Tioconazole
Structural formula | |||||||||||||||||||
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1: 1 mixture of ( R ) -form (top) and ( S ) -form (bottom) | |||||||||||||||||||
General | |||||||||||||||||||
Non-proprietary name | Tioconazole | ||||||||||||||||||
other names |
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Molecular formula | C 16 H 13 Cl 3 N 2 OS | ||||||||||||||||||
Brief description |
white to almost white, crystalline powder |
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Drug information | |||||||||||||||||||
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properties | |||||||||||||||||||
Molar mass | 387.71 g · mol -1 | ||||||||||||||||||
Physical state |
firmly |
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Melting point |
168–170 ° C (tioconazole hydrochloride ) |
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solubility |
very slightly soluble in water, very slightly soluble in dichloromethane , slightly soluble in ethanol 96% |
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safety instructions | |||||||||||||||||||
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Toxicological data | |||||||||||||||||||
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . |
Tioconazole is a medicinal substance used to treat fungal infections of the skin and mucous membranes caused by dermatophytes , yeasts and molds, as well as pityriasis versicolor and erythrasma .
Clinical information
Contraindications (contraindications)
Use on the eye.
Chemistry, isomerism
Tioconazole is a chiral drug and contains a stereocenter . So there are two stereoisomers , the ( R ) form and the ( S ) form. The commercial preparations contain the drug as a racemate [1: 1 mixture of the ( R ) and ( S ) isomers]. For synthesis, 1- (2,4-dichlorophenyl) -2- (1 H -imidazol-1-yl) -ethanol (an intermediate product of the miconazole synthesis) is deprotonated with sodium hydride and then with 2-chloro-3- (chloromethyl) -thiophene implemented.
Trade names
Mykontral (D), Trosyd (A, CH)
The named preparations are no longer available.
Individual evidence
- ↑ a b TIOCONAZOLE CRS data sheet (PDF) at EDQM , accessed on February 16, 2009.
- ^ The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition, 2006, p. 1625, ISBN 978-0-911910-00-1 .
- ↑ a b Tioconazole data sheet from Sigma-Aldrich , accessed on April 24, 2011 ( PDF ).
- ^ A b c Axel Kleemann , Jürgen Engel, Bernd Kutscher and Dietmar Reichert: Pharmaceutical Substances , 4th edition (2000), Thieme-Verlag Stuttgart, ISBN 978-1-58890-031-9 .