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Details

Stereochemistry RACEMIC
Molecular Formula C22H16F2N2
Molecular Weight 346.3735
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FLUTRIMAZOLE

SMILES

c1ccc(cc1)C(c2ccc(cc2)F)(c3ccccc3F)n4ccnc4

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
Curator's Comment:: 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.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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.
Primary
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.
Primary
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

PubMed

TitleDatePubMed
[Comparison of the efficacy of 1% flutrimazole cream twice a day with 1% flutrimazole cream once a day for the treatment of superficial dermatophytoses].
2002 Sep
Efficacy of flutrimazole 1% powder in the treatment of tinea pedis.
2003 Apr
Flutrimazole shampoo 1% versus ketoconazole shampoo 2% in the treatment of pityriasis versicolor. A randomised double-blind comparative trial.
2007 May
[Facial dermatophytide reaction].
2008 Apr
Pharmacological control of neutrophil-mediated inflammation: strategies targeting calcium handling by activated polymorphonuclear leukocytes.
2009 Feb 6
Identification of antifungal compounds active against Candida albicans using an improved high-throughput Caenorhabditis elegans assay.
2009 Sep 14
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
Patents

Patents

Sample Use Guides

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
EP   INN   MART.   MI   WHO-DD  
INN  
Official Name English
FLUTRIMAZOLE [EP MONOGRAPH]
Common Name English
FLUTRIMAZOLE [WHO-DD]
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
Classification Tree Code System Code
WHO-ATC G01AF18
Created by admin on Fri Jun 25 21:16:56 UTC 2021 , Edited by admin on Fri Jun 25 21:16:56 UTC 2021
WHO-VATC QD01AC16
Created by admin on Fri Jun 25 21:16:56 UTC 2021 , Edited by admin on Fri Jun 25 21:16:56 UTC 2021
WHO-VATC QG01AF18
Created by admin on Fri Jun 25 21:16:56 UTC 2021 , Edited by admin on Fri Jun 25 21:16:56 UTC 2021
WHO-ATC D01AC16
Created by admin on Fri Jun 25 21:16:56 UTC 2021 , Edited by admin on Fri Jun 25 21:16:56 UTC 2021
Code System Code Type Description
PUBCHEM
3401
Created by admin on Fri Jun 25 21:16:56 UTC 2021 , Edited by admin on Fri Jun 25 21:16:56 UTC 2021
PRIMARY
DRUG BANK
DB13425
Created by admin on Fri Jun 25 21:16:56 UTC 2021 , Edited by admin on Fri Jun 25 21:16:56 UTC 2021
PRIMARY
ChEMBL
CHEMBL2107430
Created by admin on Fri Jun 25 21:16:56 UTC 2021 , Edited by admin on Fri Jun 25 21:16:56 UTC 2021
PRIMARY
EVMPD
SUB07765MIG
Created by admin on Fri Jun 25 21:16:56 UTC 2021 , Edited by admin on Fri Jun 25 21:16:56 UTC 2021
PRIMARY
FDA UNII
776S0UP252
Created by admin on Fri Jun 25 21:16:56 UTC 2021 , Edited by admin on Fri Jun 25 21:16:56 UTC 2021
PRIMARY
NCI_THESAURUS
C167003
Created by admin on Fri Jun 25 21:16:56 UTC 2021 , Edited by admin on Fri Jun 25 21:16:56 UTC 2021
PRIMARY
DRUG CENTRAL
1227
Created by admin on Fri Jun 25 21:16:56 UTC 2021 , Edited by admin on Fri Jun 25 21:16:56 UTC 2021
PRIMARY
INN
6460
Created by admin on Fri Jun 25 21:16:56 UTC 2021 , Edited by admin on Fri Jun 25 21:16:56 UTC 2021
PRIMARY
RXCUI
61773
Created by admin on Fri Jun 25 21:16:56 UTC 2021 , Edited by admin on Fri Jun 25 21:16:56 UTC 2021
PRIMARY RxNorm
CAS
119006-77-8
Created by admin on Fri Jun 25 21:16:56 UTC 2021 , Edited by admin on Fri Jun 25 21:16:56 UTC 2021
PRIMARY
MESH
C076986
Created by admin on Fri Jun 25 21:16:56 UTC 2021 , Edited by admin on Fri Jun 25 21:16:56 UTC 2021
PRIMARY
MERCK INDEX
M5513
Created by admin on Fri Jun 25 21:16:56 UTC 2021 , Edited by admin on Fri Jun 25 21:16:56 UTC 2021
PRIMARY Merck Index