7-Hydroxymethotrexate (BioDeep_00000607053)

   


代谢物信息卡片


2-[[4-[(2,4-diamino-7-oxo-8H-pteridin-6-yl)methyl-methylamino]benzoyl]amino]pentanedioic acid

化学式: C20H22N8O6 (470.1662)
中文名称: 氨甲叶酸7-羟基代谢物
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CN(CC1=NC2=C(N=C(N=C2NC1=O)N)N)C3=CC=C(C=C3)C(=O)NC(CCC(=O)O)C(=O)O
InChI: InChI=1S/C20H22N8O6/c1-28(8-12-18(32)26-16-14(23-12)15(21)25-20(22)27-16)10-4-2-9(3-5-10)17(31)24-11(19(33)34)6-7-13(29)30/h2-5,11H,6-8H2,1H3,(H,24,31)(H,29,30)(H,33,34)(H5,21,22,25,26,27,32)

描述信息

D004791 - Enzyme Inhibitors > D005493 - Folic Acid Antagonists

同义名列表

2 个代谢物同义名

2-[[4-[(2,4-diamino-7-oxo-8H-pteridin-6-yl)methyl-methylamino]benzoyl]amino]pentanedioic acid; 7-Hydroxymethotrexate



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)

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)

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

  • Yurong Song, Linlin Liu, Bin Liu, Rui Liu, Youwen Chen, Chenxi Li, Guangzhi Liu, Zhiqian Song, Cheng Lu, Aiping Lu, Yuanyan Liu. Interaction of nobiletin with methotrexate ameliorates 7-OH methotrexate-induced nephrotoxicity through endoplasmic reticulum stress-dependent PERK/CHOP signaling pathway. Pharmacological research. 2021 03; 165(?):105371. doi: 10.1016/j.phrs.2020.105371. [PMID: 33460792]
  • Shenghui Mei, Yong Cui, Dongjie Zhang, Chun Zeng, Xiaohui Ren, Kefu Yu, Song Lin, Zhigang Zhao. Simultaneous Determination of Urine Methotrexate, 7-Hydroxy Methotrexate, Deoxyaminopteroic Acid, and 7-Hydroxy Deoxyaminopteroic Acid by UHPLC-MS/MS in Patients Receiving High-dose Methotrexate Therapy. Analytical sciences : the international journal of the Japan Society for Analytical Chemistry. 2020 Dec; 36(12):1479-1486. doi: 10.2116/analsci.19p481. [PMID: 32801284]
  • G J Luo, L Wang, G F Hu, C B Li, H X Liu, M T Peng. [Clinical application of the simultaneous detection of methotrexate and 7-hydroxymethotrexate in the delayed elimination for pediatric acute lymphoblastic leukemia]. Zhonghua yi xue za zhi. 2020 Jul; 100(25):1973-1978. doi: 10.3760/cma.j.cn112137-20200424-01305. [PMID: 32629599]
  • Shenghui Mei, Xiaoxu Shi, Yaming Du, Yong Cui, Chun Zeng, Xiaohui Ren, Kefu Yu, Zhigang Zhao, Song Lin. Simultaneous determination of plasma methotrexate and 7-hydroxy methotrexate by UHPLC-MS/MS in patients receiving high-dose methotrexate therapy. Journal of pharmaceutical and biomedical analysis. 2018 Sep; 158(?):300-306. doi: 10.1016/j.jpba.2018.06.011. [PMID: 29909319]
  • Le Wang, Leilei Ma, Yunfei Lin, Xing Liu, Ling Xiao, Yiting Zhang, Ye Xu, Hu Zhou, Guoyu Pan. Leflunomide Increases Hepatic Exposure to Methotrexate and Its Metabolite by Differentially Regulating Multidrug Resistance-Associated Protein Mrp2/3/4 Transporters via Peroxisome Proliferator-Activated Receptor α Activation. Molecular pharmacology. 2018 06; 93(6):563-574. doi: 10.1124/mol.117.110593. [PMID: 29618584]
  • Nicolas Fabresse, Bénédicte Devictor, Christel Pissier, Hervé Chambost, Bruno Lacarelle, Gérard Michel, Caroline Solas. Plasma 7-Hydroxymethotrexate Levels Versus Methotrexate to Predict Delayed Elimination in Children Receiving High-Dose Methotrexate. Therapeutic drug monitoring. 2018 02; 40(1):76-83. doi: 10.1097/ftd.0000000000000445. [PMID: 29120974]
  • Ryan C Schofield, Lakshmi V Ramanathan, Kazunori Murata, Martin Fleisher, Melissa S Pessin, Dean C Carlow. Development of an Assay for Methotrexate and Its Metabolites 7-Hydroxy Methotrexate and DAMPA in Serum by LC-MS/MS. Methods in molecular biology (Clifton, N.J.). 2016; 1383(?):213-22. doi: 10.1007/978-1-4939-3252-8_23. [PMID: 26660190]
  • Ryan C Schofield, Lakshmi V Ramanathan, Kazunori Murata, Marie Grace, Martin Fleisher, Melissa S Pessin, Dean C Carlow. Development and validation of a turbulent flow chromatography and tandem mass spectrometry method for the quantitation of methotrexate and its metabolites 7-hydroxy methotrexate and DAMPA in serum. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2015 Oct; 1002(?):169-75. doi: 10.1016/j.jchromb.2015.08.025. [PMID: 26322588]
  • J Bluett, I Riba-Garcia, K Hollywood, S M M Verstappen, A Barton, R D Unwin. A HPLC-SRM-MS based method for the detection and quantification of methotrexate in urine at doses used in clinical practice for patients with rheumatological disease: a potential measure of adherence. The Analyst. 2015 Mar; 140(6):1981-7. doi: 10.1039/c4an02321h. [PMID: 25671614]
  • M Řiháček, K Pilatova, J Štěrba, R Pilný, D Valík. [New Indings in Methotrexate Pharmacology -  Diagnostic Possibilities and Impact on Clinical Care]. Klinicka onkologie : casopis Ceske a Slovenske onkologicke spolecnosti. 2015; 28(3):163-70. doi: 10.14735/amko2015163. [PMID: 26062617]
  • Katalin Csordas, Marta Hegyi, Oliver T Eipel, Judit Muller, Daniel J Erdelyi, Gabor T Kovacs. Comparison of pharmacokinetics and toxicity after high-dose methotrexate treatments in children with acute lymphoblastic leukemia. Anti-cancer drugs. 2013 Feb; 24(2):189-97. doi: 10.1097/cad.0b013e32835b8662. [PMID: 23187460]
  • Masanobu Uchiyama, Takanori Matsumoto, Taichi Matsumoto, Shiro Jimi, Yasushi Takamatsu, Kazuo Tamura, Shuuji Hara. Simple and sensitive HPLC method for the fluorometric determination of methotrexate and its major metabolites in human plasma by post-column photochemical reaction. Biomedical chromatography : BMC. 2012 Jan; 26(1):76-80. doi: 10.1002/bmc.1628. [PMID: 21437923]
  • Zhan Wang, Qingyu Zhou, Gary D Kruh, James M Gallo. Dose-dependent disposition of methotrexate in Abcc2 and Abcc3 gene knockout murine models. Drug metabolism and disposition: the biological fate of chemicals. 2011 Nov; 39(11):2155-61. doi: 10.1124/dmd.111.041228. [PMID: 21841039]
  • Katalin Csordás, Olivér Eipel, Márta Hegyi, Monika Csóka, Eva Pap, Gábor Kovács. [Pharmacokinetic analysis of high-dose methotrexate treatments in children with hematologic malignancies]. Orvosi hetilap. 2011 Oct; 152(40):1609-17. doi: 10.1556/oh.2011.29143. [PMID: 21945870]
  • Maria L H Vlaming, Anita van Esch, Evita van de Steeg, Zeliha Pala, Els Wagenaar, Olaf van Tellingen, Alfred H Schinkel. Impact of abcc2 [multidrug resistance-associated protein (MRP) 2], abcc3 (MRP3), and abcg2 (breast cancer resistance protein) on the oral pharmacokinetics of methotrexate and its main metabolite 7-hydroxymethotrexate. Drug metabolism and disposition: the biological fate of chemicals. 2011 Aug; 39(8):1338-44. doi: 10.1124/dmd.111.038794. [PMID: 21566011]
  • Roland J W Meesters, Ethan den Boer, Ron A A Mathot, Robert de Jonge, Rob J van Klaveren, Jan Lindemans, Theo M Luider. Ultrafast selective quantification of methotrexate in human plasma by high-throughput MALDI-isotope dilution mass spectrometry. Bioanalysis. 2011 Jun; 3(12):1369-78. doi: 10.4155/bio.11.113. [PMID: 21679031]
  • Jirina Chládková, Jirí Hak, Jirina Martínková, Jaroslav Chládek. High-dose methotrexate in children with acute lymphoblastic leukemia: 7-hydroxymethotrexate systemic exposure and urinary concentrations at the steady state correlate well with those of methotrexate. Arzneimittel-Forschung. 2010; 60(12):769-75. doi: 10.1055/s-0031-1296353. [PMID: 21265469]
  • Maria L H Vlaming, Anita van Esch, Zeliha Pala, Els Wagenaar, Koen van de Wetering, Olaf van Tellingen, Alfred H Schinkel. Abcc2 (Mrp2), Abcc3 (Mrp3), and Abcg2 (Bcrp1) are the main determinants for rapid elimination of methotrexate and its toxic metabolite 7-hydroxymethotrexate in vivo. Molecular cancer therapeutics. 2009 Dec; 8(12):3350-9. doi: 10.1158/1535-7163.mct-09-0668. [PMID: 19996279]
  • Joseph E Baggott, Sarah L Morgan. Methotrexate catabolism to 7-hydroxymethotrexate in rheumatoid arthritis alters drug efficacy and retention and is reduced by folic acid supplementation. Arthritis and rheumatism. 2009 Aug; 60(8):2257-61. doi: 10.1002/art.24685. [PMID: 19644884]
  • Maria L H Vlaming, Zeliha Pala, Anita van Esch, Els Wagenaar, Dirk R de Waart, Koen van de Wetering, Cornelia M M van der Kruijssen, Ronald P J Oude Elferink, Olaf van Tellingen, Alfred H Schinkel. Functionally overlapping roles of Abcg2 (Bcrp1) and Abcc2 (Mrp2) in the elimination of methotrexate and its main toxic metabolite 7-hydroxymethotrexate in vivo. Clinical cancer research : an official journal of the American Association for Cancer Research. 2009 May; 15(9):3084-93. doi: 10.1158/1078-0432.ccr-08-2940. [PMID: 19383815]
  • Maria L H Vlaming, Zeliha Pala, Anita van Esch, Els Wagenaar, Olaf van Tellingen, Dirk R de Waart, Ronald P J Oude Elferink, Koen van de Wetering, Alfred H Schinkel. Impact of Abcc2 (Mrp2) and Abcc3 (Mrp3) on the in vivo elimination of methotrexate and its main toxic metabolite 7-hydroxymethotrexate. Clinical cancer research : an official journal of the American Association for Cancer Research. 2008 Dec; 14(24):8152-60. doi: 10.1158/1078-0432.ccr-08-1609. [PMID: 19088030]
  • Ping Guo, Xiaomin Wang, Liansheng Liu, Martin G Belinsky, Gary D Kruh, James M Gallo. Determination of methotrexate and its major metabolite 7-hydroxymethotrexate in mouse plasma and brain tissue by liquid chromatography-tandem mass spectrometry. Journal of pharmaceutical and biomedical analysis. 2007 Apr; 43(5):1789-95. doi: 10.1016/j.jpba.2006.12.034. [PMID: 17289326]
  • Aya Moriyasu, Kazumi Sugihara, Keiko Nakatani, Shigeru Ohta, Shigeyuki Kitamura. In vivo-in vitro relationship of methotrexate 7-hydroxylation by aldehyde oxidase in four different strain rats. Drug metabolism and pharmacokinetics. 2006 Dec; 21(6):485-91. doi: 10.2133/dmpk.21.485. [PMID: 17220564]
  • Ilaria Badagnani, Richard A Castro, Travis R Taylor, Claire M Brett, Conrad C Huang, Douglas Stryke, Michiko Kawamoto, Susan J Johns, Thomas E Ferrin, Elaine J Carlson, Esteban G Burchard, Kathleen M Giacomini. Interaction of methotrexate with organic-anion transporting polypeptide 1A2 and its genetic variants. The Journal of pharmacology and experimental therapeutics. 2006 Aug; 318(2):521-9. doi: 10.1124/jpet.106.104364. [PMID: 16702441]
  • Majid Vakily, Fouad Amer, Michael J Kukulka, Nupun Andhivarothai. Coadministration of lansoprazole and naproxen does not affect the pharmacokinetic profile of methotrexate in adult patients with rheumatoid arthritis. Journal of clinical pharmacology. 2005 Oct; 45(10):1179-86. doi: 10.1177/0091270005280100. [PMID: 16172183]
  • R M Lingg, G Hempel, M G Rots, C H Van Zantwijk, J Boos, G J L Kaspers. Effects and interaction of 7-hydroxy methotrexate and methotrexate in leukaemic cells ex vivo measured by the thymidylate synthase inhibition assay. Cancer chemotherapy and pharmacology. 2005 Sep; 56(3):322-7. doi: 10.1007/s00280-005-1032-1. [PMID: 15868145]
  • Linda S Liang, Wesley Wong, Helen M Burt. Pharmacokinetic study of methotrexate following intra-articular injection of methotrexate loaded poly(L-lactic acid) microspheres in rabbits. Journal of pharmaceutical sciences. 2005 Jun; 94(6):1204-15. doi: 10.1002/jps.20341. [PMID: 15858840]
  • Kambiz Fotoohi, Tor Skärby, Stefan Söderhäll, Curt Peterson, Freidoun Albertioni. Interference of 7-hydroxymethotrexate with the determination of methotrexate in plasma samples from children with acute lymphoblastic leukemia employing routine clinical assays. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2005 Mar; 817(2):139-44. doi: 10.1016/j.jchromb.2004.11.037. [PMID: 15686977]
  • Joseph E Baggott, S Louis Bridges, Sarah L Morgan. Evidence for two phenotypes in the metabolism of methotrexate to 7-hydroxymethotrexate in patients with rheumatoid arthritis. Arthritis and rheumatism. 2005 Jan; 52(1):356-8. doi: 10.1002/art.20742. [PMID: 15641087]
  • Stefan N Hartmann, Christiane M Rordorf, Slavica Milosavljev, Janice M Branson, Gérard H Chales, Robert R Juvin, Pierre Lafforgue, Jean Marie Le Parc, Christian G Tavernier, Olivier C Meyer. Lumiracoxib does not affect methotrexate pharmacokinetics in rheumatoid arthritis patients. The Annals of pharmacotherapy. 2004 Oct; 38(10):1582-7. doi: 10.1345/aph.1e044. [PMID: 15340127]
  • R I Fox, S L Morgan, H T Smith, B A Robbins, M G Choc, J E Baggott. Combined oral cyclosporin and methotrexate therapy in patients with rheumatoid arthritis elevates methotrexate levels and reduces 7-hydroxymethotrexate levels when compared with methotrexate alone. Rheumatology (Oxford, England). 2003 Aug; 42(8):989-94. doi: 10.1093/rheumatology/keg277. [PMID: 12730515]
  • Jaroslav Chládek, Jiøí Grim, Jiøina Martínková, Marie Simková, Jaroslava Vanìèková, Vìra Koudelková, Marie Noièková. Pharmacokinetics and pharmacodynamics of low-dose methotrexate in the treatment of psoriasis. British journal of clinical pharmacology. 2002 Aug; 54(2):147-56. doi: 10.1046/j.1365-2125.2002.01621.x. [PMID: 12207634]
  • J I Schwartz, N G Agrawal, P H Wong, K A Bachmann, A G Porras, J L Miller, D L Ebel, M R Sack, G B Holmes, J S Redfern, B J Gertz. Lack of pharmacokinetic interaction between rofecoxib and methotrexate in rheumatoid arthritis patients. Journal of clinical pharmacology. 2001 Oct; 41(10):1120-30. doi: 10.1177/00912700122012616. [PMID: 11583481]
  • G Rule, M Chapple, J Henion. A 384-well solid-phase extraction for LC/MS/MS determination of methotrexate and its 7-hydroxy metabolite in human urine and plasma. Analytical chemistry. 2001 Feb; 73(3):439-43. doi: 10.1021/ac000897i. [PMID: 11217743]
  • O M Fuskevåg, C Kristiansen, R Olsen, J Aarbakke, S Lindal. Microvascular perturbations in rats receiving the maximum tolerated dose of methotrexate or its major metabolite 7-hydroxymethotrexate. Ultrastructural pathology. 2000 Sep; 24(5):325-32. doi: 10.1080/019131200750035058. [PMID: 11071571]
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  • J E Baggott, S L Morgan, W J Koopman. The effect of methotrexate and 7-hydroxymethotrexate on rat adjuvant arthritis and on urinary aminoimidazole carboxamide excretion. Arthritis and rheumatism. 1998 Aug; 41(8):1407-10. doi: 10.1002/1529-0131(199808)41:8<1407::aid-art9>3.0.co;2-h. [PMID: 9704638]
  • T Hirai, S Matsumoto, I Kishi. Determination of methotrexate and its main metabolite 7-hydroxymethotrexate in human urine by high-performance liquid chromatography with normal solid-phase extraction. Journal of chromatography. B, Biomedical sciences and applications. 1997 Mar; 690(1-2):267-73. doi: 10.1016/s0378-4347(96)00371-4. [PMID: 9106052]
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