Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C9H12N2O6 |
| Molecular Weight | 244.2014 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N2C=CC(=O)NC2=O
InChI
InChIKey=DRTQHJPVMGBUCF-XVFCMESISA-N
InChI=1S/C9H12N2O6/c12-3-4-6(14)7(15)8(17-4)11-2-1-5(13)10-9(11)16/h1-2,4,6-8,12,14-15H,3H2,(H,10,13,16)/t4-,6-,7-,8-/m1/s1
DescriptionSources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/208169Orig1s000Lbl.pdf | https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/208159s000lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/27354750http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/208169s000lbl.pdfCurator's Comment: description was created based on several sources, including:
http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/208159s000lbl.pdf
http://www.rxlist.com/xuriden-drug.htm
https://www.drugs.com/mtm/uridine-triacetate.html
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/208169Orig1s000Lbl.pdf | https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/208159s000lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/27354750http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/208169s000lbl.pdf
Curator's Comment: description was created based on several sources, including:
http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/208159s000lbl.pdf
http://www.rxlist.com/xuriden-drug.htm
https://www.drugs.com/mtm/uridine-triacetate.html
Uridine triacetate is used to treat an overdose of capecitabine or fluorouracil. In addition, it is used as a pyrimidine analog for uridine replacement indicated for the treatment of hereditary orotic aciduria. Following oral administration, uridine triacetate is deacetylated by nonspecific esterases present throughout the body, yielding uridine in the circulation. Uridine competitively inhibits cell damage and cell death caused by fluorouracil. Uridine can be used by essentially all cells to make uridine nucleotides, compensating for the genetic deficiency in synthesis in patients with hereditary orotic aciduria. When intracellular uridine nucleotides are restored into the normal range, overproduction of orotic acid is reduced by feedback inhibition, so that urinary excretion of orotic acid is also reduced. Adverse reactions occurring in >2% of patients receiving uridine triacetate included vomiting, nausea, and diarrhea. In vitro data showed that uridine triacetate was a weak substrate for P-glycoprotein. Due to the potential for high local (gut) concentrations of the drug after dosing, the interaction of uridine triacetate with orally administered P-gp substrate drugs cannot be ruled out.
CNS Activity
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/208169Orig1s000Lbl.pdf | https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/208159s000lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/18540779https://www.ncbi.nlm.nih.gov/pubmed/16769123
Curator's Comment: Uridine triacetate is CNS penetrant and active.
Uridine triacetate is an acetylated prodrug of uridine. Circulating uridine is taken up into mammalian cells via specific nucleoside transporters, and also crosses the blood-brain barrier.
Uridine triacetate treatment may decrease symptoms of depression.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: GO:0008219 |
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Target ID: CHEMBL3542438 |
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Target ID: 151531.0 Gene Symbol: UPP2 |
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Target ID: CHEMBL2311222 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | VISTOGARD Approved UseVISTOGARD® is a pyrimidine analog indicated for the emergency treatment of adult and pediatric patients:
• following a fluorouracil or capecitabine overdose 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 earlyonset, unusually severe adverse reactions (e.g., gastrointestinal toxicity and/or neutropenia) within 96 hours following the end of fluorouracil or capecitabine administration Launch Date1.4497056E12 |
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| Curative | VISTOGARD Approved UseVISTOGARD® is a pyrimidine analog indicated for the emergency treatment of adult and pediatric patients:
• following a fluorouracil or capecitabine overdose 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 earlyonset, unusually severe adverse reactions (e.g., gastrointestinal toxicity and/or neutropenia) within 96 hours following the end of fluorouracil or capecitabine administration Launch Date1.4497056E12 |
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| Primary | XURIDEN Approved UseXURIDEN is a pyrimidine analog for uridine replacement indicated for the treatment of hereditary orotic aciduria. Launch Date1.44123835E12 |
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| Primary | XURIDEN Approved UseXURIDEN™ is indicated for the treatment of hereditary orotic aciduria. XURIDEN is a pyrimidine analog for uridine replacement indicated for the treatment of hereditary orotic aciduria. (1) Launch Date1.44132486E12 |
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| Secondary | VISTOGARD Approved UseVISTOGARD® is indicated for the emergency treatment of adult and pediatric patients:
following a fluorouracil or capecitabine overdose 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. Launch Date1.4497056E12 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
36.1 μM EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/21379380 |
4.15 g single, oral dose: 4.15 g route of administration: Oral experiment type: SINGLE co-administered: |
URIDINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
25.8 μg/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/24009876 |
450 mg/kg single, oral dose: 450 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
URIDINE plasma | Oryctolagus cuniculus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
164.1 μM × h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/21379380 |
4.15 g single, oral dose: 4.15 g route of administration: Oral experiment type: SINGLE co-administered: |
URIDINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
79 μg × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/24009876 |
450 mg/kg single, oral dose: 450 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
URIDINE plasma | Oryctolagus cuniculus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
4.6 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/21379380 |
4.15 g single, oral dose: 4.15 g route of administration: Oral experiment type: SINGLE co-administered: |
URIDINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
1.38 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/24009876 |
450 mg/kg single, oral dose: 450 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
URIDINE plasma | Oryctolagus cuniculus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Molecular cloning, functional expression and chromosomal localization of a cDNA encoding a human Na+/nucleoside cotransporter (hCNT2) selective for purine nucleosides and uridine. | 1998 Oct-Dec |
|
| Bone morphogenetic protein-2, but not bone morphogenetic protein-7, promotes dendritic growth and calbindin phenotype in cultured rat striatal neurons. | 2001 |
|
| Molecular mechanisms of apolipoprotein B mRNA editing. | 2001 Apr |
|
| In vitro glucuronidation of the cyclin-dependent kinase inhibitor flavopiridol by rat and human liver microsomes: involvement of UDP-glucuronosyltransferases 1A1 and 1A9. | 2001 Apr |
|
| Single molecule DNA sequencing in submicrometer channels: state of the art and future prospects. | 2001 Apr 13 |
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| Methyl orange antagonizes uridine 5' triphosphate and not alpha,beta-methylene-adenosine 5' triphosphate-evoked depolarization of rat superior cervical ganglia. | 2001 Feb |
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| UTP as an extracellular signaling molecule. | 2001 Feb |
|
| Identification of candidate mitochondrial RNA editing ligases from Trypanosoma brucei. | 2001 Feb |
|
| Extracellular adenosine-induced apoptosis in mouse neuroblastoma cells: studies on involvement of adenosine receptors and adenosine uptake. | 2001 Feb 15 |
|
| 5-Formyluracil and its nucleoside derivatives confer toxicity and mutagenicity to mammalian cells by interfering with normal RNA and DNA metabolism. | 2001 Feb 3 |
|
| Beta-adrenoceptor stimulation attenuates the hypertrophic effect of alpha-adrenoceptor stimulation in adult rat ventricular cardiomyocytes. | 2001 Jan |
|
| Identification of Cys140 in helix 4 as an exofacial cysteine residue within the substrate-translocation channel of rat equilibrative nitrobenzylthioinosine (NBMPR)-insensitive nucleoside transporter rENT2. | 2001 Jan 15 |
|
| Functional production of mammalian concentrative nucleoside transporters in Saccharomyces cerevisiae. | 2001 Jan-Mar |
|
| 5-(Trifluoromethyl)-beta-l-2'-deoxyuridine, the L-enantiomer of trifluorothymidine: stereospecific synthesis and antiherpetic evaluations. | 2001 Jul |
|
| Role of the hMLH1 DNA mismatch repair protein in fluoropyrimidine-mediated cell death and cell cycle responses. | 2001 Jul 1 |
|
| Nucleoside analogues as highly potent and selective inhibitors of herpes simplex virus thymidine kinase. | 2001 Jul 9 |
|
| Sarpogrelate inhibits serotonin-induced proliferation of porcine coronary artery smooth muscle cells: implications for long-term graft patency. | 2001 Jun |
|
| Possible existence of a novel receptor for uridine analogues in the central nervous system using two isomers, N3-(S)-(+)- and N3-(R)-(-)-alpha-hydroxy-beta-phenethyluridines. | 2001 Jun |
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| Differential effects of apical and basolateral uridine triphosphate on intestinal epithelial chloride secretion. | 2001 Jun |
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| Fluoropyrimidine sensitivity of human MCF-7 breast cancer cells stably transfected with human uridine phosphorylase. | 2001 Jun 15 |
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| Synthesis and separation of diastereomers of uridine 2',3'-cyclic boranophosphate. | 2001 Mar 12 |
|
| Detection of genome impairment in bovine early embryos by autoradiography: a methodological note. | 2001 May |
|
| Effects of purine and pyrimidine nucleotides on intracellular Ca2+ in human eosinophils: activation of purinergic P2Y receptors. | 2001 May |
|
| VX-497: a novel, selective IMPDH inhibitor and immunosuppressive agent. | 2001 May |
|
| Characterization of nucleoside transport systems in cultured rat epididymal epithelium. | 2001 May |
|
| Uridine receptor: discovery and its involvement in sleep mechanism. | 2001 May 1 |
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| Herpes simplex virus 1 ICP27 is required for transcription of two viral late (gamma 2) genes in infected cells. | 2001 May 10 |
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| Uracil salvage pathway in PC12 cells. | 2001 Nov 15 |
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| Uridine Triacetate. | 2016 Jun |
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| Emergency use of uridine triacetate for the prevention and treatment of life-threatening 5-fluorouracil and capecitabine toxicity. | 2017 Jan 1 |
|
| Successful use of uridine triacetate (Vistogard) three weeks after capecitabine in a patient with homozygous dihydropyrimidine dehydrogenase mutation: A case report and review of the literature. | 2019 Jan |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/208169Orig1s000Lbl.pdf https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/208159s000lbl.pdf
Curator's Comment: 10 grams orally every 6 hours for 20 doses, without regard to meals.
http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/208159s000lbl.pdf
The recommended starting dosage of oral XURIDEN for the treatment of hereditary orotic aciduria is 60 mg/kg once daily. Increase the dosage of
XURIDEN to 120 mg/kg (not to exceed 8 grams) once daily for insufficient efficacy.
The recommended dosage of VISTOGARD for the emergency treatment of fluorouracil or capecitabine overdose.
Adults: 10 grams (1 packet) orally every 6 hours for 20 doses, without regard to meals.
Pediatric: 6.2 grams/m2 of body surface area (not to exceed 10 grams per dose) orally every 6 hours
for 20 doses, without regard to meals.
Route of Administration:
Oral
Uridine dose-dependently protected cells from chemical hypoxia and ceramide, and decreased formation of reactive oxygen species and mitochondrial DNA damage due to hydrogen peroxide. These protective effects were achieved by raising uridine levels to at least 25-50 μM and serum uridine levels in this range in humans were obtained with oral uridine prodrug PN401 (Uridine triacetate).
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| Classification Tree | Code System | Code | ||
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LOINC |
59216-2
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NCI_THESAURUS |
C2080
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NDF-RT |
N0000191809
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DSLD |
3300 (Number of products:5)
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LOINC |
75159-4
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LOINC |
75130-5
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1707114
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PRIMARY | |||
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N0000175452
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PRIMARY | Analogs/Derivatives [Chemical/Ingredient] | ||
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WHI7HQ7H85
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DB02745
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11017
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PRIMARY | RxNorm | ||
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16704
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D014529
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20256
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SUB05047MIG
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58-96-8
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DTXSID40891555
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m11332
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PRIMARY | Merck Index | ||
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WHI7HQ7H85
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200-407-5
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URIDINE
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N0000007587
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PRIMARY | Pyrimidines [Chemical/Ingredient] | ||
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6029
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C922
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ACTIVE MOIETY
PARENT (METABOLITE)
PRODRUG (METABOLITE ACTIVE)
