Oxypurinol (BioDeep_00000003006)

 

Secondary id: BioDeep_00000400350

natural product human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite Volatile Flavor Compounds


代谢物信息卡片


1H,2H,4H,5H,6H-pyrazolo[3,4-d]pyrimidine-4,6-dione

化学式: C5H4N4O2 (152.0334244)
中文名称: 1H-吡唑并[3,4-d]嘧啶-4,6(2H,5H)-二酮, 奥昔嘌醇, 羟基嘌呤, 氧嘌呤醇
谱图信息: 最多检出来源 Homo sapiens(blood) 1.13%

分子结构信息

SMILES: C1=C2C(=NC(=O)NC2=O)NN1
InChI: InChI=1S/C5H4N4O2/c10-4-2-1-6-9-3(2)7-5(11)8-4/h1H,(H3,6,7,8,9,10,11)

描述信息

Oxipurinol is a xanthine oxidase inhibitor. Oxipurinol is potentially used for treatment of congestive heart failure. PMID: 15139781.
Oxipurinol is a xanthine oxidase inhibitor. Oxipurinol is potentially used for treatment of congestive heart failure.
C471 - Enzyme Inhibitor > C1637 - Xanthine Oxidase Inhibitor
D004791 - Enzyme Inhibitors
CONFIDENCE standard compound; INTERNAL_ID 864; DATASET 20200303_ENTACT_RP_MIX500; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 855; ORIGINAL_PRECURSOR_SCAN_NO 853
CONFIDENCE standard compound; INTERNAL_ID 864; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 883; ORIGINAL_PRECURSOR_SCAN_NO 881
CONFIDENCE standard compound; INTERNAL_ID 864; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 893; ORIGINAL_PRECURSOR_SCAN_NO 892
CONFIDENCE standard compound; INTERNAL_ID 864; DATASET 20200303_ENTACT_RP_MIX500; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 861; ORIGINAL_PRECURSOR_SCAN_NO 860
CONFIDENCE standard compound; INTERNAL_ID 864; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 894; ORIGINAL_PRECURSOR_SCAN_NO 892
Acquisition and generation of the data is financially supported in part by CREST/JST.
Oxipurinol (Oxipurinol), the major active metabolite of Allopurinol, is an inhibitor of xanthine oxidase. Oxipurinol can be used to regulate blood urate levels and treat gout[1].

同义名列表

12 个代谢物同义名

1H,2H,4H,5H,6H-pyrazolo[3,4-d]pyrimidine-4,6-dione; 1H-Pyrazolo[3,4-d]pyrimidine-4,6(2H,5H)-dione; 4,6-Dihydroxypyrazolo[3,4-D]pyrimidine; 1H-Pyrazolo[3,4-D]pyrimidin-4,6-diol; 1H,3H,9H-Alloxanthine; Oxoallopurinol; Alloxanthine; Oxipurinol; Oxypurinol; 1,2-dihydropyrazolo[3,4-d]pyrimidine-4,6-dione; Alloxanthine; Oxypurinol



数据库引用编号

37 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)

21 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

  • Bianca Vora, Deanna J Brackman, Ling Zou, Maria Garcia-Cremades, Marina Sirota, Radojka M Savic, Kathleen M Giacomini. Oxypurinol pharmacokinetics and pharmacodynamics in healthy volunteers: Influence of BCRP Q141K polymorphism and patient characteristics. Clinical and translational science. 2021 07; 14(4):1431-1443. doi: 10.1111/cts.12992. [PMID: 33931953]
  • Lisa K Stamp, Peter T Chapman. Allopurinol hypersensitivity: Pathogenesis and prevention. Best practice & research. Clinical rheumatology. 2020 08; 34(4):101501. doi: 10.1016/j.berh.2020.101501. [PMID: 32265121]
  • Ana Leonor P C Godoy, Clauceane de Jesus, Rafaela S Gonçalves, Francine Johansson Azeredo, Adriana Rocha, Maria P Marques, Vera L Lanchote, Daniela F Larangeira, Stella Maria Barrouin-Melo. Detection of allopurinol and oxypurinol in canine urine by HPLC/MS-MS: Focus on veterinary clinical pharmacokinetics. Journal of pharmaceutical and biomedical analysis. 2020 Jun; 185(?):113204. doi: 10.1016/j.jpba.2020.113204. [PMID: 32126445]
  • Francisco J López-Iranzo, Ana M López-Rodas, Luis Franco, Gerardo López-Rodas. Pentoxifylline and Oxypurinol: Potential Drugs to Prevent the "Cytokine Release (Storm) Syndrome" Caused by SARS-CoV-2?. Current pharmaceutical design. 2020; 26(35):4515-4521. doi: 10.2174/1381612826666200811180232. [PMID: 32787748]
  • Lisa K Stamp, Peter T Chapman, Murray Barclay, Anne Horne, Christopher Frampton, Tony R Merriman, Daniel F B Wright, Jill Drake, Nicola Dalbeth. Relationships Between Allopurinol Dose, Oxypurinol Concentration and Urate-Lowering Response-In Search of a Minimum Effective Oxypurinol Concentration. Clinical and translational science. 2020 01; 13(1):110-115. doi: 10.1111/cts.12686. [PMID: 31444839]
  • Hiroshi Arakawa, Natsumi Amezawa, Tomomichi Katsuyama, Takeo Nakanishi, Ikumi Tamai. Uric acid analogue as a possible xenobiotic marker of uric acid transporter Urat1 in rats. Drug metabolism and pharmacokinetics. 2019 Apr; 34(2):155-158. doi: 10.1016/j.dmpk.2018.12.003. [PMID: 30826184]
  • Muzaffar Iqbal, Essam Ezzeldin, Rashed Naji Herqash, Ozair Alam. Ultra-performance hydrophilic interaction liquid chromatography coupled with tandem mass spectrometry for simultaneous determination of allopurinol, oxypurinol and lesinurad in rat plasma: Application to pharmacokinetic study in rats. PloS one. 2019; 14(3):e0213786. doi: 10.1371/journal.pone.0213786. [PMID: 30870504]
  • Dongmei Zhou, Lifang Sun, Mai Nguyen, Li- Tain Yeh, David M Wilson. The Effects of Special Patient Population Plasma on Pharmacokinetic Quantifications Using LC-MS/MS. Drug metabolism letters. 2019; 13(2):111-122. doi: 10.2174/1872312813666191015162634. [PMID: 31613735]
  • Angus Lindsay, Preston M McCourt, Peter Karachunski, Dawn A Lowe, James M Ervasti. Xanthine oxidase is hyper-active in Duchenne muscular dystrophy. Free radical biology & medicine. 2018 12; 129(?):364-371. doi: 10.1016/j.freeradbiomed.2018.10.404. [PMID: 30312761]
  • Martin Kankam, Jesse Hall, Michael Gillen, Xiaojuan Yang, Zancong Shen, Caroline Lee, Sha Liu, Jeffrey N Miner, Susan Walker, Vicki Clauson, David Wilson, Mai Nguyen. Pharmacokinetics, Pharmacodynamics, and Tolerability of Concomitant Multiple Dose Administration of Verinurad (RDEA3170) and Allopurinol in Adult Male Subjects With Gout. Journal of clinical pharmacology. 2018 09; 58(9):1214-1222. doi: 10.1002/jcph.1119. [PMID: 29733447]
  • Makiko Nakamura, Kyoko Fujita, Yu Toyoda, Tappei Takada, Hiroshi Hasegawa, Kimiyoshi Ichida. Investigation of the transport of xanthine dehydrogenase inhibitors by the urate transporter ABCG2. Drug metabolism and pharmacokinetics. 2018 Feb; 33(1):77-81. doi: 10.1016/j.dmpk.2017.11.002. [PMID: 29342419]
  • Lisa K Stamp, Tony Merriman, Christopher Frampton, Mei Zhang, Mary Wallace, Jeffrey N Miner, Nicola Dalbeth. Plasma oxypurinol as a measure of adherence in clinical trials. Annals of the rheumatic diseases. 2018 02; 77(2):313-314. doi: 10.1136/annrheumdis-2016-210661. [PMID: 28057666]
  • Diluk R W Kannangara, Garry G Graham, Daniel F B Wright, Sophie L Stocker, Ian Portek, Kevin D Pile, Murray L Barclay, Kenneth M Williams, Lisa K Stamp, Richard O Day. Individualising the dose of allopurinol in patients with gout. British journal of clinical pharmacology. 2017 Sep; 83(9):2015-2026. doi: 10.1111/bcp.13307. [PMID: 28417592]
  • Daniel Fb Wright, Matthew P Doogue, Murray L Barclay, Peter T Chapman, Nicholas B Cross, John H Irvine, Lisa K Stamp. A population pharmacokinetic model to predict oxypurinol exposure in patients on haemodialysis. European journal of clinical pharmacology. 2017 Jan; 73(1):71-78. doi: 10.1007/s00228-016-2133-y. [PMID: 27683090]
  • Lisa K Stamp, Richard O Day, James Yun. Allopurinol hypersensitivity: investigating the cause and minimizing the risk. Nature reviews. Rheumatology. 2016 Apr; 12(4):235-42. doi: 10.1038/nrrheum.2015.132. [PMID: 26416594]
  • Jun Fang, Hongzhuan Yin, Long Liao, Haibo Qin, Fumiko Ueda, Kyoko Uemura, Kanami Eguchi, Gahininath Y Bharate, Hiroshi Maeda. Water soluble PEG-conjugate of xanthine oxidase inhibitor, PEG-AHPP micelles, as a novel therapeutic for ROS related inflammatory bowel diseases. Journal of controlled release : official journal of the Controlled Release Society. 2016 Feb; 223(?):188-196. doi: 10.1016/j.jconrel.2015.12.049. [PMID: 26739550]
  • Daniel F B Wright, Stephen B Duffull, Tony R Merriman, Nicola Dalbeth, Murray L Barclay, Lisa K Stamp. Predicting allopurinol response in patients with gout. British journal of clinical pharmacology. 2016 Feb; 81(2):277-89. doi: 10.1111/bcp.12799. [PMID: 26451524]
  • Wen-Hung Chung, Wan-Chun Chang, Sophie L Stocker, Chiun-Gung Juo, Garry G Graham, Ming-Han H Lee, Kenneth M Williams, Ya-Chung Tian, Kuo-Chang Juan, Yeong-Jian Jan Wu, Chih-Hsun Yang, Chee-Jen Chang, Yu-Jr Lin, Richard O Day, Shuen-Iu Hung. Insights into the poor prognosis of allopurinol-induced severe cutaneous adverse reactions: the impact of renal insufficiency, high plasma levels of oxypurinol and granulysin. Annals of the rheumatic diseases. 2015 Dec; 74(12):2157-64. doi: 10.1136/annrheumdis-2014-205577. [PMID: 25115449]
  • Jan Funke, Carsten Prasse, Christian Lütke Eversloh, Thomas A Ternes. Oxypurinol - A novel marker for wastewater contamination of the aquatic environment. Water research. 2015 May; 74(?):257-65. doi: 10.1016/j.watres.2015.02.007. [PMID: 25753675]
  • Xia Liu, Xiao-Jia Ni, De-Wei Shang, Ming Zhang, Jin-Qing Hu, Chang Qiu, Fu-Tian Luo, Yu-Guan Wen. Determination of allopurinol and oxypurinol in human plasma and urine by liquid chromatography-tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2013 Dec; 941(?):10-6. doi: 10.1016/j.jchromb.2013.09.028. [PMID: 24184830]
  • Diluk R W Kannangara, Sheena N Ramasamy, John E Ray, Graham Jones, Garry G Graham, Kenneth M Williams, Richard O Day. An audit of a therapeutic drug monitoring service for allopurinol therapy. Therapeutic drug monitoring. 2013 Dec; 35(6):863-6. doi: 10.1097/ftd.0b013e318299920a. [PMID: 24263644]
  • P A Blaker, M Arenas-Hernandez, M A Smith, E A Shobowale-Bakre, L Fairbanks, P M Irving, J D Sanderson, A M Marinaki. Mechanism of allopurinol induced TPMT inhibition. Biochemical pharmacology. 2013 Aug; 86(4):539-47. doi: 10.1016/j.bcp.2013.06.002. [PMID: 23770457]
  • Daniel F B Wright, Lisa K Stamp, Tony R Merriman, Murray L Barclay, Stephen B Duffull, Nicholas H G Holford. The population pharmacokinetics of allopurinol and oxypurinol in patients with gout. European journal of clinical pharmacology. 2013 Jul; 69(7):1411-21. doi: 10.1007/s00228-013-1478-8. [PMID: 23475133]
  • Jochen Springer, Anika Tschirner, Kai Hartman, Sandra Palus, Eva K Wirth, Silvia Busquets Ruis, Nadine Möller, Stephan von Haehling, Josep M Argiles, Josef Köhrle, Volker Adams, Stefan D Anker, Wolfram Doehner. Inhibition of xanthine oxidase reduces wasting and improves outcome in a rat model of cancer cachexia. International journal of cancer. 2012 Nov; 131(9):2187-96. doi: 10.1002/ijc.27494. [PMID: 22336965]
  • Lisa K Stamp, Murray L Barclay, John L O'Donnell, Mei Zhang, Jill Drake, Christopher Frampton, Peter T Chapman. Furosemide increases plasma oxypurinol without lowering serum urate--a complex drug interaction: implications for clinical practice. Rheumatology (Oxford, England). 2012 Sep; 51(9):1670-6. doi: 10.1093/rheumatology/kes091. [PMID: 22539486]
  • Sophie L Stocker, Andrew J McLachlan, Radojka M Savic, Carl M Kirkpatrick, Garry G Graham, Kenneth M Williams, Richard O Day. The pharmacokinetics of oxypurinol in people with gout. British journal of clinical pharmacology. 2012 Sep; 74(3):477-89. doi: 10.1111/j.1365-2125.2012.04207.x. [PMID: 22300439]
  • Diluk R W Kannangara, Darren M Roberts, Timothy J Furlong, Garry G Graham, Kenneth M Williams, Richard O Day. Oxypurinol, allopurinol and allopurinol-1-riboside in plasma following an acute overdose of allopurinol in a patient with advanced chronic kidney disease. British journal of clinical pharmacology. 2012 May; 73(5):828-9. doi: 10.1111/j.1365-2125.2011.04147.x. [PMID: 22098112]
  • Paolo Puddu, Giovanni M Puddu, Eleonora Cravero, Luca Vizioli, Antonio Muscari. Relationships among hyperuricemia, endothelial dysfunction and cardiovascular disease: molecular mechanisms and clinical implications. Journal of cardiology. 2012 May; 59(3):235-42. doi: 10.1016/j.jjcc.2012.01.013. [PMID: 22398104]
  • Ramón Rodrigo. Prevention of postoperative atrial fibrillation: novel and safe strategy based on the modulation of the antioxidant system. Frontiers in physiology. 2012; 3(?):93. doi: 10.3389/fphys.2012.00093. [PMID: 22518106]
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  • Rodrigo Frezzatti, Paulo Flavio Silveira. Allopurinol reduces the lethality associated with acute renal failure induced by Crotalus durissus terrificus snake venom: comparison with probenecid. PLoS neglected tropical diseases. 2011 Sep; 5(9):e1312. doi: 10.1371/journal.pntd.0001312. [PMID: 21909449]
  • L K Stamp, M L Barclay, J L O'Donnell, M Zhang, J Drake, C Frampton, P T Chapman. Relationship between serum urate and plasma oxypurinol in the management of gout: determination of minimum plasma oxypurinol concentration to achieve a target serum urate level. Clinical pharmacology and therapeutics. 2011 Sep; 90(3):392-8. doi: 10.1038/clpt.2011.113. [PMID: 21796116]
  • Mahesh J Fuldeore, Aylin A Riedel, Victoria Zarotsky, Bhavik J Pandya, Omar Dabbous, Eswar Krishnan. Chronic kidney disease in gout in a managed care setting. BMC nephrology. 2011 Aug; 12(?):36. doi: 10.1186/1471-2369-12-36. [PMID: 21812963]
  • Daniel Y Ng, Sophie L Stocker, Garry G Graham, Kenneth M Williams, Richard O Day. Lack of effect of hydrochlorothiazide and low-dose aspirin on the renal clearance of urate and oxypurinol after a single dose of allopurinol in normal volunteers. European journal of clinical pharmacology. 2011 Jul; 67(7):709-13. doi: 10.1007/s00228-010-0963-6. [PMID: 21181139]
  • Christiane Funk, Meriem Alami, Tania Tibiletti, Beverley R Green. High light stress and the one-helix LHC-like proteins of the cryptophyte Guillardia theta. Biochimica et biophysica acta. 2011 Jul; 1807(7):841-6. doi: 10.1016/j.bbabio.2011.03.011. [PMID: 21459077]
  • M Kurajoh, T Ka, C Okuda, A Yamamoto, Z Tsutsumi, H Koyama, Y Moriwaki, T Yamamoto. Effects of bovine milk ingestion on urinary excretion of oxypurinol and uric acid. International journal of clinical pharmacology and therapeutics. 2011 Jun; 49(6):366-70. doi: 10.5414/cp201508. [PMID: 21612743]
  • Tatsuo Hosoya, Hosoya Tatsuo, Iwao Ohno, Ohno Iwao. A repeated oral administration study of febuxostat (TMX-67), a non-purine-selective inhibitor of xanthine oxidase, in patients with impaired renal function in Japan: pharmacokinetic and pharmacodynamic study. Journal of clinical rheumatology : practical reports on rheumatic & musculoskeletal diseases. 2011 Jun; 17(4 Suppl 2):S27-34. doi: 10.1097/rhu.0b013e31821d36f2. [PMID: 21654267]
  • Sophie L Stocker, Garry G Graham, Andrew J McLachlan, Kenneth M Williams, Richard O Day. Pharmacokinetic and pharmacodynamic interaction between allopurinol and probenecid in patients with gout. The Journal of rheumatology. 2011 May; 38(5):904-10. doi: 10.3899/jrheum.101160. [PMID: 21285173]
  • Lisa K Stamp, John L O'Donnell, Mei Zhang, Jill James, Christopher Frampton, Murray L Barclay, Peter T Chapman. Using allopurinol above the dose based on creatinine clearance is effective and safe in patients with chronic gout, including those with renal impairment. Arthritis and rheumatism. 2011 Feb; 63(2):412-21. doi: 10.1002/art.30119. [PMID: 21279998]
  • Anne-Kathrin Tausche, Carsten Wunderlich, Martin Aringer. Tophaceous gout and renal insufficiency: a new solution for an old therapeutic dilemma. Case reports in medicine. 2011; 2011(?):397646. doi: 10.1155/2011/397646. [PMID: 21629805]
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