Flutrimazole

Flutrimazole
Clinical data

AHFS/Drugs.com	International Drug Names
ATC code	D01AC16 (WHO) G01AF18 (WHO)
Identifiers
IUPAC name (RS)-1-[(2-Fluorophenyl)(4-fluorophenyl)benzyl]-1H-imidazole
CAS Number	119006-77-8^Y
PubChem (CID)	3401
ChemSpider	3284^Y
UNII	776S0UP252^Y
KEGG	D07193^Y
ChEBI	CHEBI:82864^N
ChEMBL	CHEMBL2107430^N
Chemical and physical data
Formula	C₂₂H₁₆F₂N₂
Molar mass	346.373 g/mol
3D model (Jmol)	Interactive image
Chirality	Racemic mixture
SMILES Fc1ccc(cc1)C(c2c(F)cccc2)(c3ccccc3)n4ccnc4
InChI 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^Y Key:QHMWCHQXCUNUAK-UHFFFAOYSA-N^Y
^NY (what is this?) (verify)

Flutrimazole is a wide-spectrum antifungal drug. It is used for the topical treatment of superficial mycoses of the skin. Flutrimazole is an imidazole derivative. Its antifungal activity has been demonstrated in in vivo and in vitro studies to be comparable to that of clotrimazole and higher than bifonazole.^[1]

Mechanism of action

It interferes with the synthesis of ergosterol by inhibiting the activity of the enzyme lanosterol 14 α-demethylase.

References

The Merck Index, 12th Edition. 4247

↑ Alomar, A; Videla, S; Delgadillo, J; Gich, I; Izquierdo, I; Forn, J (1995). "Flutrimazole 1% Dermal Cream in the Treatment of Dermatomycoses: a Multicentre, Double-Blind, Randomized, Comparative Clinical Trial with Bifonazole 1% Cream. Efficacy of Flutrimazole 1% Dermal Cream in Dermatomycoses. Catalan Flutrimazole Study Group". Dermatology (Basel, Switzerland). 190 (4): 295–300. PMID 7655109. |access-date= requires |url= (help)

Antifungals (D01 and J02)

Wall/
membrane

Ergosterol
inhibitors

Azoles
(lanosterol 14
alpha-demethylase inhibitors)

Imidazoles	Topical: bifonazole^‡ butoconazole chlormidazole^‡ clotrimazole^# croconazole^‡ econazole fenticonazole^‡ flutrimazole isoconazole^‡ ketoconazole luliconazole miconazole^# neticonazole^‡ omoconazole^‡ oxiconazole sertaconazole sulconazole tioconazole Systemic: ketoconazole

Triazoles	Topical: efinaconazole fluconazole^# fosfluconazole terconazole Systemic: fluconazole^# hexaconazole^‡ isavuconazole itraconazole posaconazole voriconazole Unknown: albaconazole^‡ ravuconazole^†

Thiazoles	Topical: abafungin^‡

Polyene antimycotics
(ergosterol binding)

Topical: hamycin^‡
natamycin
nystatin^#
Systemic: amphotericin B^#, hamycin^‡

Squalene monooxygenase
inhibitors

Allylamines	Topical: naftifine terbinafine Systemic: terbinafine

Benzylamines	Topical: butenafine

Others

Topical: amorolfine

β-glucan synthase
inhibitors

Intracellular

Pyrimidine analogues/ thymidylate synthase inhibitors	flucytosine^#

Mitotic inhibitors	griseofulvin^#

Aminoacyl tRNA synthetase inhibitors	tavaborole

Others

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

Gynecological anti-infectives and antiseptics (G01)

Antibiotics

Arsenic compounds

Acetarsol

Quinoline derivatives

Organic acids

Sulfonamides

Sulfatolamide

Antifungals

Imidazoles	Metronidazole Clotrimazole Miconazole Econazole Ornidazole Isoconazole Tioconazole Ketoconazole Fenticonazole Azanidazole Propenidazole Butoconazole Omoconazole Oxiconazole Flutrimazole

Triazoles	Terconazole

Polyenes	Nystatin Natamycin Amphotericin B

Other	Ciclopirox Methylrosaniline

Other

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Flutrimazole

Mechanism of action

See also

References