Mercaptopurine (BioDeep_00000003406)

 

Secondary id: BioDeep_00000398029

human metabolite Endogenous blood metabolite Chemicals and Drugs


代谢物信息卡片


GlaxoSmithKline brand OF 6 mercaptopurine

化学式: C5H4N4S (152.0156664)
中文名称: 6-巯基嘌呤 (6-MP)
谱图信息: 最多检出来源 Homo sapiens(blood) 2.38%

分子结构信息

SMILES: C1=NC2=C(N1)C(=S)N=CN2
InChI: InChI=1S/C5H4N4S/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10)

描述信息

Mercaptopurine is only found in individuals that have used or taken this drug. It is an antimetabolite antineoplastic agent with immunosuppressant properties. It interferes with nucleic acid synthesis by inhibiting purine metabolism and is used, usually in combination with other drugs, in the treatment of or in remission maintenance programs for leukemia. [PubChem]Mercaptopurine competes with hypoxanthine and guanine for the enzyme hypoxanthine-guanine phosphoribosyltransferase (HGPRTase) and is itself converted to thioinosinic acid (TIMP). This intracellular nucleotide inhibits several reactions involving inosinic acid (IMP), including the conversion of IMP to xanthylic acid (XMP) and the conversion of IMP to adenylic acid (AMP) via adenylosuccinate (SAMP). In addition, 6-methylthioinosinate (MTIMP) is formed by the methylation of TIMP. Both TIMP and MTIMP have been reported to inhibit glutamine-5-phosphoribosylpyrophosphate amidotransferase, the first enzyme unique to the de novo pathway for purine ribonucleotide synthesis. Experiments indicate that radiolabeled mercaptopurine may be recovered from the DNA in the form of deoxythioguanosine. Some mercaptopurine is converted to nucleotide derivatives of 6-thioguanine (6-TG) by the sequential actions of inosinate (IMP) dehydrogenase and xanthylate (XMP) aminase, converting TIMP to thioguanylic acid (TGMP).
L - Antineoplastic and immunomodulating agents > L01 - Antineoplastic agents > L01B - Antimetabolites > L01BB - Purine analogues
C274 - Antineoplastic Agent > C186664 - Cytotoxic Chemotherapeutic Agent > C272 - Antimetabolite
D004791 - Enzyme Inhibitors > D019384 - Nucleic Acid Synthesis Inhibitors
D007155 - Immunologic Factors > D007166 - Immunosuppressive Agents
C308 - Immunotherapeutic Agent > C574 - Immunosuppressant
D009676 - Noxae > D000963 - Antimetabolites
D000970 - Antineoplastic Agents

同义名列表

31 个代谢物同义名

GlaxoSmithKline brand OF 6 mercaptopurine; GlaxoSmithKline brand OF 6-mercaptopurine; Glaxo wellcome brand OF 6-mercaptopurine; Glaxo wellcome brand OF 6 mercaptopurine; Wellcome brand OF 6 mercaptopurine; Wellcome brand OF 6-mercaptopurine; 1,7-Dihydro-6H-purine-6-thione; 6,7-dihydro-3H-purine-6-thione; 6 Mercaptopurine monohydrate; 6-Mercaptopurine monohydrate; Mercaptopurine monohydrate; Mercaptopurine anhydrous; Mercaptopurina wellcome; 6 Thiohypoxanthine; 6-Thiohypoxanthine; 3H-Purine-6-thiol; 6 Mercaptopurine; 6-Mercaptopurine; mercaptopurine; 6-Thiopurine; 6 Thiopurine; Puri-nethol; Puri nethol; Purimethol; Purinethol; Mercapurin; thiopurine; Leupurin; 6-MP; 6 MP; MP



数据库引用编号

25 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(10)

BioCyc(0)

PlantCyc(0)

代谢反应

73 个相关的代谢反应过程信息。

Reactome(66)

BioCyc(0)

WikiPathways(1)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(1)

PathBank(5)

PharmGKB(0)

11 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

  • Ahmet Doğan Ergin, Çağatay Oltulu, Büşra Koç. Enhanced Cytotoxic Activity of 6-Mercaptopurine-Loaded Solid Lipid Nanoparticles in Hepatic Cancer Treatment. Assay and drug development technologies. 2023 Jul; ?(?):. doi: 10.1089/adt.2023.007. [PMID: 37417972]
  • Yaru Zou, Wei Gao, Huizhen Jin, Chenmei Mao, Yi Zhang, Xiaoling Wang, Dong Mei, Libo Zhao. Cellular Uptake and Transport Mechanism of 6-Mercaptopurine Nanomedicines for Enhanced Oral Bioavailability. International journal of nanomedicine. 2023; 18(?):79-94. doi: 10.2147/ijn.s394819. [PMID: 36636639]
  • . Suspected Drug-induced Liver Injury Due to 6-Mercaptopurine With a Superimposed SARS-CoV-2 Infection in a Patient With B-ALL: Erratum. Journal of pediatric hematology/oncology. 2022 05; 44(4):193. doi: 10.1097/mph.0000000000002476. [PMID: 35452202]
  • Kory Cablay, Violet M Borowicz, Ryan Fulton. Suspected Drug-induced Liver Injury Due to 6-Mercaptopurine With a Superimposed SARS-CoV-2 Infection in a Patient With B-ALL. Journal of pediatric hematology/oncology. 2022 04; 44(3):e792-e794. doi: 10.1097/mph.0000000000002407. [PMID: 35091518]
  • Mirabella Zhao, Mads Damsgaard Wewer, Jacob Tveiten Bjerrum, Casper Steenholdt, Frank Schiødt, Kent Haderslev, Marianne Kiszka-Kanowitz, Pia Munkholm, Jakob Seidelin, Johan Burisch. [Practical guide to the use of thiopurinesin patients with inflammatory bowel diseases]. Ugeskrift for laeger. 2022 03; 184(11):. doi: NULL. [PMID: 35315759]
  • Rana Salari, Tooba Hallaj. A dual colorimetric and fluorometric sensor based on N, P-CDs and shape transformation of AgNPrs for the determination of 6-mercaptopurine. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2021 Dec; 262(?):120104. doi: 10.1016/j.saa.2021.120104. [PMID: 34218180]
  • Hiromu Morikubo, Taku Kobayashi, Ryo Ozaki, Shinji Okabayashi, Satoshi Kuronuma, Osamu Takeuchi, Tenyo Shiba, Hiroki Kiyohara, Mao Matsubayashi, Shintaro Sagami, Masaru Nakano, Osamu Ikezaki, Tadakazu Hisamatsu, Yoichi Tanaka, Toshifumi Hibi. Differential effects of mesalazine formulations on thiopurine metabolism through thiopurine S-methyltransferase inhibition. Journal of gastroenterology and hepatology. 2021 Aug; 36(8):2116-2124. doi: 10.1111/jgh.15411. [PMID: 33470487]
  • Zahra Alizadeh, Mahdi M Farimani, Valentina Parisi, Stefania Marzocco, Samad N Ebrahimi, Nunziatina De Tommasi. Nor-abietane Diterpenoids from Perovskia abrotanoides Roots with Anti-inflammatory Potential. Journal of natural products. 2021 04; 84(4):1185-1197. doi: 10.1021/acs.jnatprod.0c01256. [PMID: 33749273]
  • Xuanxuan An, Ruchun Chen, Qizhen Chen, Qin Tan, Shuang Pan, Hui Liu, Xiaoli Hu. A MnO2 nanosheet-assisted ratiometric fluorescence probe based on carbon quantum dots and o-phenylenediamine for determination of 6-mercaptopurine. Mikrochimica acta. 2021 04; 188(5):156. doi: 10.1007/s00604-021-04802-4. [PMID: 33825037]
  • Ryan C Ungaro, Erica J Brenner, Richard B Gearry, Gilaad G Kaplan, Michele Kissous-Hunt, James D Lewis, Siew C Ng, Jean-Francois Rahier, Walter Reinisch, Flávio Steinwurz, Fox E Underwood, Xian Zhang, Jean-Frederic Colombel, Michael D Kappelman. Effect of IBD medications on COVID-19 outcomes: results from an international registry. Gut. 2021 04; 70(4):725-732. doi: 10.1136/gutjnl-2020-322539. [PMID: 33082265]
  • Kristyna Pospisilova, Jitka Siroka, Eva Karaskova, Ondrej Hradsky, Tereza Lerchova, Kristyna Zarubova, Ivana Copova, Lucie Gonsorcikova, Maria Velganova-Veghova, Irena Francova, Lubor Urbanek, Milos Geryk, Vladimir Mihal, Jiri Bronsky. Is It Useful to Monitor Thiopurine Metabolites in Pediatric Patients with Crohn's Disease on Combination Therapy? A Multicenter Prospective Observational Study. Paediatric drugs. 2021 Mar; 23(2):183-194. doi: 10.1007/s40272-021-00439-1. [PMID: 33709340]
  • Venkatraman Radhakrishnan, Devleena Gangopadhyay. Repeat-positive SARS-CoV-2 in a child with cancer. Pediatric blood & cancer. 2021 03; 68(3):e28744. doi: 10.1002/pbc.28744. [PMID: 33009874]
  • Xueying Lu, Yandong Xie, Fengyu Wang. Application and Analysis of 6-Mercaptopurine Nanomedicine in the Treatment of Leukemia. Journal of nanoscience and nanotechnology. 2021 Feb; 21(2):1001-1007. doi: 10.1166/jnn.2021.18695. [PMID: 33183436]
  • Abeer A Sharfalddin, Abdul-Hamid Emwas, Mariusz Jaremko, Mostafa A Hussien. Complexation of uranyl (UO2)2+ with bidentate ligands: XRD, spectroscopic, computational, and biological studies. PloS one. 2021; 16(8):e0256186. doi: 10.1371/journal.pone.0256186. [PMID: 34411162]
  • Yaru Zou, Dong Mei, Jinjie Yuan, Jiaqi Han, Jiamin Xu, Ning Sun, Huan He, Changqing Yang, Libo Zhao. Preparation, Characterization, Pharmacokinetic, and Therapeutic Potential of Novel 6-Mercaptopurine-Loaded Oral Nanomedicines for Acute Lymphoblastic Leukemia. International journal of nanomedicine. 2021; 16(?):1127-1141. doi: 10.2147/ijn.s290466. [PMID: 33603372]
  • Zhao Wang, Shuting Li, Chunyan Zhou, Yingying Sun, Hui Pang, Wei Liu, Xinchun Li. Ratiometric fluorescent nanoprobe based on CdTe/SiO2/folic acid/silver nanoparticles core-shell-satellite assembly for determination of 6-mercaptopurine. Mikrochimica acta. 2020 11; 187(12):665. doi: 10.1007/s00604-020-04628-6. [PMID: 33205310]
  • Benoît Bernar, Gabriele Kropshofer, Roman Crazzolara, Klaus Kapelari, Andrea Griesmacher, Thomas Müller, Sabine Scholl-Bürgi. SARS-CoV-2 infection in a 7-year-old girl with pancytopenia during acute lymphocytic leukemia maintenance therapy. Pediatric blood & cancer. 2020 11; 67(11):e28391. doi: 10.1002/pbc.28391. [PMID: 32779856]
  • Nabeel Khan, Dhruvan Patel, Dawei Xie, James Lewis, Chinmay Trivedi, Yu-Xiao Yang. Impact of Anti-Tumor Necrosis Factor and Thiopurine Medications on the Development of COVID-19 in Patients With Inflammatory Bowel Disease: A Nationwide Veterans Administration Cohort Study. Gastroenterology. 2020 10; 159(4):1545-1546.e1. doi: 10.1053/j.gastro.2020.05.065. [PMID: 32479823]
  • Rafael Martín-Masot, María Pilar Ortiz Pérez, Natalia Ramos Rueda, Juliana Serrano Nieto, Javier Blasco-Alonso, Víctor Manuel Navas-López. [Laboratory determination of thiopurine levels in paediatric patients with inflammatory bowel disease]. Anales de pediatria. 2020 Jul; 93(1):34-40. doi: 10.1016/j.anpedi.2019.10.005. [PMID: 31784325]
  • Rikke Hebo Larsen, Lisa Lyngsie Hjalgrim, Kathrine Grell, Kim Kristensen, Line Gerner Pedersen, Emilie Damgaard Brünner, Bodil Als-Nielsen, Kjeld Schmiegelow, Jacob Nersting. Pharmacokinetics of tablet and liquid formulations of oral 6-mercaptopurine in children with acute lymphoblastic leukemia. Cancer chemotherapy and pharmacology. 2020 07; 86(1):25-32. doi: 10.1007/s00280-020-04097-x. [PMID: 32519032]
  • Thomas M Goodsall, Samuel P Costello, Robert V Bryant. COVID-19 and implications for thiopurine use. The Medical journal of Australia. 2020 06; 212(10):490-490.e1. doi: 10.5694/mja2.50613. [PMID: 32400020]
  • Mirko Kroll, Kirsten Kaupat-Bleckmann, Anja Mörickel, Julia Altenl, Denis M Schewel, Martin Stanullal, Martin Zimmermann, Martin Schrappe, Gunnar Cario. Methotrexate-associated toxicity in children with Down syndrome and acute lymphoblastic leukemia during consolidation therapy with high dose methotrexate according to ALL-BFM treatment regimen. Haematologica. 2020 04; 105(4):1013-1020. doi: 10.3324/haematol.2019.224774. [PMID: 31371414]
  • Peter Ter Horst, Elise J Smolders, Daphne den Besten-Bertholee. Mercaptopurine and Metabolites in Breast Milk. Breastfeeding medicine : the official journal of the Academy of Breastfeeding Medicine. 2020 04; 15(4):277-279. doi: 10.1089/bfm.2019.0101. [PMID: 31414890]
  • Sandra Bohn Thomsen, Kristine Højgaard Allin, Johan Burisch, Camilla Bjørn Jensen, Susanne Hansen, Lise Lotte Gluud, Klaus Theede, Marianne Kiszka-Kanowitz, Anette Mertz Nielsen, Tine Jess. Outcome of concomitant treatment with thiopurines and allopurinol in patients with inflammatory bowel disease: A nationwide Danish cohort study. United European gastroenterology journal. 2020 02; 8(1):68-76. doi: 10.1177/2050640619868387. [PMID: 32213059]
  • Jiaqi Han, Shenghui Mei, Jiamin Xu, Dongjie Zhang, Siyao Jin, Zhigang Zhao, Libo Zhao. Simultaneous UPLC-MS/MS Determination of 6-mercaptopurine, 6-methylmercaptopurine and 6-thioguanine in Plasma: Application to the Pharmacokinetic Evaluation of Novel Dosage forms in Beagle Dogs. Current pharmaceutical design. 2020; 26(46):6013-6020. doi: 10.2174/1381612826999200820161343. [PMID: 32867649]
  • Yadi Zhou, Yuan Hou, Jiayu Shen, Yin Huang, William Martin, Feixiong Cheng. Network-based drug repurposing for novel coronavirus 2019-nCoV/SARS-CoV-2. Cell discovery. 2020; 6(?):14. doi: NULL. [PMID: 32194980]
  • Marzieh Dadkhah Aseman, Shiva Aryamanesh, Zahra Shojaeifard, Bahram Hemmateenejad, S Masoud Nabavizadeh. Cycloplatinated(II) Derivatives of Mercaptopurine Capable of Binding Interactions with HSA/DNA. Inorganic chemistry. 2019 Dec; 58(23):16154-16170. doi: 10.1021/acs.inorgchem.9b02696. [PMID: 31721562]
  • Simon Pape, Christoph Schramm, Tom Jg Gevers. Clinical management of autoimmune hepatitis. United European gastroenterology journal. 2019 11; 7(9):1156-1163. doi: 10.1177/2050640619872408. [PMID: 31700628]
  • Ida Sofie Grønningsæter, Hanne Kristin Fredly, Bjørn Tore Gjertsen, Kimberley Joanne Hatfield, Øystein Bruserud. Systemic Metabolomic Profiling of Acute Myeloid Leukemia Patients before and During Disease-Stabilizing Treatment Based on All-Trans Retinoic Acid, Valproic Acid, and Low-Dose Chemotherapy. Cells. 2019 10; 8(10):. doi: 10.3390/cells8101229. [PMID: 31658693]
  • Prashanthi Kandavel, Sally J Eder, Noah E Newman, Akbar K Waljee, Emily P Whitfield, Jeremy Adler. Mean Corpuscular Volume to White Blood Cell Ratio for Thiopurine Monitoring in Pediatric Inflammatory Bowel Disease. Journal of pediatric gastroenterology and nutrition. 2019 07; 69(1):88-94. doi: 10.1097/mpg.0000000000002296. [PMID: 30747813]
  • Diana Schmidt, Kim Kristensen, Henrik Schroeder, Peder Skov Wehner, Steen Rosthøj, Jesper Heldrup, Linn Damsgaard, Kjeld Schmiegelow, Torben Stamm Mikkelsen. Plasma creatinine as predictor of delayed elimination of high-dose methotrexate in childhood acute lymphoblastic leukemia: A Danish population-based study. Pediatric blood & cancer. 2019 06; 66(6):e27637. doi: 10.1002/pbc.27637. [PMID: 30835935]
  • Nicholas M Ruel, Khanh H Nguyen, Gonzalo Vilas, James R Hammond. Characterization of 6-Mercaptopurine Transport by the SLC43A3-Encoded Nucleobase Transporter. Molecular pharmacology. 2019 06; 95(6):584-596. doi: 10.1124/mol.118.114389. [PMID: 30910793]
  • Anil Kumar, Purnendu Kumar Pathak, Bhim Bali Prasad. Electrocatalytic Imprinted Polymer of N-Doped Hollow Carbon Nanosphere-Palladium Nanocomposite for Ultratrace Detection of Anticancer Drug 6-Mercaptopurine. ACS applied materials & interfaces. 2019 May; 11(17):16065-16074. doi: 10.1021/acsami.9b02947. [PMID: 30990996]
  • Nicholas A Kennedy, Graham A Heap, Harry D Green, Benjamin Hamilton, Claire Bewshea, Gareth J Walker, Amanda Thomas, Rachel Nice, Mandy H Perry, Sonia Bouri, Neil Chanchlani, Neel M Heerasing, Peter Hendy, Simeng Lin, Daniel R Gaya, J R Fraser Cummings, Christian P Selinger, Charlie W Lees, Ailsa L Hart, Miles Parkes, Shaji Sebastian, John C Mansfield, Peter M Irving, James Lindsay, Richard K Russell, Timothy J McDonald, Dermot McGovern, James R Goodhand, Tariq Ahmad. Predictors of anti-TNF treatment failure in anti-TNF-naive patients with active luminal Crohn's disease: a prospective, multicentre, cohort study. The lancet. Gastroenterology & hepatology. 2019 05; 4(5):341-353. doi: 10.1016/s2468-1253(19)30012-3. [PMID: 30824404]
  • Miriam Saiz-Rodríguez, Dolores Ochoa, Carmen Belmonte, Manuel Román, Cristina Martínez-Ingelmo, Lucía Ortega-Ruíz, Carmen Sarmiento-Iglesias, Coral Herrador, Francisco Abad-Santos. Influence of thiopurine S-methyltransferase polymorphisms in mercaptopurine pharmacokinetics in healthy volunteers. Basic & clinical pharmacology & toxicology. 2019 Apr; 124(4):449-455. doi: 10.1111/bcpt.13153. [PMID: 30346660]
  • Anne Grosen, Jacob Nersting, Mona Bungum, Lisbet Ambrosius Christensen, Kjeld Schmiegelow, Marcello Spanò, Mette Julsgaard, Eugenia Cordelli, Giorgio Leter, Peter Braad Larsen, Christian Lodberg Hvas, Jens Kelsen. Sperm DNA Integrity is Unaffected by Thiopurine Treatment in Men With Inflammatory Bowel Disease. Journal of Crohn's & colitis. 2019 Jan; 13(1):3-11. doi: 10.1093/ecco-jcc/jjy086. [PMID: 29917107]
  • Feng Zhang, Hua Liu, Qing Liu, Xingguang Su. An enzymatic ratiometric fluorescence assay for 6-mercaptopurine by using MoS2 quantum dots. Mikrochimica acta. 2018 11; 185(12):540. doi: 10.1007/s00604-018-3039-4. [PMID: 30415422]
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  • James Guoxian Huang, Allen Eng Juh Yeoh, Paul Anantharajah Tambyah, Mas Isa Suhaila. The Conundrum in the Diagnosis and Management of Atypical Fulminant Measles in a Leukemia Survivor on Maintenance Chemotherapy. Journal of pediatric hematology/oncology. 2017 01; 39(1):e36-e38. doi: 10.1097/mph.0000000000000620. [PMID: 27992394]
  • Hassan Karimi-Maleh, Abdollah Fallah Shojaei, Khalil Tabatabaeian, Fatemeh Karimi, Shahryar Shakeri, Reza Moradi. Simultaneous determination of 6-mercaptopruine, 6-thioguanine and dasatinib as three important anticancer drugs using nanostructure voltammetric sensor employing Pt/MWCNTs and 1-butyl-3-methylimidazolium hexafluoro phosphate. Biosensors & bioelectronics. 2016 Dec; 86(?):879-884. doi: 10.1016/j.bios.2016.07.086. [PMID: 27494812]
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