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
Weitere Namen anzeigen
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
- Formalladung
- 0
- Komplexität
- 488
Experimentelle und physikochemische Eigenschaften
Solubility
Practically insoluble
6.37e-03 g/L
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
- pka
- 6.68 · 6.68±0.12(Predicted)
- Farbe
- White to Pale Yellow
- 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 Datenbank
- 99592 · 99592-32-2(CAS DataBase Reference)
Sicherheit und Regulatorisches
GHS-Klassifizierung
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.
Gefahrenhinweise
Toxikologische Informationen
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.
Sicherheitsdaten
- Alarmwort
- Warnung
- Gefahrenhinweise
- Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code H315
Chemie und Industrie
Pharmakologische Informationen
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.
Verwendung und Herstellung
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>.
Anwendungen
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.
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