Diaziquone (BioDeep_00000746747)

   


代谢物信息卡片


Carbamic acid,N,N-[2,5-bis(1-aziridinyl)-3,6-dioxo-1,4-cyclohexadiene-1,4-diyl]bis-,C,C-diethyl ester

化学式: C16H20N4O6 (364.1383)
中文名称: 亚丝醌
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CCOC(=O)NC1=C(C(=O)C(=C(C1=O)N2CC2)NC(=O)OCC)N3CC3
InChI: InChI=1S/C16H20N4O6/c1-3-25-15(23)17-9-11(19-5-6-19)14(22)10(18-16(24)26-4-2)12(13(9)21)20-7-8-20/h3-8H2,1-2H3,(H,17,23)(H,18,24)

描述信息

D019995 - Laboratory Chemicals > D007202 - Indicators and Reagents > D003432 - Cross-Linking Reagents
C274 - Antineoplastic Agent > C186664 - Cytotoxic Chemotherapeutic Agent > C2842 - DNA Binding Agent
D000970 - Antineoplastic Agents

同义名列表

2 个代谢物同义名

Carbamic acid,N,N-[2,5-bis(1-aziridinyl)-3,6-dioxo-1,4-cyclohexadiene-1,4-diyl]bis-,C,C-diethyl ester; Diaziquone



数据库引用编号

5 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

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PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

0 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。

亚细胞结构定位 关联基因列表


文献列表

  • Karel Smejkal, Jana Svacinová, Tereza Slapetová, Kristýna Schneiderová, Stefano Dall'acqua, Gabbriella Innocenti, Veronika Závalová, Peter Kollár, Stanislav Chudík, Radek Marek, Ondrej Julínek, Marie Urbanová, Murat Kartal, Marek Csöllei, Karel Dolezal. Cytotoxic activities of several geranyl-substituted flavanones. Journal of natural products. 2010 Apr; 73(4):568-72. doi: 10.1021/np900681y. [PMID: 20192247]
  • Gudrun Fleischhack, Ulrich Jaehde, Udo Bode. Pharmacokinetics following intraventricular administration of chemotherapy in patients with neoplastic meningitis. Clinical pharmacokinetics. 2005; 44(1):1-31. doi: 10.2165/00003088-200544010-00001. [PMID: 15634030]
  • P E Kintzel. Anticancer drug-induced kidney disorders. Drug safety. 2001 Jan; 24(1):19-38. doi: 10.2165/00002018-200124010-00003. [PMID: 11219485]
  • X Qiu, H J Forman, A H Schönthal, E Cadenas. Induction of p21 mediated by reactive oxygen species formed during the metabolism of aziridinylbenzoquinones by HCT116 cells. The Journal of biological chemistry. 1996 Dec; 271(50):31915-21. doi: 10.1074/jbc.271.50.31915. [PMID: 8943236]
  • L C Hartmann, M M Ames, J M Reid, R L Richardson. Phase I trial of diaziquone (AZQ) plus GM-CSF. Investigational new drugs. 1995; 13(2):175-6. doi: 10.1007/bf00872869. [PMID: 8617583]
  • J J Schlager, B J Hoerl, J Riebow, D P Scott, P Gasdaska, R E Scott, G Powis. Increased NAD(P)H:(quinone-acceptor)oxidoreductase activity is associated with density-dependent growth inhibition of normal but not transformed cells. Cancer research. 1993 Mar; 53(6):1338-42. doi: NULL. [PMID: 8443814]
  • P J Stiff, R S McKenzie, L D Potempa, K Albain, D Koch, E Braud, V K Bansal, M K Weidner, V J Lanzotti, H G Chun. A phase I trial of high-dose diaziquone and autologous bone marrow transplantation: an Illinois Cancer Council study. Journal of clinical oncology : official journal of the American Society of Clinical Oncology. 1991 Aug; 9(8):1487-94. doi: 10.1200/jco.1991.9.8.1487. [PMID: 2072148]
  • G R Fisher, P L Gutierrez. The reductive metabolism of diaziquone (AZQ) in the S9 fraction of MCF-7 cells: free radical formation and NAD(P)H: quinone-acceptor oxidoreductase (DT-diaphorase) activity. Free radical biology & medicine. 1991; 10(6):359-70. doi: 10.1016/0891-5849(91)90044-4. [PMID: 1654286]
  • P J O'Brien, H K Kaul, A M Rauth. Differential cytotoxicity of diaziquone toward Chinese hamster ovary cells under hypoxic and aerobic exposure conditions. Cancer research. 1990 Mar; 50(5):1516-20. doi: NULL. [PMID: 2302714]
  • J M Silva, P J O'Brien. Diaziquone-induced cytotoxicity in isolated rat hepatocytes. Cancer research. 1989 Oct; 49(20):5550-4. doi: . [PMID: 2790779]
  • R P Pugh, T Fleming, J T Guy, J K Weick, J H Ward. Phase II study of diaziquone in untreated advanced gastric carcinoma. A Southwest Oncology Group Study. American journal of clinical oncology. 1989 Feb; 12(1):11-3. doi: 10.1097/00000421-198902000-00003. [PMID: 2912017]
  • R F Betteridge, A G Bosanquet, P Hunt, E D Gilby. Determination of diaziridinyl-3,6-bis(2-hydroxyethylamino)-1,4-benzoquinone in plasma by solid-phase extraction and high-performance liquid chromatography. Journal of chromatography. 1988 Nov; 432(?):352-7. doi: 10.1016/s0378-4347(00)80665-9. [PMID: 3220904]
  • A D Kligerman, G L Erexson, M F Bryant. Sister chromatid exchange induction by diaziquone in human and mouse lymphocytes following both in vivo and in vitro exposures. Cancer research. 1988 Jan; 48(1):27-31. doi: ". [PMID: 3334997]
  • B H Kushner, S Siena, H Castro-Malaspina. Myeloablation with diaziquone: in vitro assessment. Blood. 1987 Jun; 69(6):1747-52. doi: NULL. [PMID: 3555652]
  • A D Kligerman, G L Erexson, J L Wilmer, S C Schold. Sister chromatid exchange induction in patients with anaplastic gliomas undergoing treatment with radiation plus diaziquone or 1,3-bis(2-chloroethyl)-1-nitrosourea. Cancer research. 1987 Jan; 47(2):631-5. doi: ". [PMID: 3791247]
  • D A Decker, J Kish, M Al-Sarraf, S Goldfarb. Phase II clinical evaluation of AZQ in renal cell carcinoma. American journal of clinical oncology. 1986 Apr; 9(2):126-8. doi: 10.1097/00000421-198604000-00004. [PMID: 3717078]
  • E J Lee, D A Van Echo, M J Egorin, M S Nayar, P Shulman, C A Schiffer. Diaziquone given as a continuous infusion is an active agent for relapsed adult acute nonlymphocytic leukemia. Blood. 1986 Jan; 67(1):182-7. doi: NULL. [PMID: 3940546]
  • R L Stephens, R Kirby, E D Crawford, R Bukowski, S E Rivkin, R M O'Bryan. High dose AZQ in renal cancer. A Southwest Oncology Group phase II study. Investigational new drugs. 1986; 4(1):57-9. doi: 10.1007/bf00172018. [PMID: 3700042]
  • D J Moore, G Powis, R L Richardson, M R Pittelkow. Topical chemotherapy of intradermal Walker 256 carcinosarcoma with diaziquone and doxorubicin in the rat. Cancer research. 1985 Nov; 45(11 Pt 1):5466-72. doi: NULL. [PMID: 4053022]
  • K A Kennedy, J D McGurl, L Leondaridis, O Alabaster. pH dependence of mitomycin C-induced cross-linking activity in EMT6 tumor cells. Cancer research. 1985 Aug; 45(8):3541-7. doi: NULL. [PMID: 3926302]
  • M J Egorin, B M Fox, J F Spiegel, P L Gutierrez, R D Friedman, N R Bachur. Cellular pharmacology in murine and human leukemic cell lines of diaziquone (NSC 182986). Cancer research. 1985 Mar; 45(3):992-9. doi: NULL. [PMID: 3971389]
  • L J Ettinger, S E Siegel, J B Belasco, A E Evans, K S Ruccione, D C Jamin, T M Rohrbaugh, G R Higgins. Phase I clinical evaluation of diaziquone in childhood cancer. Cancer treatment reports. 1985 Mar; 69(3):323-7. doi: ". [PMID: 3856480]
  • S Frytak, R T Eagan, M M Ames, E T Creagan, W C Nichols. Phase I study of diaziquone. Cancer treatment reports. 1984 Jul; 68(7-8):975-8. doi: NULL. [PMID: 6744349]
  • M Hansen, W M Gallmeier, J Vermorken, E Holdener, H H Hansen, J Renard, M Rozencweig. Phase II trial of diaziquone in advanced renal adenocarcinoma. Cancer treatment reports. 1984 Jul; 68(7-8):1055-6. doi: NULL. [PMID: 6744342]
  • S C Schold, H S Friedman, T D Bjornsson, D D Bigner. Treatment of human glioma and medulloblastoma tumor lines in athymic mice with diaziquone and diaziquone-based drug combinations. Cancer research. 1984 Jun; 44(6):2352-7. doi: NULL. [PMID: 6722774]
  • M J Egorin, E H Bellis, M Salcman, J M Collins, J F Spiegel, N R Bachur. The pharmacology of diaziquone given in intravenous or intracarotid infusion to normal and intracranial tumor-bearing puppies. Journal of neurosurgery. 1984 May; 60(5):1005-13. doi: 10.3171/jns.1984.60.5.1005. [PMID: 6716135]
  • S C Schold, H S Friedman, T D Bjornsson, J M Falletta. Treatment of patients with recurrent primary brain tumors with AZQ. Neurology. 1984 May; 34(5):615-9. doi: 10.1212/wnl.34.5.615. [PMID: 6538653]
  • G A Curt, J A Kelley, C V Kufta, B H Smith, P L Kornblith, R C Young, J M Collins. Phase II and pharmacokinetic study of aziridinylbenzoquinone [2,5-diaziridinyl-3,6-bis(carboethoxyamino)-1,4-benzoquinone, diaziquone, NSC 182986] in high-grade gliomas. Cancer research. 1983 Dec; 43(12 Pt 1):6102-5. doi: NULL. [PMID: 6640549]
  • M A Oberc-Greenwood, B H Smith, C Cooke, J R Ellis, P L Kornblith, P E McKeever. Mitochondrial toxicity of 2,5-diaziridinyl-3,6-bis-(carboethoxyamino)-1,4-benzoquinone. Journal of the National Cancer Institute. 1983 Oct; 71(4):725-33. doi: ". [PMID: 6578368]
  • K Lu, N Savaraj, B S Yap, A Y Bedikian, L Feun, R S Benjamin, T L Loo. Clinical pharmacology of 2,5'-diaziridinyl-3,6-biscarboethoxyamino-1,4-benzoquinone (AZQ). European journal of cancer & clinical oncology. 1983 May; 19(5):603-6. doi: 10.1016/0277-5379(83)90175-x. [PMID: 6683631]
  • J F Spiegel, M J Egorin, J M Collins, B D Lerner, N R Bachur. The murine disposition and pharmacokinetics of the antineoplastic agent, diaziquone (NSC 182986). Drug metabolism and disposition: the biological fate of chemicals. 1983 Jan; 11(1):41-6. doi: NULL. [PMID: 6132794]
  • N Savaraj, K Lu, L G Feun, M E Leavens, D Stewart, M A Burgess, R S Benjamin, T L Loo. Intracerebral penetration and tissue distribution of 2,5-diaziridinyl 3,6-bis(carboethoxyamino) 1,4-benzoquinone (AZQ, NSC-182986). Journal of neuro-oncology. 1983; 1(1):15-9. doi: 10.1007/bf00153636. [PMID: 6678302]
  • L G Feun, N Savaraj, K Lu, Z Guo, L G Raulston, R S Benjamin, W S Fields, T L Loo. The pharmacologic fate of 2,5-diaziridinyl-3,6-bis(carboethoxyamino) 1,4-benzoquinone (AZQ NSC-182986) by intracarotid or intravenous administration in beagles. Journal of neuro-oncology. 1983; 1(3):219-24. doi: 10.1007/bf00165606. [PMID: 6678971]
  • J F Bender, A J Grillo-Lopez, J G Posada. Diaziquone (AZQ). Investigational new drugs. 1983; 1(1):71-84. doi: 10.1007/bf00180194. [PMID: 6381377]
  • N R Bachur, J M Collins, J A Kelley, D A Van Echo, R S Kaplan, M Whitacre. Diaziquone, 2,5-diaziridinyl-3,6-biscarboethoxyamino-1,4-benzoquinone, plasma and cerebrospinal fluid kinetics. Clinical pharmacology and therapeutics. 1982 May; 31(5):650-5. doi: 10.1038/clpt.1982.90. [PMID: 7075113]
  • R L Schilsky, J A Kelley, D C Ihde, D M Howser, R S Cordes, R C Young. Phase I trial and pharmacokinetics of aziridinylbenzoquinone (NSC 182986) in humans. Cancer research. 1982 Apr; 42(4):1582-6. doi: NULL. [PMID: 7060028]
  • P E Gormley, J H Wood, D G Poplack. Ability of a new antitumor agent, AZQ, to penetrate into cerebrospinal fluid. Pharmacology. 1981; 22(3):196-8. doi: 10.1159/000137490. [PMID: 7208602]