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(blood) 27.06%

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

Reactome(0)

BioCyc(0)

PlantCyc(0)

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)

COVID-19 Disease Map(0)

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]
  • Sarah F Cook, Chris Stockmann, Samira Samiee-Zafarghandy, Amber D King, Nina Deutsch, Elaine F Williams, Diana G Wilkins, Catherine M T Sherwin, John N van den Anker. Neonatal Maturation of Paracetamol (Acetaminophen) Glucuronidation, Sulfation, and Oxidation Based on a Parent-Metabolite Population Pharmacokinetic Model. Clinical pharmacokinetics. 2016 11; 55(11):1395-1411. doi: 10.1007/s40262-016-0408-1. [PMID: 27209292]
  • 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]
  • Yanli Zhao, Jerold S Harmatz, Carol R Epstein, Yukako Nakagawa, Chie Kurosaki, Tetsuro Nakamura, Takumi Kadota, Dennis Giesing, Michael H Court, David J Greenblatt. Favipiravir inhibits acetaminophen sulfate formation but minimally affects systemic pharmacokinetics of acetaminophen. British journal of clinical pharmacology. 2015 Nov; 80(5):1076-85. doi: 10.1111/bcp.12644. [PMID: 25808818]
  • Stephen F Previs, David E Kelley. Tracer-based assessments of hepatic anaplerotic and TCA cycle flux: practicality, stoichiometry, and hidden assumptions. American journal of physiology. Endocrinology and metabolism. 2015 Oct; 309(8):E727-35. doi: 10.1152/ajpendo.00216.2015. [PMID: 26330343]
  • K Taguchi, M Tokuno, K Yamasaki, D Kadowaki, H Seo, M Otagiri. Establishment of a model of acetaminophen-induced hepatotoxicity in different weekly-aged ICR mice. Laboratory animals. 2015 Oct; 49(4):294-301. doi: 10.1177/0023677215573041. [PMID: 25675952]
  • Elke H J Krekels, Saskia van Ham, Karel Allegaert, Jan de Hoon, Dick Tibboel, Meindert Danhof, Catherijne A J Knibbe. Developmental changes rather than repeated administration drive paracetamol glucuronidation in neonates and infants. European journal of clinical pharmacology. 2015 Sep; 71(9):1075-82. doi: 10.1007/s00228-015-1887-y. [PMID: 26139379]
  • J Jones, S Kahl, F Carvalho, C Barosa, M Roden. Simplified analysis of acetaminophen glucuronide for quantifying gluconeogenesis and glycogenolysis using deuterated water. Analytical biochemistry. 2015 Jun; 479(?):37-9. doi: 10.1016/j.ab.2015.03.018. [PMID: 25800563]
  • Mark J Canet, Matthew D Merrell, Rhiannon N Hardwick, Amy M Bataille, Sarah N Campion, Daniel W Ferreira, Stavra A Xanthakos, Jose E Manautou, H Hesham A-Kader, Robert P Erickson, Nathan J Cherrington. Altered regulation of hepatic efflux transporters disrupts acetaminophen disposition in pediatric nonalcoholic steatohepatitis. Drug metabolism and disposition: the biological fate of chemicals. 2015 Jun; 43(6):829-35. doi: 10.1124/dmd.114.062703. [PMID: 25788542]
  • 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]
  • Yan Zhang, Yanyan Jia, Xinyou Liu, Linna Liu, Qingwei Wang, Aidong Wen. The effect of transcatheter arterial chemoembolization on phase II drug metabolism enzymes in patients with hepatocellular carcinoma. Cancer chemotherapy and pharmacology. 2010 Jan; 65(2):347-52. doi: 10.1007/s00280-009-1040-7. [PMID: 19517110]
  • T Andrew Clayton, David Baker, John C Lindon, Jeremy R Everett, Jeremy K Nicholson. Pharmacometabonomic identification of a significant host-microbiome metabolic interaction affecting human drug metabolism. Proceedings of the National Academy of Sciences of the United States of America. 2009 Aug; 106(34):14728-33. doi: 10.1073/pnas.0904489106. [PMID: 19667173]
  • Ian D Wilson. Drugs, bugs, and personalized medicine: pharmacometabonomics enters the ring. Proceedings of the National Academy of Sciences of the United States of America. 2009 Aug; 106(34):14187-8. doi: 10.1073/pnas.0907721106. [PMID: 19706501]
  • Jinchun Sun, Laura K Schnackenberg, Richard D Beger. Studies of acetaminophen and metabolites in urine and their correlations with toxicity using metabolomics. Drug metabolism letters. 2009 Aug; 3(3):130-6. doi: 10.2174/187231209789352139. [PMID: 19702550]
  • Rita Basu, Visvanthan Chandramouli, William Schumann, Ananda Basu, Bernard R Landau, Robert A Rizza. Additional evidence that transaldolase exchange, isotope discrimination during the triose-isomerase reaction, or both occur in humans: effects of type 2 diabetes. Diabetes. 2009 Jul; 58(7):1539-43. doi: 10.2337/db08-1300. [PMID: 19366865]
  • Irena Baranowska, Andrzej Wilczek. Simultaneous RP-HPLC determination of sotalol, metoprolol, alpha-hydroxymetoprolol, paracetamol and its glucuronide and sulfate metabolites in human urine. Analytical sciences : the international journal of the Japan Society for Analytical Chemistry. 2009 Jun; 25(6):769-72. doi: 10.2116/analsci.25.769. [PMID: 19531885]
  • Carolina I Ghanem, María L Ruiz, Silvina S M Villanueva, Marcelo Luquita, Susana Llesuy, Viviana A Catania, Laura A Bengochea, Aldo D Mottino. Effect of repeated administration with subtoxic doses of acetaminophen to rats on enterohepatic recirculation of a subsequent toxic dose. Biochemical pharmacology. 2009 May; 77(10):1621-8. doi: 10.1016/j.bcp.2009.02.006. [PMID: 19426699]
  • Scott A Reisman, Iván L Csanaky, Lauren M Aleksunes, Curtis D Klaassen. Altered disposition of acetaminophen in Nrf2-null and Keap1-knockdown mice. Toxicological sciences : an official journal of the Society of Toxicology. 2009 May; 109(1):31-40. doi: 10.1093/toxsci/kfp047. [PMID: 19246624]
  • David Reith, Natalie J Medlicott, Rohana Kumara De Silva, Lin Yang, Jeremy Hickling, Mathew Zacharias. Simultaneous modelling of the Michaelis-Menten kinetics of paracetamol sulphation and glucuronidation. Clinical and experimental pharmacology & physiology. 2009 Jan; 36(1):35-42. doi: 10.1111/j.1440-1681.2008.05029.x. [PMID: 18759860]
  • Khalid M Alkharfy, Samuel M Poloyac, Mario Congiu, Paul V Desmond, Reginald F Frye. Effect of the acute phase response induced by endotoxin administration on the expression and activity of UGT isoforms in rats. Drug metabolism letters. 2008 Dec; 2(4):248-55. doi: 10.2174/187231208786734085. [PMID: 19356101]
  • T C Delgado, C Barosa, M M C A Castro, C F G C Geraldes, M Bastos, C Baptista, A Fagulha, L Barros, A Mota, M Carvalheiro, J G Jones, Matthew Merritt. Sources of hepatic glucose production by 2H2O ingestion and Bayesian analysis of 2H glucuronide enrichment. Magnetic resonance in medicine. 2008 Sep; 60(3):517-23. doi: 10.1002/mrm.21681. [PMID: 18727053]
  • Silvina S M Villanueva, María L Ruiz, Carolina I Ghanem, Marcelo G Luquita, Viviana A Catania, Aldo D Mottino. Hepatic synthesis and urinary elimination of acetaminophen glucuronide are exacerbated in bile duct-ligated rats. Drug metabolism and disposition: the biological fate of chemicals. 2008 Mar; 36(3):475-80. doi: 10.1124/dmd.107.018127. [PMID: 18096675]
  • A K Hewavitharana, S Lee, P A Dawson, D Markovich, P N Shaw. Development of an HPLC-MS/MS method for the selective determination of paracetamol metabolites in mouse urine. Analytical biochemistry. 2008 Mar; 374(1):106-11. doi: 10.1016/j.ab.2007.11.011. [PMID: 18082126]
  • S Koling, G Hempel, C Lanvers, J Boos, G Würthwein. Monitoring paracetamol metabolism after single and repeated administration in pediatric patients with neoplastic diseases. International journal of clinical pharmacology and therapeutics. 2007 Sep; 45(9):496-503. doi: 10.5414/cpp45496. [PMID: 17907592]
  • K Allegaert, R Verbesselt, M Rayyan, A Debeer, J de Hoon. Urinary metabolites to assess in vivo ontogeny of hepatic drug metabolism in early neonatal life. Methods and findings in experimental and clinical pharmacology. 2007 May; 29(4):251-6. doi: 10.1358/mf.2007.29.4.1106408. [PMID: 17609736]
  • Jeeranut Tankanitlert, Thad A Howard, Anusorn Temsakulphong, Pornpan Sirankapracha, Noppawan Phumala Morales, Yupin Sanvarinda, Pranee Fucharoen, Russell E Ware, Suthat Fucharoen, Udom Chantharaksri. A pharmacokinetic study of paracetamol in Thai beta-thalassemia/HbE patients. European journal of clinical pharmacology. 2006 Sep; 62(9):743-8. doi: 10.1007/s00228-006-0167-2. [PMID: 16845508]
  • John G Jones, Ana Fagulha, Cristina Barosa, Margarida Bastos, Luisa Barros, Carla Baptista, M Madalena Caldeira, Manuela Carvalheiro. Noninvasive analysis of hepatic glycogen kinetics before and after breakfast with deuterated water and acetaminophen. Diabetes. 2006 Aug; 55(8):2294-300. doi: 10.2337/db06-0304. [PMID: 16873693]
  • A W Nicholls, I D Wilson, M Godejohann, J K Nicholson, J P Shockcor. Identification of phenacetin metabolites in human urine after administration of phenacetin-C2H3: measurement of futile metabolic deacetylation via HPLC/MS-SPE-NMR and HPLC-ToF MS. Xenobiotica; the fate of foreign compounds in biological systems. 2006 Jul; 36(7):615-29. doi: 10.1080/00498250600711113. [PMID: 16864507]
  • Stanton Segal, Suzanne Wehrli, Claire Yager, Robert Reynolds. Pathways of galactose metabolism by galactosemics: evidence for galactose conversion to hepatic UDPglucose. Molecular genetics and metabolism. 2006 Feb; 87(2):92-101. doi: 10.1016/j.ymgme.2005.09.012. [PMID: 16260165]
  • K Allegaert, D Tibboel. Comments on 'shift from biliary to urinary elimination of acetaminophen-glucuronide in acetaminophen-pretreated rats'. The Journal of pharmacology and experimental therapeutics. 2006 Feb; 316(2):966-7. doi: 10.1124/jpet.105.096024. [PMID: 16428678]
  • José E Manautou, Dirk R de Waart, Cindy Kunne, Noam Zelcer, Michael Goedken, Piet Borst, Ronald Oude Elferink. Altered disposition of acetaminophen in mice with a disruption of the Mrp3 gene. Hepatology (Baltimore, Md.). 2005 Nov; 42(5):1091-8. doi: 10.1002/hep.20898. [PMID: 16250050]
  • Karel Allegaert, Jan de Hoon, Rene Verbesselt, Christine Vanhole, Hugo Devlieger, Dick Tibboel. Intra- and interindividual variability of glucuronidation of paracetamol during repeated administration of propacetamol in neonates. Acta paediatrica (Oslo, Norway : 1992). 2005 Sep; 94(9):1273-9. doi: 10.1111/j.1651-2227.2005.tb02088.x. [PMID: 16278989]
  • Ja Yong Lee, Da Woon Jung, Hyun Ah Park, Soo Jeong Kim, Jin Ho Chung, Chang Kiu Moon, Young Chul Kim. Effect of taurine on biliary excretion and metabolism of acetaminophen in male hamsters. Biological & pharmaceutical bulletin. 2004 Nov; 27(11):1792-6. doi: 10.1248/bpb.27.1792. [PMID: 15516725]
  • Brian C Weis, David Margolis, Shawn C Burgess, Matthew E Merritt, Holly Wise, A Dean Sherry, Craig R Malloy. Glucose production pathways by 2H and 13C NMR in patients with HIV-associated lipoatrophy. Magnetic resonance in medicine. 2004 Apr; 51(4):649-54. doi: 10.1002/mrm.20057. [PMID: 15065235]
  • L S Jensen, J Valentine, R W Milne, A M Evans. The quantification of paracetamol, paracetamol glucuronide and paracetamol sulphate in plasma and urine using a single high-performance liquid chromatography assay. Journal of pharmaceutical and biomedical analysis. 2004 Feb; 34(3):585-93. doi: 10.1016/s0731-7085(03)00573-9. [PMID: 15127815]
  • A L Slitt, N J Cherrington, J M Maher, C D Klaassen. Induction of multidrug resistance protein 3 in rat liver is associated with altered vectorial excretion of acetaminophen metabolites. Drug metabolism and disposition: the biological fate of chemicals. 2003 Sep; 31(9):1176-86. doi: 10.1124/dmd.31.9.1176. [PMID: 12920174]
  • Caroline D van der Marel, Brian J Anderson, Richard A van Lingen, Nicholas H G Holford, Marien A L Pluim, Frank G A Jansman, John N van den Anker, Dick Tibboel. Paracetamol and metabolite pharmacokinetics in infants. European journal of clinical pharmacology. 2003 Jul; 59(3):243-51. doi: 10.1007/s00228-003-0608-0. [PMID: 12761605]
  • Chuan Chen, Gayle E Hennig, Jose E Manautou. Hepatobiliary excretion of acetaminophen glutathione conjugate and its derivatives in transport-deficient (TR-) hyperbilirubinemic rats. Drug metabolism and disposition: the biological fate of chemicals. 2003 Jun; 31(6):798-804. doi: 10.1124/dmd.31.6.798. [PMID: 12756215]
  • Jeong M Park, Yvonne S Lin, Justina C Calamia, Kenneth E Thummel, John T Slattery, Thomas F Kalhorn, Robert L Carithers, Adam E Levy, Christopher L Marsh, Mary F Hebert. Transiently altered acetaminophen metabolism after liver transplantation. Clinical pharmacology and therapeutics. 2003 Jun; 73(6):545-53. doi: 10.1016/s0009-9236(03)00062-6. [PMID: 12811364]
  • Shawn C Burgess, Brian Weis, John G Jones, Erin Smith, Matthew E Merritt, David Margolis, A Dean Sherry, Craig R Malloy. Noninvasive evaluation of liver metabolism by 2H and 13C NMR isotopomer analysis of human urine. Analytical biochemistry. 2003 Jan; 312(2):228-34. doi: 10.1016/s0003-2697(02)00465-7. [PMID: 12531210]
  • Hao Xiong, Hiroshi Suzuki, Yuichi Sugiyama, Peter J Meier, Gary M Pollack, Kim L R Brouwer. Mechanisms of impaired biliary excretion of acetaminophen glucuronide after acute phenobarbital treatment or phenobarbital pretreatment. Drug metabolism and disposition: the biological fate of chemicals. 2002 Sep; 30(9):962-9. doi: 10.1124/dmd.30.9.962. [PMID: 12167560]
  • Hiroki Itoh, Toshiaki Nagano, Masaharu Takeyama. Effect of nizatidine on paracetamol and its metabolites in human plasma. The Journal of pharmacy and pharmacology. 2002 Jun; 54(6):869-73. doi: 10.1211/0022357021779050. [PMID: 12079004]
  • J G Jones, M A Solomon, S M Cole, A D Sherry, C R Malloy. An integrated (2)H and (13)C NMR study of gluconeogenesis and TCA cycle flux in humans. American journal of physiology. Endocrinology and metabolism. 2001 Oct; 281(4):E848-56. doi: 10.1152/ajpendo.2001.281.4.e848. [PMID: 11551863]
  • H Itoh, T Nagano, M Takeyama. Cisapride raises the bioavailability of paracetamol by inhibiting its glucuronidation in man. The Journal of pharmacy and pharmacology. 2001 Jul; 53(7):1041-5. doi: 10.1211/0022357011776298. [PMID: 11480539]
  • D Bougie, R Aster. Immune thrombocytopenia resulting from sensitivity to metabolites of naproxen and acetaminophen. Blood. 2001 Jun; 97(12):3846-50. doi: 10.1182/blood.v97.12.3846. [PMID: 11389025]
  • A Vella, P Shah, R Basu, A Basu, M Camilleri, W F Schwenk, R A Rizza. Type I diabetes mellitus does not alter initial splanchnic glucose extraction or hepatic UDP-glucose flux during enteral glucose administration. Diabetologia. 2001 Jun; 44(6):729-37. doi: 10.1007/s001250051682. [PMID: 11440366]
  • M B Fisher, M Vandenbranden, K Findlay, B Burchell, K E Thummel, S D Hall, S A Wrighton. Tissue distribution and interindividual variation in human UDP-glucuronosyltransferase activity: relationship between UGT1A1 promoter genotype and variability in a liver bank. Pharmacogenetics. 2000 Nov; 10(8):727-39. doi: 10.1097/00008571-200011000-00007. [PMID: 11186135]
  • H Xiong, K C Turner, E S Ward, P L Jansen, K L Brouwer. Altered hepatobiliary disposition of acetaminophen glucuronide in isolated perfused livers from multidrug resistance-associated protein 2-deficient TR(-) rats. The Journal of pharmacology and experimental therapeutics. 2000 Nov; 295(2):512-8. doi: NULL. [PMID: 11046083]
  • S H Cha, T Sekine, H Kusuhara, E Yu, J Y Kim, D K Kim, Y Sugiyama, Y Kanai, H Endou. Molecular cloning and characterization of multispecific organic anion transporter 4 expressed in the placenta. The Journal of biological chemistry. 2000 Feb; 275(6):4507-12. doi: 10.1074/jbc.275.6.4507. [PMID: 10660625]
  • S G Kulkarni, A A Pegram, P C Smith. Disposition of acetaminophen and indocyanine green in cystic fibrosis-knockout mice. AAPS pharmSci. 2000; 2(2):E18. doi: 10.1208/ps020218. [PMID: 11741234]
  • A Alberti, P Pirrone, M Elia, R H Waring, C Romano. Sulphation deficit in 'low-functioning' autistic children: a pilot study. Biological psychiatry. 1999 Aug; 46(3):420-4. doi: 10.1016/s0006-3223(98)00337-0. [PMID: 10435209]
  • F Bohnenstengel, H K Kroemer, B Sperker. In vitro cleavage of paracetamol glucuronide by human liver and kidney beta-glucuronidase: determination of paracetamol by capillary electrophoresis. Journal of chromatography. B, Biomedical sciences and applications. 1999 Jan; 721(2):295-9. doi: 10.1016/s0378-4347(98)00464-2. [PMID: 10052702]
  • R A van Lingen, J T Deinum, J M Quak, A J Kuizenga, J G van Dam, K J Anand, D Tibboel, A Okken. Pharmacokinetics and metabolism of rectally administered paracetamol in preterm neonates. Archives of disease in childhood. Fetal and neonatal edition. 1999 Jan; 80(1):F59-63. doi: 10.1136/fn.80.1.f59. [PMID: 10325815]
  • R P Tonge, E J Kelly, S A Bruschi, T Kalhorn, D L Eaton, D W Nebert, S D Nelson. Role of CYP1A2 in the hepatotoxicity of acetaminophen: investigations using Cyp1a2 null mice. Toxicology and applied pharmacology. 1998 Nov; 153(1):102-8. doi: 10.1006/taap.1998.8543. [PMID: 9875304]
  • A W Nicholls, J C Lindon, S Caddick, R D Farrant, I D Wilson, J K Nicholson. NMR spectroscopic studies on the metabolism and futile deacetylation of phenacetin in the rat. Xenobiotica; the fate of foreign compounds in biological systems. 1997 Nov; 27(11):1175-86. doi: 10.1080/004982597239930. [PMID: 9413921]
  • J P Shockcor, S E Unger, I D Wilson, P J Foxall, J K Nicholson, J C Lindon. Combined HPLC, NMR spectroscopy, and ion-trap mass spectrometry with application to the detection and characterization of xenobiotic and endogenous metabolites in human urine. Analytical chemistry. 1996 Dec; 68(24):4431-5. doi: 10.1021/ac9606463. [PMID: 8972626]
  • W F Schwenk, J C Kahl. Acetaminophen glucuronidation accurately reflects gluconeogenesis in fasted dogs. The American journal of physiology. 1996 Sep; 271(3 Pt 1):E529-34. doi: 10.1152/ajpendo.1996.271.3.e529. [PMID: 8843747]
  • R B Raftogianis, M R Franklin, R E Galinsky. Effect of lipid-free total parenteral nutrition on hepatic drug conjugation in rats. The Journal of pharmacology and experimental therapeutics. 1996 Feb; 276(2):602-8. doi: . [PMID: 8632327]
  • K I Rother, W F Schwenk. Hepatic glycogen accurately reflected by acetaminophen glucuronide in dogs refed after fasting. The American journal of physiology. 1995 Oct; 269(4 Pt 1):E766-73. doi: 10.1152/ajpendo.1995.269.4.e766. [PMID: 7485493]
  • R E Kane, A P Li, D R Kaminski. Sulfation and glucuronidation of acetaminophen by human hepatocytes cultured on Matrigel and type 1 collagen reproduces conjugation in vivo. Drug metabolism and disposition: the biological fate of chemicals. 1995 Mar; 23(3):303-7. doi: NULL. [PMID: 7628293]
  • G S Lau, J A Critchley. The estimation of paracetamol and its major metabolites in both plasma and urine by a single high-performance liquid chromatography assay. Journal of pharmaceutical and biomedical analysis. 1994 Dec; 12(12):1563-72. doi: 10.1016/0731-7085(94)00859-0. [PMID: 7696381]
  • P R Gwilt, C L Lear, M A Tempero, D D Birt, A C Grandjean, R W Ruddon, D L Nagel. The effect of garlic extract on human metabolism of acetaminophen. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 1994 Mar; 3(2):155-60. doi: NULL. [PMID: 8049637]
  • K L Brouwer. Acute phenobarbital administration alters the disposition of acetaminophen metabolites in the rat. Drug metabolism and disposition: the biological fate of chemicals. 1993 Nov; 21(6):1129-33. doi: NULL. [PMID: 7905395]
  • S D Studenberg, K L Brouwer. Hepatic disposition of acetaminophen and metabolites. Pharmacokinetic modeling, protein binding and subcellular distribution. Biochemical pharmacology. 1993 Aug; 46(4):739-46. doi: 10.1016/0006-2952(93)90562-b. [PMID: 8363647]
  • J O Miners, D J Birkett. The misuse of urinary metabolite excretion data in drug metabolism studies. Pharmacogenetics. 1993 Feb; 3(1):58-9. doi: 10.1097/00008571-199302000-00007. [PMID: 8329069]
  • U Martin, R M Temple, R J Winney, L F Prescott. The disposition of paracetamol and its conjugates during multiple dosing in patients with end-stage renal failure maintained on haemodialysis. European journal of clinical pharmacology. 1993; 45(2):141-5. doi: 10.1007/bf00315495. [PMID: 8223835]
  • S M de Morais, S Y Chow, P G Wells. Biotransformation and toxicity of acetaminophen in congenic RHA rats with or without a hereditary deficiency in bilirubin UDP-glucuronosyltransferase. Toxicology and applied pharmacology. 1992 Nov; 117(1):81-7. doi: 10.1016/0041-008x(92)90220-m. [PMID: 1440617]
  • P M Savina, K L Brouwer. Probenecid-impaired biliary excretion of acetaminophen glucuronide and sulfate in the rat. Drug metabolism and disposition: the biological fate of chemicals. 1992 Jul; 20(4):496-501. doi: NULL. [PMID: 1356724]
  • Y P Liu, J Liu, X S Jia, Q Mao, C Madhu, C D Klaassen. Protective effects of fulvotomentosides on acetaminophen-induced hepatotoxicity. Zhongguo yao li xue bao = Acta pharmacologica Sinica. 1992 May; 13(3):209-12. doi: . [PMID: 1442100]
  • L A Skoglund, K Ingebrigtsen, P Lausund, I Nafstad. Plasma concentration of paracetamol and its major metabolites after p.o. dosing with paracetamol or concurrent administration of paracetamol and its N-acetyl-DL-methionine ester in mice. General pharmacology. 1992 Mar; 23(2):155-8. doi: 10.1016/0306-3623(92)90002-2. [PMID: 1639228]
  • M Patel, B K Tang, W Kalow. Variability of acetaminophen metabolism in Caucasians and Orientals. Pharmacogenetics. 1992 Feb; 2(1):38-45. doi: 10.1097/00008571-199202000-00007. [PMID: 1302042]
  • T Gin, A M Cho, J K Lew, G S Lau, P M Yuen, J A Critchley, T E Oh. Gastric emptying in the postpartum period. Anaesthesia and intensive care. 1991 Nov; 19(4):521-4. doi: 10.1177/0310057x9101900405. [PMID: 1750631]
  • C Madhu, C D Klaassen. Protective effect of pregnenolone-16 alpha-carbonitrile on acetaminophen-induced hepatotoxicity in hamsters. Toxicology and applied pharmacology. 1991 Jun; 109(2):305-13. doi: 10.1016/0041-008x(91)90177-g. [PMID: 2068728]
  • M H Davies, R C Schnell. Oltipraz-induced amelioration of acetaminophen hepatotoxicity in hamsters. II. Competitive shunt in metabolism via glucuronidation. Toxicology and applied pharmacology. 1991 Jun; 109(1):29-40. doi: 10.1016/0041-008x(91)90188-k. [PMID: 2038747]
  • A C Schoots, G C Koomen, D G Struijk, R T Krediet, L Arisz. Isolation, identification, and analysis of 4-acetylaminophenol-glucuronide in body fluids of dialyzed renal patients; a molecular mass marker for peritoneal diffusive transport. Clinica chimica acta; international journal of clinical chemistry. 1990 Apr; 188(1):15-29. doi: 10.1016/0009-8981(90)90142-f. [PMID: 2347081]
  • J Hirate, C Y Zhu, I Horikoshi, V O Bhargava. First-pass metabolism of acetaminophen in rats after low and high doses. Biopharmaceutics & drug disposition. 1990 Apr; 11(3):245-52. doi: 10.1002/bdd.2510110309. [PMID: 2328311]
  • K L Brouwer, J A Jones. Altered hepatobiliary disposition of acetaminophen metabolites after phenobarbital pretreatment and renal ligation: evidence for impaired biliary excretion and a diffusional barrier. The Journal of pharmacology and experimental therapeutics. 1990 Feb; 252(2):657-64. doi: NULL. [PMID: 2313593]
  • L F Prescott, G C Speirs, J A Critchley, R M Temple, R J Winney. Paracetamol disposition and metabolite kinetics in patients with chronic renal failure. European journal of clinical pharmacology. 1989; 36(3):291-7. doi: 10.1007/bf00558162. [PMID: 2744070]
  • D J Ecobichon, S Hidvegi, A M Comeau, D R Varma. Acetaminophen metabolism in vivo by pregnant, fetal, and neonatal guinea pigs. Journal of biochemical toxicology. 1989; 4(4):235-40. doi: 10.1002/jbt.2570040406. [PMID: 2634094]