Sertaconazole

HCID 65863CAS 99592-32-2

Grundinformationen

Standard-SMILES
Clc1ccc(C(Cn2ccnc2)OCc2csc3c(Cl)cccc23)c(Cl)c1
InChIKey
JLGKQTAYUIMGRK-UHFFFAOYSA-N
Summenformel
C20H15Cl3N2OS
Durchschnittliche Molmasse
437,8 g/mol
Monoisotopische Masse
435,99706714

Überblick

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.

Namen und Bezeichner

Bevorzugter Name
Sertaconazole
IUPAC
1-[2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl]imidazole
Englischer Name
Sertaconazole
Summenformel
C20H15Cl3N2OS
Molmasse
437.77

Namen und Synonyme

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
Weitere Namen anzeigen
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

Datenbank-Bezeichner

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

Eigenschaften

Berechnete Struktureigenschaften

XLogP
6,3
Polarare Oberfläche (TPSA)
55,3 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
6
Schwere Atome
27

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals
LogP6.2
Solubility · 2 Einträge

Practically insoluble

6.37e-03 g/L

Endocrine DisruptorsPotential endocrine disrupting compound
Physical DescriptionSolid

Physikochemische Eigenschaften

Schmelzpunkt
146 · 146-147°
Siedepunkt
614.1 · 614.1±55.0 °C(Predicted)
Dichte
1.43 · 1.43±0.1 g/cm3(Predicted)
storage temp.
Refrigerator
Löslichkeit
DMSO (Slightly), Methanol (Slightly)
Aggregatzustand
Solid

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

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.

Gefahrenhinweise

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Toxikologische Informationen

Exposure RoutesBioavailability is negligible.
Toxicity Summary · 1 Eintrag

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).

Sicherheitsdaten

Alarmwort
Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code H315

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 4 Einträge

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 Eintrag

Sertaconazole is an imidazole/triazole type antifungal agent. Sertaconazole is a highly selective inhibitor of fungal cytochrome P-450 sterol C-14 &alpha;-demethylation via the inhibition of the enzyme cytochrome P450 14&alpha;-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 &alpha;-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 · 1 Eintrag

Sertaconazole interacts with 14-&alpha; 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 Einträge

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.

Verwendung und Herstellung

Uses · 2 Einträge

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>.

Anwendungen · 2 Einträge

BeschreibungSertaconazole 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.

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

Anbieter50 Anbieter

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]

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