daunomycinol (BioDeep_00000009323)

   

Volatile Flavor Compounds


代谢物信息卡片


(13S)-13-Dihydrodaunorubicin

化学式: C27H31NO10 (529.1947866)
中文名称: 柔红霉素
谱图信息: 最多检出来源 Macaca mulatta(otcml) 2.48%

分子结构信息

SMILES: C12C[C@@](C[C@H](O[C@@H]3O[C@H]([C@@H](O)[C@@H](N)C3)C)C1=C(O)C1=C(C(=O)C3C(=C(OC)C=CC=3)C1=O)C=2O)(O)[C@@H](O)C
InChI: InChI=1S/C27H31NO10/c1-10-22(30)14(28)7-17(37-10)38-16-9-27(35,11(2)29)8-13-19(16)26(34)21-20(24(13)32)23(31)12-5-4-6-15(36-3)18(12)25(21)33/h4-6,10-11,14,16-17,22,29-30,32,34-35H,7-9,28H2,1-3H3/t10-,11-,14-,16-,17-,22+,27-/m0/s1

描述信息

C274 - Antineoplastic Agent > C2189 - Signal Transduction Inhibitor > C129824 - Antineoplastic Protein Inhibitor
C274 - Antineoplastic Agent > C186664 - Cytotoxic Chemotherapeutic Agent > C259 - Antineoplastic Antibiotic
C471 - Enzyme Inhibitor > C129825 - Antineoplastic Enzyme Inhibitor > C1748 - Topoisomerase Inhibitor
C274 - Antineoplastic Agent > C186664 - Cytotoxic Chemotherapeutic Agent > C2842 - DNA Binding Agent
The (13S)-diastereomer of 13-dihydrodaunorubicin.
An aminoglycoside antibiotic that is (1S,3S)-3,5,12-trihydroxy-3-(1-hydroxyethyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene having a 3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl residue attached at position 1 via a glycosidic linkage.

同义名列表

5 个代谢物同义名

(13S)-13-Dihydrodaunorubicin; 13-Dihydrodaunorubicin; Daunorubicinol; daunomycinol; (13S)-13-Dihydrodaunorubicin



数据库引用编号

23 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

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)

2 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

  • Milena Locci de Oliveira, Adriana Rocha, Glauco Henrique Balthazar Nardotto, Leandro Francisco Pippa, Belinda Pinto Simões, Vera Lucia Lanchote. Analysis of daunorubicin and its metabolite daunorubicinol in plasma and urine with application in the evaluation of total, renal and metabolic formation clearances in patients with acute myeloid leukemia. Journal of pharmaceutical and biomedical analysis. 2020 Nov; 191(?):113576. doi: 10.1016/j.jpba.2020.113576. [PMID: 32889347]
  • Savitha Varatharajan, John C Panetta, Ajay Abraham, Sreeja Karathedath, Ezhilpavai Mohanan, Kavitha M Lakshmi, Nancy Arthur, Vivi M Srivastava, Sandeep Nemani, Biju George, Alok Srivastava, Vikram Mathews, Poonkuzhali Balasubramanian. Population pharmacokinetics of Daunorubicin in adult patients with acute myeloid leukemia. Cancer chemotherapy and pharmacology. 2016 Nov; 78(5):1051-1058. doi: 10.1007/s00280-016-3166-8. [PMID: 27738808]
  • Jan Hintzpeter, Jan Hornung, Bettina Ebert, Hans-Jörg Martin, Edmund Maser. Curcumin is a tight-binding inhibitor of the most efficient human daunorubicin reductase--Carbonyl reductase 1. Chemico-biological interactions. 2015 Jun; 234(?):162-8. doi: 10.1016/j.cbi.2014.12.019. [PMID: 25541467]
  • Patrick Thompson, Heather E Wheeler, Shannon M Delaney, Rachel Lorier, Ulrich Broeckel, Meenakshi Devidas, Gregory H Reaman, Kathleen Scorsone, Lillian Sung, M Eileen Dolan, Stacey L Berg. Pharmacokinetics and pharmacogenomics of daunorubicin in children: a report from the Children's Oncology Group. Cancer chemotherapy and pharmacology. 2014 Oct; 74(4):831-8. doi: 10.1007/s00280-014-2535-4. [PMID: 25119182]
  • Onkar S Bains, András Szeitz, Joanna M Lubieniecka, Gina E Cragg, Thomas A Grigliatti, K Wayne Riggs, Ronald E Reid. A correlation between cytotoxicity and reductase-mediated metabolism in cell lines treated with doxorubicin and daunorubicin. The Journal of pharmacology and experimental therapeutics. 2013 Nov; 347(2):375-87. doi: 10.1124/jpet.113.206805. [PMID: 23995598]
  • Savitha Varatharajan, Ajay Abraham, Wei Zhang, R V Shaji, Rayaz Ahmed, Aby Abraham, Biju George, Alok Srivastava, Mammen Chandy, Vikram Mathews, Poonkuzhali Balasubramanian. Carbonyl reductase 1 expression influences daunorubicin metabolism in acute myeloid leukemia. European journal of clinical pharmacology. 2012 Dec; 68(12):1577-86. doi: 10.1007/s00228-012-1291-9. [PMID: 22562609]
  • Georg Hempel, Mary V Relling, Giulio de Rossi, Jan Stary, Paola De Lorenzo, Maria Grazia Valsecchi, Elena Barisone, Joachim Boos, Rob Pieters. Pharmacokinetics of daunorubicin and daunorubicinol in infants with leukemia treated in the interfant 99 protocol. Pediatric blood & cancer. 2010 Mar; 54(3):355-60. doi: 10.1002/pbc.22266. [PMID: 19731319]
  • M Furlanut, G de Manzoni, F Pasini, S Tasselli, A Tomezzoli, D Poz, L Franceschi. Daunorubicin and daunorubicinol tissue concentrations in gastric cancer patients after local administration of a liposomal preparation. Pharmacological research. 2007 Oct; 56(4):344-9. doi: 10.1016/j.phrs.2007.08.005. [PMID: 17904378]
  • Yuanhang Lu, Anguo Deng, Xiao Yang, Jianshe Liu, Zhonghua Zhu. A potential pathological role of angiopoietins expression in glomeruli during progressive glomerulisclerosis related to podocyte injury. Journal of Huazhong University of Science and Technology. Medical sciences = Hua zhong ke ji da xue xue bao. Yi xue Ying De wen ban = Huazhong keji daxue xuebao. Yixue Yingdewen ban. 2006; 26(3):294-7. doi: 10.1007/bf02829555. [PMID: 16961273]
  • Nina Griese, Gottfried Blaschke, Joachim Boos, Georg Hempel. Determination of free and liposome-associated daunorubicin and daunorubicinol in plasma by capillary electrophoresis. Journal of chromatography. A. 2002 Dec; 979(1-2):379-88. doi: 10.1016/s0021-9673(02)01440-1. [PMID: 12498269]
  • A E van Ede, R F J M Laan, H J Blom, G H J Boers, C J Haagsma, C M G Thomas, T M De Boo, L B A van de Putte. Homocysteine and folate status in methotrexate-treated patients with rheumatoid arthritis. Rheumatology (Oxford, England). 2002 Jun; 41(6):658-65. doi: 10.1093/rheumatology/41.6.658. [PMID: 12048292]
  • G Hempel, P Schulze-Westhoff, S Flege, J Boos. Quantification of daunorubicin and daunorubicinol in plasma by capillary electrophoresis. Journal of chromatography. B, Biomedical sciences and applications. 2001 Jul; 758(2):221-8. doi: 10.1016/s0378-4347(01)00185-2. [PMID: 11486832]
  • R Bellott, A Auvrignon, T Leblanc, Y Pérel, V Gandemer, Y Bertrand, F Méchinaud, P Bellenger, J Vernois, G Leverger, A Baruchel, J Robert. Pharmacokinetics of liposomal daunorubicin (DaunoXome) during a phase I-II study in children with relapsed acute lymphoblastic leukaemia. Cancer chemotherapy and pharmacology. 2001; 47(1):15-21. doi: 10.1007/s002800000206. [PMID: 11221955]
  • J K Schröder, S Kasimir-Bauer, S Seeber, M E Scheulen. In vitro effect of multidrug resistance modifiers on idarubicinol efflux in blasts of acute myeloid leukemia. Journal of cancer research and clinical oncology. 2000 Feb; 126(2):111-6. doi: 10.1007/s004320050019. [PMID: 10664252]
  • L Fumagalli, M Zucchetti, I Parisi, M G Viganò, B Zecca, A Careddu, M D'Incalci, A Lazzarin. The pharmacokinetics of liposomal encapsulated daunorubicin are not modified by HAART in patients with HIV-associated Kaposi's sarcoma. Cancer chemotherapy and pharmacology. 2000; 45(6):495-501. doi: 10.1007/s002800051025. [PMID: 10854138]
  • P H Houba, E Boven, I H van der Meulen-Muileman, R G Leenders, J W Scheeren, H M Pinedo, H J Haisma. Distribution and pharmacokinetics of the prodrug daunorubicin-GA3 in nude mice bearing human ovarian cancer xenografts. Biochemical pharmacology. 1999 Mar; 57(6):673-80. doi: 10.1016/s0006-2952(98)00343-8. [PMID: 10037453]
  • M Zucchetti, A Boiardi, A Silvani, I Parisi, S Piccolrovazzi, M D'Incalci. Distribution of daunorubicin and daunorubicinol in human glioma tumors after administration of liposomal daunorubicin. Cancer chemotherapy and pharmacology. 1999; 44(2):173-6. doi: 10.1007/s002800050964. [PMID: 10412954]
  • B J Cusack, S P Young, R E Vestal, R D Olson. Age-related pharmacokinetics of daunorubicin and daunorubicinol following intravenous bolus daunorubicin administration in the rat. Cancer chemotherapy and pharmacology. 1997; 39(6):505-12. doi: 10.1007/s002800050606. [PMID: 9118462]
  • D D Ross, L A Doyle, W Yang, Y Tong, B Cornblatt. Susceptibility of idarubicin, daunorubicin, and their C-13 alcohol metabolites to transport-mediated multidrug resistance. Biochemical pharmacology. 1995 Nov; 50(10):1673-83. doi: 10.1016/0006-2952(95)02069-1. [PMID: 7503771]
  • B J Cusack, S P Young, R D Olson. Daunorubicin and daunorubicinol pharmacokinetics in plasma and tissues in the rat. Cancer chemotherapy and pharmacology. 1995; 35(3):213-8. doi: 10.1007/bf00686550. [PMID: 7805179]
  • P Galettis, J Boutagy, D D Ma. Daunorubicin pharmacokinetics and the correlation with P-glycoprotein and response in patients with acute leukaemia. British journal of cancer. 1994 Aug; 70(2):324-9. doi: 10.1038/bjc.1994.301. [PMID: 7914424]
  • U Tidefelt, B Sundman-Engberg, C Paul. Comparison of the intracellular pharmacokinetics of daunorubicin and idarubicin in patients with acute leukemia. Leukemia research. 1994 Apr; 18(4):293-7. doi: 10.1016/0145-2126(94)90032-9. [PMID: 8170171]
  • B J Cusack, P S Mushlin, L D Voulelis, X Li, R J Boucek, R D Olson. Daunorubicin-induced cardiac injury in the rabbit: a role for daunorubicinol?. Toxicology and applied pharmacology. 1993 Feb; 118(2):177-85. doi: 10.1006/taap.1993.1023. [PMID: 8441996]
  • J Dubois, M Hanocq, G Atassi, R Arnould, F Abikhalil. Pharmacokinetics of daunorubicin and daunorubicinol in plasma, P388 and B16 tumours. Comparison with in vitro cytotoxicity data. European journal of drug metabolism and pharmacokinetics. 1991 Apr; 16(2):119-27. doi: 10.1007/bf03189948. [PMID: 1936071]
  • B Schott, J Robert. Comparative activity of anthracycline 13-dihydrometabolites against rat glioblastoma cells in culture. Biochemical pharmacology. 1989 Nov; 38(22):4069-74. doi: 10.1016/0006-2952(89)90688-6. [PMID: 2597184]
  • C Paul, J Liliemark, U Tidefelt, G Gahrton, C Peterson. Pharmacokinetics of daunorubicin and doxorubicin in plasma and leukemic cells from patients with acute nonlymphoblastic leukemia. Therapeutic drug monitoring. 1989; 11(2):140-8. doi: 10.1097/00007691-198903000-00004. [PMID: 2718219]
  • C Paul, U Tidefelt, J Liliemark, C Peterson. Increasing the accumulation of daunorubicin in human leukemic cells by prolonging the infusion time. Leukemia research. 1989; 13(2):191-6. doi: 10.1016/0145-2126(89)90145-8. [PMID: 2927175]
  • E Kokenberg, P Sonneveld, W Sizoo, A Hagenbeek, B Löwenberg. Cellular pharmacokinetics of daunorubicin: relationships with the response to treatment in patients with acute myeloid leukemia. Journal of clinical oncology : official journal of the American Society of Clinical Oncology. 1988 May; 6(5):802-12. doi: 10.1200/jco.1988.6.5.802. [PMID: 3163363]
  • T Gessner, H D Preisler, N Azarnia, W Bolanowska, W R Vogler, H Grunwald, R Joyce, J Goldberg. Plasma levels of daunorubicin metabolites and the outcome of ANLL therapy. Medical oncology and tumor pharmacotherapy. 1987; 4(1):23-31. doi: 10.1007/bf02934931. [PMID: 3600054]
  • K Nooter, R Oostrum, J Deurloo. Effects of verapamil on the pharmacokinetics of daunomycin in the rat. Cancer chemotherapy and pharmacology. 1987; 20(2):176-8. doi: 10.1007/bf00253975. [PMID: 3664935]
  • J J Nguyen-Huu, P Turk, B Diquet. Determination of rubidazone and its metabolites in human plasma and urine by reversed-phase ion-pair high-performance liquid chromatography. Journal of chromatography. 1986 Aug; 380(2):455-61. doi: 10.1016/s0378-4347(00)83679-8. [PMID: 3760077]
  • K Nooter, P Sonneveld, A Martens, A Hagenbeek, F Schultz. Tissue distribution and myelotoxicity of daunomycin in the rat: rapid bolus injection vs continuous infusion. European journal of cancer & clinical oncology. 1986 Jul; 22(7):801-6. doi: 10.1016/0277-5379(86)90366-4. [PMID: 3770038]
  • N Erb, R Erttmann, G Landbeck. A rapid chromatographic procedure for the determination of adriamycin, daunomycin and their 13-OH metabolites adriamycinol and daunomycinol. Cancer chemotherapy and pharmacology. 1986; 17(1):53-5. doi: 10.1007/bf00299866. [PMID: 3698178]
  • D M Maniez-Devos, R Baurain, M Lesne, A Trouet. Doxorubicin and daunorubicin plasmatic, hepatic and renal disposition in the rabbit with or without enterohepatic circulation. Journal de pharmacologie. 1986 Jan; 17(1):1-13. doi: NULL. [PMID: 3713196]
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  • J T Hjelle, R Baurain, M Masquelier, A Trouet. Cellular pharmacology of amino acid derivatives of daunorubicin and doxorubicin in suspension of renal proximal tubules. The Journal of pharmacology and experimental therapeutics. 1984 May; 229(2):372-80. doi: NULL. [PMID: 6585548]
  • K Nooter, P Sonneveld, J Deurloo, R Oostrum, F Schultz, A Martens, A Hagenbeek. Repeated daunomycin administration in rats. Pharmacokinetics and bone marrow toxicity. Cancer chemotherapy and pharmacology. 1984; 12(3):187-9. doi: 10.1007/bf00256543. [PMID: 6705136]
  • M W DeGregorio, W M Holleran, B A Macher, C A Linker, J R Wilbur. Kinetics and sensitivity of daunorubicin in patients with acute leukemia. Cancer chemotherapy and pharmacology. 1984; 13(3):230-4. doi: 10.1007/bf00269036. [PMID: 6488444]
  • C Akpofure, C A Riley, J A Sinkule, W E Evans. Quantitation of daunorubicin and its metabolites by high-performance liquid chromatography with electrochemical detection. Journal of chromatography. 1982 Nov; 232(2):377-83. doi: 10.1016/s0378-4347(00)84177-8. [PMID: 7153284]
  • S Eksborg, H Ehrsson, B Andersson, M Beran. Liquid chromatographic determination of daunorubicin and daunorubicinol in plasma from leukemic patients. Journal of chromatography. 1978 Jun; 153(1):211-8. doi: 10.1016/s0021-9673(00)89874-x. [PMID: 659557]
  • R Hulhoven, J P Desager. Quantitative determination of low levels of daunomycin and daunomycinol in plasma by high-performance liquid chromatography. Journal of chromatography. 1976 Sep; 125(1):369-74. doi: 10.1016/s0021-9673(00)93832-9. [PMID: 977683]