Sertaconazole (HCID 65863)

概要

1-{2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl}imidazole is a member of the class of imidazoles that carries a 2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl group at position 1. It is a dichlorobenzene, a member of imidazoles, an ether and a member of 1-benzothiophenes.

名称と識別子

優先名称: Sertaconazole
IUPAC: 1-[2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl]imidazole
現地名: セルタコナゾール
英語名: Sertaconazole
分子式: C20H15Cl3N2OS
分子量: 437.77

名称と別名

Sertaconazole99592-32-2SertaconazolSertaconazolumFI-7045Demofix72W71I16EG1-(2-((7-Chlorobenzo(b)thien-3-yl)methoxy)-2-(2,4-dichlorophenyl)ethyl)-1H-imidazole1-{2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl}-1H-imidazole7-Chloro-3-(1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxy-methyl)benzo(b)thiopheneDTXSID0048551Ginedermofix

名称をさらに表示

1-[2-[(7-クロロベンゾ[b]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-イミダゾールセルタコナゾール7-クロロ-3-[[1-(2,4-ジクロロフェニル)-2-(1H-イミダゾール-1-イル)エトキシ]メチル]-1-ベンゾチオフェン1-[β-[(7-クロロベンゾ[b]チオフェン-3-イル)メトキシ]-2,4-ジクロロフェネチル]-1H-イミダゾール1-{2-[(7-クロロ-1-ベンゾチオフェン-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Sertaconazole nitrateeno(RS)-1-(2-((7-chloro-1-benzothiophen-3-yl)methoxy)-2-(2,4-dichlorophenyl)ethyl) -1H-imidazoleZalainFI-7056DermofixEnolase γ

1H-Imidazole, 1-(2-((7-chlorobenzo(b)thien-3-yl)methoxy)-2-(2,4-dichlorophenyl)ethyl)-7-Chloro-3-[1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxy-methyl]benzo[b]thiophene1-(2-((7-chloro-1-benzothiophen-3-yl)methoxy)-2-(2,4-dichlorophenyl)ethyl)-1H-imidazole1H-Imidazole, 1-[2-[(7-chlorobenzo[b]thien-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl]-RefChem:56490DTXCID6028107CHEBI:82866D01AC14

データベース識別子

CAS: 99592-32-2
PubChem CID: 65863
DTXSID: DTXSID0048551
ChEMBL: CHEMBL1201196
ChEBI: CHEBI:83682
UNII: 72W71I16EG
EC Number: 841-355-9
Nikkaji: J369.930G

物性

構造計算による物性

XLogP: 6.3
極性表面積: 55.3 Å²
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: 27
形式電荷: 0
複雑度: 488

実験および物理化学的性質

DrugsPharmaceuticals

LogP6.2

Solubility · 2 件

Practically insoluble

6.37e-03 g/L

Endocrine DisruptorsPotential endocrine disrupting compound

Physical DescriptionSolid

物理化学的性質

融点: 146 · 146-147°
沸点: 614.1 · 614.1±55.0 °C(Predicted)
比重(密度): 1.43 · 1.43±0.1 g/cm3(Predicted)
貯蔵温度: Refrigerator
溶解性: DMSO（微量）、メタノール（微量）
外見: 個体
酸解離定数(Pka): 6.68 · 6.68±0.12(Predicted)
色: 白色～淡黄色
InChI: InChI=1S/C20H15Cl3N2OS/c21-14-4-5-16(18(23)8-14)19(9-25-7-6-24-12-25)26-10-13-11-27-20-15(13)2-1-3-17(20)22/h1-8,11-12,19H,9-10H2
InChIKey: JLGKQTAYUIMGRK-UHFFFAOYSA-N
SMILES: C1N(CC(OCC2=CSC3=C(Cl)C=CC=C32)C2=CC=C(Cl)C=C2Cl)C=CN=1
CAS データベース: 99592 · 99592-32-2(CAS DataBase Reference)

安全と法規制

GHS分類

GHS Classification · 4 件

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

危険有害性情報

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

毒性情報

Exposure RoutesBioavailability is negligible.

Toxicity Summary · 1 件

Sertaconazole interacts with 14-α demethylase, a cytochrome P-450 enzyme necessary to convert lanosterol to ergosterol. 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. Sertaconazole may also inhibit endogenous respiration, interact with membrane phospholipids, inhibit the transformation of yeasts to mycelial forms, inhibit purine uptake, and impair triglyceride and/or phospholipid biosynthesis.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

安全データ

危険有害性情報: コード危険有害性情報危険有害性クラス区分注意喚起語シンボル P コード H315

化学と産業

薬理情報

ATC Code · 4 件

D - Dermatologicals

G - Genito urinary system and sex hormones

QD - Dermatologicals

QG - Genito urinary system and sex hormones

Protein Binding>99% to plasma

Pharmacodynamics · 1 件

Sertaconazole is an imidazole/triazole type antifungal agent. Sertaconazole is a highly selective inhibitor of fungal cytochrome P-450 sterol C-14 α-demethylation via the inhibition of the enzyme cytochrome P450 14α-demethylase. This enzyme converts lanosterol to ergosterol, and is required in fungal cell wall synthesis. The subsequent loss of normal sterols correlates with the accumulation of 14 α-methyl sterols in fungi and may be partly responsible for the fungistatic activity of fluconazole. Mammalian cell demethylation is much less sensitive to fluconazole inhibition. Sertaconazole exhibits in vitro activity against Cryptococcus neoformans and Candida spp. Fungistatic activity has also been demonstrated in normal and immunocompromised animal models for systemic and intracranial fungal infections due to Cryptococcus neoformans and for systemic infections due to Candida albicans.

Mechanism of Action · 1 件

Sertaconazole interacts with 14-α demethylase, a cytochrome P-450 enzyme necessary to convert lanosterol to ergosterol. 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. Sertaconazole may also inhibit endogenous respiration, interact with membrane phospholipids, inhibit the transformation of yeasts to mycelial forms, inhibit purine uptake, and impair triglyceride and/or phospholipid biosynthesis.

FDA Pharmacological Classification · 5 件

72W71I16EG

SERTACONAZOLE

Established Pharmacologic Class [EPC] - Azole Antifungal

Chemical Structure [CS] - Azoles

Sertaconazole is an Azole Antifungal.

MeSH Pharmacological ClassificationSubstances 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.

用途と製造

Uses · 2 件

Use (kg; approx.) in Germany (2009): >100

For the topical treatment of interdigital tinea pedis in immunocompetent patients 12 years of age and older, caused by Trichophyton rubrum, Trichophyton mentagrophytes, and Epidermophyton floccosum.

応用分野 · 2 件

説明Sertaconazole has been developed and launched for the treatment of dermatological fungal infections by Ferrer Internacional S. A. Mylan received FDA approval for sertaconazole nitrate cream for the treatment of athlete's foot (tinea pedis) at the end of 2003.

使用An imidazole antifungal agent, inhibits the synthesis of ergosterol, an essential cell wall component of fungi.

上流・下流製品情報

上流原料

ベンゾ[b]チオフェン水素化ナトリウムヘキサメチルりん酸トリアミドシリカゲル 2-bromomethylbenzene

サプライヤー50 社

北京华美互利生物化工010-56205725 · [email protected]

杭州品高化工有限公司0571-87658025 · [email protected]

普善实业（陕西）有限公司029-81310890 18165209495 · [email protected]

T&W GROUP021-61551611 13296011611 · [email protected]

Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]

セルタコナゾール

基本情報

概要