2',3',5'-tri-O-acetyluridine
Basic information
- CAS
4105-38-8- Standard SMILES
CC(=O)OC[C@H]1O[C@@H](n2ccc(=O)[nH]c2=O)[C@H](OC(C)=O)[C@@H]1OC(C)=O- InChIKey
AUFUWRKPQLGTGF-FMKGYKFTSA-N- Molecular formula
- C15H18N2O9
- Average molar mass
- 370.31 g/mol
- Monoisotopic mass
- 370.10123016
Overview
Uridine triacetate is an acetate ester that is uracil in which the three hydroxy hydrogens are replaced by acetate group. A prodrug for uridine, it is used for the treatment of hereditary orotic aciduria and for management of fluorouracil toxicity. It has a role as a prodrug, a neuroprotective agent and an orphan drug. It is a member of uridines and an acetate ester.
Names & identifiers
- Preferred name
- 2',3',5'-tri-O-acetyluridine
- IUPAC
- [(2R,3R,4R,5R)-3,4-diacetyloxy-5-(2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl acetate
- English name
- 2',3',5'-Tri-O-acetyluridine
- Molecular formula
- C15H18N2O9
- Molecular weight
- 370.31
Names & synonyms
Uridine triacetate2',3',5'-Tri-O-acetyluridine4105-38-8TriacetyluridineVistonuridinePN401Tri-O-acetyluridineVistogardPN-401RG2133Triacetate d'uridineRG 2133
Show more names
TAU(2R,3R,4R,5R)-2-(AcetoxyMethyl)-5-(2,4-dioxo-3,4-dihydropyriMidin-1(2H)-yl)tetrahydrofuran-3,4-diyl diacetateMSTDPPNDFTDPMAPTLMTBT1DDPACMTBT2
Triacetato de uridinaCHEBI:90914DTXSID409614092WP61F175MNSC79269[(2R,3R,4R,5R)-3,4-bis(acetyloxy)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methyl acetateuridini triacetas((2R,3R,4R,5R)-3,4-bis(acetyloxy)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl)methyl acetate
Database identifiers
- CAS
4105-38-8- PubChem CID
- 20058
- DTXSID
DTXSID40961409- ChEMBL
CHEMBL2107381
Properties
Computed structural properties
- XLogP
- -0.5
- Topological polar surface area
- 138 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 8
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 660
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
LogP-0.36
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Physicochemical properties
- Melting point
- 127 to · 127.0 to 131.0 °C
- Density
- 1.43 · 1.43±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · Inert atmosphere,Store in freezer, under -20°C
- solubility
- Chloroform (Slightly), Dichloromethane (Slightly), DMSO (Slightly)
- form
- Solid
- pka
- 9.39 · 9.39±0.10(Predicted)
- color
- Off-White
- biological source
- synthetic (organic)
- InChI
- InChI=1S/C15H18N2O9/c1-7(18)23-6-10-12(24-8(2)19)13(25-9(3)20)14(26-10)17-5-4-11(21)16-15(17)22/h4-5,10,12-14H,6H2,1-3H3,(H,16,21,22)/t10-,12-,13-,14-/m1/s1
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Uridine triacetate
vNo-DILI-concern
0
No match
DOI:10.1016/j.drudis.2016.02.015
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- hs_code
- 29349990
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 24/25
- Storage Class
- 13 - Non Combustible Solids
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P301+P312-P302+P352-P304+P340-P305+P351+P338
Chemistry & industry
Pharmacology
ATC Code
A - Alimentary tract and metabolism
QA - Alimentary tract and metabolism
Mechanism of Action
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 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.
Biological Half-Life2 to 2.5 hours
Metabolism/MetabolitesFollowing oral administration, uridine triacetate is deacetylated by nonspecific esterases present throughout the body, yielding uridine in the circulation.
FDA Pharmacological Classification
URIDINE TRIACETATE
Analogs/Derivatives [Chemical/Ingredient]; Pyrimidine Analog [EPC]; Pyrimidines [Chemical/Ingredient]
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