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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
Structure of URIDINE

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

HIDE SMILES / InChI

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

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 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

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

2015
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

2015
Primary
XURIDEN

Approved Use

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

Launch Date

2015
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

2015
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

2015
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
Anemia of azaribine in the treatment of psoriasis.
1976 Dec
Nucleoside transport in human colonic epithelial cell lines: evidence for two Na+-independent transport systems in T84 and Caco-2 cells.
1999 Jun 9
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
Analysis of RNA synthesis by cytometry.
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
Synthesis of novel 3'-C-methylene thymidine and 5-methyluridine/cytidine H-phosphonates and phosphonamidites for new backbone modification of oligonucleotides.
2001 Apr 20
Uridine phosphorylase association with vimentin. Intracellular distribution and localization.
2001 Apr 20
Thiosugars. Part 9: synthesis and biological evaluation of some 4'-thio-L-arabino nucleoside analogues.
2001 Apr 23
Natural and synthetic inhibitors of UDP-glucuronosyltransferase.
2001 Feb
Terminal uridine nick end labelling and mitosis in breast carcinoma. Correlation with tumor grade and p53 overexpression.
2001 Feb
Purine and pyrimidine nucleotide-sensitive phospholipase A(2) in ampulla from frog semicircular canal.
2001 Feb
A novel proton-dependent nucleoside transporter, CeCNT3, from Caenorhabditis elegans.
2001 Feb
The effects of P2Y receptor agonists and adenosine on prostaglandin production by the guinea-pig uterus.
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
The eosinophil peroxidase-hydrogen peroxide-bromide system of human eosinophils generates 5-bromouracil, a mutagenic thymine analogue.
2001 Feb 20
Synthesis using ring closure metathesis and effect on nucleoside transport of a (N)-methanocarba S-(4-nitrobenzyl)thioinosine derivative.
2001 Feb 22
5-Formyluracil and its nucleoside derivatives confer toxicity and mutagenicity to mammalian cells by interfering with normal RNA and DNA metabolism.
2001 Feb 3
Determination of nucleosides in natural Cordyceps sinensis and cultured Cordyceps mycelia by capillary electrophoresis.
2001 Jan
Reduced cellular transport and activation of fluoropyrimidine nucleosides and resistance in human lymphocytic cell lines selected for arabinosylcytosine resistance.
2001 Jan 1
Functional production of mammalian concentrative nucleoside transporters in Saccharomyces cerevisiae.
2001 Jan-Mar
Poly(A) polymerase activity and RNA polyadenylation in Streptomyces coelicolor A3(2).
2001 Jun
Differential effects of apical and basolateral uridine triphosphate on intestinal epithelial chloride secretion.
2001 Jun
Active intestinal absorption of nucleosides by Na+-dependent transport across the brush border membrane in cows.
2001 Mar
P2Y receptor-mediated inhibition of voltage-activated Ca(2+) currents in PC12 cells.
2001 Mar
Synergistic efficacy of 3n-butyrate and 5-fluorouracil in human colorectal cancer xenografts via modulation of DNA synthesis.
2001 Mar
Ontogenic and longitudinal activity of Na(+)-nucleoside transporters in the human intestine.
2001 Mar
HuR, a RNA stability factor, is expressed in malignant brain tumors and binds to adenine- and uridine-rich elements within the 3' untranslated regions of cytokine and angiogenic factor mRNAs.
2001 Mar 1
Synthesis and separation of diastereomers of uridine 2',3'-cyclic boranophosphate.
2001 Mar 12
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
Identification and quantification of base and nucleoside markers in extracts of Ganoderma lucidum, Ganoderma japonicum and Ganoderma capsules by micellar electrokinetic chromatography.
2001 Mar 9
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
Phosphorylation of uridine and cytidine nucleoside analogs by two human uridine-cytidine kinases.
2001 May
Localization of GFP-tagged concentrative nucleoside transporters in a renal polarized epithelial cell line.
2001 May
VX-497: a novel, selective IMPDH inhibitor and immunosuppressive agent.
2001 May
Uridine receptor: discovery and its involvement in sleep mechanism.
2001 May 1
Bacteriophage T7 RNA polymerase transcription elongation is inhibited by site-specific, stereospecific benzo[c]phenanthrene diol epoxide DNA lesions.
2001 May 1
High-performance liquid chromatographic method combining radiochemical and ultraviolet detection for determination of low activities of uridine 5'-diphosphate-glucuronosyltransferase.
2001 May 15
Uracil salvage pathway in PC12 cells.
2001 Nov 15
Uridine Triacetate.
2016 Jun
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
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).
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:17:34 GMT 2023
Edited
by admin
on Fri Dec 15 15:17:34 GMT 2023
Record UNII
WHI7HQ7H85
Record Status Validated (UNII)
Record Version
  • Download
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
URIDINE [USP IMPURITY]
Common Name English
1-.BETA.-D-RIBOFURANOSYLURACIL
Common Name English
ADENOSINE IMPURITY F [EP IMPURITY]
Common Name English
NSC-20256
Code English
URIDINE [USP-RS]
Common Name English
1-.BETA.-D-RIBOFURANOSYLPYRIMIDINE-2,4(1H,3H)-DIONE
Systematic Name English
URIDINE [MART.]
Common Name English
Classification Tree Code System Code
LOINC 59216-2
Created by admin on Fri Dec 15 15:17:34 GMT 2023 , Edited by admin on Fri Dec 15 15:17:34 GMT 2023
NCI_THESAURUS C2080
Created by admin on Fri Dec 15 15:17:34 GMT 2023 , Edited by admin on Fri Dec 15 15:17:34 GMT 2023
NDF-RT N0000191809
Created by admin on Fri Dec 15 15:17:34 GMT 2023 , Edited by admin on Fri Dec 15 15:17:34 GMT 2023
DSLD 3300 (Number of products:5)
Created by admin on Fri Dec 15 15:17:34 GMT 2023 , Edited by admin on Fri Dec 15 15:17:34 GMT 2023
LOINC 75159-4
Created by admin on Fri Dec 15 15:17:34 GMT 2023 , Edited by admin on Fri Dec 15 15:17:34 GMT 2023
LOINC 75130-5
Created by admin on Fri Dec 15 15:17:34 GMT 2023 , Edited by admin on Fri Dec 15 15:17:34 GMT 2023
Code System Code Type Description
RS_ITEM_NUM
1707114
Created by admin on Fri Dec 15 15:17:34 GMT 2023 , Edited by admin on Fri Dec 15 15:17:34 GMT 2023
PRIMARY
NDF-RT
N0000175452
Created by admin on Fri Dec 15 15:17:34 GMT 2023 , Edited by admin on Fri Dec 15 15:17:34 GMT 2023
PRIMARY Analogs/Derivatives [Chemical/Ingredient]
DAILYMED
WHI7HQ7H85
Created by admin on Fri Dec 15 15:17:34 GMT 2023 , Edited by admin on Fri Dec 15 15:17:34 GMT 2023
PRIMARY
DRUG BANK
DB02745
Created by admin on Fri Dec 15 15:17:34 GMT 2023 , Edited by admin on Fri Dec 15 15:17:34 GMT 2023
PRIMARY
RXCUI
11017
Created by admin on Fri Dec 15 15:17:34 GMT 2023 , Edited by admin on Fri Dec 15 15:17:34 GMT 2023
PRIMARY RxNorm
CHEBI
16704
Created by admin on Fri Dec 15 15:17:34 GMT 2023 , Edited by admin on Fri Dec 15 15:17:34 GMT 2023
PRIMARY
MESH
D014529
Created by admin on Fri Dec 15 15:17:34 GMT 2023 , Edited by admin on Fri Dec 15 15:17:34 GMT 2023
PRIMARY
NSC
20256
Created by admin on Fri Dec 15 15:17:34 GMT 2023 , Edited by admin on Fri Dec 15 15:17:34 GMT 2023
PRIMARY
EVMPD
SUB05047MIG
Created by admin on Fri Dec 15 15:17:34 GMT 2023 , Edited by admin on Fri Dec 15 15:17:34 GMT 2023
PRIMARY
CAS
58-96-8
Created by admin on Fri Dec 15 15:17:34 GMT 2023 , Edited by admin on Fri Dec 15 15:17:34 GMT 2023
PRIMARY
EPA CompTox
DTXSID40891555
Created by admin on Fri Dec 15 15:17:34 GMT 2023 , Edited by admin on Fri Dec 15 15:17:34 GMT 2023
PRIMARY
MERCK INDEX
m11332
Created by admin on Fri Dec 15 15:17:34 GMT 2023 , Edited by admin on Fri Dec 15 15:17:34 GMT 2023
PRIMARY Merck Index
FDA UNII
WHI7HQ7H85
Created by admin on Fri Dec 15 15:17:34 GMT 2023 , Edited by admin on Fri Dec 15 15:17:34 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-407-5
Created by admin on Fri Dec 15 15:17:34 GMT 2023 , Edited by admin on Fri Dec 15 15:17:34 GMT 2023
PRIMARY
WIKIPEDIA
URIDINE
Created by admin on Fri Dec 15 15:17:34 GMT 2023 , Edited by admin on Fri Dec 15 15:17:34 GMT 2023
PRIMARY
NDF-RT
N0000007587
Created by admin on Fri Dec 15 15:17:34 GMT 2023 , Edited by admin on Fri Dec 15 15:17:34 GMT 2023
PRIMARY Pyrimidines [Chemical/Ingredient]
PUBCHEM
6029
Created by admin on Fri Dec 15 15:17:34 GMT 2023 , Edited by admin on Fri Dec 15 15:17:34 GMT 2023
PRIMARY
NCI_THESAURUS
C922
Created by admin on Fri Dec 15 15:17:34 GMT 2023 , Edited by admin on Fri Dec 15 15:17:34 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> METABOLITE
Mediator Substance is AOX1
PRODRUG -> METABOLITE ACTIVE
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC ORAL ADMINISTRATION

Biological Half-life PHARMACOKINETIC ORAL ADMINISTRATION