基本情報
- CAS
4105-38-8- 標準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- 分子式
- C15H18N2O9
- 平均分子量
- 370.31 g/mol
- 単同位体質量
- 370.10123016
概要
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.
名称と識別子
- 優先名称
- 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
- 現地名
- ウリジントリアセタート
- 英語名
- 2',3',5'-Tri-O-acetyluridine
- 分子式
- C15H18N2O9
- 分子量
- 370.31
名称と別名
Uridine triacetate2',3',5'-Tri-O-acetyluridine4105-38-8TriacetyluridineVistonuridinePN401Tri-O-acetyluridineVistogardPN-401RG2133Triacetate d'uridineRG 2133
名称をさらに表示
1-(2-O,3-O,5-O-トリアセチル-β-D-リボフラノシル)ピリミジン-2,4(1H,3H)-ジオンウリジン2',3',5'-トリアセタート1-(2-O,3-O,5-O-トリアセチル-β-D-リボフラノシル)-4-ヒドロキシピリミジン-2(1H)-オン2'-O,3'-O,5'-O-トリアセチルウリジン2',3',5'-トリ-O-アセチルウリジンウリジン 2',3',5'-トリアセタート2',3',5'-トリアセチルウリジンウリジントリアセタートウリジン2′,3′,5′-トリアセタート[(2R,3R,4R,5R)-3,4-ビス(アセチルオキシ)-5-(2,4-ジオキソ-1,2,3,4-テトラヒドロピリミジン-1-イル)オキソラン-2-イル]メチル アセタート2′-O,3′-O,5′-O-トリアセチルウリジンTAU(2R,3R,4R,5R)-2-(AcetoxyMethyl)-5-(2,4-dioxo-3,4-dihydropyriMidin-1(2H)-yl)tetrahydrofuran-3,4-diyl diacetateMSTDPPNDFTDPMAPTLMTBT1DDPAC
物性
構造計算による物性
- XLogP
- -0.5
- 極性表面積
- 138 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 9
- 回転可能結合数
- 8
- 重原子数
- 26
- 形式電荷
- 0
- 複雑度
- 660
実験および物理化学的性質
DrugsPharmaceuticals -> Listed in ZINC15
LogP-0.36
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
物理化学的性質
- 融点
- 127 to · 127.0 to 131.0 °C
- 比重(密度)
- 1.43 · 1.43±0.1 g/cm3(Predicted)
- 貯蔵温度
- -20 °C · Inert atmosphere,Store in freezer, under -20°C
- 溶解性
- クロロホルム（微量）、ジクロロメタン（微量）、DMSO（微量）
- 外見
- 個体
- 酸解離定数(Pka)
- 9.39 · 9.39±0.10(Predicted)
- 色
- オフホワイト
- 由来生物
- 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
- 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
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
毒性情報
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
安全データ
- wgk
- 3
- hs_code
- 29349990
- safety_code
- 24/25
- ストレージクラス
- 13 - Non Combustible Solids
化学と産業
薬理情報
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]
関連反応
2 件
化合物ノート
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