fosfluconazole

{{Short description|Chemical compound}}

{{more citations needed|date=April 2020}}

{{Infobox drug

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| verifiedrevid = 447618215

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| IUPAC_name = {[2-(2,4-Difluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-yl]oxy}phosphonic acid

| image = Fosfluconazol.svg

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| Drugs.com = {{drugs.com|international|fosfluconazole}}

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| legal_status = Rx-only

| routes_of_administration = IV

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| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 194798-83-9

| ATC_prefix = none

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| PubChem = 214356

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

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| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 1908301

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 185843

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 3JIJ299EWH

| synonyms =

| 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_Ref = {{stdinchicite|correct|chemspider}}

| 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_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = GHJWNRRCRIGGIO-UHFFFAOYSA-N

}}

Fosfluconazole ({{abbrlink|INN|International Nonproprietary Name}}) is a water-soluble phosphate prodrug of fluconazole{{cite journal| vauthors = Bentley A, Butters M, Green SP, Learmonth WJ, MacRae JA, Morland MC, O'Conno G, Skuse J |date=2002|title=The Discovery and Process Development of a Commercial Route to the Water Soluble Prodrug, Fosfluconazole|journal=Organic Process Research & Development|volume=6|issue=2|pages=109–112|doi=10.1021/op010064+|issn=1083-6160}} — a triazole antifungal drug used in the treatment and prevention of superficial and systemic fungal infections.{{cite journal | vauthors = Takahashi D, Nakamura T, Shigematsu R, Matsui M, Araki S, Kubo K, Sato H, Shirahata A | display-authors = 6 | title = Fosfluconazole for antifungal prophylaxis in very low birth weight infants | journal = International Journal of Pediatrics | volume = 2009 | issue = 2009 | pages = 274768 | date = 2009-05-25 | pmid = 19946419 | pmc = 2778452 | doi = 10.1155/2009/274768 | doi-access = free }}

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).{{cite journal | vauthors = Lee CC, Schrier WH, Nagyvary J | title = The enzymatic hydrolysis of the phosphate ester bond in some thionucleotides | journal = Biochimica et Biophysica Acta (BBA) - Nucleic Acids and Protein Synthesis | volume = 561 | issue = 1 | pages = 223–231 | date = January 1979 | pmid = 84687 | doi = 10.1016/0005-2787(79)90505-7 }}