Acetimidoquinone (BioDeep_00001874392)
代谢物信息卡片
N-Acetylimidoquinone
化学式: C8H7NO2 (149.0476762)
中文名称: N-乙酰苯醌亚胺
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CC(=O)N=C1C=CC(=O)C=C1
InChI: InChI=1S/C8H7NO2/c1-6(10)9-7-2-4-8(11)5-3-7/h2-5H,1H3
相关代谢途径
Reactome(6)
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)
1 个相关的物种来源信息
- 9606 - Homo sapiens: 10.1007/S11306-016-1051-4
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
- Wen-Zhang Dai, Zhao-Fang Bai, Ting-Ting He, Xiao-Yan Zhan, Qiang Li, Jing Zhao, Xiao-He Xiao. [Schisandrin C improves acetaminophen-induced liver injury in mice by regulating Nrf2 signaling pathway].
Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica.
2022 Oct; 47(19):5299-5305. doi:
10.19540/j.cnki.cjcmm.20220421.704. [PMID: 36472037] - Cosby G Arnold, Layne Dylla, Andrew A Monte, Kennon Heard, Susan Heard, Angelo D'Alessandro, Kate Reynolds, Richard Dart, Barry Rumack, Brandon Sonn. Metabolomic Evaluation of N-Acetyl-p-Benzoquinone Imine Protein Adduct Formation with Therapeutic Acetaminophen Administration: Sex-based Physiologic Differences.
Journal of medical toxicology : official journal of the American College of Medical Toxicology.
2022 10; 18(4):297-310. doi:
10.1007/s13181-022-00903-5. [PMID: 35751009] - Chuan-Hua Ding, He Zhu. Isatidis Folium alleviates acetaminophen-induced liver injury in mice by enhancing the endogenous antioxidant system.
Environmental toxicology.
2020 Nov; 35(11):1251-1259. doi:
10.1002/tox.22990. [PMID: 32677766] - Xiqian Zhang, Ting Wang, Yujie Yang, Ruina Li, Ya Chen, Rong Li, Xuehua Jiang, Ling Wang. Tanshinone IIA attenuates acetaminophen-induced hepatotoxicity through HOTAIR-Nrf2-MRP2/4 signaling pathway.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie.
2020 Oct; 130(?):110547. doi:
10.1016/j.biopha.2020.110547. [PMID: 32777703] - Sacha Bohler, Xiaosong Liu, Julian Krauskopf, Florian Caiment, Jiri Aubrecht, Gerry A F Nicolaes, Jos C S Kleinjans, Jacco J Briedé. Acetaminophen Overdose as a Potential Risk Factor for Parkinson's Disease.
Clinical and translational science.
2019 11; 12(6):609-616. doi:
10.1111/cts.12663. [PMID: 31305025] - Ravindrababu Pingili, A Krishnamanjari Pawar, Siva Reddy Challa. Quercetin reduced the formation of N-acetyl-p-benzoquinoneimine, a toxic metabolite of paracetamol in rats and isolated rat hepatocytes.
Phytotherapy research : PTR.
2019 Jul; 33(7):1770-1783. doi:
10.1002/ptr.6365. [PMID: 31155811] - Ravindra Babu Pingili, A Krishnamanjari Pawar, Siva R Challa. Effect of chrysin on the formation of N-acetyl-p-benzoquinoneimine, a toxic metabolite of paracetamol in rats and isolated rat hepatocytes.
Chemico-biological interactions.
2019 Apr; 302(?):123-134. doi:
10.1016/j.cbi.2019.02.014. [PMID: 30794797] - Masashi Ozawa, Takashi Kubo, Seon Hwa Lee, Tomoyuki Oe. LC-MS analyses of N-acetyl-p-benzoquinone imine-adducts of glutathione, cysteine, N-acetylcysteine, and albumin in a plasma sample: A case study from a patient with a rare acetaminophen-induced acute swelling rash.
The Journal of toxicological sciences.
2019; 44(8):559-563. doi:
10.2131/jts.44.559. [PMID: 31378767] - Johan L Å Nilsson, Anders Blomgren, Ulf J Nilsson, Edward D Högestätt, Lars Grundemar. N,N'-Bis(2-mercaptoethyl)isophthalamide Binds Electrophilic Paracetamol Metabolites and Prevents Paracetamol-Induced Liver Toxicity.
Basic & clinical pharmacology & toxicology.
2018 Nov; 123(5):589-593. doi:
10.1111/bcpt.13058. [PMID: 29908097] - 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] - Daniel P Heruth, Katherine Shortt, Nini Zhang, Ding-You Li, Li Q Zhang, Shui Qing Ye. Genetic Association of Single Nucleotide Polymorphisms with Acetaminophen-Induced Hepatotoxicity.
The Journal of pharmacology and experimental therapeutics.
2018 10; 367(1):95-100. doi:
10.1124/jpet.118.248583. [PMID: 30076262] - Ege Arzuk, Burak Turna, Murat Sözbilen, Hilmi Orhan. Inter-individual and inter-organ variability in the bioactivation of paracetamol by human liver and kidney tissues.
Environmental toxicology and pharmacology.
2018 Jul; 61(?):8-17. doi:
10.1016/j.etap.2018.05.015. [PMID: 29803978] - Hongyu Yan, Zhenlin Huang, Qingyun Bai, Yuchen Sheng, Zhanxia Hao, Zhengtao Wang, Lili Ji. Natural product andrographolide alleviated APAP-induced liver fibrosis by activating Nrf2 antioxidant pathway.
Toxicology.
2018 03; 396-397(?):1-12. doi:
10.1016/j.tox.2018.01.007. [PMID: 29355602] - Syu-Ichi Kanno, Ayako Tomizawa, Shin Yomogida, Akiyoshi Hara. Glutathione peroxidase 3 is a protective factor against acetaminophen‑induced hepatotoxicity in vivo and in vitro.
International journal of molecular medicine.
2017 Sep; 40(3):748-754. doi:
10.3892/ijmm.2017.3049. [PMID: 28677736] - Qingyun Bai, Hongyu Yan, Yuchen Sheng, Yao Jin, Liang Shi, Lili Ji, Zhengtao Wang. Long-term acetaminophen treatment induced liver fibrosis in mice and the involvement of Egr-1.
Toxicology.
2017 05; 382(?):47-58. doi:
10.1016/j.tox.2017.03.008. [PMID: 28286204] - Satoshi Tamai, Takuma Iguchi, Noriyo Niino, Kei Mikamoto, Ken Sakurai, Ayako Sayama, Hitomi Shimoda, Wataru Takasaki, Kazuhiko Mori. A monkey model of acetaminophen-induced hepatotoxicity; phenotypic similarity to human.
The Journal of toxicological sciences.
2017; 42(1):73-84. doi:
10.2131/jts.42.73. [PMID: 28070111] - Isao Ishii, Shotaro Kamata, Yoshifumi Hagiya, Yumi Abiko, Tadashi Kasahara, Yoshito Kumagai. Protective effects of hydrogen sulfide anions against acetaminophen-induced hepatotoxicity in mice.
The Journal of toxicological sciences.
2015 Dec; 40(6):837-41. doi:
10.2131/jts.40.837. [PMID: 26558465] - Estella M Alonso, Laura P James, Song Zhang, Robert H Squires. Acetaminophen Adducts Detected in Serum of Pediatric Patients With Acute Liver Failure.
Journal of pediatric gastroenterology and nutrition.
2015 Jul; 61(1):102-7. doi:
10.1097/mpg.0000000000000814. [PMID: 25859823] - Ravindra Babu Pingili, A Krishnamanjari Pawar, Siva R Challa. Systemic exposure of Paracetamol (acetaminophen) was enhanced by quercetin and chrysin co-administration in Wistar rats and in vitro model: risk of liver toxicity.
Drug development and industrial pharmacy.
2015; 41(11):1793-800. doi:
10.3109/03639045.2015.1008012. [PMID: 25678313] - Yiming Jiang, Xiaomei Fan, Ying Wang, Pan Chen, Hang Zeng, Huasen Tan, Frank J Gonzalez, Min Huang, Huichang Bi. Schisandrol B protects against acetaminophen-induced hepatotoxicity by inhibition of CYP-mediated bioactivation and regulation of liver regeneration.
Toxicological sciences : an official journal of the Society of Toxicology.
2015 Jan; 143(1):107-15. doi:
10.1093/toxsci/kfu216. [PMID: 25319358] - Astrid Jordet Langhammer, Odd Georg Nilsen. Fennel and raspberry leaf as possible inhibitors of acetaminophen oxidation.
Phytotherapy research : PTR.
2014 Oct; 28(10):1573-6. doi:
10.1002/ptr.5124. [PMID: 24458977] - André LeBlanc, Tze Chieh Shiao, René Roy, Lekha Sleno. Absolute quantitation of NAPQI-modified rat serum albumin by LC-MS/MS: monitoring acetaminophen covalent binding in vivo.
Chemical research in toxicology.
2014 Sep; 27(9):1632-9. doi:
10.1021/tx500284g. [PMID: 25168029] - Arne Trettin, Sandor Batkai, Thomas Thum, Jens Jordan, Dimitrios Tsikas. Trapping of NAPQI, the intermediate toxic paracetamol metabolite, by aqueous sulfide (S²⁻) and analysis by GC-MS/MS.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2014 Jul; 963(?):99-105. doi:
10.1016/j.jchromb.2014.05.050. [PMID: 24950097] - Fumio Osaki, Takaaki Goto, Seon Hwa Lee, Tomoyuki Oe. Predicted multiple selected reaction monitoring to screen activated drug-mediated modifications on human serum albumin.
Analytical biochemistry.
2014 Mar; 449(?):59-67. doi:
10.1016/j.ab.2013.12.016. [PMID: 24361714] - 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] - Mohamed I Sakeran, Nahla Zidan, Hasibur Rehman, Al Thbiani Aziz, Shalini Saggu. Abrogation by Trifolium alexandrinum root extract on hepatotoxicity induced by acetaminophen in rats.
Redox report : communications in free radical research.
2014 Jan; 19(1):26-33. doi:
10.1179/1351000213y.0000000068. [PMID: 24191932] - Jeffrey L Woodhead, Brett A Howell, Yuching Yang, Alison H Harrill, Harvey J Clewell, Melvin E Andersen, Scott Q Siler, Paul B Watkins. An analysis of N-acetylcysteine treatment for acetaminophen overdose using a systems model of drug-induced liver injury.
The Journal of pharmacology and experimental therapeutics.
2012 Aug; 342(2):529-40. doi:
10.1124/jpet.112.192930. [PMID: 22593093] - Jean-Matthieu Prot, Andrei Bunescu, Bénédicte Elena-Herrmann, Caroline Aninat, Leila Choucha Snouber, Laurent Griscom, Florence Razan, Frederic Y Bois, Cécile Legallais, Céline Brochot, Anne Corlu, Marc Emmanuel Dumas, Eric Leclerc. Predictive toxicology using systemic biology and liver microfluidic "on chip" approaches: application to acetaminophen injury.
Toxicology and applied pharmacology.
2012 Mar; 259(3):270-80. doi:
10.1016/j.taap.2011.12.017. [PMID: 22230336] - Shingo Arakawa, Takanori Maejima, Kazunori Fujimoto, Takashi Yamaguchi, Masae Yagi, Tomomi Sugiura, Ryo Atsumi, Yasushi Yamazoe. Resistance to acetaminophen-induced hepatotoxicity in glutathione S-transferase Mu 1-null mice.
The Journal of toxicological sciences.
2012; 37(3):595-605. doi:
10.2131/jts.37.595. [PMID: 22687999] - Seon Mi Jin, Hong Ryang Kil, Kwangsik Park, Chung Il Noh. Gene expression in rat hearts following oral administration of a single hepatotoxic dose of acetaminophen.
Yonsei medical journal.
2012 Jan; 53(1):172-80. doi:
10.3349/ymj.2012.53.1.172. [PMID: 22187249] - Nam-Hun Lee, Chang-Seob Seo, Ho-Young Lee, Da-Young Jung, Jun-Kyung Lee, Jin-Ah Lee, Kye Yong Song, Hyeun-Kyoo Shin, Mee-Young Lee, Young Bae Seo, Hokyoung Kim, Hyekyung Ha. Hepatoprotective and Antioxidative Activities of Cornus officinalis against Acetaminophen-Induced Hepatotoxicity in Mice.
Evidence-based complementary and alternative medicine : eCAM.
2012; 2012(?):804924. doi:
10.1155/2012/804924. [PMID: 21869901] - Anil U Tatiya, Sanjay J Surana, Manisha P Sutar, Nehal H Gamit. Hepatoprotective effect of poly herbal formulation against various hepatotoxic agents in rats.
Pharmacognosy research.
2012 Jan; 4(1):50-6. doi:
10.4103/0974-8490.91040. [PMID: 22224062] - Runkuan Yang, Shutian Zhang, Henri Kajander, Shengtao Zhu, Marja-Leena Koskinen, Jyrki Tenhunen. Ringer's lactate improves liver recovery in a murine model of acetaminophen toxicity.
BMC gastroenterology.
2011 Nov; 11(?):125. doi:
10.1186/1471-230x-11-125. [PMID: 22085740] - Jinah Hwang, Yun-Hee Chang, Jung Hwa Park, Soo Yeon Kim, Haeyon Chung, Eugene Shim, Hye Jin Hwang. Dietary saturated and monounsaturated fats protect against acute acetaminophen hepatotoxicity by altering fatty acid composition of liver microsomal membrane in rats.
Lipids in health and disease.
2011 Oct; 10(?):184. doi:
10.1186/1476-511x-10-184. [PMID: 22011590] - María Eugenia Letelier, Miguel López-Valladares, Liliana Peredo-Silva, Daniel Rojas-Sepúlveda, Paula Aracena. Microsomal oxidative damage promoted by acetaminophen metabolism.
Toxicology in vitro : an international journal published in association with BIBRA.
2011 Oct; 25(7):1310-3. doi:
10.1016/j.tiv.2011.04.022. [PMID: 21569833] - Katsunori Yamaura, Maki Shimada, Noriyuki Nakayama, Koichi Ueno. Protective effects of goldenseal (Hydrastis canadensis L.) on acetaminophen-induced hepatotoxicity through inhibition of CYP2E1 in rats.
Pharmacognosy research.
2011 Oct; 3(4):250-5. doi:
10.4103/0974-8490.89745. [PMID: 22224048] - Andreas Leffler, Anja Lattrell, Sergej Kronewald, Florian Niedermirtl, Carla Nau. Activation of TRPA1 by membrane permeable local anesthetics.
Molecular pain.
2011 Aug; 7(?):62. doi:
10.1186/1744-8069-7-62. [PMID: 21861907] - H Najafzadeh, A Rezaie, A M Masoodi, S Mehrzadi. Comparison of the effect of vanadium and deferoxamine on acetaminophen toxicity in rats.
Indian journal of pharmacology.
2011 Jul; 43(4):429-32. doi:
10.4103/0253-7613.83115. [PMID: 21844999] - Carmen Flores-Pérez, Juan Luis Chávez-Pacheco, Blanca Ramírez-Mendiola, Radamés Alemón-Medina, Raquel García-Álvarez, Hugo Juárez-Olguín, Janett Flores-Pérez. A reliable method of liquid chromatography for the quantification of acetaminophen and identification of its toxic metabolite N-acetyl-p-benzoquinoneimine for application in pediatric studies.
Biomedical chromatography : BMC.
2011 Jul; 25(7):760-6. doi:
10.1002/bmc.1511. [PMID: 20878659] - Sujata Singh, Shanker K Singh, Mritunjay Kumar, Kalpana Chandra, Rashmi Singh. Ameliorative Potential of Quercetin Against Paracetamol-induced Oxidative Stress in Mice Blood.
Toxicology international.
2011 Jul; 18(2):140-5. doi:
10.4103/0971-6580.84267. [PMID: 21976820] - Ayyasamy Manimaran, Souvendra Nath Sarkar, Palanisamy Sankar. Repeated preexposure or coexposure to arsenic differentially alters acetaminophen-induced oxidative stress in rat kidney.
Environmental toxicology.
2011 Jun; 26(3):250-9. doi:
10.1002/tox.20551. [PMID: 19950220] - Dimitrios Tsikas, Arne Trettin, Alexander A Zörner, Frank-Mathias Gutzki. In-source formation of N-acetyl-p-benzoquinone imine (NAPQI), the putatively toxic acetaminophen (paracetamol) metabolite, after derivatization with pentafluorobenzyl bromide and GC-ECNICI-MS analysis.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2011 May; 879(17-18):1476-84. doi:
10.1016/j.jchromb.2011.01.025. [PMID: 21353649] - Rakhee Agarwal, Lee Ann MacMillan-Crow, Tonya M Rafferty, Hamida Saba, Dean W Roberts, E Kim Fifer, Laura P James, Jack A Hinson. Acetaminophen-induced hepatotoxicity in mice occurs with inhibition of activity and nitration of mitochondrial manganese superoxide dismutase.
The Journal of pharmacology and experimental therapeutics.
2011 Apr; 337(1):110-6. doi:
10.1124/jpet.110.176321. [PMID: 21205919] - Ali Özcan, Yücel Sahin. A novel approach for the determination of paracetamol based on the reduction of N-acetyl-p-benzoquinoneimine formed on the electrochemically treated pencil graphite electrode.
Analytica chimica acta.
2011 Jan; 685(1):9-14. doi:
10.1016/j.aca.2010.11.004. [PMID: 21168545] - Kiyoshi Fukuhara, Akiko Ohno, Yosuke Ando, Takashi Yamoto, Haruhiro Okuda. A 1H NMR-based metabolomics approach for mechanistic insight into acetaminophen-induced hepatotoxicity.
Drug metabolism and pharmacokinetics.
2011; 26(4):399-406. doi:
10.2133/dmpk.dmpk-11-rg-005. [PMID: 21670543] - Jean Matthieu Prot, Anne-Sophie Briffaut, Franck Letourneur, Philippe Chafey, Franck Merlier, Yves Grandvalet, Cécile Legallais, Eric Leclerc. Integrated proteomic and transcriptomic investigation of the acetaminophen toxicity in liver microfluidic biochip.
PloS one.
2011; 6(8):e21268. doi:
10.1371/journal.pone.0021268. [PMID: 21857903] - Inmaculada Posadas, Pablo Santos, Almudena Blanco, Maríangeles Muñoz-Fernández, Valentín Ceña. Acetaminophen induces apoptosis in rat cortical neurons.
PloS one.
2010 Dec; 5(12):e15360. doi:
10.1371/journal.pone.0015360. [PMID: 21170329] - Robert A Ettlin, Junji Kuroda, Stephanie Plassmann, Makoto Hayashi, David E Prentice. Successful drug development despite adverse preclinical findings part 2: examples.
Journal of toxicologic pathology.
2010 Dec; 23(4):213-34. doi:
10.1293/tox.23.213. [PMID: 22272032] - Adeline Yl Lim, Ignacio Segarra, Srikumar Chakravarthi, Sufyan Akram, John P Judson. Histopathology and biochemistry analysis of the interaction between sunitinib and paracetamol in mice.
BMC pharmacology.
2010 Oct; 10(?):14. doi:
10.1186/1471-2210-10-14. [PMID: 20950441] - Candasamy Mayuren, Vudumula Varun Reddy, Srikakulam Vishnu Priya, Vallampatla Anusha Devi. Protective effect of Livactine against CCl(4) and paracetamol induced hepatotoxicity in adult Wistar rats.
North American journal of medical sciences.
2010 Oct; 2(10):491-5. doi:
10.4297/najms.2010.2491. [PMID: 22558553] - Chieko Saito, John J Lemasters, Hartmut Jaeschke. c-Jun N-terminal kinase modulates oxidant stress and peroxynitrite formation independent of inducible nitric oxide synthase in acetaminophen hepatotoxicity.
Toxicology and applied pharmacology.
2010 Jul; 246(1-2):8-17. doi:
10.1016/j.taap.2010.04.015. [PMID: 20423716] - K S Gopi, A Gopala Reddy, K Jyothi, B Anil Kumar. Acetaminophen-induced Hepato- and Nephrotoxicity and Amelioration by Silymarin and Terminalia chebula in Rats.
Toxicology international.
2010 Jul; 17(2):64-6. doi:
10.4103/0971-6580.72672. [PMID: 21170247] - J H Winnike, Z Li, F A Wright, J M Macdonald, T M O'Connell, P B Watkins. Use of pharmaco-metabonomics for early prediction of acetaminophen-induced hepatotoxicity in humans.
Clinical pharmacology and therapeutics.
2010 Jul; 88(1):45-51. doi:
10.1038/clpt.2009.240. [PMID: 20182423] - Joydeep Das, Jyotirmoy Ghosh, Prasenjit Manna, Parames C Sil. Acetaminophen induced acute liver failure via oxidative stress and JNK activation: protective role of taurine by the suppression of cytochrome P450 2E1.
Free radical research.
2010 Mar; 44(3):340-55. doi:
10.3109/10715760903513017. [PMID: 20166895] - Chieko Saito, Hui-Min Yan, Antonio Artigues, Maria T Villar, Anwar Farhood, Hartmut Jaeschke. Mechanism of protection by metallothionein against acetaminophen hepatotoxicity.
Toxicology and applied pharmacology.
2010 Jan; 242(2):182-90. doi:
10.1016/j.taap.2009.10.006. [PMID: 19835899] - Rick D Fannin, Mark Russo, Thomas M O'Connell, Kevin Gerrish, Jason H Winnike, Jeffrey Macdonald, Jack Newton, Shahid Malik, Stella O Sieber, Joel Parker, Ruchir Shah, Tong Zhou, Paul B Watkins, Richard S Paules. Acetaminophen dosing of humans results in blood transcriptome and metabolome changes consistent with impaired oxidative phosphorylation.
Hepatology (Baltimore, Md.).
2010 Jan; 51(1):227-36. doi:
10.1002/hep.23330. [PMID: 19918972] - Tadashi Nishida, Shuzo Ohata, Chiaki Kusumoto, Shinsuke Mochida, Junya Nakada, Yoshimi Inagaki, Yoshiji Ohta, Tatsuya Matsura. Zinc Supplementation with Polaprezinc Protects Mouse Hepatocytes against Acetaminophen-Induced Toxicity via Induction of Heat Shock Protein 70.
Journal of clinical biochemistry and nutrition.
2010 Jan; 46(1):43-51. doi:
10.3164/jcbn.09-60. [PMID: 20104264] - Juan Mayordomo-Colunga, Elene Larrea, Mónica García, Sonsoles Suárez, Julián Rodríguez. Life-threatening hyponatremia due to intravenous n-acetylcysteine treatment in an infant: a case report.
Cases journal.
2009 Sep; 2(?):8347. doi:
10.4076/1757-1626-2-8347. [PMID: 19918421] - Inthisham Nassar, Thanikachalam Pasupati, John Paul Judson, Ignacio Segarra. Reduced exposure of imatinib after coadministration with acetaminophen in mice.
Indian journal of pharmacology.
2009 Aug; 41(4):167-72. doi:
10.4103/0253-7613.56071. [PMID: 20523867] - M Anoush, M A Eghbal, F Fathiazad, H Hamzeiy, N S Kouzehkonani. The protective effects of garlic extract against acetaminophen-induced oxidative stress and glutathione depletion.
Pakistan journal of biological sciences : PJBS.
2009 May; 12(10):765-71. doi:
10.3923/pjbs.2009.765.771. [PMID: 19806806] - 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] - Christian Huber, Bernadett Bartha, Rudolf Harpaintner, Peter Schröder. Metabolism of acetaminophen (paracetamol) in plants--two independent pathways result in the formation of a glutathione and a glucose conjugate.
Environmental science and pollution research international.
2009 Mar; 16(2):206-13. doi:
10.1007/s11356-008-0095-z. [PMID: 19145453] - Runkuan Yang, Keita Miki, Xin He, Meaghan E Killeen, Mitchell P Fink. Prolonged treatment with N-acetylcystine delays liver recovery from acetaminophen hepatotoxicity.
Critical care (London, England).
2009; 13(2):R55. doi:
10.1186/cc7782. [PMID: 19358737] - Kelly K Andringa, Mary Lynn Bajt, Hartmut Jaeschke, Shannon M Bailey. Mitochondrial protein thiol modifications in acetaminophen hepatotoxicity: effect on HMG-CoA synthase.
Toxicology letters.
2008 Apr; 177(3):188-97. doi:
10.1016/j.toxlet.2008.01.010. [PMID: 18313239] - M Tolulope Olaleye, B T João Rocha. Acetaminophen-induced liver damage in mice: effects of some medicinal plants on the oxidative defense system.
Experimental and toxicologic pathology : official journal of the Gesellschaft fur Toxikologische Pathologie.
2008 Mar; 59(5):319-27. doi:
10.1016/j.etp.2007.10.003. [PMID: 18054472] - Johannes S Hoos, Micaela C Damsten, Jon S B de Vlieger, Jan N M Commandeur, Nico P E Vermeulen, Wilfried M A Niessen, Henk Lingeman, Hubertus Irth. Automated detection of covalent adducts to human serum albumin by immunoaffinity chromatography, on-line solution phase digestion and liquid chromatography-mass spectrometry.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2007 Nov; 859(2):147-56. doi:
10.1016/j.jchromb.2007.09.015. [PMID: 17913598] - Lisa A McConnachie, Isaac Mohar, Francesca N Hudson, Carol B Ware, Warren C Ladiges, Carolina Fernandez, Sam Chatterton-Kirchmeier, Collin C White, Robert H Pierce, Terrance J Kavanagh. Glutamate cysteine ligase modifier subunit deficiency and gender as determinants of acetaminophen-induced hepatotoxicity in mice.
Toxicological sciences : an official journal of the Society of Toxicology.
2007 Oct; 99(2):628-36. doi:
10.1093/toxsci/kfm165. [PMID: 17584759] - 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] - Micaela C Damsten, Jan N M Commandeur, Alex Fidder, Albert G Hulst, Daan Touw, Daan Noort, Nico P E Vermeulen. Liquid chromatography/tandem mass spectrometry detection of covalent binding of acetaminophen to human serum albumin.
Drug metabolism and disposition: the biological fate of chemicals.
2007 Aug; 35(8):1408-17. doi:
10.1124/dmd.106.014233. [PMID: 17510247] - E K Kuffner, J L Green, G M Bogdan, P C Knox, R B Palmer, K Heard, J T Slattery, R C Dart. The effect of acetaminophen (four grams a day for three consecutive days) on hepatic tests in alcoholic patients--a multicenter randomized study.
BMC medicine.
2007 May; 5(?):13. doi:
10.1186/1741-7015-5-13. [PMID: 17537264] - Shigeo Shinoda, Takahiko Aoyama, Yukio Aoyama, Sachiko Tomioka, Yoshiaki Matsumoto, Yoko Ohe. Pharmacokinetics/pharmacodynamics of acetaminophen analgesia in Japanese patients with chronic pain.
Biological & pharmaceutical bulletin.
2007 Jan; 30(1):157-61. doi:
10.1248/bpb.30.157. [PMID: 17202677] - Xin Gen Lei, Jian-Hong Zhu, James P McClung, Manuel Aregullin, Carol A Roneker. Mice deficient in Cu,Zn-superoxide dismutase are resistant to acetaminophen toxicity.
The Biochemical journal.
2006 Nov; 399(3):455-61. doi:
10.1042/bj20060784. [PMID: 16831125] - H Balaji Raghavendran, A Sathivel, T Devaki. Defensive nature of Sargassum polycystum (Brown alga) against acetaminophen-induced toxic hepatitis in rats: role of drug metabolizing microsomal enzyme system, tumor necrosis factor-alpha and fate of liver cell structural integrity.
World journal of gastroenterology.
2006 Jun; 12(24):3829-34. doi:
10.3748/wjg.v12.i24.3829. [PMID: 16804966] - Yuri N Clement, Arlene F Williams. Protection against paracetamol-induced hepatic injury by prazosin pre-treatment in CD-1 mice.
Mutation research.
2005 Nov; 579(1-2):182-8. doi:
10.1016/j.mrfmmm.2005.03.028. [PMID: 16054166] - Stephan T Stern, Mary K Bruno, Robert A Horton, Dennis W Hill, Jeanette C Roberts, Steven D Cohen. Contribution of acetaminophen-cysteine to acetaminophen nephrotoxicity II. Possible involvement of the gamma-glutamyl cycle.
Toxicology and applied pharmacology.
2005 Jan; 202(2):160-71. doi:
10.1016/j.taap.2004.06.029. [PMID: 15629191] - Marco L A Sivilotti, Angela M Good, Mark C Yarema, David N Juurlink, David W Johnson. A new predictor of toxicity following acetaminophen overdose based on pretreatment exposure.
Clinical toxicology (Philadelphia, Pa.).
2005; 43(4):229-34. doi:
10.1081/clt-66056. [PMID: 16035198] - Yasuhiro Masubuchi, Chieko Suda, Toshiharu Horie. Involvement of mitochondrial permeability transition in acetaminophen-induced liver injury in mice.
Journal of hepatology.
2005 Jan; 42(1):110-6. doi:
10.1016/j.jhep.2004.09.015. [PMID: 15629515] - Grace L Guo, Jeff S Moffit, Christopher J Nicol, Jerrold M Ward, Lauren A Aleksunes, Angela L Slitt, Steven A Kliewer, Jose E Manautou, Frank J Gonzalez. Enhanced acetaminophen toxicity by activation of the pregnane X receptor.
Toxicological sciences : an official journal of the Society of Toxicology.
2004 Dec; 82(2):374-80. doi:
10.1093/toxsci/kfh286. [PMID: 15456926] - Karen Bedard, Nicole MacDonald, Jodie Collins, Alastair Cribb. Cytoprotection following endoplasmic reticulum stress protein induction in continuous cell lines.
Basic & clinical pharmacology & toxicology.
2004 Mar; 94(3):124-31. doi:
10.1111/j.1742-7843.2004.pto940305.x. [PMID: 15049342] - Laura P James, Philip R Mayeux, Jack A Hinson. Acetaminophen-induced hepatotoxicity.
Drug metabolism and disposition: the biological fate of chemicals.
2003 Dec; 31(12):1499-506. doi:
10.1124/dmd.31.12.1499. [PMID: 14625346] - 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] - Paul I Dargan, Alison L Jones. Acetaminophen poisoning: an update for the intensivist.
Critical care (London, England).
2002 Apr; 6(2):108-10. doi:
10.1186/cc1465. [PMID: 11983032] - Shengrong Lin, Lakhdar Gasmi, Yi Xie, Kang Ying, Shaohua Gu, Zhao Wang, Hua Jin, Yueqiong Chao, Chaoqun Wu, Zongxiang Zhou, Rong Tang, Yumin Mao, Alexander G McLennan. Cloning, expression and characterisation of a human Nudix hydrolase specific for adenosine 5'-diphosphoribose (ADP-ribose).
Biochimica et biophysica acta.
2002 Jan; 1594(1):127-35. doi:
10.1016/s0167-4838(01)00296-5. [PMID: 11825615] - Stefan U Ruepp, Robert P Tonge, Joanne Shaw, Nicola Wallis, François Pognan. Genomics and proteomics analysis of acetaminophen toxicity in mouse liver.
Toxicological sciences : an official journal of the Society of Toxicology.
2002 Jan; 65(1):135-50. doi:
10.1093/toxsci/65.1.135. [PMID: 11752693] - Y Li, G W Dai, Y Li, G T Liu. [Effect of bicyclol on acetaminophen-induced hepatotoxicity: energetic metabolism and mitochondrial injury in acetaminophen-intoxicated mice].
Yao xue xue bao = Acta pharmaceutica Sinica.
2001 Oct; 36(10):723-6. doi:
". [PMID: 12579967] - P J Ferret, R Hammoud, M Tulliez, A Tran, H Trébéden, P Jaffray, B Malassagne, Y Calmus, B Weill, F Batteux. Detoxification of reactive oxygen species by a nonpeptidyl mimic of superoxide dismutase cures acetaminophen-induced acute liver failure in the mouse.
Hepatology (Baltimore, Md.).
2001 May; 33(5):1173-80. doi:
10.1053/jhep.2001.24267. [PMID: 11343246] - A Tran, J M Tréluyer, E Rey, J Barbet, G Ferracci, P d'Athis, J Vincent, G Pons. Protective effect of stiripentol on acetaminophen-induced hepatotoxicity in rat.
Toxicology and applied pharmacology.
2001 Feb; 170(3):145-52. doi:
10.1006/taap.2000.9091. [PMID: 11162779] - J F Sinclair, J G Szakacs, S G Wood, H S Walton, J L Bement, F J Gonzalez, E H Jeffery, S A Wrighton, W J Bement, P R Sinclair. Short-term treatment with alcohols causes hepatic steatosis and enhances acetaminophen hepatotoxicity in Cyp2e1(-/-) mice.
Toxicology and applied pharmacology.
2000 Oct; 168(2):114-22. doi:
10.1006/taap.2000.9023. [PMID: 11032766] - M Hojo, K Hanioka, M Miyata, Y Yamazoe. Hepatotoxicity of acetaminophen and N-acetyl-p-benzoquinone imine and enhancement by fructose.
Xenobiotica; the fate of foreign compounds in biological systems.
2000 Sep; 30(9):933-41. doi:
10.1080/004982500433345. [PMID: 11055270] - K E Thummel, J T Slattery, H Ro, J Y Chien, S D Nelson, K E Lown, P B Watkins. Ethanol and production of the hepatotoxic metabolite of acetaminophen in healthy adults.
Clinical pharmacology and therapeutics.
2000 Jun; 67(6):591-9. doi:
10.1067/mcp.2000.106574. [PMID: 10872641] - P T Manyike, E D Kharasch, T F Kalhorn, J T Slattery. Contribution of CYP2E1 and CYP3A to acetaminophen reactive metabolite formation.
Clinical pharmacology and therapeutics.
2000 Mar; 67(3):275-82. doi:
10.1067/mcp.2000.104736. [PMID: 10741631] - P McCloskey, R J Edwards, R Tootle, C Selden, E Roberts, H J Hodgson. Resistance of three immortalized human hepatocyte cell lines to acetaminophen and N-acetyl-p-benzoquinoneimine toxicity.
Journal of hepatology.
1999 Nov; 31(5):841-51. doi:
10.1016/s0168-8278(99)80285-2. [PMID: 10580581] - J A Lawson, M A Fisher, C A Simmons, A Farhood, H Jaeschke. Inhibition of Fas receptor (CD95)-induced hepatic caspase activation and apoptosis by acetaminophen in mice.
Toxicology and applied pharmacology.
1999 May; 156(3):179-86. doi:
10.1006/taap.1999.8635. [PMID: 10222310] - O Mirochnitchenko, M Weisbrot-Lefkowitz, K Reuhl, L Chen, C Yang, M Inouye. Acetaminophen toxicity. Opposite effects of two forms of glutathione peroxidase.
The Journal of biological chemistry.
1999 Apr; 274(15):10349-55. doi:
10.1074/jbc.274.15.10349. [PMID: 10187823] - C Zhao, H Shichi. Prevention of acetaminophen-induced cataract by a combination of diallyl disulfide and N-acetylcysteine.
Journal of ocular pharmacology and therapeutics : the official journal of the Association for Ocular Pharmacology and Therapeutics.
1998 Aug; 14(4):345-55. doi:
10.1089/jop.1998.14.345. [PMID: 9715438] - M C Lin, E J Wang, C Patten, M J Lee, F Xiao, K R Reuhl, C S Yang. Protective effect of diallyl sulfone against acetaminophen-induced hepatotoxicity in mice.
Journal of biochemical toxicology.
1996; 11(1):11-20. doi:
10.1002/(sici)1522-7146(1996)11:1<11::aid-jbt2>3.0.co;2-y. [PMID: 8806047] - F M Fouad, F Shahidi, O A Mamer. Comparison of thermally oxidized lipids and acetaminophen with concurrent consumption of ethanol as inducers of liver cirrhosis.
Journal of toxicology and environmental health.
1995 Oct; 46(2):217-32. doi:
10.1080/15287399509532030. [PMID: 7563219] - Q J Li, J G Bessems, J N Commandeur, B Adams, N P Vermeulen. Mechanism of protection of ebselen against paracetamol-induced toxicity in rat hepatocytes.
Biochemical pharmacology.
1994 Oct; 48(8):1631-40. doi:
10.1016/0006-2952(94)90208-9. [PMID: 7980628] - P Nasseri-Sina, D J Fawthrop, J Wilson, A R Boobis, D S Davies. Cytoprotection by iloprost against paracetamol-induced toxicity in hamster isolated hepatocytes.
British journal of pharmacology.
1992 Feb; 105(2):417-23. doi:
10.1111/j.1476-5381.1992.tb14268.x. [PMID: 1373102]