Nelarabine (BioDeep_00000027080)

   

human metabolite blood metabolite Chemicals and Drugs Cytotoxicity


代谢物信息卡片


(2R,3S,4S,5R)-2-(2-amino-6-methoxy-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

化学式: C11H15N5O5 (297.10731400000003)
中文名称: 奈拉滨
谱图信息: 最多检出来源 Homo sapiens(blood) 10.26%

分子结构信息

SMILES: COC1=NC(=NC2=C1N=CN2C3C(C(C(O3)CO)O)O)N
InChI: InChI=1S/C11H15N5O5/c1-20-9-5-8(14-11(12)15-9)16(3-13-5)10-7(19)6(18)4(2-17)21-10/h3-4,6-7,10,17-19H,2H2,1H3,(H2,12,14,15)/t4-,6-,7+,10-/m1/s1

描述信息

Nelarabine is only found in individuals that have used or taken this drug. It is a chemotherapy drug used in T-cell acute lymphoblastic leukemia. Nelarabine is a purine nucleoside analog converted to its corresponding arabinosylguanine nucleotide triphosphate (araGTP), resulting in inhibition of DNA synthesis and cytotoxicity.Once nelarabine is metabolized into ara-GTP, the metabolite accumulates in leukemic blasts and incorporates into DNA to exert its S phase-specific cytotoxic effects, leading to the induction of fragmentation and apoptosis. Ara-GTP competes with endogenous deoxyGTP (dGTP) for incorporation into DNA. Once ara-GTP is incorporated at the 3 end of DNA, further DNA elongation is inhibited, which signals apoptosis and leads to cellular destruction. Additional cytotoxic activities may exist, but these are not fully understood.
L - Antineoplastic and immunomodulating agents > L01 - Antineoplastic agents > L01B - Antimetabolites > L01BB - Purine analogues
C274 - Antineoplastic Agent > C186664 - Cytotoxic Chemotherapeutic Agent > C272 - Antimetabolite
Nelarabine (506U78) is a nucleoside analogue and can be used for the research of T cell acute lymphoblastic leukemia (T-ALL)[1].

同义名列表

14 个代谢物同义名

(2R,3S,4S,5R)-2-(2-amino-6-methoxy-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol; 2-Amino-9-beta-D-arabinofuranosyl-6-methoxy-9H-purine; 2-Amino-9-b-D-arabinofuranosyl-6-methoxy-9H-purine; 2-Amino-9-β-D-arabinofuranosyl-6-methoxy-9H-purine; GlaxoSmithKline brand OF nelarabine; 2-Amino-6-methoxypurine arabinoside; o6-methylguanosine; Compound 506u78; Nelzarabine; Nelarabine; GW-506U78; Arranon; 506U78; GW 506U78



数据库引用编号

11 个数据库交叉引用编号

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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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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

  • James A Whitlock, Jemily Malvar, Luciano Dalla-Pozza, John M Goldberg, Lewis B Silverman, David S Ziegler, Andishe Attarbaschi, Patrick A Brown, Rebecca A Gardner, Paul S Gaynon, Raymond Hutchinson, Van T Huynh, Sima Jeha, Leigh Marcus, Yoav Messinger, Kirk R Schultz, Jeannette Cassar, Franco Locatelli, C Michel Zwaan, Brent L Wood, Richard Sposto, Lia Gore. Nelarabine, etoposide, and cyclophosphamide in relapsed pediatric T-acute lymphoblastic leukemia and T-lymphoblastic lymphoma (study T2008-002 NECTAR). Pediatric blood & cancer. 2022 Nov; 69(11):e29901. doi: 10.1002/pbc.29901. [PMID: 35989458]
  • Balázs Vaskó, Viktória Juhász, Beáta Tóth, Anita Kurunczi, Zsolt Fekete, Joseph Krisjanis Zolnerciks, Emese Kis, Rémi Magnan, Axel Bidon-Chanal Badia, Marçal Pastor-Anglada, Eszter Hazai, Zsolt Bikadi, Ferenc Fülöp, Peter Krajcsi. Inhibitor selectivity of CNTs and ENTs. Xenobiotica; the fate of foreign compounds in biological systems. 2019 Jul; 49(7):840-851. doi: 10.1080/00498254.2018.1501832. [PMID: 30022699]
  • Douglas A Canning. Re: Unilateral multicystic dysplastic kidney: does initial size matter?. The Journal of urology. 2013 Jun; 189(6):2305. doi: 10.1016/j.juro.2013.02.108. [PMID: 23663641]
  • Glen E Kisby, Rebecca C Fry, Michael R Lasarev, Theodor K Bammler, Richard P Beyer, Mona Churchwell, Daniel R Doerge, Lisiane B Meira, Valerie S Palmer, Ana-Luiza Ramos-Crawford, Xuefeng Ren, Robert C Sullivan, Terrance J Kavanagh, Leona D Samson, Helmut Zarbl, Peter S Spencer. The cycad genotoxin MAM modulates brain cellular pathways involved in neurodegenerative disease and cancer in a DNA damage-linked manner. PloS one. 2011; 6(6):e20911. doi: 10.1371/journal.pone.0020911. [PMID: 21731631]
  • R Scott Obach, Franco Lombardo, Nigel J Waters. Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds. Drug metabolism and disposition: the biological fate of chemicals. 2008 Jul; 36(7):1385-405. doi: 10.1124/dmd.108.020479. [PMID: 18426954]
  • Varsha Gandhi, Constantine Tam, Susan O'Brien, Roxanne C Jewell, Carlos O Rodriguez, Susan Lerner, William Plunkett, Michael J Keating. Phase I trial of nelarabine in indolent leukemias. Journal of clinical oncology : official journal of the American Society of Clinical Oncology. 2008 Mar; 26(7):1098-105. doi: 10.1200/jco.2007.14.1986. [PMID: 18309944]
  • Bruce D Cheson. Clinical management of T-cell malignancies: current perspectives, key issues, and emerging therapies. Seminars in oncology. 2007 Dec; 34(6 Suppl 5):S3-7. doi: 10.1053/j.seminoncol.2007.11.001. [PMID: 18086345]
  • Stacey L Berg, Claudia Brueckner, Jed G Nuchtern, Robert Dauser, Leticia McGuffey, Susan M Blaney. Plasma and cerebrospinal fluid pharmacokinetics of nelarabine in nonhuman primates. Cancer chemotherapy and pharmacology. 2007 May; 59(6):743-7. doi: 10.1007/s00280-006-0328-0. [PMID: 16953392]
  • Alex H Beesley, Misty-Lee Palmer, Jette Ford, Renae E Weller, Aaron J Cummings, Joseph R Freitas, Martin J Firth, Kanchana U Perera, Nicholas H de Klerk, Ursula R Kees. In vitro cytotoxicity of nelarabine, clofarabine and flavopiridol in paediatric acute lymphoblastic leukaemia. British journal of haematology. 2007 Apr; 137(2):109-16. doi: 10.1111/j.1365-2141.2007.06527.x. [PMID: 17391490]
  • Farhad Ravandi, Varsha Gandhi. Novel purine nucleoside analogues for T-cell-lineage acute lymphoblastic leukaemia and lymphoma. Expert opinion on investigational drugs. 2006 Dec; 15(12):1601-13. doi: 10.1517/13543784.15.12.1601. [PMID: 17107284]
  • Tadeusz Robak, Ewa Lech-Maranda, Anna Korycka, Ewa Robak. Purine nucleoside analogs as immunosuppressive and antineoplastic agents: mechanism of action and clinical activity. Current medicinal chemistry. 2006; 13(26):3165-89. doi: 10.2174/092986706778742918. [PMID: 17168705]
  • J Kurtzberg, T J Ernst, M J Keating, V Gandhi, J P Hodge, D F Kisor, J J Lager, C Stephens, J Levin, T Krenitsky, G Elion, B S Mitchell. Phase I study of 506U78 administered on a consecutive 5-day schedule in children and adults with refractory hematologic malignancies. Journal of clinical oncology : official journal of the American Society of Clinical Oncology. 2005 May; 23(15):3396-403. doi: 10.1200/jco.2005.03.199. [PMID: 15908652]
  • V Gandhi, W Plunkett, S Weller, M Du, M Ayres, C O Rodriguez, P Ramakrishna, G L Rosner, J P Hodge, S O'Brien, M J Keating. Evaluation of the combination of nelarabine and fludarabine in leukemias: clinical response, pharmacokinetics, and pharmacodynamics in leukemia cells. Journal of clinical oncology : official journal of the American Society of Clinical Oncology. 2001 Apr; 19(8):2142-52. doi: 10.1200/jco.2001.19.8.2142. [PMID: 11304766]
  • D F Kisor, W Plunkett, J Kurtzberg, B Mitchell, J P Hodge, T Ernst, M J Keating, V Gandhi. Pharmacokinetics of nelarabine and 9-beta-D-arabinofuranosyl guanine in pediatric and adult patients during a phase I study of nelarabine for the treatment of refractory hematologic malignancies. Journal of clinical oncology : official journal of the American Society of Clinical Oncology. 2000 Mar; 18(5):995-1003. doi: 10.1200/jco.2000.18.5.995. [PMID: 10694549]
  • A Aguayo, J E Cortes, H M Kantarjian, M Beran, V Gandhi, W Plunkett, J Kurtzberg, M J Keating. Complete hematologic and cytogenetic response to 2-amino-9-beta-D-arabinosyl-6-methoxy-9H-guanine in a patient with chronic myelogenous leukemia in T-cell blastic phase: a case report and review of the literature. Cancer. 1999 Jan; 85(1):58-64. doi: 10.1002/(sici)1097-0142(19990101)85:1<58::aid-cncr8>3.0.co;2-e. [PMID: 9921974]
  • V Gandhi, W Plunkett, C O Rodriguez, B J Nowak, M Du, M Ayres, D F Kisor, B S Mitchell, J Kurtzberg, M J Keating. Compound GW506U78 in refractory hematologic malignancies: relationship between cellular pharmacokinetics and clinical response. Journal of clinical oncology : official journal of the American Society of Clinical Oncology. 1998 Nov; 16(11):3607-15. doi: 10.1200/jco.1998.16.11.3607. [PMID: 9817282]