Valrubicin (BioDeep_00000027132)

   

human metabolite blood metabolite Chemicals and Drugs


代谢物信息卡片


2,2,2-Trifluoro-N-(3-hydroxy-2-methyl-6-{[(1S,3S)-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-3-[2-(pentanoyloxy)acetyl]-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}oxan-4-yl)ethanimidate

化学式: C34H36F3NO13 (723.2138642)
中文名称: 戊柔比星
谱图信息: 最多检出来源 Homo sapiens(blood) 91.3%

分子结构信息

SMILES: CCCCC(=O)OCC(=O)C1(CC(C2=C(C1)C(=C3C(=C2O)C(=O)C4=C(C3=O)C=CC=C4OC)O)OC5CC(C(C(O5)C)O)NC(=O)C(F)(F)F)O
InChI: InChI=1S/C34H36F3NO13/c1-4-5-9-21(40)49-13-20(39)33(47)11-16-24(19(12-33)51-22-10-17(27(41)14(2)50-22)38-32(46)34(35,36)37)31(45)26-25(29(16)43)28(42)15-7-6-8-18(48-3)23(15)30(26)44/h6-8,14,17,19,22,27,41,43,45,47H,4-5,9-13H2,1-3H3,(H,38,46)/t14?,17?,19-,22?,27?,33-/m0/s1

描述信息

Valrubicin is only found in individuals that have used or taken this drug. It is a chemotherapy drug used to treat bladder cancer. Valrubicin is a semisynthetic analog of the anthracycline doxorubicin, and is administered by infusion directly into the bladder. [Wikipedia]Valrubicin is an anthracycline that affects a variety of inter-related biological functions, most of which involve nucleic acid metabolism. It readily penetrates into cells, where after DNA intercalation, it inhibits the incorporation of nucleosides into nucleic acids, causes extensive chromosomal damage, and arrests cell cycle in G2. Although valrubicin does not bind strongly to DNA, a principal mechanism of its action, mediated by valrubicin metabolites, is interference with the normal DNA breaking-resealing action of DNA topoisomerase II.

同义名列表

10 个代谢物同义名

2,2,2-Trifluoro-N-(3-hydroxy-2-methyl-6-{[(1S,3S)-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-3-[2-(pentanoyloxy)acetyl]-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}oxan-4-yl)ethanimidate; 2-oxo-2-[(2S,4S)-2,5,12-trihydroxy-4-{[5-hydroxy-6-methyl-4-(trifluoroacetamido)oxan-2-yl]oxy}-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-2-yl]ethyl pentanoate; N-Trifluoroacetyladriamycin 14-valerate; Paladin brand OF valrubicin; Antibiotic ad 32; Valrubicin; Valtaxin; Valstar; AD-32; AD 32



数据库引用编号

9 个数据库交叉引用编号

分类词条

相关代谢途径

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代谢反应

0 个相关的代谢反应过程信息。

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INOH(0)

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1 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。



文献列表

  • Krishnaprasad Baby, Swastika Maity, Chetan H Mehta, Akhil Suresh, Usha Y Nayak, Yogendra Nayak. SARS-CoV-2 entry inhibitors by dual targeting TMPRSS2 and ACE2: An in silico drug repurposing study. European journal of pharmacology. 2021 Apr; 896(?):173922. doi: 10.1016/j.ejphar.2021.173922. [PMID: 33539819]
  • Sunil Shah, Rahul Chib, Sangram Raut, Jaclyn Bermudez, Nirupama Sabnis, Divya Duggal, Joseph D Kimball, Andras G Lacko, Zygmunt Gryczynski, Ignacy Gryczynski. Photophysical characterization of anticancer drug valrubicin in rHDL nanoparticles and its use as an imaging agent. Journal of photochemistry and photobiology. B, Biology. 2016 Feb; 155(?):60-5. doi: 10.1016/j.jphotobiol.2015.12.007. [PMID: 26735001]
  • R Hajian, Z Mehrayin, M Mohagheghian, M Zafari, P Hosseini, N Shams. Fabrication of an electrochemical sensor based on carbon nanotubes modified with gold nanoparticles for determination of valrubicin as a chemotherapy drug: valrubicin-DNA interaction. Materials science & engineering. C, Materials for biological applications. 2015 Apr; 49(?):769-775. doi: 10.1016/j.msec.2015.01.072. [PMID: 25687007]
  • Ina Groenkjaer Laugesen, Eva Hauge, Stine Maria Andersen, Karin Stenderup, Elisabeth de Darkó, Tomas Norman Dam, Cecilia Rosada. Valrubicin activates PKCa in keratinocytes: a conceivable mode of action in treating hyper-proliferative skin diseases. Journal of drugs in dermatology : JDD. 2013 Oct; 12(10):1156-62. doi: ". [PMID: 24085052]
  • Gary D Steinberg, Norm D Smith, Kevin Ryder, Nicole M Strangman, Simon J Slater. Factors affecting valrubicin response in patients with bacillus Calmette-Guérin-refractory bladder carcinoma in situ. Postgraduate medicine. 2011 May; 123(3):28-34. doi: 10.3810/pgm.2011.05.2281. [PMID: 21566413]
  • G Steinberg, R Bahnson, S Brosman, R Middleton, Z Wajsman, M Wehle. Efficacy and safety of valrubicin for the treatment of Bacillus Calmette-Guerin refractory carcinoma in situ of the bladder. The Valrubicin Study Group. The Journal of urology. 2000 Mar; 163(3):761-7. doi: NULL. [PMID: 10687972]
  • M Masquelier, S Vitols, M Pålsson, U Mårs, B S Larsson, C O Peterson. Low density lipoprotein as a carrier of cytostatics in cancer chemotherapy: study of stability of drug-carrier complexes in blood. Journal of drug targeting. 2000; 8(3):155-64. doi: 10.3109/10611860008996861. [PMID: 10938525]
  • R E Greenberg, R R Bahnson, D Wood, S J Childs, C Bellingham, M Edson, M H Bamberger, G D Steinberg, M Israel, T Sweatman, B Giantonio, P J O'Dwyer. Initial report on intravesical administration of N-trifluoroacetyladriamycin-14-valerate (AD 32) to patients with refractory superficial transitional cell carcinoma of the urinary bladder. Urology. 1997 Mar; 49(3):471-5. doi: 10.1016/s0090-4295(96)00621-8. [PMID: 9123721]
  • A Gerke, K Westesen, M H Koch. Physicochemical characterization of protein-free low density lipoprotein models and influence of drug loading. Pharmaceutical research. 1996 Jan; 13(1):44-51. doi: 10.1023/a:1016069031411. [PMID: 8668677]
  • K Westesen, A Gerke, M H Koch. Characterization of native and drug-loaded human low density lipoproteins. Journal of pharmaceutical sciences. 1995 Feb; 84(2):139-47. doi: 10.1002/jps.2600840204. [PMID: 7738790]
  • A Mori, S J Kennel, L Huang. Immunotargeting of liposomes containing lipophilic antitumor prodrugs. Pharmaceutical research. 1993 Apr; 10(4):507-14. doi: 10.1023/a:1018933632318. [PMID: 8483832]
  • T W Sweatman, R F Parker, M Israel. Pharmacologic rationale for intravesical N-trifluoroacetyladriamycin-14-valerate (AD 32): a preclinical study. Cancer chemotherapy and pharmacology. 1991; 28(1):1-6. doi: 10.1007/bf00684948. [PMID: 2040028]
  • P P Constantinides, N Inouchi, T R Tritton, A C Sartorelli, J M Sturtevant. A scanning calorimetric study of the interaction of anthracyclines with neutral and acidic phospholipids alone and in binary mixtures. The Journal of biological chemistry. 1986 Aug; 261(22):10196-203. doi: 10.1016/s0021-9258(18)67510-6. [PMID: 3460992]
  • M Masquelier, S Vitols, C Peterson. Low-density lipoprotein as a carrier of antitumoral drugs: in vivo fate of drug-human low-density lipoprotein complexes in mice. Cancer research. 1986 Aug; 46(8):3842-7. doi: NULL. [PMID: 3731059]
  • R Seshadri, J M Idriss, M Israel. Adriamycin analogues. Preparation and biological evaluation of some thio ester analogues of adriamycin and N-(trifluoroacetyl)adriamycin 14-valerate. Journal of medicinal chemistry. 1986 Jul; 29(7):1269-73. doi: 10.1021/jm00157a025. [PMID: 3806575]
  • M Israel, D Taube, R Seshadri, J M Idriss. Adriamycin analogues. Preparation and biological evaluation of some N-(trifluoroacetyl)-14-O-[(N-acetylamino)acyl]adriamycin derivatives. Journal of medicinal chemistry. 1986 Jul; 29(7):1273-6. doi: 10.1021/jm00157a026. [PMID: 3806576]
  • G Zini, G P Vicario, M Lazzati, F Arcamone. Radioactive species in rat urines and tissues after [14C] AD 32 administration. Cancer chemotherapy and pharmacology. 1984; 12(3):154-6. doi: 10.1007/bf00256537. [PMID: 6705133]
  • M Israel, A M Karkowsky, V K Khetarpal. Distribution of radioactivity and anthracycline-fluorescence in tissues of mice one hour after [14C]-labeled AD 32 administration. Evidence for tissue aglycone formation. Cancer chemotherapy and pharmacology. 1981; 6(1):25-30. doi: 10.1007/bf00253006. [PMID: 6944160]
  • M Israel, A M Karkowsky, W J Pegg. Pharmacologic studies with radiolabeled N-trifluoroacetyladriamycin-14-valerate (AD 32). Comparison of total anthracycline fluorescence and radioactivity in mouse serum and urine. Cancer chemotherapy and pharmacology. 1980; 4(2):79-82. doi: 10.1007/bf00254026. [PMID: 7389059]