27314-97-2

• 常用中文名：替拉扎明
• 常用英文名：Tirapazamine
• CAS号：27314-97-2
• 分子式：C₇H₆N₄O₂
• 分子量：178.148
• 相关类别： 研究领域 癌症
• 发布时间：2018-07-04 15:46:40
• 更新时间：2025-08-20 18:02:07
• Tirapazamine(SR259075; Win59075; SR4233)可在低氧水平下被活化为毒性自由基，是一种实验性抗癌化合物。

名称

• 中文名: 替拉扎明
• 英文名: tirapazamine
• 中文别名: 3-氨基-1,2,4-苯并三嗪-1,4-二氧; 替扎拉明
• 英文别名: 4-hydroxy-1-oxido-1,2,4-benzotriazin-1-ium-3-imine; 1,2,4-Benzotriazin-3-amine, 1,4-dioxide; 3-Amino-1,2,4-benzotriazine 1,4-Dioxide; 1,4-Dioxido-1,2,4-benzotriazin-3-ylamine; SR 259075; 1,2,4-Benzotriazin-3-amine 1,4-dioxide; 4-Hydroxy-1-oxido-1,2,4-benzotriazin-1-ium-3-imine SR 259075 SR 4233 Tirazone Win 59075; Tirazone; Tirapazamine; 3-Aminobenzo[e][1,2,4]triazine 1,4-dioxide

物化性质

• 密度: 1.7±0.1 g/cm3
• 沸点: 493.6±28.0 °C at 760 mmHg
• 熔点: 220ºC
• 分子式: C₇H₆N₄O₂
• 分子量: 178.148
• 闪点: 252.3±24.0 °C
• 精确质量: 178.049072
• PSA: 89.83000
• LogP: -0.31
• 外观性状: 橙色-红色结晶粉末
• 蒸汽压: 0.0±1.3 mmHg at 25°C
• 折射率: 1.777
• 储存条件: 0-10°C;避免加热

生物活性

• 描述: Tirapazamine是一种抗癌剂,对实体瘤中的缺氧细胞具有选择性细胞毒性,从而诱导DNA中的单链和双链断裂,碱基损伤和细胞死亡。
• 相关类别:
  信号通路 >> 其他 >> 其他
  研究领域 >> 癌症
• 参考文献:

  [1]. Cai TY, et al. Tirapazamine sensitizes hepatocellular carcinoma cells to topoisomerase I inhibitors via cooperative modulation of hypoxia-inducible factor-1α. Mol Cancer Ther. 2014 Mar;13(3):630-42.

  [2]. Sliwinska J, et al. Tirapazamine-doxorubicin interaction referring to heart oxidative stress and Ca2? balance protein levels. Oxid Med Cell Longev. 2012;2012:890826.

毒性和生态

CHEMICAL IDENTIFICATION RTECS NUMBER : DM0671500 CHEMICAL NAME : 1,2,4-Benzotriazine, 3-amino-, 1,4-dioxide CAS REGISTRY NUMBER : 27314-97-2 BEILSTEIN REFERENCE NO. : 0179322 LAST UPDATED : 199712 DATA ITEMS CITED : 8 MOLECULAR FORMULA : C7-H6-N4-O2 MOLECULAR WEIGHT : 178.17 HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 59390 ug/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : LD - Lethal dose ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : >36 mg/kg TOXIC EFFECTS : Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Endocrine - other changes Blood - changes in bone marrow (not otherwise specified) TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 89 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 101 mg/kg TOXIC EFFECTS : Behavioral - somnolence (general depressed activity) Skin and Appendages - hair Nutritional and Gross Metabolic - weight loss or decreased weight gain TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 19 mg/kg/2W-C TOXIC EFFECTS : Related to Chronic Data - death MUTATION DATA TYPE OF TEST : Unscheduled DNA synthesis TEST SYSTEM : Rodent - rat Mammary gland DOSE/DURATION : 500 umol/L REFERENCE : CRNGDP Carcinogenesis (London). (Oxford Univ. Press, Pinkhill House, Southfield Road, Eynsham, Oxford OX8 1JJ, UK) V.1- 1980- Volume(issue)/page/year: 11,1407,1990

安全

• 符号: GHS07
• 信号词: Warning
• 危害声明: H315-H319-H335
• 警示性声明: P261-P305 + P351 + P338
• 危害码 (欧洲): Xi: Irritant;
• 风险声明 (欧洲): 36/37/38
• 安全声明 (欧洲): 26-36
• 危险品运输编码: NONH for all modes of transport
• RTECS号: DM0671500

合成路线

5424-06-6 ~79% 27314-97-2

文献：Suzuki, Hitomi; Kawakami, Takehiko Synthesis, 1997 , # 8 p. 855 - 857

20028-79-9 ~75% 27314-97-2

文献：Gatenyo, Julia; Johnson, Kevin; Rajapakse, Anuruddha; Gates, Kent S.; Rozen, Shlomo Tetrahedron, 2012 , vol. 68, # 43 p. 8942 - 8944

5424-06-6 ~% 27446-08-8 27314-97-2

文献：Gatenyo, Julia; Johnson, Kevin; Rajapakse, Anuruddha; Gates, Kent S.; Rozen, Shlomo Tetrahedron, 2012 , vol. 68, # 43 p. 8942 - 8944

20028-80-2 ~0% 5424-06-6 27238-43-3 27314-97-2 详细

文献：Fuchs; Chowdhury; Barnes; Gates Journal of Organic Chemistry, 2001 , vol. 66, # 1 p. 107 - 114

88-74-4 ~% 27314-97-2

文献：Fuchs; Chowdhury; Barnes; Gates Journal of Organic Chemistry, 2001 , vol. 66, # 1 p. 107 - 114

528-29-0 ~% 27314-97-2

文献：Suzuki, Hitomi; Kawakami, Takehiko Synthesis, 1997 , # 8 p. 855 - 857

67692-91-5 ~% 27314-97-2

文献：Robbins; Schofield Journal of the Chemical Society, 1957 , p. 3186,3191

27446-08-8 ~% 27314-97-2

文献：Robbins; Schofield Journal of the Chemical Society, 1957 , p. 3186,3191

20028-80-2 ~% 27314-97-2

文献：Fuchs; Chowdhury; Barnes; Gates Journal of Organic Chemistry, 2001 , vol. 66, # 1 p. 107 - 114

上下游产品

上游产品  6
5424-06-6 20028-80-2 88-74-4 528-29-0
67692-91-5 27446-08-8
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5424-06-6 34371-14-7 20028-80-2