Tioconazole

Structural formula
	1: 1 mixture of ( R ) -form (top) and ( S ) -form (bottom)
General
Non-proprietary name	Tioconazole
other names	( RS ) -1- {2 - [(2-chloro-3-thienyl) methoxy] -2- (2,4-dichlorophenyl) ethyl} -1 H -imidazole; rac -1- {2 - [(2-chloro-3-thienyl) methoxy] -2- (2,4-dichlorophenyl) ethyl} -1 H -imidazole; DL -1- {2 - [(2-chloro-3-thienyl) methoxy] -2- (2,4-dichlorophenyl) ethyl} -1 H -imidazole; (±) -1- {2 - [(2-Chloro-3-thienyl) methoxy] -2- (2,4-dichlorophenyl) ethyl} -1 H -imidazole; ( RS ) -1- {2,4-dichloro-β - [(2-chloro-3-thienyl) oxy] phenylethyl} imidazole; DL -1- {2,4-dichloro-β - [(2-chloro-3-thienyl) oxy] phenylethyl} imidazole; rac -1- {2,4-dichloro-β - [(2-chloro-3-thienyl) oxy] phenylethyl} imidazole; (±) -1- {2,4-dichloro-β - [(2-chloro-3-thienyl) oxy] phenylethyl} imidazole; Tioconazolum;
Molecular formula	C 16 H 13 Cl 3 N 2 OS
Brief description	white to almost white, crystalline powder
External identifiers / databases
EC number	265-973-8
ECHA InfoCard	100.059.958
PubChem	5482
DrugBank	DB01007
Wikidata	Q260326
Drug information
ATC code	D01 AC07 G01 AF08
Drug class	Antifungal agent
properties
Molar mass	387.71 g · mol -1
Physical state	firmly
Melting point	168–170 ° C (tioconazole hydrochloride )
solubility	very slightly soluble in water, very slightly soluble in dichloromethane , slightly soluble in ethanol 96%
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Caution
H and P phrases	H: 302-413
	P: no P-phrases
Toxicological data	1870 mg kg −1 ( LD 50 , mouse , oral ) ; 770 mg kg −1 ( LD 50 , rat , oral ) ;
	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

Monopreparations

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 .

Web links

Commons : Tioconazole - collection of images, videos and audio files

[Ph._Eur.-1] TIOCONAZOLE CRS data sheet (PDF) at EDQM , accessed on February 16, 2009.

[MerckIndex-2] The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition, 2006, p. 1625, ISBN 978-0-911910-00-1 .

[Sigma-3] Tioconazole data sheet from Sigma-Aldrich , accessed on April 24, 2011 ( PDF ).

[A._Kleemann-4] 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 .