4-acetaminophen sulfate (BioDeep_00000024214)

   

human metabolite Endogenous blood metabolite Chemicals and Drugs


代谢物信息卡片


Acetaminophen sulfate ester, monopotassium salt

化学式: C8H9NO5S (231.0201424)
中文名称: 4-乙酰氨基硫酸菲, 4-乙酰氨基苯酚硫酸酯
谱图信息: 最多检出来源 Homo sapiens(feces) 2.27%

Reviewed

Last reviewed on 2024-09-14.

Cite this Page

4-acetaminophen sulfate. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/4-acetaminophen_sulfate (retrieved 2024-11-22) (BioDeep RN: BioDeep_00000024214). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CC(=O)NC1=CC=C(C=C1)OS(=O)(=O)O
InChI: InChI=1S/C8H9NO5S/c1-6(10)9-7-2-4-8(5-3-7)14-15(11,12)13/h2-5H,1H3,(H,9,10)(H,11,12,13)

描述信息

Paracetamol sulfate, also known as paracetamol sulfuric acid or 4-acetaminophen sulfate, is classified as a phenylsulfate. Phenylsulfates are compounds containing a sulfuric acid group conjugated to a phenyl group. Paracetamol sulfate is considered a slightly soluble (in water), acidic compound. Paracetamol sulfate is a metabolite of paracetamol, a common drug used for the relief of pain as an antipyretic. After paracetamol is absorbed from the gastrointestinal tract, it forms paracetamol sulfate by conjugation with sulfuric acid. Paracetamol sulfate can be found in both plasma and urine (PMID: 15127815).

同义名列表

25 个代谢物同义名

Acetaminophen sulfate ester, monopotassium salt; (4-acetamidophenyl)oxidanesulfonic acid; N-Acetyl-4-aminophenol sulphuric acid; N-Acetyl-4-aminophenol sulfuric acid; Acetaminophen sulphuric acid ester; Acetaminophen sulfuric acid ester; N-(4-(Sulphooxy)phenyl)acetamide; N-Acetyl-4-aminophenol sulphate; N-(4-(Sulfooxy)phenyl)acetamide; 4-Acetaminophen sulphuric acid; N-Acetyl-4-aminophenol sulfate; 4-Acetaminophen sulfuric acid; Acetaminophen sulphuric acid; Acetaminophen sulphate ester; Acetaminophen sulfate ester; Acetaminophen sulfuric acid; Paracetamol sulphuric acid; Paracetamol sulfuric acid; 4-Acetaminophen sulphate; 4-ACETAMINOPHEN SULFATE; Acetaminophen sulphate; Acetaminophen sulfate; Acetaminophen-sulfate; Paracetamol sulphate; Paracetamol sulfate



数据库引用编号

7 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(6)

BioCyc(0)

PlantCyc(0)

代谢反应

61 个相关的代谢反应过程信息。

Reactome(60)

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

  • 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]
  • 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]
  • 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]
  • 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]
  • 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]
  • 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]
  • 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]
  • 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]
  • 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]
  • 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]
  • Sun J Kim, Min Y Lee, Do Y Kwon, Sung Y Kim, Young C Kim. Alteration in metabolism and toxicity of acetaminophen upon repeated administration in rats. Journal of pharmacological sciences. 2009 Oct; 111(2):175-81. doi: 10.1254/jphs.09151fp. [PMID: 19834287]
  • 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]
  • 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]
  • 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]
  • 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]
  • Hayati Filik, Izzet Sener, Sema Demirci Cekiç, Emine Kiliç, Reşat Apak. Spectrophotometric determination of paracetamol in urine with tetrahydroxycalix[4]arene as a coupling reagent and preconcentration with triton X-114 using cloud point extraction. Chemical & pharmaceutical bulletin. 2006 Jun; 54(6):891-6. doi: 10.1248/cpb.54.891. [PMID: 16755066]
  • 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]
  • 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]
  • Anthony N Lucas, Roger L Nation, Robert W Milne, Geoffrey D Reynolds, Allan M Evans. The effects of phytoestrogenic isoflavones on the formation and disposition of paracetamol sulfate in the isolated perfused rat liver. The Journal of pharmacy and pharmacology. 2003 May; 55(5):639-46. doi: 10.1211/002235703765344540. [PMID: 12831506]
  • 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]
  • Y Ohkawa, Y Kiyohara, T Asoh, H Maeda, M Kurumi, K Sasaki, Y Kurosaki, M Matsumura, T Nakayama. Application of 4-hydroxyantipyrine and acetaminophen O-sulfate as biodistribution promoter. Biological & pharmaceutical bulletin. 2001 Dec; 24(12):1404-10. doi: 10.1248/bpb.24.1404. [PMID: 11767111]
  • 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]
  • 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 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]
  • 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]
  • 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]
  • B H Ali, Z Cheng, G el Hadrami, A K Bashir, Q A McKellar. Comparative pharmacokinetics of paracetamol (acetaminophen) and its sulphate and glucuronide metabolites in desert camels and goats. Journal of veterinary pharmacology and therapeutics. 1996 Jun; 19(3):238-44. doi: 10.1111/j.1365-2885.1996.tb00044.x. [PMID: 8803883]
  • 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]
  • 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]
  • 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]
  • 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]
  • C A Goresky, K S Pang, A J Schwab, F Barker, W F Cherry, G G Bach. Uptake of a protein-bound polar compound, acetaminophen sulfate, by perfused rat liver. Hepatology (Baltimore, Md.). 1992 Jul; 16(1):173-90. doi: 10.1002/hep.1840160129. [PMID: 1618470]
  • 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]
  • 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]
  • 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]
  • 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]
  • J Nakamura, S Baba, T Nakamura, H Sasaki, J Shibasaki. A method for the preparation of calibration curves for acetaminophen glucuronide and acetaminophen sulfate in rabbit urine without use of authentic compounds in high-performance liquid chromatography. Journal of pharmacobio-dynamics. 1987 Nov; 10(11):673-7. doi: 10.1248/bpb1978.10.673. [PMID: 3446775]
  • G B Corcoran, B K Wong, L Shum, R E Galinsky. Acetaminophen sulfation deficit in obese rats overfed an energy-dense cafeteria diet. Endocrine research. 1987; 13(2):101-21. doi: 10.3109/07435808709023667. [PMID: 3622404]
  • I Roberts, R J Flanagan, J Strang, L F Prescott. Toxicological studies in a Distalgesic addict. Human toxicology. 1986 May; 5(3):207-10. doi: 10.1177/096032718600500310. [PMID: 3710498]
  • R E Galinsky, G B Corcoran. Influence of advanced age on the formation and elimination of acetaminophen metabolites by male rats. Pharmacology. 1986; 32(6):313-20. doi: 10.1159/000138186. [PMID: 3755243]
  • D Jung, N U Zafar. Micro high-performance liquid chromatographic assay of acetaminophen and its major metabolites in plasma and urine. Journal of chromatography. 1985 Apr; 339(1):198-202. doi: 10.1016/s0378-4347(00)84644-7. [PMID: 4019667]
  • L F Prescott. Kinetics and metabolism of paracetamol and phenacetin. British journal of clinical pharmacology. 1980 Oct; 10 Suppl 2(?):291S-298S. doi: 10.1111/j.1365-2125.1980.tb01812.x. [PMID: 7002186]