5-fluoro-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione

• ChemBase编号: 207
• 分子式: C9H11FN2O5
• 平均质量: 246.1924432
• 单一同位素质量: 246.06519968
• SMILES: Fc1cn([C@@H]2O[C@@H]([C@@H](O)C2)CO)c(=O)[nH]c1=O
• Canonical SMILES: OC[C@H]1O[C@H](C[C@@H]1O)n1cc(F)c(=O)[nH]c1=O
• InChI: InChI=1S/C9H11FN2O5/c10-4-2-12(9(16)11-8(4)15)7-1-5(14)6(3-13)17-7/h2,5-7,13-14H,1,3H2,(H,11,15,16)/t5-,6+,7+/m0/s1
• InChIKey: ODKNJVUHOIMIIZ-RRKCRQDMSA-N

名称和登记号

名称

• IUPAC标准名: 5-fluoro-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC传统名: floxuridine
• 商标名: FUDR
• 别名: 2′-Deoxy-5-fluorouridine; FUDR; Floxuridine; 5-Fluoro-2′-deoxyuridine; 5-Fluoro-2'-deoxyuridine; 5 Fluorodeoxyuridine; 5FDU; Deoxyfluorouridine; FDUR; FDURD; Floxiridina [INN-Spanish]; Floxuridinum [INN-Latin]; Floxuridin; Fluorodeoxyuridine; Fluoruridine Deoxyribose; Floxuridine; 5-fluoro-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione; 5-fluoro-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione

登记号

• CAS号: 50-91-9
• EC号: 200-072-5
• MDL号: MFCD00006530
• Beilstein号: 90221
• PubChem SID: 160963670; 46508645; 24894724
• PubChem CID: 5790

理论计算性质

JChem

• Acid pKa: 6.6786437
• 质子受体: 5
• 质子供体: 3
• LogD (pH = 5.5): -1.3427026
• LogD (pH = 7.4): -2.0867264
• Log P: -1.3151612
• 摩尔折射率: 51.2578 cm^3
• 极化性: 20.081879 Å^3
• 极化表面积: 99.1 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -1.15
• LOG S: -0.78
• 溶解度: 4.08e+01 g/l

分子性质

理化性质

• 溶解度: 1.19E+004 mg/L
• 熔点: 148 °C(lit.); 148-150 °C; 149 - 151°C
• 比旋光度: [α]20/D +38±1°, c = 1% in H2O
• 疏水性(logP): -1.4; -1.405

安全信息

• RTECS编号: YU7525000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 联合国危险货物编号: 2811
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 3
• 危险公开号: 22
• 安全公开号: 22-36
• GHS危险品标识: GHS06
• GHS警示词: Danger
• GHS危险声明: H301
• GHS警示性声明: P301 + P310
• 个人保护装置: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3
• 保存温度: 2-8°C

药理学性质

• 相关基因信息: mouse ... Tyms(22171)

产品相关信息

• 纯度: ≥98.0% (HPLC); 95%; 97%; 98%
• Empirical Formula (Hill Notation): C9H11FN2O5
• 分类: Rare Derivatives of Natural Compounds

详细说明

DrugBank - DB00322

• Drug Groups: approved
• Description: An antineoplastic antimetabolite that is metabolized to fluorouracil when administered by rapid injection. Floxuridine is available as a sterile, nonpyrogenic, lyophilized powder for reconstitution. When administered by slow, continuous, intra-arterial infusion, it is converted to floxuridine monophosphate. It has been used to treat hepatic metastases of gastrointestinal adenocarcinomas and for palliation in malignant neoplasms of the liver and gastrointestinal tract. [PubChem]
• Indication: For palliative management of gastrointestinal adenocarcinoma metastatic to the liver, when given by continuous regional intra-arterial infusion in carefully selected patients who are considered incurable by surgery or other means. Also for the palliative management of liver cancer (usually administered by hepatic intra-arterial infusion).
• Pharmacology: Floxuridine is a pyrimidine analog that acts as an inhibitor of the S-phase of cell division. This selectively kills rapidly dividing cells. Floxuridine is an anti-metabolite. Anti-metabolites masquerade as pyramidine-like molecules which prevents normal pyrimidines from being incorporated into DNA during the S phase of the cell cycle. Flurouracil (the end-product of catabolism of floxuridine) blocks an enzyme which converts cytosine nucleosides into the deoxy derivative. In addition, DNA synthesis is further inhibited because fluoruracil blocks the incorporation of the thymdine nucleotide into the DNA strand.
• Toxicity: Oral, rat LD₅₀: 215 mg/kg. Signs of overdose include nausea, vomiting, diarrhea, gastrointestinal ulceration and bleeding, and bone marrow depression (including thrombocytopenia, leukopenia and agranulocytosis).
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Elimination: The drug is excreted intact and as urea, fluorouracil, a-fluoro-bureidopropionic acid, dihydrofluorouracil, a-fluoro-b-guanidopropionic acid and a-fluoro-b-alanine in the urine; it is also expired as respiratory carbon dioxide.
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - F0503

Biochem/physiol Actions
Antineoplastic drug that acts as a potent inhibitor of thymidylate synthetase1 Resistance to FUdR can develop in cancer cell cultures, among other means, by low-level Mycoplasma infection.2
包装
1 g in poly bottle
100, 250 mg in poly bottle

Sigma Aldrich - 46875

Biochem/physiol Actions
Antineoplastic drug that acts as a potent inhibitor of thymidylate synthetase1 Resistance to FUdR can develop in cancer cell cultures, among other means, by low-level Mycoplasma infection.2
Other Notes
Inhibits DNA synthesis by prior inhibition of thymidylate synthetase3