Fosfluconazole

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Fosfluconazole

Systematic (IUPAC) name
{[2-(2,4-difluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-yl]oxy}phosphonic acid
Clinical data
AHFS/Drugs.com	International Drug Names
Legal status	℞ Prescription only
Routes	IV
Identifiers

ATC code	None
PubChem	CID 214356
ChemSpider	185843^Y
UNII	3JIJ299EWH^Y
ChEMBL	CHEMBL1614657^N
Chemical data
Formula	C₁₃H₁₃F₂N₆O₄P
Mol. mass	386.25 g/mol
SMILES Fc1ccc(c(F)c1)C(OP(=O)(O)O)(Cn2ncnc2)Cn3ncnc3
InChI InChI=1S/C13H13F2N6O4P/c14-10-1-2-11(12(15)3-10)13(25-26(22,23)24,4-20-8-16-6-18-20)5-21-9-17-7-19-21/h1-3,6-9H,4-5H2,(H2,22,23,24)^Y Key:GHJWNRRCRIGGIO-UHFFFAOYSA-N^Y
N (what is this?) (verify)

Fosfluconazole (INN) is a water-soluble phosphate prodrug of fluconazole - a triazole antifungal drug used in the treatment and prevention of superficial and systemic fungal infections. The phosphate ester bond is hydrolysed by the action of a phosphatase - an enzyme that removes a phosphate group from its substrate by hydrolysing phosphoric acid monoesters into a phosphate ion and a molecule with a free hydroxyl group (see dephosphorylation).

Antifungals (D01 and J02)

Wall/
membrane

Ergosterol
inhibitors

Azoles
(lanosterol 14
alpha-demethylase inhibitors)

Imidazoles	topical: Bifonazole Butoconazole Clomidazole Clotrimazole^#, Croconazole Econazole Fenticonazole Ketoconazole Isoconazole Miconazole^#, Neticonazole Omoconazole Oxiconazole Sertaconazole Sulconazole Tioconazole

Triazoles	topical: (Fluconazole^#, Fosfluconazole Terconazole) systemic: (Fluconazole Hexaconazole Isavuconazole^†, Itraconazole Posaconazole Voriconazole) unknown: (Albaconazole)

Thiazoles	topical: (Abafungin)

Polyene antimycotics
(ergosterol binding)

topical: (Hamycin
Natamycin
Nystatin^#)
systemic: (Amphotericin B^#, Hamycin)

Allylamines
(squalene monooxygenase
inhibitors)

β-glucan synthase
inhibitors

Intracellular

Pyrimidine analogues/ Thymidylate synthase inhibitors	Flucytosine^#

Mitotic inhibitors	Griseofulvin^#

Others

Tea tree oil
citronella oil
lemon grass
orange oil
patchouli
lemon myrtle

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^‡Withdrawn from market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

M: MYC

fung, clas

fung

drug (fung)

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