30868-30-5

• 常用中文名：吡唑啉
• 常用英文名：Pyrazofurin
• CAS号：30868-30-5
• 分子式：C₉H₁₃N₃O₆
• 分子量：259.21600
• 相关类别： 信号通路 细胞周期/DNA损伤 DNA/RNA合成
• 发布时间：2018-02-20 08:00:00
• 更新时间：2024-01-02 14:19:07
• Pyrazofurin 是一种具有抗肿瘤活性的嘧啶核苷类似物,通过抑制尿苷5'-磷酸 (UMP) 合酶抑制细胞增殖和细胞内 DNA 合成。 Pyrazofurin 是一种活性,敏感的乳清酸-磷酸核糖基转移酶 (orotate-phosphoribosyltransferase) 抑制剂,在三种鳞状细胞癌 (SCC) 细胞系 Hep-2,HNSCC-14B 和 HNSCC-14C 的 IC50s 在 0.06-0.37 μM 之间。

名称

• 中文名: 吡唑霉素
• 英文名: 5-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-1H-pyrazole-3-carboxamide
• 中文别名: 吡唑呋林
• 英文别名: Pirazofurin; Pyrazofurin; Pyrazomycin

物化性质

• 密度: 1.786g/cm3
• 沸点: 584.397ºC at 760 mmHg
• 分子式: C₉H₁₃N₃O₆
• 分子量: 259.21600
• 闪点: 307.232ºC
• 精确质量: 259.08000
• PSA: 161.92000
• 折射率: 1.718
• 储存条件: -20°C
• 计算化学:

  1.疏水参数计算参考值（XlogP）:-2.2

  2.氢键供体数量:6

  3.氢键受体数量:7

  4.可旋转化学键数量:3

  5.互变异构体数量:17

  6.拓扑分子极性表面积:162

  7.重原子数量:18

  8.表面电荷:0

  9.复杂度:329

  10.同位素原子数量:0

  11.确定原子立构中心数量:4

  12.不确定原子立构中心数量:0

  13.确定化学键立构中心数量:0

  14.不确定化学键立构中心数量:0

  15.共价键单元数量:1

生物活性

• 描述: Pyrazofurin 是一种具有抗肿瘤活性的嘧啶核苷类似物,通过抑制尿苷5'-磷酸 (UMP) 合酶抑制细胞增殖和细胞内 DNA 合成。 Pyrazofurin 是一种活性,敏感的乳清酸-磷酸核糖基转移酶 (orotate-phosphoribosyltransferase) 抑制剂,在三种鳞状细胞癌 (SCC) 细胞系 Hep-2,HNSCC-14B 和 HNSCC-14C 的 IC50s 在 0.06-0.37 μM 之间。
• 相关类别:
  研究领域 >> 癌症
  信号通路 >> 细胞周期/DNA损伤 >> DNA/RNA合成
• 参考文献:

  [1]. Ringer DP, et al. Alteration in de novo pyrimidine biosynthesis during uridine reversal of pyrazofurin-inhibited DNA synthesis. Neuropsychopharmacology. J Biochem Toxicol. 1991 Spring;6(1):19-27.

  [2]. Peters GJ, et al. Antipyrimidine effects of five different pyrimidine de novo synthesis inhibitors in three head and neck cancer cell lines. Nucleosides Nucleotides Nucleic Acids. 2018;37(6):329-339.

毒性和生态

CHEMICAL IDENTIFICATION RTECS NUMBER : UQ6360000 CHEMICAL NAME : 1H-Pyrazole-5-carboxamide, 4-hydroxy-3-beta-D-ribofuranosyl- CAS REGISTRY NUMBER : 30868-30-5 LAST UPDATED : 199112 DATA ITEMS CITED : 11 MOLECULAR FORMULA : C9-H13-N3-O6 MOLECULAR WEIGHT : 259.25 WISWESSER LINE NOTATION : T5OTJ B1Q CQ DQ E- CT5MNJ DQ EVZ HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Human DOSE/DURATION : 108 mg/kg/5D TOXIC EFFECTS : Gastrointestinal - hypermotility, diarrhea Gastrointestinal - nausea or vomiting Skin and Appendages - dermatitis, other (after systemic exposure) TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Human DOSE/DURATION : 48 mg/kg/5D TOXIC EFFECTS : Gastrointestinal - other changes Blood - changes in bone marrow (not otherwise specified) TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Human DOSE/DURATION : 84 mg/kg/5D TOXIC EFFECTS : Blood - changes in bone marrow (not otherwise specified) Skin and Appendages - dermatitis, other (after systemic exposure) TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Human DOSE/DURATION : 108 mg/kg/5D TOXIC EFFECTS : Gastrointestinal - other changes Blood - changes in bone marrow (not otherwise specified) TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Human DOSE/DURATION : 144 mg/kg/5D TOXIC EFFECTS : Gastrointestinal - other changes Blood - changes in bone marrow (not otherwise specified) Skin and Appendages - dermatitis, other (after systemic exposure) TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Unreported SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 70 mg/kg TOXIC EFFECTS : Behavioral - food intake (animal) Gastrointestinal - hypermotility, diarrhea Nutritional and Gross Metabolic - dehydration TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Unreported SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 10 mg/kg TOXIC EFFECTS : Sense Organs and Special Senses (Eye) - ptosis Lungs, Thorax, or Respiration - dyspnea Nutritional and Gross Metabolic - body temperature decrease MUTATION DATA TYPE OF TEST : DNA inhibition TEST SYSTEM : Rodent - guinea pig Lymphocyte DOSE/DURATION : 10 umol/L REFERENCE : JBTOEB Journal of Biochemical Toxicology. (VCH Publishers, Inc., 220 E. 23rd St., Suite 909, New York, NY USA 10010) V.1- 1986- Volume(issue)/page/year: 6,19,1991

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