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
| Molecular Formula | C9H12N2O6 |
| Molecular Weight | 244.2014 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionSources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/208169s000lbl.pdfhttps://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/27354750Curator'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: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/208169s000lbl.pdfhttps://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/27354750
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 (formally PN401) is an acetylated prodrug of uridine. Following oral administration, uridine triacetate is deacetylated by nonspecific esterases present throughout the body, yielding uridine in the circulation. Uridine triacetate under VISTOGARD trade name is a uridine replacement agent approved for the emergency treatment of fluorouracil or capecitabine overdose (regardless of the presence of symptoms) or early-onset severe or life-threatening cardiac or central nervous system (CNS) toxicity and/or early-onset unusually severe adverse reactions (eg, gastrointestinal [GI] toxicity and/or neutropenia) within 96 hours following the end of fluorouracil or capecitabine administration in adult and pediatric patients. Uridine competitively inhibits cell damage and cell death caused by fluorouracil. Fluorouracil is a cytotoxic antimetabolite that interferes with nucleic acid metabolism in normal and cancer cells. Cells anabolize fluorouracil to the cytotoxic intermediates 5-fluoro-2’-deoxyuridine-5’- monophosphate (FdUMP) and 5-fluorouridine triphosphate (FUTP). FdUMP inhibits thymidylate synthase, blocking thymidine synthesis. Thymidine is required for DNA replication and repair. Uridine is not found in DNA. The second source of fluorouracil cytotoxicity is the incorporation of its metabolite, FUTP, into RNA. This incorporation of FUTP into RNA is proportional to systemic fluorouracil exposure. Excess circulating uridine derived from VISTOGARD is converted into uridine triphosphate (UTP), which competes with FUTP for incorporation into RNA. Uridine triacetate is also approved for the treatment of hereditary orotic aciduria under XURIDEN trade name. Uridine triacetate provides uridine in the systemic circulation of patients with hereditary orotic aciduria who cannot synthesize adequate quantities of uridine due to a genetic defect in uridine nucleotide synthesis.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16769123https://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/18540779
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 |
|||
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 Date2015 |
|||
| 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 Date2015 |
|||
| Primary | XURIDEN Approved UseXURIDEN is a pyrimidine analog for uridine replacement indicated for the treatment of hereditary orotic aciduria. Launch Date2015 |
|||
| 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 Date2015 |
|||
| 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 Date2015 |
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 |
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 |
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 |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| unlikely |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Effect of 17-beta estradiol and epidermal growth factor on DNA and RNA labeling in astroglial cells during development, maturation and differentiation in culture. | 2001-07-31 |
|
| Subcellular distribution and membrane topology of the mammalian concentrative Na+-nucleoside cotransporter rCNT1. | 2001-07-27 |
|
| Intracellular trafficking determinants in APOBEC-1, the catalytic subunit for cytidine to uridine editing of apolipoprotein B mRNA. | 2001-07-15 |
|
| Activation pathways of 5-fluorouracil in rat organs and in PC12 cells. | 2001-07-15 |
|
| Equilibrative nucleoside transporters: mapping regions of interaction for the substrate analogue nitrobenzylthioinosine (NBMPR) using rat chimeric proteins. | 2001-07-10 |
|
| Structure of an RNA hairpin from HRV-14. | 2001-07-10 |
|
| Nucleoside analogues as highly potent and selective inhibitors of herpes simplex virus thymidine kinase. | 2001-07-09 |
|
| Role of the hMLH1 DNA mismatch repair protein in fluoropyrimidine-mediated cell death and cell cycle responses. | 2001-07-01 |
|
| 5-(Trifluoromethyl)-beta-l-2'-deoxyuridine, the L-enantiomer of trifluorothymidine: stereospecific synthesis and antiherpetic evaluations. | 2001-07 |
|
| Role of the hepatic function in the development of the pyrogenic tolerance to muramyl dipeptide. | 2001-07 |
|
| Apical P2Y4 purinergic receptor controls K+ secretion by vestibular dark cell epithelium. | 2001-07 |
|
| Fluoropyrimidine sensitivity of human MCF-7 breast cancer cells stably transfected with human uridine phosphorylase. | 2001-06-15 |
|
| Functional production of mammalian concentrative nucleoside transporters in Saccharomyces cerevisiae. | 2001-06-09 |
|
| Delayed re-endothelialization and T-cell infiltration following intracoronary radiation therapy in the porcine model. | 2001-06-01 |
|
| Structure of a C-rich strand fragment of the human centromeric satellite III: a pH-dependent intercalation topology. | 2001-06-01 |
|
| Sarpogrelate inhibits serotonin-induced proliferation of porcine coronary artery smooth muscle cells: implications for long-term graft patency. | 2001-06 |
|
| 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. | 2001-06 |
|
| Poly(A) polymerase activity and RNA polyadenylation in Streptomyces coelicolor A3(2). | 2001-06 |
|
| Elucidation of the initial step of oligonucleotide fragmentation in matrix-assisted laser desorption/ionization using modified nucleic acids. | 2001-06 |
|
| Differential effects of apical and basolateral uridine triphosphate on intestinal epithelial chloride secretion. | 2001-06 |
|
| Probing Tat peptide-TAR RNA interactions by psoralen photo-cross-linking. | 2001-05-29 |
|
| Liquid-core waveguide technology for coupling column liquid chromatography and Raman spectroscopy. | 2001-05-18 |
|
| High-performance liquid chromatographic method combining radiochemical and ultraviolet detection for determination of low activities of uridine 5'-diphosphate-glucuronosyltransferase. | 2001-05-15 |
|
| Herpes simplex virus 1 ICP27 is required for transcription of two viral late (gamma 2) genes in infected cells. | 2001-05-10 |
|
| Uridine receptor: discovery and its involvement in sleep mechanism. | 2001-05-01 |
|
| Bacteriophage T7 RNA polymerase transcription elongation is inhibited by site-specific, stereospecific benzo[c]phenanthrene diol epoxide DNA lesions. | 2001-05-01 |
|
| The UDPase activity of the Kluyveromyces lactis Golgi GDPase has a role in uridine nucleotide sugar transport into Golgi vesicles. | 2001-05 |
|
| Detection of genome impairment in bovine early embryos by autoradiography: a methodological note. | 2001-05 |
|
| Effects of purine and pyrimidine nucleotides on intracellular Ca2+ in human eosinophils: activation of purinergic P2Y receptors. | 2001-05 |
|
| Lethality of glnD null mutations in Azotobacter vinelandii is suppressible by prevention of glutamine synthetase adenylylation. | 2001-05 |
|
| Phosphorylation of uridine and cytidine nucleoside analogs by two human uridine-cytidine kinases. | 2001-05 |
|
| Biphasic cytotoxic mechanism of extracellular ATP on U-937 human histiocytic leukemia cells: involvement of adenosine generation. | 2001-04-23 |
|
| Thiosugars. Part 9: synthesis and biological evaluation of some 4'-thio-L-arabino nucleoside analogues. | 2001-04-23 |
|
| Synthesis of novel 3'-C-methylene thymidine and 5-methyluridine/cytidine H-phosphonates and phosphonamidites for new backbone modification of oligonucleotides. | 2001-04-20 |
|
| Methylenetetrahydrofolate reductase polymorphism is associated with folate pool in gastrointestinal cancer tissue. | 2001-04-13 |
|
| High-performance liquid chromatographic assay for acetaminophen glucuronide in human liver microsomes. | 2001-04-05 |
|
| Effects of ATP on intracellular calcium dynamics of neurons and satellite cells in rat superior cervical ganglia. | 2001-04 |
|
| Tuber physiology and properties of starch from tubers of transgenic potato plants with altered plastidic adenylate transporter activity. | 2001-04 |
|
| The effect of cytidine on the structure and function of an RNA ligase ribozyme. | 2001-03 |
|
| An extended structural signature for the tRNA anticodon loop. | 2001-03 |
|
| A base change in the catalytic core of the hairpin ribozyme perturbs function but not domain docking. | 2001-02-27 |
|
| Importance of specific nucleotides in the folding of the natural form of the hairpin ribozyme. | 2001-02-20 |
|
| The eosinophil peroxidase-hydrogen peroxide-bromide system of human eosinophils generates 5-bromouracil, a mutagenic thymine analogue. | 2001-02-20 |
|
| Methyl orange antagonizes uridine 5' triphosphate and not alpha,beta-methylene-adenosine 5' triphosphate-evoked depolarization of rat superior cervical ganglia. | 2001-02 |
|
| UTP as an extracellular signaling molecule. | 2001-02 |
|
| Gap-junctional communication between feeder cells and recipient normal epithelial cells correlates with growth stimulation. | 2001-02 |
|
| Natural and synthetic inhibitors of UDP-glucuronosyltransferase. | 2001-02 |
|
| Synthesis of 2'-modified oligodeoxynucleotides via on-column conjugation. | 2001-01-26 |
|
| Bone morphogenetic protein-2, but not bone morphogenetic protein-7, promotes dendritic growth and calbindin phenotype in cultured rat striatal neurons. | 2001 |
|
| [Oogenesis of Mozambique tilapia. II. Synthesis of RNA and development of the nucleoli]. | 2001 |
Patents
Sample Use Guides
In Vivo Use Guide
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 starting dosage is 60 mg/kg once daily; the dose may be increased to120 mg/kg (not to exceed 8 grams) once daily for insufficient efficacy.
Route of Administration:
Oral
| Substance Class |
Chemical
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WHI7HQ7H85
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Validated (UNII)
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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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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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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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100000084782
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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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| Related Record | Type | Details | ||
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PARENT -> METABOLITE |
Mediator Substance is AOX1
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PRODRUG -> METABOLITE ACTIVE |
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| Related Record | Type | Details | ||
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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| Related Record | Type | Details | ||
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ACTIVE MOIETY |
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| Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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| Tmax | PHARMACOKINETIC |
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ORAL ADMINISTRATION |
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| Biological Half-life | PHARMACOKINETIC |
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ORAL ADMINISTRATION |
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