2',3',5'-Tri-O-acetyluridine
- Product Name
- 2',3',5'-Tri-O-acetyluridine
- CAS No.
- 4105-38-8
- Chemical Name
- 2',3',5'-Tri-O-acetyluridine
- Synonyms
- TAU;Uridine triacetate;(2R,3R,4R,5R)-2-(AcetoxyMethyl)-5-(2,4-dioxo-3,4-dihydropyriMidin-1(2H)-yl)tetrahydrofuran-3,4-diyl diacetate;MAPTL;MTBT1;RG 2133;Vistonuridine;2',3',5'-TriacetyL;Tri-O-acetyl uridine;2',3',5'-Tri-O-acety
- CBNumber
- CB0687805
- Molecular Formula
- C15H18N2O9
- Formula Weight
- 370.31
- MOL File
- 4105-38-8.mol
2',3',5'-Tri-O-acetyluridine Property
- Melting point:
- 127.0 to 131.0 °C
- Density
- 1.43±0.1 g/cm3(Predicted)
- storage temp.
- Inert atmosphere,Store in freezer, under -20°C
- solubility
- Chloroform (Slightly), Dichloromethane (Slightly), DMSO (Slightly)
- form
- Solid
- pka
- 9.39±0.10(Predicted)
- color
- Off-White
- 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-QRMSVCKNSA-N
- SMILES
- C(OC(=O)C)[C@H]1O[C@@H](N2C=CC(=O)NC2=O)[C@H](OC(=O)C)[C@@H]1OC(=O)C
- CAS DataBase Reference
- 4105-38-8(CAS DataBase Reference)
Safety
- Safety Statements
- 24/25
- WGK Germany
- 3
- HS Code
- 29349990
N-Bromosuccinimide Price
- Product number
- SAB1306711
- Product name
- ANTI-TAU(C-TERMINAL) antibody produced in rabbit
- Purity
- IgG fraction of antiserum, buffered aqueous solution
- Packaging
- 400μL
- Price
- $481
- Updated
- 2024/03/01
- Product number
- SAB1306682
- Product name
- ANTI-TAU (MAPT) (S720) antibody produced in rabbit
- Purity
- affinity isolated antibody, buffered aqueous solution
- Packaging
- 400μL
- Price
- $481
- Updated
- 2024/03/01
- Product number
- S451738
- Product name
- 2'',3'',5''-TRIACETYLURIDINE
- Purity
- AldrichCPR
- Packaging
- 250MG
- Price
- $179
- Updated
- 2024/03/01
- Product number
- T2549
- Product name
- 2',3',5'-Tri-O-acetyluridine
- Purity
- >98.0%(HPLC)(T)
- Packaging
- 5g
- Price
- $28
- Updated
- 2024/03/01
- Product number
- T2549
- Product name
- 2',3',5'-Tri-O-acetyluridine
- Purity
- >98.0%(HPLC)(T)
- Packaging
- 25g
- Price
- $90
- Updated
- 2024/03/01
2',3',5'-Tri-O-acetyluridine Chemical Properties,Usage,Production
Description
Uridine triacetate is an orally available pro-drug of uridine approved by the FDA for the treatment of the rare autosomal recessive disorder called hereditary orotic aciduria. The drug was also approved for treating overdose of two chemotherapies (fluorouracil and capecitabine). Uridine triacetate was developed by Wellstat Therapeutics and licensed to BTG.
Chemical Properties
White or almost white crystalline powder
Uses
2’,3’,5’-Triacetyluridine is used in the treatment of Alzheimer’s disease in mice and provide neuroprotective effects. Shown to also decrease depressive symptoms and increases in brain pH bipolar patients.
Definition
ChEBI: 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.
Synthesis
Commercially available uridine (167) was treated with acetic
anhydride in the presence of catalytic boron trifluoride-etherate,
and the crude product was recrystallized from ethanol to give
uridine triacetate (XX) in 74-78% yield.
Research
Administration of 200 mg/kg of 5-fluorouracil (FUra) to mice bearing human colon carcinoma DLD-1 xenografts resulted in 100% mortality. Oral administration of 2000 mg/kg of 2‘,3’,5‘-tri-O-acetyluridine (TAU), a prodrug of uridine, in combination with 120 mg/kg of 5-(benzyloxy benzyl)barbituric acid acyclonucleoside (BBBA), the most potent known inhibitor of uridine phosphorylase (UrdPase, EC 2.4.2.3), 2 hr after the administration of the same dose of FUra completely protected the mice (100% survival) from the toxicity of FUra. This combination also reduced tumor weight by 67% compared with 46% achieved by the maximum tolerated dose (50 mg/kg) of FUra alone. Similarly, administration of BBBA plus TAU 1 hr before or 4 hr after the administration of FUra reduced the tumor weight by 53 and 37%, respectively. TAU alone did not protect from FUra host toxicity. The efficiency of the BBBA plus TAU combination in rescuing from FUra host toxicities is attributed to the exceptional effectiveness of this combination in raising and maintaining higher plasma uridine concentrations than those achieved by TAU alone or by equimolar doses of uridine. The present results suggest that the BBBA plus TAU combination can provide a better substitute for the massive doses of uridine required to achieve the high levels of uridine necessary to rescue or protect from FUra host toxicities without the toxic side-effects associated with such doses of uridine[2].
References
[1] E.D. Gudio, M.L. Ferreira, L.E. Iglesias . “A rational approach to the regioselective deacetylation of 2′,3′,5′-tri-O-acetyluridine by Novozym 435 catalysed alcoholysis.” Biochimica et biophysica acta. Proteins and proteomics 1824 4 (2012): Pages 627-636.
[2] Osama M Ashour . “Modulation of 5-fluorouracil host toxicity by 5-(benzyloxybenzyl)barbituric acid acyclonucleoside, a uridine phosphorylase inhibitor, and 2′,3′,5′-tri-O-acetyluridine, a prodrug of uridine.” Biochemical pharmacology 60 3 (2000): Pages 427-431.
2',3',5'-Tri-O-acetyluridine Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from 2',3',5'-Tri-O-acetyluridine manufacturers
- Product
- 2',3',5'-Tri-O-acetyluridine 4105-38-8
- Price
- US $0.00/Kg/Drum
- Min. Order
- 1KG
- Purity
- 98%min HPLC
- Supply Ability
- 100kg
- Release date
- 2021-08-06
- Product
- 2',3',5'-Tri-O-acetyluridine 4105-38-8
- Price
- US $10.00/KG
- Min. Order
- 100KG
- Purity
- 99%
- Supply Ability
- 100 mt
- Release date
- 2024-11-22
- Product
- TAU;2',3',5'-Tri-O-acetyluridine 4105-38-8
- Price
- US $0.00-0.00/g
- Min. Order
- 100g
- Purity
- 98%+
- Supply Ability
- 100kgs
- Release date
- 2021-05-21