5-fluoro-1,2,3,4-tetrahydropyrimidine-2,4-dione

• ChemBase编号: 426
• 分子式: C4H3FN2O2
• 平均质量: 130.0772232
• 单一同位素质量: 130.01785557
• SMILES: Fc1c(=O)[nH]c(=O)[nH]c1
• Canonical SMILES: Fc1c[nH]c(=O)[nH]c1=O
• InChI: InChI=1S/C4H3FN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9)
• InChIKey: GHASVSINZRGABV-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 5-fluoro-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC传统名: fluorouracil
• 商标名: 5 Fluorouracil; Adrucil; Arumel; Carac; Carzonal; Effluderm; Efudex; Efudix; Efurix; FU; Fluoroblastin; Fluoroplex; Fluracil; Fluracilum; Fluri; Fluril; Fluro Uracil; Ftoruracil; Kecimeton; Phthoruracil; Phtoruracil; Queroplex; Timazin; URF; Ulup
• 别名: 2,4-二羟基-5-氟嘧啶; 5-氟-2,4(1H,3H)-嘧啶二酮; 5-氟脲嘧啶; 5-氟尿嘧啶; 5-Fluoro-2,4(1H,3H)pyrimidinedione; 5-Fluoropyrimidine-2,4-diol; Adrucil; Arumel; Flurablastin; Queroplex; Ro 2-9757; Timazin; U 8953; Ulup; 5-Fluoro Uracil; 5-fluoropyrimidine-2,4(1H,3H)-dione; Fluorouracil; 5-Fluorouracil; 2,4-Dihydroxy-5-fluoropyrimidine; 5-Fluoro-2,4(1H,3H)-pyrimidinedione; 5-Fluorouracil; Fluorouracil; 5-FU; Carac; Efudex; Fluoroplex; Adrucil(Fluorouracil); 5-Fluoropyrimidine-2,4(1H,3H)-dione; 5-Fluorouracil 99%; 5-Fluorouracil

登记号

• CAS号: 51-21-8
• EC号: 200-085-6
• MDL号: MFCD00006018
• Beilstein号: 127172
• 默克索引号: 144181
• PubChem SID: 46508557; 160963889; 24888466; 24871165
• PubChem CID: 3385

理论计算性质

JChem

• Acid pKa: 6.7786403
• 质子受体: 2
• 质子供体: 2
• LogD (pH = 5.5): -0.6778695
• LogD (pH = 7.4): -1.3501022
• Log P: -0.6558481
• 摩尔折射率: 26.1722 cm^3
• 极化性: 9.588146 Å^3
• 极化表面积: 58.2 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -0.58
• LOG S: -1.35
• 溶解度: 5.86e+00 g/l

分子性质

理化性质

• 溶解度: < 0.1 g/100 mL at 19 °C; DMSO; H2O: soluble10 mg/mL, clear; Water
• 外观: off-white to white powder; White Solid
• 熔点: 130.5 °C; 280-282°C(dec); 280-282°C; 282-286 °C (dec.); 282-286 °C (dec.)(lit.); 282-286(dec.)°C; ca 282°C dec.
• 沸点: 190-200°C/0.1mm
• 疏水性(logP): -0.8

安全信息

• 保存条件: -20°C; Refrigerator; Room Temperature (15-30°C), Protect from light
• 保存注意事项: IRRITANT, TOXIC, CORROSIVE; Light Sensitive; Toxic/Light Sensitive/Keep Cold
• RTECS编号: YR0350000
• 欧盟危险性物质标志: 腐蚀性(Corrosive) (C); 有毒(Toxic) (T); 有害性(Harmful) (Xn)
• 联合国危险货物编号: 2811; 2928; UN2811
• 德国WGK号: 3
• 联合国危险货物等级: 6.1; 8
• 联合国危险货物包装类别(PG): 3; II; III
• 澳大利亚Hazchem: 2XE
• 危险公开号: 22; 61-22-48/22-68; R:22-34
• 安全公开号: 53-45; S:26-27/28-36/37/39-46-64
• 欧盟危险货物分类: TC2
• 欧盟危险识别号(EUHIN): 6.1B
• 美国ERG指导号: 154
• TSCA收录: true; 是
• GHS危险品标识: GHS07; GHS08
• GHS危险声明: H360-H341-H373-H302
• GHS警示性声明: P260-P281-P301+P312-P308+P313-P405-P501A
• RID/ADR: UN 2811 6.1/PG 3

药理学性质

• 作用靶点: Antimetabolites

产品相关信息

• 纯度: ~99%; ≥99.0% (HPLC); 97%; 98.5%; 98+%; 99%
• 成盐信息: Free Base
• Empirical Formula (Hill Notation): C4H3FN2O2

详细说明

MP Biomedicals - 02101722

Crystalline
Purity: ~99%

DrugBank - DB00544

• Drug Groups: approved
• Description: A pyrimidine analog that is an antineoplastic antimetabolite. It interferes with DNA synthesis by blocking the thymidylate synthetase conversion of deoxyuridylic acid to thymidylic acid. [PubChem]
• Indication: For the topical treatment of multiple actinic or solar keratoses. In the 5% strength it is also useful in the treatment of superficial basal cell carcinomas when conventional methods are impractical, such as with multiple lesions or difficult treatment sites. Fluorouracil injection is indicated in the palliative management of some types of cancer, including colon, esophageal, gastric, rectum, breast, biliary tract, stomach, head and neck, cervical, pancreas, renal cell, and carcinoid.
• Pharmacology: Fluorouracil is an antineoplastic anti-metabolite. Anti-metabolites masquerade as purine or pyrimidine - which become the building blocks of DNA. They prevent these substances from becoming incorporated into DNA during the "S" phase (of the cell cycle), stopping normal development and division. Fluorouracil blocks an enzyme which converts the cytosine nucleotide into the deoxy derivative. In addition, DNA synthesis is further inhibited because Fluorouracil blocks the incorporation of the thymidine nucleotide into the DNA strand.
• Toxicity: LD₅₀=230mg/kg (orally in mice)
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: 28-100%
• Half Life: 10-20 minutes
• Protein Binding: 8-12%
• Elimination: Seven percent to 20% of the parent drug is excreted unchanged in the urine in 6 hours; of this over 90% is excreted in the first hour.; The remaining percentage of the administered dose is metabolized, primarily in the liver.
• References: Longley DB, Harkin DP, Johnston PG: 5-fluorouracil: mechanisms of action and clinical strategies. Nat Rev Cancer. 2003 May;3(5):330-8. [Pubmed] ; Petty RD, Cassidy J: Novel fluoropyrimidines: improving the efficacy and tolerability of cytotoxic therapy. Curr Cancer Drug Targets. 2004 Mar;4(2):191-204. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Apollo Scientific Ltd - PC4380

Antineoplastic agent. Not USP. Not for drug use.

Selleck Chemicals - S1209

Research Area: Cancer
Biological Activity:
Fluorouracil (5-FU or f5U) is a chemotherapy drug that is a pyrimidine analog which is used in the treatment of cancer. It works through noncompetitive inhibition of thymidylate synthase. Due to its noncompetitive nature and effects on thymidine synthesis, 5-FU is frequently referred to as the "suicide inactivator". It belongs to the family of drugs called antimetabolites. It is typically administered with leucovorin. [1] Fluorouracil IC50 values were observed across the National Cancer Institute NCI60 panel of human tumor cell lines, which exhibit a mean IC50 of 17.6 μM, with a range of 1–501 μM. [2]

Sigma Aldrich - 858471

包装
5 g in glass bottle
Application
Inhibitor of DNA synthesis.1,2

Sigma Aldrich - 47576

Other Notes
Potent antineoplastic agent. Its determination in tissue with microbore HPLC and fluorescence detection1; Metabolised to fluoro-2′-deoxyuridine monophosphate which inhibits DNA synthesis by blocking thymidylate synthetase2

Toronto Research Chemicals - F596000

5-Fluoro Uracil is an active metabolite of Doxifluridine (D556750).

参考文献

• Longley DB, Harkin DP, Johnston PG: 5-fluorouracil: mechanisms of action and clinical strategies. Nat Rev Cancer. 2003 May;3(5):330-8. Pubmed
• Petty RD, Cassidy J: Novel fluoropyrimidines: improving the efficacy and tolerability of cytotoxic therapy. Curr Cancer Drug Targets. 2004 Mar;4(2):191-204. Pubmed
• http://en.wikipedia.org/wiki/Fluorouracil
• Bollag, W., et al.: Eur. J. Cancer, 16, 427 (1980)
• Pinedo, H., et al.: J. Clin. Oncol., 6, 1653 (1980)
• Ishikawa, T., et al.: Biochem. Pharmacol., 55, 1091 (1980)
• Schuller, J., et al.: Cancer Chemother. Pharmacol., 45, 291 (1980)
• Antineoplastic agent. Not for drug use.