기본 정보
- 표준 SMILES
Clc1ccc(C(Cn2ccnc2)OCc2csc3c(Cl)cccc23)c(Cl)c1- InChIKey
JLGKQTAYUIMGRK-UHFFFAOYSA-N- 분자식
- C20H15Cl3N2OS
- 평균 분자량
- 437.8 g/mol
- 단동위원소 질량
- 435.99706714
개요
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.
이름 및 식별자
- 우선 이름
- Sertaconazole
- IUPAC
- 1-[2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl]imidazole
- 영어명
- Sertaconazole
- 분자식
- C20H15Cl3N2OS
- 분자량
- 437.77
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- CAS
99592-32-2- PubChem CID
- 65863
- DTXSID
DTXSID0048551- ChEMBL
CHEMBL1201196- ChEBI
CHEBI:83682- UNII
- 72W71I16EG
- EC Number
- 841-355-9
- Nikkaji
- J369.930G
물성
구조 계산 물성
- XLogP
- 6.3
- 극성 표면적
- 55.3 Ų
- 수소 결합 공여자 수
- 0
- 수소 결합 수용자 수
- 3
- 회전 가능 결합 수
- 6
- 무거운 원자 수
- 27
- 형식 전하
- 0
- 복잡도
- 488
실험 및 물리화학적 성질
Solubility
Practically insoluble
6.37e-03 g/L
물리화학적 성질
- 녹는점
- 146 · 146-147°
- 끓는 점
- 614.1 · 614.1±55.0 °C(Predicted)
- 밀도
- 1.43 · 1.43±0.1 g/cm3(Predicted)
- 저장 조건
- Refrigerator
- 용해도
- DMSO(약간 용해됨), 메탄올(약간 용해됨)
- 물리적 상태
- 고체
- 산도 계수 (pKa)
- 6.68 · 6.68±0.12(Predicted)
- 색상
- 흰색에서 연한 노란색
- 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
안전 및 규제
GHS 분류
GHS Classification
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.
유해성 정보
독성 정보
Toxicity Summary
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.
안전 데이터
- 신호 어
- Warning
- 유해·위험 문구
- 암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드 H315
화학 및 산업
약리 정보
ATC Code
D - Dermatologicals
G - Genito urinary system and sex hormones
QD - Dermatologicals
QG - Genito urinary system and sex hormones
Pharmacodynamics
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 <i>in vitro</i> activity against <i>Cryptococcus neoformans</i> and <i>Candida spp.</i> Fungistatic activity has also been demonstrated in normal and immunocompromised animal models for systemic and intracranial fungal infections due to <i>Cryptococcus neoformans</i> and for systemic infections due to Candida albicans.
Mechanism of Action
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
72W71I16EG
SERTACONAZOLE
Established Pharmacologic Class [EPC] - Azole Antifungal
Chemical Structure [CS] - Azoles
Sertaconazole is an Azole Antifungal.
용도 및 제조
Uses
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 <i>Trichophyton rubrum</i>, <i>Trichophyton mentagrophytes</i>, and <i>Epidermophyton floccosum</i>.
응용 분야
개요Sertaconazole 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.
용도An imidazole antifungal agent, inhibits the synthesis of ergosterol, an essential cell wall component of fungi.
상·하류 제품 정보
상류 원료
공급사50 곳
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