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Uridine triacetate

CAT: 0804-HY-14905-01Size: 10 mM - 1 mLDry Ice: NoHazardous: No
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CAT#:0804-HY-14905-01Size:10 mM - 1 mL
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Description
Uridine triacetate (Tri-O-acetyl uridine) is an orally active proagent of Uridine. Uridine triacetate is quickly absorbed in the gut, and is rapidly deacetylated in the circulation to yield free uridine. Uridine triacetate is used for the research of 5-fluorouracil (5-FU) and capecitabine toxicity, or early-onset cardiac or central nervous system (CNS)[2].
CAS Number
4105-38-8
Product Name Alternative
Tri-O-acetyl uridine
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
Drug Derivative
Type
Reference compound
Related Pathways
Others
Applications
Neuroscience-Neuromodulation
Field of Research
Neurological Disease
Assay Protocol
https://www.medchemexpress.com/uridine-triacetate.html
Concentration
10mM
Purity
99.95
Solubility
DMSO : ≥ 100 mg/mL|H2O : 10 mg/mL (ultrasonic)
Smiles
O=C1NC(C=CN1[C@H]2[C@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O2)=O
Molecular Formula
C15H18N2O9
Molecular Weight
370.31
Precautions
H302, H315, H319, H335
References & Citations
[1]Ma WW, et al. Emergency use of uridine triacetate for the prevention and treatment of life-threatening 5-fluorouracil and capecitabine toxicity. Cancer. 2017 Jan 1;123 (2) :345-356.|[2]Cada DJ, et al. Uridine Triacetate. Hosp Pharm. 2016 Jun;51 (6) :484-8.|[3]Rolando A G Garcia, et al. Prompt treatment with uridine triacetate improves survival and reduces toxicity due to fluorouracil and capecitabine overdose or dihydropyrimidine dehydrogenase deficiency. Toxicol Appl Pharmacol. 2018 Aug 15;353:67-73. |[4]Siennah R Miller, et al. Predicting Drug Interactions with Human Equilibrative Nucleoside Transporters 1 and 2 Using Functional Knockout Cell Lines and Bayesian Modeling. Mol Pharmacol. 2021 Feb;99 (2) :147-162.
Shipping Conditions
Blue Ice
Storage Conditions
-20°C, 3 years (Powder)
Scientific Category
Reference compound1
Clinical Information
Launched

Chemical Information

2',3',5'-tri-O-acetyluridine

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.

CAS Number4105-38-8
PubChem CID20058
IUPAC Name[(2R,3R,4R,5R)-3,4-diacetyloxy-5-(2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl acetate
Molecular FormulaC15H18N2O9
Molecular Weight370.31
XLogP-0.5
Topological Polar Surface Area138
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count9
Rotatable Bond Count8
Heavy Atom Count26
Formal Charge0
Complexity660
SMILES
CC(=O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=CC(=O)NC2=O)OC(=O)C)OC(=O)C
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
InChIKey
AUFUWRKPQLGTGF-FMKGYKFTSA-N
Chemical Structure
2D Structure
2D structure of 2',3',5'-tri-O-acetyluridine
CAS: 4105-38-8
CID: 20058
Formula: C15H18N2O9
MW: 370.31
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight370.31
XLogP3-0.5
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count9
Rotatable Bond Count8
Exact Mass370.10123016
Monoisotopic Mass370.10123016
Topological Polar Surface Area138 Ų
Heavy Atom Count26
Formal Charge0
Complexity660
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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