Sertaconazole

Bezeichnung:Sertaconazole

CAS-Nr99592-32-2

Englisch Name:Sertaconazole

CBNumberCB6701774

SummenformelC20H15Cl3N2OS

Molgewicht437.77

MOL-Datei99592-32-2.mol

Sertaconazole physikalisch-chemischer Eigenschaften

Schmelzpunkt	146-147°
Siedepunkt	614.1±55.0 °C(Predicted)
Dichte	1.43±0.1 g/cm3(Predicted)
storage temp.	Refrigerator
Löslichkeit	DMSO (Slightly), Methanol (Slightly)
Aggregatzustand	Solid
pka	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	99592-32-2(CAS DataBase Reference)

Gefahreninformationscode (GHS)

Sertaconazole Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung
Sertaconazole 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.
Verwenden
An imidazole antifungal agent, inhibits the synthesis of ergosterol, an essential cell wall component of fungi.
Definition
ChEBI: 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, an ether, a member of imidazoles and a member of 1-benzothiophenes.
Indications
Topical treatment of mycoses of the skin induced or sustained by fungi such as yeasts and dermatophytes. New formulations for the treatment of vaginal mycoses are in development.
Antimicrobial activity
Sertaconazole is a rather new broad-spectrum imidazole antimycotic with activity against almost all species of pathogenic fungi. It also has excellent activity against pathogenic yeasts.
Synthese
2,4-Dichloro acetophenone 169 was brominated at low temperature to give bromide intermediate 170, which was used without isolation. To the same pot, five-fold excess of imidazole was added to give imidazolylacetophenone 171 in 71% yield from 169. Sodium borohydride was employed to reduce ketone 171 to alcohol 172 in 78% yield. Racemic alcohol 172 was resolved with (-)-DIP-chloride to give its corresponding chiral R-alcohol 173 in 80% yield. Compound 173 was then alkylated with 3-bromomethyl-7-chlorobenzo[b]thiophene (174) in dry DMF in the presence of potassium t-butoxide to give the alkylation product in 68% yield. Finally, 60% nitric acid was used to make sertaconazole mononitrate (XXI) in 89% yield.
Solubility in organics
Fairly soluble in ethanol (1.7 %), chloroform (1.5 %); slightly soluble in acetone (0.95 %); very slightly soluble in noctanol (0.069 %). Practically insoluble in water (< 0.01 %).

Sertaconazole Upstream-Materialien And Downstream Produkte

Sertaconazole Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

99592-32-2, Sertaconazole Verwandte Suche:

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