Fosfluconazole

Fosfluconazole
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of; administration	IV
ATC code	none;
Legal status
Legal status	In general: ℞ (Prescription only);
Identifiers
	IUPAC name {[2-(2,4-Difluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-yl]oxy}phosphonic acid;
CAS Number	194798-83-9 ;
PubChem CID	214356;
ChemSpider	185843 ;
UNII	3JIJ299EWH;
ChEMBL	ChEMBL1908301 ;
CompTox Dashboard (EPA)	DTXSID3048601 ;
Chemical and physical data
Formula	C13H13F2N6O4P
Molar mass	386.256 g·mol−1
3D model (JSmol)	Interactive image;
	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) ; Key:GHJWNRRCRIGGIO-UHFFFAOYSA-N ;
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Fosfluconazole (INNTooltip International Nonproprietary Name) 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]

References

^ 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. doi:10.1021/op010064+. ISSN 1083-6160.
^ Takahashi D, Nakamura T, Shigematsu R, Matsui M, Araki S, Kubo K, et al. (2009-05-25). "Fosfluconazole for antifungal prophylaxis in very low birth weight infants". International Journal of Pediatrics. 2009 (2009): 274768. doi:10.1155/2009/274768. PMC 2778452. PMID 19946419.
^ Lee CC, Schrier WH, Nagyvary J (January 1979). "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. doi:10.1016/0005-2787(79)90505-7. PMID 84687.

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[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. doi:10.1021/op010064+. ISSN 1083-6160.

[2] Takahashi D, Nakamura T, Shigematsu R, Matsui M, Araki S, Kubo K, et al. (2009-05-25). "Fosfluconazole for antifungal prophylaxis in very low birth weight infants". International Journal of Pediatrics. 2009 (2009): 274768. doi:10.1155/2009/274768. PMC 2778452. PMID 19946419.

[3] Lee CC, Schrier WH, Nagyvary J (January 1979). "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. doi:10.1016/0005-2787(79)90505-7. PMID 84687.

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