydTrosylTioconazolTioconazolumUK-203491-(2-((2-chlorothiophen-3-yl)methoxy)-2-(2,4-dichlorophenyl)ethyl)-1H-imidazole(+-)-TioconazoleDTXSID3046619
名称をさらに表示
1-[2,4-ジクロロ-β-[(2-クロロ-3-テニル)オキシ]フェネチル]-1H-イミダゾール1-[2,4-ジクロロ-β-[(2-クロロ-3-チエニル)メチルオキシ]フェネチル]-1H-イミダゾールチオコナゾール1-[β-[(2-クロロ-3-チエニル)メトキシ]-2,4-ジクロロフェネチル]-1H-イミダゾール1-(1H-イミダゾール-1-イル)-2-(2,4-ジクロロフェニル)-2-[(2-クロロ-3-チエニル)メトキシ]エタンチオコナゾール (JAN)1-{2-[(2-クロロチオフェン-3-イル)メトキシ]-2-(2,4-ジクロロフェニル)エチル}-1H-イミダゾール1-[(S)-β-[(2-クロロ-3-チエニル)メチルオキシ]-2,4-ジクロロフェネチル]-1H-イミダゾール(S)-チオコナゾール1-[(2S)-2-[(2-クロロチオフェン-3-イル)メトキシ]-2-(2,4-ジクロロフェニル)エチル]-1H-イミダゾールZonidenFungibacidVagistat 1ioconazoleGyno-Trosyd
UK 20349UK-20,349NSC-759169S57Y5X1117(+-)-1-(2,4-Dichloro-beta-((2-chloro-3-ethenyl)oxy)phenethyl)imidazoleDTXCID10266191H-Imidazole, 1-(2-((2-chloro-3-thienyl)methoxy)-2-(2,4-dichlorophenyl)ethyl)-1-{2-[(2-chlorothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl}-1H-imidazole

物性

構造計算による物性

XLogP
5.3
極性表面積
55.3 Ų
水素結合供与体数
0
水素結合受容体数
3
回転可能結合数
6
重原子数
23
形式電荷
0
複雑度
379

実験および物理化学的性質

LogP4.4
Solubility1.65e-02 g/L
Human Drugs · 3 件

Breast Feeding; Lactation; Anti-Infective Agents; Antifungal Agents; Dermatologic Agents;

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Physical DescriptionSolid
Collision Cross Section · 2 件

180.7 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

179.43 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

物理化学的性質

融点
79 · 79-81oC
沸点
534.5 · 534.5±50.0 °C(Predicted)
比重(密度)
1.3115 · 1.3115 (rough estimate)
屈折率
1.6 · 1.6000 (estimate)
貯蔵温度
Keep in dark place,Inert atmosphere,Room temperature
溶解性
水に極めて溶けにくく、塩化メチレンに極めて溶けやすく、アルコールに溶けやすい。
外見
粉
酸解離定数(Pka)

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 4 件

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P261, P264, P270, P272, P273, P280, P301+P317, P302+P352, P318, P321, P330, P333+P317, P362+P364, P391, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 100 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Hazard Classes and CategoriesAcute Tox. 4 (100%)

毒性情報

Exposure RoutesSystemic absorption following a single intravaginal application of tioconazole in nonpregnant patients is negligible.
Toxicity Summary · 1 件

Tioconazole interacts with 14-α 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. Tioconazole may also inhibit endogenous respiration, interact with membrane phospholipids, inhibit the transformation of yeasts to mycelial forms and the uptake of purine, impair triglyceride and/or phospholipid biosynthesis, and inhibit the movement of calcium and potassium ions across the cell membrane by blocking the ion transport pathway known as the Gardos channel.

Signs and SymptomsSymptoms of overdose include erythema, stinging, blistering, peeling, edema, pruritus, urticaria, burning, and general irritation of the skin, and cramps.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

化学と産業

薬理情報

ATC Code · 4 件

D - Dermatologicals

G - Genito urinary system and sex hormones

QG - Genito urinary system and sex hormones

QD - Dermatologicals

Pharmacodynamics · 1 件

Tioconazole is a broad-spectrum imidazole antifungal agent that inhibits the growth of human pathogenic yeasts. Tioconazole exhibits fungicidal activity in vitro against <i>Candida albicans</i>, other species of the genus Candida, and against <i>Torulopsis glabrata</i>. Tioconazole prevents the growth and function of some fungal organisms by interfering with the production of substances needed to preserve the cell membrane. In addition to its broad spectrum antifungal effects with tioconazole being effective against commonly occurring dermatophyte and yeast-like fungal species, tioconazole also has antibacterial effects on certain Gram-positive cocci bacteria.

Mechanism of Action · 1 件

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. Tioconazole may also inhibit endogenous respiration, interact with membrane phospholipids, inhibit the transformation of yeasts to mycelial forms and the uptake of purine, impair triglyceride and/or phospholipid biosynthesis, and inhibit the movement of calcium and potassium ions across the cell membrane by blocking the ion transport pathway known as the Gardos channel.

Metabolism/Metabolites · 2 件

Orally administered tioconazole is extensively metabolized. The major metabolites are glucuronide conjugates.

Orally administered tioconazole is extensively metabolized. The major metabolites are glucuronide conjugates.

FDA Pharmacological Classification · 6 件

S57Y5X1117

TIOCONAZOLE

Established Pharmacologic Class [EPC] - Azole Antifungal

Chemical Structure [CS] - Azoles

Tioconazole is an Azole Antifungal.

TIOCONAZOLE

関連反応

3 件
反応記録を作成
HRID 1265340 の反応式
HRID 1265340生成物としてuspto-grants-2003_04
HRID 1265341 の反応式
HRID 1265341生成物としてuspto-grants-2003_04
HRID 1265342 の反応式
HRID 1265342生成物としてuspto-grants-2003_04

化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート

データベース識別子

CAS
65899-73-2
PubChem CID
5482
DTXSID
DTXSID3046619
ChEMBL
CHEMBL1200438
ChEBI
CHEBI:77898
UNII
S57Y5X1117
EC Number
265-973-8
Nikkaji
J3.525D
6.66 · 6.66±0.12(Predicted)
色
ホワイトからオフホワイト
化粧品成分の機能
抗菌剤
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
SMILES
C1N(CC(OCC2C=CSC=2Cl)C2=CC=C(Cl)C=C2Cl)C=CN=1
CAS データベース
65899 · 65899-73-2(CAS DataBase Reference)

化学的性質

化学的特性White powder EINECS: 265-973-8

Effects During Pregnancy and Lactation
◉ Summary of Use during Lactation

安全データ

wgk
3
ridadr
UN3077
hs_code
2934990002
risk_code
22
hazard_code
Xn
hazard_class
9
Hazard Classifications
Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Repr. 2Skin Sens. 1
ストレージクラス
11 - Combustible Solids
MeSH Pharmacological Classification · 2 件

Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues.

Compounds that specifically inhibit STEROL 14-DEMETHYLASE. A variety of azole-derived ANTIFUNGAL AGENTS act through this mechanism.

Absorption, Distribution and ExcretionSystemic absorption following a single intravaginal application of tioconazole in nonpregnant patients is negligible.
Cellular LocationsCytoplasm

用途と製造

UsesFor the local treatment of vulvovaginal candidiasis (moniliasis).

応用分野

説明Tioconazole is an antifungal agent, closely related to miconazole. Tioconazole is effective in the topical treatment of superficial fungal infections and appears to be more potent than miconazole against Candida and Trichophyton species.

使用antithrombotic

上流・下流製品情報

上流原料

2-クロロ-3-(クロロメチル)チオフェン水素化ナトリウム1-(2,4-ジクロロフェニル)-2-(1-イミダゾリル)エタノール

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補足説明

定義ChEBI: A member of the class of imidazoles that comprises 2-(2,4-dichlorophenyl)ethylimidazole carrying an additional (2-chloro-3-thienyl)methoxy substituent at position 2.