U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C9H12N2O6
Molecular Weight 244.2017
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of URIDINE

SMILES

c1cn([C@@]2([H])[C@@]([H])([C@@]([H])([C@@]([H])(CO)O2)O)O)c(=O)nc1O

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

HIDE SMILES / InChI

Description
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

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

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
VISTOGARD

Approved Use

VISTOGARD® 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 Date

1.4497056E12
Curative
VISTOGARD

Approved Use

VISTOGARD® 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 Date

1.4497056E12
Primary
XURIDEN

Approved Use

XURIDEN is a pyrimidine analog for uridine replacement indicated for the treatment of hereditary orotic aciduria.

Launch Date

1.44123835E12
Primary
XURIDEN

Approved Use

XURIDEN™ 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 Date

1.44132486E12
Secondary
VISTOGARD

Approved Use

VISTOGARD® 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 Date

1.4497056E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
36.1 μM
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
164.1 μM × h
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
4.6 h
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
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
Overview

Overview

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
unlikely
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
PubMed

PubMed

TitleDatePubMed
Bone morphogenetic protein-2, but not bone morphogenetic protein-7, promotes dendritic growth and calbindin phenotype in cultured rat striatal neurons.
2001
Effects of ATP on intracellular calcium dynamics of neurons and satellite cells in rat superior cervical ganglia.
2001 Apr
Synthesis of novel 3'-C-methylene thymidine and 5-methyluridine/cytidine H-phosphonates and phosphonamidites for new backbone modification of oligonucleotides.
2001 Apr 20
Thiosugars. Part 9: synthesis and biological evaluation of some 4'-thio-L-arabino nucleoside analogues.
2001 Apr 23
High-performance liquid chromatographic assay for acetaminophen glucuronide in human liver microsomes.
2001 Apr 5
Methyl orange antagonizes uridine 5' triphosphate and not alpha,beta-methylene-adenosine 5' triphosphate-evoked depolarization of rat superior cervical ganglia.
2001 Feb
Natural and synthetic inhibitors of UDP-glucuronosyltransferase.
2001 Feb
Identification of candidate mitochondrial RNA editing ligases from Trypanosoma brucei.
2001 Feb
Terminal uridine nick end labelling and mitosis in breast carcinoma. Correlation with tumor grade and p53 overexpression.
2001 Feb
The RNA structures engaged in replication and transcription of the A59 strain of mouse hepatitis virus.
2001 Feb
Uridine uptake inhibition as a cytotoxicity test for a human hepatoma cell line (HepG2 cells): comparison with the neutral red assay.
2001 Feb 14
Reduced cellular transport and activation of fluoropyrimidine nucleosides and resistance in human lymphocytic cell lines selected for arabinosylcytosine resistance.
2001 Jan 1
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
Synthesis of 2'-modified oligodeoxynucleotides via on-column conjugation.
2001 Jan 26
Molecular identification and characterization of novel human and mouse concentrative Na+-nucleoside cotransporter proteins (hCNT3 and mCNT3) broadly selective for purine and pyrimidine nucleosides (system cib).
2001 Jan 26
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 hepatic function in the development of the pyrogenic tolerance to muramyl dipeptide.
2001 Jul
Apical P2Y4 purinergic receptor controls K+ secretion by vestibular dark cell epithelium.
2001 Jul
Role of the hMLH1 DNA mismatch repair protein in fluoropyrimidine-mediated cell death and cell cycle responses.
2001 Jul 1
Equilibrative nucleoside transporters: mapping regions of interaction for the substrate analogue nitrobenzylthioinosine (NBMPR) using rat chimeric proteins.
2001 Jul 10
Structure of an RNA hairpin from HRV-14.
2001 Jul 10
Intracellular trafficking determinants in APOBEC-1, the catalytic subunit for cytidine to uridine editing of apolipoprotein B mRNA.
2001 Jul 15
Activation pathways of 5-fluorouracil in rat organs and in PC12 cells.
2001 Jul 15
Subcellular distribution and membrane topology of the mammalian concentrative Na+-nucleoside cotransporter rCNT1.
2001 Jul 27
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 Jul 31
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
Poly(A) polymerase activity and RNA polyadenylation in Streptomyces coelicolor A3(2).
2001 Jun
Elucidation of the initial step of oligonucleotide fragmentation in matrix-assisted laser desorption/ionization using modified nucleic acids.
2001 Jun
Delayed re-endothelialization and T-cell infiltration following intracoronary radiation therapy in the porcine model.
2001 Jun 1
Structure of a C-rich strand fragment of the human centromeric satellite III: a pH-dependent intercalation topology.
2001 Jun 1
Fluoropyrimidine sensitivity of human MCF-7 breast cancer cells stably transfected with human uridine phosphorylase.
2001 Jun 15
Active intestinal absorption of nucleosides by Na+-dependent transport across the brush border membrane in cows.
2001 Mar
Uridine insertion/deletion RNA editing in Leishmania tarentolae mitochondria shows cell cycle dependence.
2001 Mar
Successful living-donor liver transplantation from an asymptomatic carrier mother in ornithine transcarbamylase deficiency.
2001 Mar
Synergistic efficacy of 3n-butyrate and 5-fluorouracil in human colorectal cancer xenografts via modulation of DNA synthesis.
2001 Mar
Nucleotides U28-A42 and A37 in unmodified yeast tRNA(Trp) as negative identity elements for bovine tryptophanyl-tRNA synthetase.
2001 Mar 16
A cis-dominant cyclic nucleotide-dependent regulatory domain in the 3'-untranslated region of Na(+)/glucose cotransporter (SGLT1) mRNA.
2001 Mar 16
Cytosolic high K(m) 5'-nucleotidase and 5'(3')-deoxyribonucleotidase in substrate cycles involved in nucleotide metabolism.
2001 Mar 2
An expressed sequence tag (EST) data mining strategy succeeding in the discovery of new G-protein coupled receptors.
2001 Mar 30
Indomethacin prevents the induction of inducible nitric oxide synthase in murine peritoneal macrophages and decreases their nitric oxide production.
2001 Mar 9
Dynamic changes in glucose metabolism accompanying the expression of the neural phenotype after differentiation in PC12 cells.
2001 Mar 9
The UDPase activity of the Kluyveromyces lactis Golgi GDPase has a role in uridine nucleotide sugar transport into Golgi vesicles.
2001 May
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
Lethality of glnD null mutations in Azotobacter vinelandii is suppressible by prevention of glutamine synthetase adenylylation.
2001 May
Liquid-core waveguide technology for coupling column liquid chromatography and Raman spectroscopy.
2001 May 18
Probing Tat peptide-TAR RNA interactions by psoralen photo-cross-linking.
2001 May 29
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
At very high levels (10–200 ìM) in vitro uridine decreases azide and H2O2 toxicity in fibroblasts from patients with Alzheimer disease and in human neuroprogenitor cells.
Name Type Language
URIDINE
INCI   MART.   MI   USP-RS   WHO-DD  
INCI  
Official Name English
URACIL RIBOSIDE
Common Name English
URIDINE [INCI]
Common Name English
URIDINE [WHO-DD]
Common Name English
URIDINE [MI]
Common Name English
ADENOSINE IMPURITY F [EP]
Common Name English
1-.BETA.-D-RIBOFURANOSYLURACIL
Common Name English
NSC-20256
Code English
URIDINE [USP-RS]
Common Name English
URIDINE [MART.]
Common Name English
Classification Tree Code System Code
LOINC 59216-2
Created by admin on Sat Jun 26 14:00:53 UTC 2021 , Edited by admin on Sat Jun 26 14:00:53 UTC 2021
NCI_THESAURUS C2080
Created by admin on Sat Jun 26 14:00:53 UTC 2021 , Edited by admin on Sat Jun 26 14:00:53 UTC 2021
NDF-RT N0000191809
Created by admin on Sat Jun 26 14:00:53 UTC 2021 , Edited by admin on Sat Jun 26 14:00:53 UTC 2021
DSLD 3300 (Number of products:5)
Created by admin on Sat Jun 26 14:00:53 UTC 2021 , Edited by admin on Sat Jun 26 14:00:53 UTC 2021
LOINC 75159-4
Created by admin on Sat Jun 26 14:00:53 UTC 2021 , Edited by admin on Sat Jun 26 14:00:53 UTC 2021
LOINC 75130-5
Created by admin on Sat Jun 26 14:00:53 UTC 2021 , Edited by admin on Sat Jun 26 14:00:53 UTC 2021
Code System Code Type Description
NDF-RT
N0000175452
Created by admin on Sat Jun 26 14:00:53 UTC 2021 , Edited by admin on Sat Jun 26 14:00:53 UTC 2021
PRIMARY Analogs/Derivatives [Chemical/Ingredient]
DRUG BANK
DB02745
Created by admin on Sat Jun 26 14:00:53 UTC 2021 , Edited by admin on Sat Jun 26 14:00:53 UTC 2021
PRIMARY
RXCUI
11017
Created by admin on Sat Jun 26 14:00:53 UTC 2021 , Edited by admin on Sat Jun 26 14:00:53 UTC 2021
PRIMARY RxNorm
MESH
D014529
Created by admin on Sat Jun 26 14:00:53 UTC 2021 , Edited by admin on Sat Jun 26 14:00:53 UTC 2021
PRIMARY
USP_CATALOG
1707114
Created by admin on Sat Jun 26 14:00:53 UTC 2021 , Edited by admin on Sat Jun 26 14:00:53 UTC 2021
PRIMARY USP-RS
EVMPD
SUB05047MIG
Created by admin on Sat Jun 26 14:00:53 UTC 2021 , Edited by admin on Sat Jun 26 14:00:53 UTC 2021
PRIMARY
CAS
58-96-8
Created by admin on Sat Jun 26 14:00:53 UTC 2021 , Edited by admin on Sat Jun 26 14:00:53 UTC 2021
PRIMARY
MERCK INDEX
M11332
Created by admin on Sat Jun 26 14:00:53 UTC 2021 , Edited by admin on Sat Jun 26 14:00:53 UTC 2021
PRIMARY Merck Index
FDA UNII
WHI7HQ7H85
Created by admin on Sat Jun 26 14:00:53 UTC 2021 , Edited by admin on Sat Jun 26 14:00:53 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-407-5
Created by admin on Sat Jun 26 14:00:53 UTC 2021 , Edited by admin on Sat Jun 26 14:00:53 UTC 2021
PRIMARY
WIKIPEDIA
URIDINE
Created by admin on Sat Jun 26 14:00:53 UTC 2021 , Edited by admin on Sat Jun 26 14:00:53 UTC 2021
PRIMARY
NDF-RT
N0000007587
Created by admin on Sat Jun 26 14:00:53 UTC 2021 , Edited by admin on Sat Jun 26 14:00:53 UTC 2021
PRIMARY Pyrimidines [Chemical/Ingredient]
PUBCHEM
6029
Created by admin on Sat Jun 26 14:00:53 UTC 2021 , Edited by admin on Sat Jun 26 14:00:53 UTC 2021
PRIMARY
NCI_THESAURUS
C922
Created by admin on Sat Jun 26 14:00:53 UTC 2021 , Edited by admin on Sat Jun 26 14:00:53 UTC 2021
PRIMARY