General
Preferred name
uridine triacetate
Synonyms
Vistonuridine ()
Xuriden ()
vistonuridine, PN401 ()
Uridine triacetateUridine, 2,3,5-triacetate(2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl diacetate ()
RG-2133 ()
PN-401 ()
RG2133 ()
Vistogard ()
Triacetate d'uridine ()
Triacetato de uridina ()
PN401 ()
2',3',5'-Triacetyluridine ()
P&D ID
PD009031
CAS
293738-13-3
4105-38-8
Tags
available
prodrug
drug
Drug Status
approved
investigational
Max Phase
4.0
Drug indication
Neoplasm
First approval
2015
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
INDICATION Marketed as the product Xuriden (FDA), uridine triacetate is indicated for the treatment of hereditary orotic aciduria.; ; Marketed as the product Vistogard (FDA), uridine triacetate is indicated for the emergency treatment of adult and pediatric patients in the following situations: 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.
MOA Uridine triacetate is a synthetic uridine pro-drug that is converted to uridine in vivo. When used for the treatment or prevention of toxicity associated with fluorouracil and other antimetabolites, uridine triacetate is utilized for its ability to compete with 5-fluorouracil (5-FU) metabolites for incorporation into the genetic material of non-cancerous cells. It reduces toxicity and cell-death associated with two cytotoxic intermediates: 5-fluoro-2'-deoxyuridine-5'-monophosphate (FdUMP) and 5-fluorouridine triphosphate (FUTP). By pre-administering with uridine (as the prodrug uridine triacetate), higher doses of 5-FU can be given allowing for improved efficacy and a reduction in toxic side effects [A18578] such as neutropenia, mucositis, diarrhea, and hand–foot syndrome. ; ; Uridine triacetate is also used for replacement therapy in the treatment of hereditary orotic aciduria, also known as uridine monophosphate synthase (UMPS) deficiency. As a result of UMPS deficiency, patients experience a systemic deficiency of pyrimidine nucleotides, accounting for most symptoms of the disease. Additionally, orotic acid from the de novo pyrimidine pathway that cannot be converted to UMP is excreted in the urine, accounting for the common name of the disorder, orotic aciduria. Furthermore, orotic acid crystals in the urine can cause episodes of obstructive uropathy. When administered as the prodrug uridine triacetate, uridine can be used by essentially all cells to make uridine nucleotides, which compensates for the genetic deficiency in synthesis in patients with hereditary orotic aciduria.
Compound Sets
11
Axon Medchem Screening Library
3362
Cayman Chemical Bioactives
27445
ChEMBL Approved Drugs
CHEMBL2107381
ChEMBL Drugs
CHEMBL2107381
Drug Repurposing Hub
DrugBank
DB09144
DrugBank Approved Drugs
DB09144
Natural product-based probes and drugs
NIH Approved Oncology Drugs
440812152
ReFrame library
Selleckchem Bioactive Compound Library
uridine-triacetate
External IDs
34
Properties
(calculated by RDKit )
Molecular Weight
370.1
Hydrogen Bond Acceptors
10
Hydrogen Bond Donors
1
Rotatable Bonds
5
Ring Count
2
Aromatic Ring Count
1
cLogP
-1.14
TPSA
142.99
Fraction CSP3
0.53
Chiral centers
4.0
Largest ring
6.0
QED
0.5
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Indication
orotic aciduria
Target
Uridine prodrug
Biosynthetic Origin
Nucleoside
Therapeutic Indication
Orotic Aciduria
Therapeutic Class
Metabolic Disorders
Source data