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Tioconazol

Tioconazole

HCID 5482
NotizenReaktionen
GrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
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Grundinformationen

CAS
65899-73-2
Standard-SMILES
Clc1ccc(C(Cn2ccnc2)OCc2ccsc2Cl)c(Cl)c1
InChIKey
QXHHHPZILQDDPS-UHFFFAOYSA-N
Summenformel
C16H13Cl3N2OS
Durchschnittliche Molmasse
387,7 g/mol
Monoisotopische Masse
385,98141708

Überblick

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.

Namen und Bezeichner

Bevorzugter Name
Tioconazole
IUPAC
1-[2-[(2-chlorothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl]imidazole
Lokaler Name
Tioconazol
Englischer Name
Vagistat
Summenformel
C16H13Cl3N2OS
Molmasse
387.71

Namen und Synonyme

tioconazole65899-73-2VagistatVagistat-1TrosydTrosylTioconazolTioconazolumUK-203491-(2-((2-chlorothiophen-3-yl)methoxy)-2-(2,4-dichlorophenyl)ethyl)-1H-imidazole(+-)-TioconazoleDTXSID3046619
Weitere Namen anzeigen
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

Datenbank-Bezeichner

CAS
65899-73-2
PubChem CID
5482
DTXSID
DTXSID3046619
ChEMBL
CHEMBL1200438
ChEBI
CHEBI:77898
UNII
S57Y5X1117
EC Number

Eigenschaften

Berechnete Struktureigenschaften

XLogP
5,3
Polarare Oberfläche (TPSA)
55,3 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
6
Schwere Atome
23
Formalladung
0
Komplexität
379

Experimentelle und physikochemische Eigenschaften

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

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 Einträge

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]

Physikochemische Eigenschaften

Schmelzpunkt
79 · 79-81oC
Siedepunkt
534.5 · 534.5±50.0 °C(Predicted)
Dichte
1.3115 · 1.3115 (rough estimate)
Brechungsindex
1.6 · 1.6000 (estimate)

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 4 Einträge

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.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Toxikologische Informationen

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

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.

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 4 Einträge

D - Dermatologicals

G - Genito urinary system and sex hormones

QG - Genito urinary system and sex hormones

QD - Dermatologicals

Pharmacodynamics · 1 Eintrag

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 Eintrag

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 Einträge

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 Einträge

S57Y5X1117

TIOCONAZOLE

Established Pharmacologic Class [EPC] - Azole Antifungal

Chemical Structure [CS] - Azoles

Tioconazole is an Azole Antifungal.

TIOCONAZOLE

Zugehörige Reaktionen

3
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 1265340
HRID 1265340als Produktuspto-grants-2003_04
Reaktionsgleichung von HRID 1265341
HRID 1265341als Produktuspto-grants-2003_04
Reaktionsgleichung von HRID 1265342
HRID 1265342als Produktuspto-grants-2003_04

Notizen zur Verbindung

Wird geladen…

Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
265-973-8
Nikkaji
J3.525D
storage temp.
Keep in dark place,Inert atmosphere,Room temperature
Löslichkeit
Very slightly soluble in water, very soluble in methylene chloride, freely soluble in alcohol.
Aggregatzustand
powder
pka
6.66 · 6.66±0.12(Predicted)
Farbe
white to off-white
Kosmetik-Inhaltsstoffe Funktionen
ANTIMICROBIAL
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 Datenbank
65899 · 65899-73-2(CAS DataBase Reference)
Carcinogen Classification
No indication of carcinogenicity to humans (not listed by IARC).
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Sicherheitsdaten

wgk
3
ridadr
UN3077
hs_code
2934990002
risk_code
22
hazard_code
Xn
hazard_class
9
Speicherklasse
11 - Combustible Solids
Hazard Classifications
Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Repr. 2Skin Sens. 1
MeSH Pharmacological Classification · 2 Einträge

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

Verwendung und Herstellung

UsesFor the local treatment of vulvovaginal candidiasis (moniliasis).

Anwendungen

BeschreibungTioconazole 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.

Verwendenantithrombotic

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

2-Chloro-3-chloromethylthiopheneNatriumhydridα-(2,4-Dichlorphenyl)-1H-imidazol-1-ethanol

Anbieter100 Anbieter

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Ergänzende Hinweise

DefinitionChEBI: 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.