Isoconazole

Structural formula
	1: 1 mixture of ( R ) -form (left) and ( S ) -form (right)
General
Non-proprietary name	Isoconazole
other names	( RS ) -1- {2- (2,4-dichlorophenyl) -2 - [(2,6) -dichlorobenzyl) -oxy] phenylethyl} imidazole
Molecular formula	C 18 H 14 Cl 4 N 2 O (isoconazole) ; C 18 H 14 Cl 4 N 2 O HNO 3 (isoconazole nitrate) ;
Brief description	white to almost white powder
External identifiers / databases
EC number	248-508-3
ECHA InfoCard	100.044.084
PubChem	3760
ChemSpider	3629
DrugBank	DB08943
Wikidata	Q262210
Drug information
ATC code	G01 AF07 ; D01 AC05 ;
Drug class	Antifungal drugs
Mechanism of action	Inhibition of the biosynthesis of ergosterol in mushrooms
properties
Molar mass	416.13 g · mol -1 (isoconazole) ; 479.14 g · mol -1 (· isoconazole nitrate) ;
Physical state	firmly
Melting point	182–183 ° C (isoconazole nitrate)
solubility	practically insoluble in water, very easily soluble in methanol , easily soluble in ethanol
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS hazard labeling ; no classification available
Toxicological data	189 mg kg −1 ( LD 50 , mouse , ip )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Isoconazole is a drug from the group of azole - antifungal agents . The nitrate salt of this substance is used for the local treatment of dermatomycoses . Isoconazole is an isomer of miconazole . Isoconazole was patented by Janssen in 1970 .

Clinical information

Application areas (indications)

Isoconazole is used to treat superficial fungal infections of the skin, including classic athlete's foot and the genital region, as well as Baerensprung's disease .

Contraindications (contraindications)

Isoconazole is contraindicated in cases of known hypersensitivity to this active ingredient .

Interactions

When applied locally, no interactions with other drugs are known.

Side effects

With local application with isoconazole, itching, burning, erythema or vesicle formation as well as allergic skin reactions could be observed in individual cases .

pharmacology

Mode of action (pharmacodynamics)

Isoconazole is a topically applied antifungal drug. Its spectrum of activity includes dermatophytes, yeasts, yeast-like fungi and molds. In addition, isoconazole has a growth-inhibiting effect on gram-positive bacteria and trichomonads . Its effect is based, among other things, on the destruction of cell membrane structures with a loss of ATP as a result.

chemistry

Stereoisomerism

Isoconazole contains a stereocenter, so it is chiral. So there are two enantiomers, ( R ) - and ( S ) -1- {2- (2,4-dichlorophenyl) -2 - [(2,6) -dichlorobenzyl) oxy] phenylethyl} imidazole. The drug isoconazole is used as a racemate [1: 1 mixture of the ( R ) form and the ( S ) form].

Commercial preparations

Travogen (A, CH), Gyno-Travogen (A, CH)
Combination with diflucortolone valerate : Travocort (D, A, CH)

literature

Hubert snow man, Ros Batty, Wolfgang Blaschek, Walter Reuss: goods and services . Birkhäuser, 1995, ISBN 3-540-52688-9 , pp. 601 ( limited preview in Google Book search).
Fromtling RA: Overview of medically important antifungal azole derivatives . In: Clinical Microbiology Reviews . 1, No. 2, April 1988, pp. 187-217. PMID 3069196 . PMC 358042 (free full text).

Individual evidence

↑ ^a ^b ISOCONAZOLE CRS data sheet (PDF) at EDQM , accessed on June 26, 2010.

^ The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals , 14th Edition (Merck & Co., Inc.), Whitehouse Station, NJ, USA, 2006; ISBN 978-0-911910-00-1 , p. 893.

↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

↑ Entry on isoconazole in the ChemIDplus database of the United States National Library of Medicine (NLM) .

↑ ^a ^b ^c ^d compendium.ch: Technical information Travogen-Creme. Stand 2011. . Retrieved February 14, 2013.

↑ Fromtling RA: Overview of medically important antifungal azole derivative . In: Clin. Microbiol. Rev. . 1, No. 2, April 1988, pp. 187-217. PMID 3069196 . PMC 358042 (free full text).

[Ph._Eur.-1] ISOCONAZOLE CRS data sheet (PDF) at EDQM , accessed on June 26, 2010.

[MERCK_Index-2] The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals , 14th Edition (Merck & Co., Inc.), Whitehouse Station, NJ, USA, 2006; ISBN 978-0-911910-00-1 , p. 893.

[NV-3] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[ChemIDplus-4] Entry on isoconazole in the ChemIDplus database of the United States National Library of Medicine (NLM) .

[AGES-5] ↑ ^a ^b ^c ^d compendium.ch: Technical information Travogen-Creme. Stand 2011. . Retrieved February 14, 2013.

[pmid3069196-6] Fromtling RA: Overview of medically important antifungal azole derivative . In: Clin. Microbiol. Rev. . 1, No. 2, April 1988, pp. 187-217. PMID 3069196 . PMC 358042 (free full text).