Flutrimazole

Chemical compound

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

KEGG

D07193^Y

ChEBI

CHEBI:82864^N

ChEMBL

ChEMBL2107430^N

CompTox Dashboard (EPA)

DTXSID30869622

ECHA InfoCard100.170.770

Chemical and physical dataFormulaC₂₂H₁₆F₂N₂Molar mass346.381 g·mol⁻¹3D model (JSmol)

Interactive image

ChiralityRacemic 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.^{[citation needed]}

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. 190 (4): 295–300. doi:10.1159/000246720. PMID 7655109.

Antifungals (D01 and J02)

Wall/
membrane

Ergosterol
inhibitors

Azoles (lanosterol 14α-
demethylase inhibitors)

Imidazoles	Topical: bifonazole^‡ butoconazole chlormidazole^‡ climbazole clotrimazole^# croconazole^‡ eberconazole econazole fenticonazole^‡ flutrimazole isoconazole ketoconazole luliconazole miconazole^# neticonazole^‡ omoconazole^‡ oxiconazole sertaconazole sulconazole tioconazole Systemic: ketoconazole
Triazoles	Topical: efinaconazole fluconazole^# terconazole Systemic: fluconazole^# fosfluconazole fosravuconazole hexaconazole^‡ isavuconazole itraconazole^# oteseconazole 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	Systemic: flucytosine^#
Mitotic inhibitors	Systemic: griseofulvin^#
Aminoacyl tRNA synthetase inhibitors	Topical: 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