Acetaminophen glucuronide (BioDeep_00000017789)

   

human metabolite Endogenous blood metabolite


代谢物信息卡片


(2S,3S,4S,5R,6S)-6-(4-acetamidophenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

化学式: C14H17NO8 (327.0954122)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(feces) 6.72%

分子结构信息

SMILES: CC(=O)NC1=CC=C(C=C1)OC2C(C(C(C(O2)C(=O)O)O)O)O
InChI: InChI=1S/C14H17NO8/c1-6(16)15-7-2-4-8(5-3-7)22-14-11(19)9(17)10(18)12(23-14)13(20)21/h2-5,9-12,14,17-19H,1H3,(H,15,16)(H,20,21)

描述信息

Acetaminophen glucuronide is a natural human metabolite of Acetaminophen generated in the liver by UDP glucuonyltransferase. Glucuronidation is used to assist in the excretion of toxic substances, drugs or other substances that cannot be used as an energy source. Glucuronic acid is attached via a glycosidic bond to the substance, and the resulting glucuronide, which has a much higher water solubility than the original substance, is eventually excreted by the kidneys. Acetaminophen glucuronide is found to be associated with beta-thalassemia, which is an inborn error of metabolism.
Acetaminophen glucuronide is a natural human metabolite of Acetaminophen generated in the liver by UDP glucuonyltransferase. Glucuronidation is used to assist in the excretion of toxic substances, drugs or other substances that cannot be used as an energy source. Glucuronic acid is attached via a glycosidic bond to the substance, and the resulting glucuronide, which has a much higher water solubility than the original substance, is eventually excreted by the kidneys. [HMDB]

同义名列表

28 个代谢物同义名

(2S,3S,4S,5R,6S)-6-(4-acetamidophenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid; 4-(Acetylamino)phenyl beta-delta-glucopyranosiduronic acid; 4-Acetamidophenyl beta-delta-glucopyranosiduronic acid; 4-(Acetylamino)phenyl beta-D-glucopyranosiduronic acid; 4-(Acetylamino)phenyl β-D-glucopyranosiduronic acid; 4-Acetamidophenyl b-delta-glucopyranosiduronic acid; 4-Acetamidophenyl beta-D-glucopyranosiduronic acid; 4-Acetamidophenyl b-D-glucopyranosiduronic acid; p-Acetamidophenyl D-glucosiduronic acid; p-Acetamidophenyl glucosiduronic acid; N-Acetyl-4-aminophenol glucuronide; N-Acetyl-p-aminophenyl glucuronide; p-Acetamidophenyl β-D-glucuronide; 4-Hydroxyacetanilide glucuronide; N-Acetyl-4-glucuronosidoaniline; 4-(Glucuronosyloxy)-acetanilide; p-Acetamidophenyl glucuronide; Deethylphenacetin glucuronide; 4-Acetamidophenol glucuronide; Paracetamol beta-glucuronide; p-acetamidophenylglucuronide; 4-Glucuronosidoacetanilide; Paracetamol O-glucuronide; Paracetamol β-glucuronide; Acetaminophen glucuronide; Paracetamol glucuronide; Acetanilide glucuronide; PCM-g



数据库引用编号

11 个数据库交叉引用编号

分类词条

相关代谢途径

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代谢反应

1 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)

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PathBank(1)

PharmGKB(0)

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

  • Takumi Noda, Ryuji Kato, Yasuyuki Ozato, Yuka Kawai, Masato Yamamoto, Yuya Kagawa, Misa Azuma, Kojiro Yamamoto, Mika Kusanagi, Kiyoaki Uryu, Hiromasa Harada, Yoshio Ijiri, Tetsuya Hayashi, Kazuhiko Tanaka. Decreased plasma acetaminophen glucuronide/acetaminophen concentration ratio warns the onset of acetaminophen-induced liver injury. Biopharmaceutics & drug disposition. 2022 Jun; 43(3):108-116. doi: 10.1002/bdd.2316. [PMID: 35508086]
  • Tianling Wang, Lei Tang, Ruili Lin, Dian He, Yanqing Wu, Yang Zhang, Pingrong Yang, Junquan He. Individual variability in human urinary metabolites identifies age-related, body mass index-related, and sex-related biomarkers. Molecular genetics & genomic medicine. 2021 08; 9(8):e1738. doi: 10.1002/mgg3.1738. [PMID: 34293245]
  • Yuelong Ji, Romuladus E Azuine, Yan Zhang, Wenpin Hou, Xiumei Hong, Guoying Wang, Anne Riley, Colleen Pearson, Barry Zuckerman, Xiaobin Wang. Association of Cord Plasma Biomarkers of In Utero Acetaminophen Exposure With Risk of Attention-Deficit/Hyperactivity Disorder and Autism Spectrum Disorder in Childhood. JAMA psychiatry. 2020 02; 77(2):180-189. doi: 10.1001/jamapsychiatry.2019.3259. [PMID: 31664451]
  • Ayako Tokunaga, Hirotaka Miyamoto, Shintaro Fumoto, Koyo Nishida. Effect of Chronic Kidney Disease on Hepatic Clearance of Drugs in Rats. Biological & pharmaceutical bulletin. 2020; 43(9):1324-1330. doi: 10.1248/bpb.b20-00124. [PMID: 32879206]
  • Monica Abadier, Anselm Wong, Paul Stathakis, John Singsit, Melanie Pillay, Andis Graudins. A case of accidental neonatal paracetamol overdose with prolonged half-life and measured metabolites. Clinical toxicology (Philadelphia, Pa.). 2019 Dec; 57(12):1154-1156. doi: 10.1080/15563650.2019.1587450. [PMID: 30856016]
  • Xiqian Zhang, Ruina Li, Wenya Hu, Jin Zeng, Xuehua Jiang, Ling Wang. A reliable LC-MS/MS method for the quantification of N-acetyl-p-benzoquinoneimine, acetaminophen glutathione and acetaminophen glucuronide in mouse plasma, liver and kidney: Method validation and application to a pharmacokinetic study. Biomedical chromatography : BMC. 2018 Nov; 32(11):e4331. doi: 10.1002/bmc.4331. [PMID: 29978489]
  • Laureen A Lammers, Roos Achterbergh, Marcel C M Pistorius, Johannes A Romijn, Ron A A Mathôt. Quantitative Method for Simultaneous Analysis of Acetaminophen and 6 Metabolites. Therapeutic drug monitoring. 2017 04; 39(2):172-179. doi: 10.1097/ftd.0000000000000373. [PMID: 28045783]
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  • Anaïs Michaut, Dounia Le Guillou, Caroline Moreau, Simon Bucher, Mitchell R McGill, Sophie Martinais, Thomas Gicquel, Isabelle Morel, Marie-Anne Robin, Hartmut Jaeschke, Bernard Fromenty. A cellular model to study drug-induced liver injury in nonalcoholic fatty liver disease: Application to acetaminophen. Toxicology and applied pharmacology. 2016 Feb; 292(?):40-55. doi: 10.1016/j.taap.2015.12.020. [PMID: 26739624]
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  • Agnieszka Karbownik, Edyta Szałek, Katarzyna Sobańska, Wojciech Połom, Tomasz Grabowski, Anna Biczysko-Murawa, Marcin Matuszewski, Anna Wolc, Edmund Grześkowiak. The effect of sunitinib on the plasma exposure of intravenous paracetamol and its major metabolite: paracetamol glucuronide. European journal of drug metabolism and pharmacokinetics. 2015 Jun; 40(2):163-70. doi: 10.1007/s13318-014-0191-z. [PMID: 24676873]
  • Malkanthi Evans, Elaine Paterson, David M Barnes. An open label pilot study to evaluate the efficacy of Spanish black radish on the induction of phase I and phase II enzymes in healthy male subjects. BMC complementary and alternative medicine. 2014 Dec; 14(?):475. doi: 10.1186/1472-6882-14-475. [PMID: 25490898]
  • Ruijuan Xu, Qian Wang, Jing Zhang, Min Zang, Xiaoquan Liu, Jin Yang. Changes in pharmacokinetic profiles of acetaminophen and its glucuronide after pretreatment with combinations of N-acetylcysteine and either glycyrrhizin, silibinin or spironolactone in rat. Xenobiotica; the fate of foreign compounds in biological systems. 2014 Jun; 44(6):541-6. doi: 10.3109/00498254.2013.858849. [PMID: 24251357]
  • John Mach, Aniko Huizer-Pajkos, Victoria C Cogger, Catriona McKenzie, David G Le Couteur, Brett E Jones, Rafael de Cabo, Sarah N Hilmer. The effect of aging on acetaminophen pharmacokinetics, toxicity and Nrf2 in Fischer 344 rats. The journals of gerontology. Series A, Biological sciences and medical sciences. 2014 Apr; 69(4):387-97. doi: 10.1093/gerona/glt095. [PMID: 23863315]
  • Michel Galinski, Stephane-Xavier Racine, Anne-Elisabeth Bossard, Maher Fleyfel, Lilia Hamza, Nadia Bouchemal, Frédéric Adnet, Laurence Le Moyec. Detection and follow-up, after partial liver resection, of the urinary paracetamol metabolites by proton NMR spectroscopy. Pharmacology. 2014; 93(1-2):18-23. doi: 10.1159/000357095. [PMID: 24401842]
  • Cristina Barosa, John G Jones, Robert Rizza, Ananda Basu, Rita Basu. Acetaminophen glucuronide and plasma glucose report identical estimates of gluconeogenesis and glycogenolysis for healthy and prediabetic subjects using the deuterated water method. Magnetic resonance in medicine. 2013 Aug; 70(2):315-9. doi: 10.1002/mrm.24485. [PMID: 23023691]
  • Aida Kulo, Mariska Y Peeters, Karel Allegaert, Anne Smits, Jan de Hoon, Rene Verbesselt, Liesbeth Lewi, Marc van de Velde, Catherijne A J Knibbe. Pharmacokinetics of paracetamol and its metabolites in women at delivery and post-partum. British journal of clinical pharmacology. 2013 Mar; 75(3):850-60. doi: 10.1111/j.1365-2125.2012.04402.x. [PMID: 22845052]
  • Katie H Owens, Natalie J Medlicott, Mathew Zacharias, Neil Curran, Sree Chary, Mark Thompson-Fawcett, David M Reith. The pharmacokinetic profile of intravenous paracetamol in adult patients undergoing major abdominal surgery. Therapeutic drug monitoring. 2012 Dec; 34(6):713-21. doi: 10.1097/ftd.0b013e31826a70ea. [PMID: 23149443]
  • Anneliese M Rittau, Andrew J McLachlan. Investigating paracetamol pharmacokinetics using venous and capillary blood and saliva sampling. The Journal of pharmacy and pharmacology. 2012 May; 64(5):705-11. doi: 10.1111/j.2042-7158.2012.01459.x. [PMID: 22471366]
  • Qin-you Tan, Rong-hua Zhu, Huan-de Li, Feng Wang, Miao Yan, Li-bo Dai. Simultaneous quantitative determination of paracetamol and its glucuronide conjugate in human plasma and urine by liquid chromatography coupled to electrospray tandem mass spectrometry: application to a clinical pharmacokinetic study. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2012 Apr; 893-894(?):162-7. doi: 10.1016/j.jchromb.2012.02.027. [PMID: 22445307]
  • Nicole J Barshop, Edmund V Capparelli, Claude B Sirlin, Jeffrey B Schwimmer, Joel E Lavine. Acetaminophen pharmacokinetics in children with nonalcoholic fatty liver disease. Journal of pediatric gastroenterology and nutrition. 2011 Feb; 52(2):198-202. doi: 10.1097/mpg.0b013e3181f9b3a0. [PMID: 21240014]
  • Antti Liukas, Kristiina Kuusniemi, Riku Aantaa, Petri Virolainen, Mikko Niemi, Pertti J Neuvonen, Klaus T Olkkola. Pharmacokinetics of intravenous paracetamol in elderly patients. Clinical pharmacokinetics. 2011 Feb; 50(2):121-9. doi: 10.2165/11537240-000000000-00000. [PMID: 21241071]
  • Dong-Wook Kim, Eugene Y Tan, Yu Jin, Sahee Park, Michael Hayes, Eren Demirhan, Horst Schran, Yanfeng Wang. Effects of imatinib mesylate on the pharmacokinetics of paracetamol (acetaminophen) in Korean patients with chronic myelogenous leukaemia. British journal of clinical pharmacology. 2011 Feb; 71(2):199-206. doi: 10.1111/j.1365-2125.2010.03810.x. [PMID: 21219400]
  • Edyta Szałek, Agnieszka Kamińska, Dawid Murawa, Karol Połom, Bartosz Urbaniak, Matylda Sobiech, Edmund Grześkowiak, Tomasz Grabowski, Anna Wolc, Zenon J Kokot, Paweł Murawa. Comparison of the pharmacokinetics of paracetamol from two generic products in patients after total gastric resection. Pharmacological reports : PR. 2011; 63(6):1518-25. doi: 10.1016/s1734-1140(11)70715-0. [PMID: 22358099]
  • Wen Jian Xiong, Hui Jin, Shui Jun Li, Jia Chen Jin, Bei Na Ji, Chen Yu. Evaluating human liver reserve function by measuring serum concentrations of phenacetin and its metabolites. Journal of digestive diseases. 2010 Dec; 11(6):358-63. doi: 10.1111/j.1751-2980.2010.00463.x. [PMID: 21091898]
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