FLUTRIMAZOLE

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

Structure Search

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

Description
Sources: http://www.vademecum.es/medicamento-flusporan_ficha_1616
Curator's Comment: description was created based on several sources, including https://www.drugs.com/international/flutrimazole.html | https://www.ncbi.nlm.nih.gov/pubmed/8569815 | https://www.old.health.gov.il/units/pharmacy/trufot/alonim/197.pdf | https://www.ncbi.nlm.nih.gov/pubmed/21718579

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 Target ID: CHEMBL3307221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1418042	Inhibitor 8297
Bile acid receptor FXR 31 Target ID: CHEMBL2047 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23688559	Antagonist 2778	13.8 µM [IC50]
Pregnane X receptor 35 Target ID: CHEMBL3401 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23688559	Agonist 2678	6.1 µM [EC50]

Conditions

Condition	Modality	Highest Phase	Product
Superficial mycoses of the skin 1 Sources: http://www.vademecum.es/medicamento-flusporan_ficha_1616	Primary	Approved 8429	Flutrimazole Approved Use FLUSPORAN dermal cream is indicated for the topical treatment of superficial mycoses of the skin, such as ringworm in its varieties: tinea pedis (athlete's foot), tinea cruris, tinea corporis, tinea faciei et barbae and tinea inguinalis , caused by Trichophyton (eg T. rubrum, T. mentagrophytes, T. tonsurans), Microsporum (eg M. canis, M. gypseum) and Epidermophyton floccosum . In the treatment of cutaneous candidiasis mainly produced by yeasts of the genus Candida (eg C. albicans, C. parapsilosis, C. guillermondi, C. tropicalis). It is also indicated for the treatment of pityriasis versicolor caused by Malassezia furfur or also known as Pityrosporum ovale.
Cutaneous candidiasis 3 Sources: http://www.vademecum.es/medicamento-flusporan_ficha_1616	Primary	Approved 8429	Flutrimazole Approved Use FLUSPORAN dermal cream is indicated for the topical treatment of superficial mycoses of the skin, such as ringworm in its varieties: tinea pedis (athlete's foot), tinea cruris, tinea corporis, tinea faciei et barbae and tinea inguinalis , caused by Trichophyton (eg T. rubrum, T. mentagrophytes, T. tonsurans), Microsporum (eg M. canis, M. gypseum) and Epidermophyton floccosum . In the treatment of cutaneous candidiasis mainly produced by yeasts of the genus Candida (eg C. albicans, C. parapsilosis, C. guillermondi, C. tropicalis). It is also indicated for the treatment of pityriasis versicolor caused by Malassezia furfur or also known as Pityrosporum ovale.
Pityriasis versicolor 4 Sources: http://www.vademecum.es/medicamento-flusporan_ficha_1616	Primary	Approved 8429	Flutrimazole Approved Use FLUSPORAN dermal cream is indicated for the topical treatment of superficial mycoses of the skin, such as ringworm in its varieties: tinea pedis (athlete's foot), tinea cruris, tinea corporis, tinea faciei et barbae and tinea inguinalis , caused by Trichophyton (eg T. rubrum, T. mentagrophytes, T. tonsurans), Microsporum (eg M. canis, M. gypseum) and Epidermophyton floccosum . In the treatment of cutaneous candidiasis mainly produced by yeasts of the genus Candida (eg C. albicans, C. parapsilosis, C. guillermondi, C. tropicalis). It is also indicated for the treatment of pityriasis versicolor caused by Malassezia furfur or also known as Pityrosporum ovale.

PubMed

Title	Date	PubMed
Flutrimazole shampoo 1% versus ketoconazole shampoo 2% in the treatment of pityriasis versicolor. A randomised double-blind comparative trial.	2007 May	17472615
[Facial dermatophytide reaction].	2008 Apr	18394396
Study to compare the efficacy and safety of fluconazole cream with flutrimazole cream in the treatment of superficial mycosis: a multicentre, randomised, double-blind, phase III trial.	2010 Nov	19558428

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.

Name

Type

Language

FLUTRIMAZOLE

Official Name

English

FLUTRIMAZOLE [EP MONOGRAPH]

Common Name

English

FLUTRIMAZOLE [MI]

Common Name

English

FLUTRIMAZOLE [MART.]

Common Name

English

flutrimazole [INN]

Common Name

English

1-(O-FLUORO-.ALPHA.-(P-FLUOROPHENYL)-.ALPHA.-PHENYLBENZYL)IMIDAZOLE

Common Name

English

UR-4056

Code

English

Flutrimazole [WHO-DD]

Common Name

English

Classification Tree Code System Code

WHO-ATC

G01AF18