Fosfluconazole Explained

Verifiedfields:	changed
Watchedfields:	changed
Verifiedrevid:	447618215
Iupac Name:	phosphonic acid
Legal Status:	Rx-only
Routes Of Administration:	IV
Cas Number:	194798-83-9
Atc Prefix:	none
Pubchem:	214356
Chembl:	1908301
Chemspiderid:	185843
Unii:	3JIJ299EWH
C:	13
H:	13
F:	2
N:	6
O:	4
P:	1
Smiles:	Fc1ccc(c(F)c1)C(OP(=O)(O)O)(Cn2ncnc2)Cn3ncnc3
Stdinchi:	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)
Stdinchikey:	GHJWNRRCRIGGIO-UHFFFAOYSA-N

Fosfluconazole is a water-soluble phosphate prodrug of fluconazole^[1] — a triazole antifungal drug used in the treatment and prevention of superficial and systemic fungal infections.^[2]

The phosphate ester bond is hydrolyzed by the action of a phosphatase — an enzyme that removes a phosphate group from its substrate by hydrolyzing phosphoric acid monoesters into a phosphate ion and a molecule with a free hydroxyl group (dephosphorylation).^[3]

Notes and References

1. Bentley A, Butters M, Green SP, Learmonth WJ, MacRae JA, Morland MC, O'Conno G, Skuse J . 2002. The Discovery and Process Development of a Commercial Route to the Water Soluble Prodrug, Fosfluconazole. Organic Process Research & Development. 6. 2. 109–112. 10.1021/op010064+. 1083-6160.
2. Takahashi D, Nakamura T, Shigematsu R, Matsui M, Araki S, Kubo K, Sato H, Shirahata A . 6 . Fosfluconazole for antifungal prophylaxis in very low birth weight infants . International Journal of Pediatrics . 2009 . 2009 . 274768 . 2009-05-25 . 19946419 . 2778452 . 10.1155/2009/274768 . free .
3. Lee CC, Schrier WH, Nagyvary J . The enzymatic hydrolysis of the phosphate ester bond in some thionucleotides . Biochimica et Biophysica Acta (BBA) - Nucleic Acids and Protein Synthesis . 561 . 1 . 223–231 . January 1979 . 84687 . 10.1016/0005-2787(79)90505-7 .