Fosfluconazole

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
Routes of administration	IV
Legal status	℞ (Prescription only)
Identifiers
CAS Number	194798-83-9^Y
ATC code	none
PubChem	CID 214356
ChemSpider	185843^Y
UNII	3JIJ299EWH^Y
ChEMBL	CHEMBL1908301^Y
Chemical data
Formula	C₁₃H₁₃F₂N₆O₄P
Molar 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
^NY (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^‡ chlormidazole^‡ croconazole^‡ fenticonazole^‡ isoconazole^‡ luliconazole neticonazole^‡ omoconazole^‡ butoconazole clotrimazole^# econazole ketoconazole miconazole^# oxiconazole sertaconazole sulconazole tioconazole Systemic: ketoconazole

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

Thiazoles	Topical: abafungin^‡

Polyene antimycotics
(ergosterol binding)

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

Allylamines
(squalene monooxygenase
inhibitors)

Topical: amorolfine^‡
butenafine
naftifine
terbinafine
Systemic: terbinafine

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^‡Withdrawn from market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

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