Raltitrexed (BioDeep_00000003172)

human metabolite blood metabolite Chemicals and Drugs

代谢物信息卡片

(2S)-2-[(5-{methyl[(2-methyl-4-oxo-1,4-dihydroquinazolin-6-yl)methyl]amino}thiophen-2-yl)formamido]pentanedioic acid

化学式: C21H22N4O6S (458.1259992)
中文名称: 雷替曲塞
谱图信息: 最多检出来源 Mentha canadensis(plant) 86.21%

分子结构信息

SMILES: CC1=NC2=C(C=C(C=C2)CN(C)C3=CC=C(S3)C(=O)NC(CCC(=O)O)C(=O)O)C(=O)N1
InChI: InChI=1S/C21H22N4O6S/c1-11-22-14-4-3-12(9-13(14)19(28)23-11)10-25(2)17-7-6-16(32-17)20(29)24-15(21(30)31)5-8-18(26)27/h3-4,6-7,9,15H,5,8,10H2,1-2H3,(H,24,29)(H,26,27)(H,30,31)(H,22,23,28)/t15-/m0/s1

描述信息

Raltitrexed is only found in individuals that have used or taken this drug. It is a chemotherapy drug manufactured AstraZeneca Company, is an antimetabolite used in chemotherapy. It is an inhibitor of thymidylate synthase.Raltitrexed is an antineoplastic Agents and folic acid antagonists. Raltitrexed inhibits thymidylate synthase (TS) leading to DNA fragmentation and cell death. It is transported into cells via a reduced folate carrier. Inside the cell Raltitrexed is extensively polyglutamated, which enhances thymidylate synthase inhibitory power and duration. Inhibition of this enzyme results in decreased synthesis of thymidine triphosphate which is required for DNA synthesis.
L - Antineoplastic and immunomodulating agents > L01 - Antineoplastic agents > L01B - Antimetabolites > L01BA - Folic acid analogues
C274 - Antineoplastic Agent > C186664 - Cytotoxic Chemotherapeutic Agent > C272 - Antimetabolite
C471 - Enzyme Inhibitor > C2021 - Thymidylate Synthase Inhibitor
D004791 - Enzyme Inhibitors > D005493 - Folic Acid Antagonists
D009676 - Noxae > D000963 - Antimetabolites
D000970 - Antineoplastic Agents
Same as: D01064

同义名列表

13 个代谢物同义名

(2S)-2-[(5-{methyl[(2-methyl-4-oxo-1,4-dihydroquinazolin-6-yl)methyl]amino}thiophen-2-yl)formamido]pentanedioic acid; 2-[[5-[methyl-[(2-methyl-4-oxo-1H-quinazolin-6-yl)methyl]amino]thiophene-2-carbonyl]amino]pentanedioic acid; N-(5-(N-(3,4-Dihydro-2-methyl-4-oxoquinazolin-6-ylmethyl)-N-methylamino)-2-thenoyl)-L-glutamic acid; AstraZeneca brand OF raltitrexed; Arkomédika brand OF raltitrexed; Zeneca brand OF raltitrexed; Raltitrexed; ICI-D1694; ICI D1694; ZD-1694; Tomudex; ZD1694; ICI D1694

数据库引用编号

17 个数据库交叉引用编号

ChEBI: CHEBI:5847
KEGG: C11372
PubChem: 135400182
PubChem: 135450461
PubChem: 104758
HMDB: HMDB0014438
Metlin: METLIN69021
DrugBank: DB00293
ChEMBL: CHEMBL225071
Wikipedia: Raltitrexed
chemspider: 94568
CAS: 112887-68-0
PMhub: MS000008367
PubChem: 13546
PDB-CCD: D16
NIKKAJI: J409.820J
KNApSAcK: 5847

分类词条

Glutamic acid and derivatives

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)

1 个相关的物种来源信息

9606 - Homo sapiens: -

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

Fouzia Gul, Nousheen Parvaiz, Syed Sikander Azam. Deciphering the relational dynamics of AF-2 domain of PAN PPAR through drug repurposing and comparative simulations. PloS one. 2023; 18(3):e0283743. doi: 10.1371/journal.pone.0283743. [PMID: 37000796]
Shuxuan Wang, Yao Chen, Houshun Fang, Yan Xu, Ming Ding, Chunshuang Ma, Yanyan Lin, Zhiyan Cui, Huiying Sun, Qun Niu, Shuzhang Sun, Bin-Bing S Zhou, Ning Xiao, Hui Li. A γ-glutamyl hydrolase lacking the signal peptide confers susceptibility to folates/antifolates in acute lymphoblastic leukemia cells. FEBS letters. 2022 02; 596(4):437-448. doi: 10.1002/1873-3468.14285. [PMID: 35040120]
Jasmine Giani, Michael B Sawyer, Carole Chambers. Tolerability of pemetrexed and oxaliplatin in the treatment of stage III colon cancer during raltitrexed shortage. Journal of oncology pharmacy practice : official publication of the International Society of Oncology Pharmacy Practitioners. 2021 Mar; 27(2):477-479. doi: 10.1177/1078155220934163. [PMID: 32588749]
Kayoko Kanamitsu, Hiroyuki Kusuhara, John D Schuetz, Kenji Takeuchi, Yuichi Sugiyama. Investigation of the Importance of Multidrug Resistance-Associated Protein 4 (Mrp4/Abcc4) in the Active Efflux of Anionic Drugs Across the Blood-Brain Barrier. Journal of pharmaceutical sciences. 2017 09; 106(9):2566-2575. doi: 10.1016/j.xphs.2017.04.040. [PMID: 28456721]
Stefano Kim, Amaëlle Bisch, Damien Montange, Marie-Justine Paillard, Thierry Nguyen, Marine Jary, Marion Jacquin, Betsy Winkfield, Christophe Borg, Bernard Royer. A simple and fast LC-MS/MS method with a very high sensitivity for the measurement of raltitrexed in human plasma. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2017 Aug; 1060(?):240-246. doi: 10.1016/j.jchromb.2017.06.021. [PMID: 28628839]
Rong Xing, Biao Qu, Jia-Wei Song, Kai Zhou, Qiao Liao. [Pharmacokinetics behavior of raltitrexed in rats after repeatedly injected with Huangqi injection]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2014 Jun; 39(11):2140-3. doi: NULL. [PMID: 25272859]
Daniel Martinez Molina, Rozbeh Jafari, Marina Ignatushchenko, Takahiro Seki, E Andreas Larsson, Chen Dan, Lekshmy Sreekumar, Yihai Cao, Pär Nordlund. Monitoring drug target engagement in cells and tissues using the cellular thermal shift assay. Science (New York, N.Y.). 2013 Jul; 341(6141):84-7. doi: 10.1126/science.1233606. [PMID: 23828940]
Rong Xing, Kai Zhou, Jia-Wei Song. [Pharmacokinetics behavior of raltitrexed in rats after single injected with astragali radix]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2013 Jun; 38(11):1823-6. doi: NULL. [PMID: 24010304]
Jie Shen, Hao Wang, Jia Wei, Lixia Yu, Li Xie, Xiaoping Qian, Zhengyun Zou, Baorui Liu, Wenxian Guan. Thymidylate synthase mRNA levels in plasma and tumor as potential predictive biomarkers for raltitrexed sensitivity in gastric cancer. International journal of cancer. 2012 Sep; 131(6):E938-45. doi: 10.1002/ijc.27530. [PMID: 22422354]
Li Tang, Lie-Jun Mei, Xiao-Jun Yang, Chao-Qun Huang, Yun-Feng Zhou, Yutaka Yonemura, Yan Li. Cytoreductive surgery plus hyperthermic intraperitoneal chemotherapy improves survival of gastric cancer with peritoneal carcinomatosis: evidence from an experimental study. Journal of translational medicine. 2011 May; 9(?):53. doi: 10.1186/1479-5876-9-53. [PMID: 21548973]
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Monika Jagiello, Urszula Kanska, Dmitry Nevozhay, Janusz Boratynski. Synthesis and biological activity of raltitrexed-carrier conjugates. Acta biochimica Polonica. 2010; 57(1):83-7. doi: 10.18388/abp.2010_2376. [PMID: 20349025]
Robert Mauritz, Godefridus J Peters, Ietje Kathmann, Habte Teshale, Paul Noordhuis, Elizabeth M Comijn, Herbert M Pinedo, Gerrit Jansen. Dynamics of antifolate transport via the reduced folate carrier and the membrane folate receptor in murine leukaemia cells in vitro and in vivo. Cancer chemotherapy and pharmacology. 2008 Nov; 62(6):937-48. doi: 10.1007/s00280-008-0683-0. [PMID: 18283461]
K M Li, L P Rivory, S J Clarke. Pemetrexed pharmacokinetics and pharmacodynamics in a phase I/II study of doublet chemotherapy with vinorelbine: implications for further optimisation of pemetrexed schedules. British journal of cancer. 2007 Oct; 97(8):1071-6. doi: 10.1038/sj.bjc.6603995. [PMID: 17912246]
J H Beumer, R C Garner, M B Cohen, S Galbraith, G F Duncan, T Griffin, J H Beijnen, J H M Schellens. Human mass balance study of the novel anticancer agent ixabepilone using accelerator mass spectrometry. Investigational new drugs. 2007 Aug; 25(4):327-34. doi: 10.1007/s10637-007-9041-z. [PMID: 17347871]
Jingjing Hu, Li Ding, Qinxin Song, Ying Gao, Shukui Qing. Determination of raltitrexed in human plasma by high performance liquid chromatography-electrospray ionization-mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2007 Jun; 853(1-2):147-53. doi: 10.1016/j.jchromb.2007.03.028. [PMID: 17459788]
Claire L Graham-Cole, Huw D Thomas, Gordon A Taylor, David R Newell, Roger G Melton, Richard Hesp, Alan V Boddy. An evaluation of thymidine phosphorylase as a means of preventing thymidine rescue from the thymidylate synthase inhibitor raltitrexed. Cancer chemotherapy and pharmacology. 2007 Feb; 59(2):197-206. doi: 10.1007/s00280-006-0258-x. [PMID: 16721548]
Cristina Müller, Matthias Brühlmeier, P August Schubiger, Roger Schibli. Effects of antifolate drugs on the cellular uptake of radiofolates in vitro and in vivo. Journal of nuclear medicine : official publication, Society of Nuclear Medicine. 2006 Dec; 47(12):2057-64. doi: . [PMID: 17138750]
Ze-Ping Hu, Xiao-Xia Yang, Sui Yung Chan, An-Long Xu, Wei Duan, Yi-Zhun Zhu, Fwu-Shan Sheu, Urs Alex Boelsterli, Eli Chan, Qiang Zhang, Jian-Cheng Wang, Pui Lai Rachel Ee, Hwee Ling Koh, Min Huang, Shu-Feng Zhou. St. John's wort attenuates irinotecan-induced diarrhea via down-regulation of intestinal pro-inflammatory cytokines and inhibition of intestinal epithelial apoptosis. Toxicology and applied pharmacology. 2006 Oct; 216(2):225-37. doi: 10.1016/j.taap.2006.05.020. [PMID: 17015070]
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T Benepal, A Jackman, L Pyle, S Bate, A Hardcastle, W Aherne, F Mitchell, L Simmons, R Ruddle, F Raynaud, M Gore. A phase I pharmacokinetic and pharmacodynamic study of BGC9331 and carboplatin in relapsed gynaecological malignancies. British journal of cancer. 2005 Oct; 93(8):868-75. doi: 10.1038/sj.bjc.6602811. [PMID: 16222320]
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Assaf Shafran, Ilan Ifergan, Eran Bram, Gerrit Jansen, Ietje Kathmann, Godefridus J Peters, Robert W Robey, Susan E Bates, Yehuda G Assaraf. ABCG2 harboring the Gly482 mutation confers high-level resistance to various hydrophilic antifolates. Cancer research. 2005 Sep; 65(18):8414-22. doi: 10.1158/0008-5472.can-04-4547. [PMID: 16166320]
Roberto Díaz, Jorge Aparicio, Regina Gironés, Jorge Molina, Laura Palomar, Angel Segura, Joaquin Montalar. Analysis of prognostic factors and applicability of Kohne's prognostic groups in patients with metastatic colorectal cancer treated with first-line irinotecan or oxaliplatin-based chemotherapy. Clinical colorectal cancer. 2005 Sep; 5(3):197-202. doi: 10.3816/ccc.2005.n.031. [PMID: 16197623]
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Vijaya L Damaraju, Katherine F Hamilton, Michelle L Seth-Smith, Carol E Cass, Michael B Sawyer. Characterization of binding of folates and antifolates to brush-border membrane vesicles isolated from human kidney. Molecular pharmacology. 2005 Feb; 67(2):453-9. doi: 10.1124/mol.104.004978. [PMID: 15509714]
Joëlle Egreteau, Eveline Boucher, Sophie de Guibert, Christian Jacquelinet, Bernard Meunier, Karim Boudjema, Jean-Luc Raoul. New drugs for colorectal cancer (irinotecan, oxaliplatin, raltitrexed) meet expectations in routine practice: a single center's experience before and after their introduction. International journal of gastrointestinal cancer. 2005; 35(1):69-76. doi: 10.1385/ijgc:35:1:069. [PMID: 15722576]
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Gianluca Masi, Alfredo Falcone, Antonello Di Paolo, Giacomo Allegrini, Romano Danesi, Cecilia Barbara, Samanta Cupini, Mario Del Tacca. A phase I and pharmacokinetic study of irinotecan given as a 7-day continuous infusion in metastatic colorectal cancer patients pretreated with 5-fluorouracil or raltitrexed. Clinical cancer research : an official journal of the American Association for Cancer Research. 2004 Mar; 10(5):1657-63. doi: 10.1158/1078-0432.ccr-1585-3. [PMID: 15014016]
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C Fleck, R Hilger, S Jurkutat, E Karge, U Merkel, A Schimske, J Schubert. Ex vivo stimulation of renal transport of the cytostatic drugs methotrexate, cisplatin, topotecan (Hycamtin) and raltitrexed (Tomudex) by dexamethasone, T3 and EGF in intact human and rat kidney tissue and in human renal cell carcinoma. Urological research. 2002 Sep; 30(4):256-62. doi: 10.1007/s00240-002-0265-2. [PMID: 12202944]
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N Horikoshi, K Aiba, M Fukuoka, S Akazawa, Y Sakata, K Furuse, R Kanamaru, S Kudoh, T Konishi, M Kurihara, H Niitani, H Furue, S Tsukagoshi, T Taguchi, S Yoshida, K Ota, T Kotake, A Wakui. [Phase I study of raltitrexed (ZD-1694)]. Gan to kagaku ryoho. Cancer & chemotherapy. 1998 Nov; 25(13):2075-84. doi: NULL. [PMID: 9838910]
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