uridine triacetate

{{Short description|Chemical compound}}

{{Use dmy dates|date=December 2019}}

{{Infobox drug

| drug_name =

| image = Uridine triacetate structure.svg

| width = 150

| alt =

| caption =

| pronounce =

| tradename = Vistogard, Xuriden

| Drugs.com = {{drugs.com|monograph|uridine-triacetate}}

| MedlinePlus = a616020

| DailyMedID = Uridine%20triacetate

| pregnancy_AU =

| pregnancy_AU_comment =

| pregnancy_US = N

| pregnancy_category=

| routes_of_administration = By mouth

| ATCvet =

| ATC_prefix = A16

| ATC_suffix = AX13

| legal_AU =

| legal_AU_comment =

| legal_CA =

| legal_DE =

| legal_NZ =

| legal_UK =

| legal_US = Rx-only

| legal_UN =

| legal_status =

| bioavailability =

| protein_bound =

| metabolism = Pyrimidine catabolic pathway

| metabolites =

| onset = T_max = 2–3 hours

| elimination_half-life = 2–2.5 hours

| duration_of_action =

| excretion = Kidney

| CAS_number = 4105-38-8

| PubChem = 20058

| PubChemSubstance =

| IUPHAR_ligand =

| DrugBank = DB09144

| ChemSpiderID = 18897

| KEGG = D09985

| UNII = 2WP61F175M

| ChEBI = 90914

| ChEMBL = 2107381

| NIAID_ChemDB =

| PDB_ligand =

| synonyms = vistonuridine

| IUPAC_name = [(2R,3R,4R,5R)-3,4-diacetyloxy-5-(2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl acetate

| C=15 | H=18 | N=2 | O=9

| SMILES = CC(=O)OCC1C(C(C(O1)N2C=CC(=O)NC2=O)OC(=O)C)OC(=O)C

| StdInChI = 1S/C15H18N2O9/c1-7(18)23-6-10-12(24-8(2)19)13(25-9(3)20)14(26-10)17-5-4-11(21)16-15(17)22/h4-5,10,12-14H,6H2,1-3H3,(H,16,21,22)/t10-,12-,13-,14-/m1/s1

| StdInChIKey = AUFUWRKPQLGTGF-FMKGYKFTSA-N

}}

Uridine triacetate (INN),{{cite web|title=International Nonproprietary Names for Pharmaceutical Substances (INN). Recommended International Nonproprietary Names: List 65|url=https://www.who.int/medicines/publications/druginformation/innlists/RL65.pdf|publisher=World Health Organization|access-date=12 March 2017|page=92}} formerly known as vistonuridine, is an orally active tri-acetylated prodrug of uridine{{cite web|title=Uridine triacetate — DrugBank Page|url=https://www.drugbank.ca/drugs/DB09144|date=12 March 2017}} used:

• in the treatment of hereditary orotic aciduria (brand name Xuriden {{IPAc-en|ˈ|z|ʊər|ə|d|ɛ|n}} {{respell|ZOOR|ə|den}});{{cite web | title=Xuriden- uridine triacetate granule | website=DailyMed | date=16 December 2019 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=40606ca9-4f14-45b7-8632-fc2d17d11a2e | access-date=20 October 2020}}
• to treat people following an overdose of chemotherapy drugs 5-fluorouracil (5-FU) or capecitabine regardless of the presence of symptoms, or who exhibit early-onset, severe or life-threatening toxicity affecting the cardiac or central nervous system, and/or early-onset, unusually severe adverse reactions (e.g., gastrointestinal toxicity and/or neutropenia) within 96 hours following the end of fluorouracil or capecitabine administration (brand name Vistogard).{{cite web | title=Vistogard- uridine triacetate granule | website=DailyMed | date=15 November 2018 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=5a0ba417-8a4a-4d7f-b85a-1839ee8bd3f1 | access-date=20 October 2020}}{{cite news|title=BTG Announces FDA Approval of Vistogard (Uridine Triacetate) as Antidote to Overdose and Early Onset, Severe, or Life-Threatening Toxicities from Chemotherapy Drugs 5-Fluorouracil (5-FU) or Capecitabine|url=https://www.btgplc.com/media/press-releases/btg-announces-fda-approval-of-vistogard/|access-date=12 March 2017|publisher=BTG International Ltd.|date=11 December 2015}}{{cite web|title=Approved Drugs — Uridine Triacetate|url=https://www.fda.gov/Drugs/InformationOnDrugs/ApprovedDrugs/ucm476930.htm|archive-url=https://web.archive.org/web/20160303213704/http://www.fda.gov/Drugs/InformationOnDrugs/ApprovedDrugs/ucm476930.htm|url-status=dead|archive-date=3 March 2016|publisher=U.S. Food and Drug Administration|access-date=12 March 2017}}{{cite journal | vauthors = Cada DJ, Mbogu U, Bindler RJ, Baker DE | title = Uridine Triacetate | journal = Hospital Pharmacy | volume = 51 | issue = 6 | pages = 484–8 | date = June 2016 | pmid = 27354750 | pmc = 4911989 | doi = 10.1310/hpj5106-484 }}{{cite journal | vauthors = Ison G, Beaver JA, McGuinn WD, Palmby TR, Dinin J, Charlab R, Marathe A, Jin R, Liu Q, Chen XH, Ysern X, Stephens O, Bai G, Wang Y, Dorff SE, Cheng J, Tang S, Sridhara R, Pierce W, McKee AE, Ibrahim A, Kim G, Pazdur R | display-authors = 6 | title = FDA Approval: Uridine Triacetate for the Treatment of Patients Following Fluorouracil or Capecitabine Overdose or Exhibiting Early-Onset Severe Toxicities Following Administration of These Drugs | journal = Clinical Cancer Research | volume = 22 | issue = 18 | pages = 4545–4549 | date = September 2016 | pmid = 27401247 | doi = 10.1158/1078-0432.CCR-16-0638 | s2cid = 25746700 | doi-access = free }}

Uridine triacetate was developed, manufactured and distributed by Wellstat Therapeutics. It was granted breakthrough therapy designation by the U.S. Food and Drug Administration (FDA) and approved for use in the United States in 2015.{{cite web | title=Xuriden (uridine triacetate) oral granules | website=U.S. Food and Drug Administration (FDA) | date=8 October 2015 | url=https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/208169Orig1s000TOC.cfm | access-date=7 December 2019 | archive-url=https://web.archive.org/web/20191208063612/https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/208169Orig1s000TOC.cfm | archive-date=8 December 2019 | url-status=live }} {{PD-notice}}{{cite web | title=Drug Trials Snapshots: Xuriden | website=U.S. Food and Drug Administration (FDA) | date=4 September 2015 | url=https://www.fda.gov/drugs/drug-approvals-and-databases/drug-trials-snapshots-xuriden | access-date=8 December 2019 | archive-url=https://web.archive.org/web/20191208063549/https://www.fda.gov/drugs/drug-approvals-and-databases/drug-trials-snapshots-xuriden | archive-date=8 December 2019 | url-status=live }} {{PD-notice}}{{cite web | url=https://www.fda.gov/media/95302/download | format=PDF | title=Previous Cumulative CY CDER BT Approvals | website=U.S. Food and Drug Administration (FDA) | access-date=7 December 2019 | archive-url=https://web.archive.org/web/20191208063439/https://www.fda.gov/media/95302/download | archive-date=8 December 2019 | url-status=live }} {{PD-notice}}