FLUTRIMAZOLE

Possibly Marketed Outside US

Details

Stereochemistry	RACEMIC
Molecular Formula	C22H16F2N2
Molecular Weight	346.3726
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

FC1=CC=C(C=C1)C(N2C=CN=C2)(C3=CC=CC=C3)C4=C(F)C=CC=C4

InChI

InChIKey=QHMWCHQXCUNUAK-UHFFFAOYSA-N

InChI=1S/C22H16F2N2/c23-19-12-10-18(11-13-19)22(26-15-14-25-16-26,17-6-2-1-3-7-17)20-8-4-5-9-21(20)24/h1-16H

HIDE SMILES / InChI

Molecular Formula	C22H16F2N2
Molecular Weight	346.3726
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description

Flutrimazole (trade names Flusporan, Funcenal, Micetal, Topiderm) is an imidazole derivative, a wide-spectrum antifungal drug used for the topical treatment of superficial mycoses of the skin. Flutrimazole interferes with the synthesis of ergosterol by inhibiting the activity of the enzyme lanosterol 14 α-demethylase. Flutrimazole’s antifungal activity has been demonstrated in in vivo and in vitro studies to be comparable to that of clotrimazole and higher than bifonazole. During clinical trials the incidence of adverse reactions in relation to the use of Flutrimazole skin cream was 8%, being the most frequent those described as slight burning, irritation, itching, and erythema in the area of application.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Lanosterol 14-alpha demethylase 13	Inhibitor 8,297
Bile acid receptor FXR 31	Antagonist 2,778	13.8 µM [IC50]
Pregnane X receptor 35	Agonist 2,678	6.1 µM [EC50]

Conditions

Condition	Modality	Highest Phase	Product
Superficial mycoses of the skin 1	Primary	Approved 8,429	Flutrimazole
Cutaneous candidiasis 3	Primary	Approved 8,429	Flutrimazole
Pityriasis versicolor 4	Primary	Approved 8,429	Flutrimazole

PubMed

Show entries

Title	Date	PubMed
Efficacy of flutrimazole 1% powder in the treatment of tinea pedis.	2003 Apr	12870201
Identification of antifungal compounds active against Candida albicans using an improved high-throughput Caenorhabditis elegans assay.	2009 Sep 14	19750012

Showing 1 to 2 of 2 entries

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Patents

Sample Use Guides

In Vivo Use Guide

1 g for 7 days

Route of Administration: Topical

In Vitro Use Guide

A total of 23 M. furfur isolates were tested for susceptibility to the various azole antifungal agents in vitro. The isolates all came originally from clinical samples and had been maintained at – 70 C with glycerol as cryoprotectant. Inocula were prepared as 4-day static cultures in Dixon broth incubated at 37 C. The suspensions were diluted with sterile water so that a l0-fold dilution gave an OD of 0.1 at 530 nm. A 25-loop multiple inoculating device was used to place volumes of approximately 30 mkl on the test media (Flutrimazole). The cultures were incubated at 37 C for 4 days and minimum inhibitory concentrations (MICs) were recorded as the lowest concentrations at which no growth of M. furfur was visible.