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Tioconazole

HCID 5482
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
65899-73-2
표준 SMILES
Clc1ccc(C(Cn2ccnc2)OCc2ccsc2Cl)c(Cl)c1
InChIKey
QXHHHPZILQDDPS-UHFFFAOYSA-N
분자식
C16H13Cl3N2OS
평균 분자량
387.7 g/mol
단동위원소 질량
385.98141708

개요

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.

이름 및 식별자

우선 이름
Tioconazole
IUPAC
1-[2-[(2-chlorothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl]imidazole
영어명
Vagistat
분자식
C16H13Cl3N2OS
분자량
387.71

이름 및 동의어

tioconazole65899-73-2VagistatVagistat-1TrosydTrosylTioconazolTioconazolumUK-203491-(2-((2-chlorothiophen-3-yl)methoxy)-2-(2,4-dichlorophenyl)ethyl)-1H-imidazole(+-)-TioconazoleDTXSID3046619
이름 더 보기
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

데이터베이스 식별자

CAS
65899-73-2
PubChem CID
5482
DTXSID
DTXSID3046619
ChEMBL
CHEMBL1200438
ChEBI
CHEBI:77898
UNII
S57Y5X1117
EC Number
265-973-8
Nikkaji
J3.525D

물성

구조 계산 물성

XLogP
5.3
극성 표면적
55.3 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
3
회전 가능 결합 수
6
무거운 원자 수
23
형식 전하
0
복잡도
379

실험 및 물리화학적 성질

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

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 · 2건

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]

물리화학적 성질

녹는점
79 · 79-81oC
끓는 점
534.5 · 534.5±50.0 °C(Predicted)
밀도
1.3115 · 1.3115 (rough estimate)
굴절률
1.6 · 1.6000 (estimate)
저장 조건
Keep in dark place,Inert atmosphere,Room temperature
용해도
물에 아주 약간 용해되고, 염화메틸렌에 매우 용해되며, 알코올에는 잘 용해됩니다.
물리적 상태
가루

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 4건

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.

유해성 정보

Hazard Classes and CategoriesAcute Tox. 4 (100%)

독성 정보

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

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).

화학 및 산업

약리 정보

ATC Code · 4건

D - Dermatologicals

G - Genito urinary system and sex hormones

QG - Genito urinary system and sex hormones

QD - Dermatologicals

Pharmacodynamics · 1건

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 · 1건

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 · 2건

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 · 6건

S57Y5X1117

TIOCONAZOLE

Established Pharmacologic Class [EPC] - Azole Antifungal

Chemical Structure [CS] - Azoles

Tioconazole is an Azole Antifungal.

TIOCONAZOLE

관련 반응

3건
반응 기록 만들기
HRID 1265340 반응식
HRID 1265340생성물로uspto-grants-2003_04
HRID 1265341 반응식
HRID 1265341생성물로uspto-grants-2003_04
HRID 1265342 반응식
HRID 1265342생성물로uspto-grants-2003_04

화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
산도 계수 (pKa)
6.66 · 6.66±0.12(Predicted)
색상
흰색에서 황백색까지
화장품 원료 기능
항균
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

화학적 성질

White powder EINECS: 265-973-8

Effects During Pregnancy and Lactation
◉ Summary of Use during Lactation

안전 데이터

wgk
3
ridadr
UN3077
HS 번호
2934990002
risk_code
22
hazard_code
Xn
위험 등급
9
Hazard Classifications
Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Repr. 2Skin Sens. 1
스토리지 클래스
11 - Combustible Solids
MeSH Pharmacological Classification · 2건

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

용도 및 제조

UsesFor the local treatment of vulvovaginal candidiasis (moniliasis).

응용 분야

개요Tioconazole 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.

용도antithrombotic

상·하류 제품 정보

상류 원료

2-클로로-3-클로로메틸티오펜수소화나트륨alpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanol

공급사100 곳

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추가 설명

정의ChEBI: 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.