Fialuridine: Difference between revisions

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 443996139

| IUPAC_name = 1-[(2''R'',3''S'',4''R'',5''R'')-3-Fluoro-4-hydroxy-5-(hydroxymethyl)- 2-tetrahydrofuranyl]-5-iodopyrimidine-2,4-dione

| image = Fialuridine.png

| alt = Skeletal formula

| image2 = Fialuridine-3D-balls.png

| alt2 = Ball-and-stick model

<!--Clinical data-->

| tradename =

| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->

| pregnancy_US = <!-- A / B / C / D / X -->

| pregnancy_category =

| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->

| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->

| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->

| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->

| legal_status =

| routes_of_administration =

<!--Pharmacokinetic data-->

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

<!--Identifiers-->

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

| CAS_number = 69123-98-4

| ATC_prefix = none

| ATC_suffix =

| PubChem = 50313

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

| DrugBank =

| NIAID_ChemDB = 070971

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

| ChEMBL = 271475

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 45627

<!--Chemical data-->

| C=9 | H=10 | F=1 | I=1 | N=2 | O=5

| synonyms = 2′-Fluoro-5-iodouracil

| smiles = c1c(c(=O)[nH]c(=O)n1[C@H]2[C@H]([C@@H]([C@H](O2)CO)O)F)I

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C9H10FIN2O5/c10-5-6(15)4(2-14)18-8(5)13-1-3(11)7(16)12-9(13)17/h1,4-6,8,14-15H,2H2,(H,12,16,17)/t4-,5+,6-,8-/m1/s1

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = IPVFGAYTKQKGBM-BYPJNBLXSA-N

'''Fialuridine''', or 1-(2-deoxy-2-fluoro-1-<small>D</small>-arabinofuranosyl)-5-iodouracil (FIAU), is a [[nucleoside analogue]] that was investigated as a potential therapy for [[hepatitis B virus]] infection. In a 1993 clinical study at the [[NIH]], unexpected toxicity led to the death of 5 out of 15 patients from [[liver failure]] alongside [[lactic acidosis]]; two further participants required [[liver transplantation]]. It is suspected that the toxicity of fialuridine was a result of mitochondrial damage caused by the incorporation of fialuridine into [[mitochondrial DNA]] via its 3'-hydroxyl moiety, leading to impaired DNA synthesis. This toxicity was unusual in that it was not predicted by animal studies.<ref>{{cite journal | vauthors = Tujios S, Fontana RJ | title = Mechanisms of drug-induced liver injury: from bedside to bench | journal = Nature Reviews. Gastroenterology & Hepatology | volume = 8 | issue = 4 | pages = 202–11 | date = April 2011 | pmid = 21386809 | doi = 10.1038/nrgastro.2011.22 | s2cid = 1329655 }}</ref><ref>{{cite journal | vauthors = McKenzie R, Fried MW, Sallie R, Conjeevaram H, Di Bisceglie AM, Park Y, Savarese B, Kleiner D, Tsokos M, Luciano C | display-authors = 6 | title = Hepatic failure and lactic acidosis due to fialuridine (FIAU), an investigational nucleoside analogue for chronic hepatitis B | journal = The New England Journal of Medicine | volume = 333 | issue = 17 | pages = 1099–105 | date = October 1995 | pmid = 7565947 | doi = 10.1056/NEJM199510263331702 | doi-access = free }}</ref><Ref>{{cite journal|last=Thomson|first=Larry | name-list-style = vanc |title=The Cure that Killed|journal=Discover Magazine |date=1 March 1994 |url = http://discovermagazine.com/1994/mar/thecurethatkille345#.UnVB6ErVlkd |access-date=2 November 2013}}</ref>

== References ==

{{Reflist}}

[[Category:Antiviral drugs]]

[[Category:withdrawn drugs]]

[[Category:Diols]]

[[Category:Arabinosides]]

[[Category:Clinical trial disasters]]

[[Category:Hydroxymethyl compounds]]

{{antiinfective-drug-stub}}