Acetylhydrazine (BioDeep_00000006497)

 

Secondary id: BioDeep_00001868005

human metabolite Endogenous blood metabolite


代谢物信息卡片


Acetylhydrazine, (e)-2-fumarate (1:1)

化学式: C2H6N2O (74.0480106)
中文名称: 乙酰肼
谱图信息: 最多检出来源 Viridiplantae(plant) 4.51%

分子结构信息

SMILES: CC(=O)NN
InChI: InChI=1S/C2H6N2O/c1-2(5)4-3/h3H2,1H3,(H,4,5)

描述信息

The acetylhydrazine metabolite was found to be much less cytotoxic than hydrazine in this hepatocyte inflammation model. (PMID: 18295292) In the pathogenesis of isoniazid-induced hepatic injury, cytochrome P450-dependent metabolic activation of the metabolite, acetylhydrazine (AcHz), is the crucial step. (PMID: 8852701) The mechanism of action of acetylphosphabenzide is likely to involve the formation of acetylhydrazine, capable of producing active electrophiles attacking DNA. (PMID: 9589859)
D009676 - Noxae > D002273 - Carcinogens

同义名列表

16 个代谢物同义名

Acetylhydrazine, (e)-2-fumarate (1:1); Acetylhydrazine monohydrochloride; Ethanehydrazonic acid; Acetic acid hydrazide; Monoacetyl hydrazine; Monoacetylhydrazine; Ethanehydrazonate; N-Acetylhydrazine; Acetate hydrazide; Acetyl hydrazide; Acetic hydrazide; Acetylhydrazine; Acetylhydrazide; acetohydrazide; Acethydrazide; Acethydrazine



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

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)

2 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

  • Mahmoud F Ismail, Amira A El-Sayed, Eslam M Hosni, Aya I Hassaballah. Synthesis and evaluation of larvicidal efficacy against C. pipiens of some new heterocyclic compounds emanated from 2-cyano-N'-(2-(2,4-dichlorophenoxy)acetyl)acetohydrazide. Chemistry & biodiversity. 2024 Feb; 21(2):e202301560. doi: 10.1002/cbdv.202301560. [PMID: 38251927]
  • Suhail Razak, Tayyaba Afsar, Nousheen Bibi, Mahmoud Abulmeaty, Mashooq Ahmad Bhat, Anam Inam, Janeen H Trembley, Ali Almajwal, Maria Shabbir, Nawaf W Alruwaili, Abdulrahman Algarni. Sulindac acetohydrazide derivative attenuates against cisplatin induced organ damage by modulation of antioxidant and inflammatory signaling pathways. Scientific reports. 2022 07; 12(1):11749. doi: 10.1038/s41598-022-15950-9. [PMID: 35817806]
  • Xiaobin Wang, Mengqi Wang, Ling Han, Fei Jin, Jian Jiao, Min Chen, Chunlong Yang, Wei Xue. Novel Pyrazole-4-acetohydrazide Derivatives Potentially Targeting Fungal Succinate Dehydrogenase: Design, Synthesis, Three-Dimensional Quantitative Structure-Activity Relationship, and Molecular Docking. Journal of agricultural and food chemistry. 2021 Aug; 69(33):9557-9570. doi: 10.1021/acs.jafc.1c03399. [PMID: 34382800]
  • Fouzia Naz, Kanwal, Mehreen Latif, Uzma Salar, Khalid Mohammed Khan, Mariya Al-Rashida, Irfan Ali, Basharat Ali, Muhammad Taha, Shahnaz Perveen. 4-Oxycoumarinyl linked acetohydrazide Schiff bases as potent urease inhibitors. Bioorganic chemistry. 2020 12; 105(?):104365. doi: 10.1016/j.bioorg.2020.104365. [PMID: 33091669]
  • Tanveer A Wani, Ahmed H Bakheit, Seema Zargar, Mashooq A Bhat, Abdulrahman A Al-Majed. Molecular docking and experimental investigation of new indole derivative cyclooxygenase inhibitor to probe its binding mechanism with bovine serum albumin. Bioorganic chemistry. 2019 08; 89(?):103010. doi: 10.1016/j.bioorg.2019.103010. [PMID: 31132602]
  • Raghu Ramanathan, Karthikeyan Sivanesan. Investigations on the Influence of Zidovudine in the Pharmacokinetics of Isoniazid and Its Hepatotoxic Metabolites in Rats. Journal of pharmacy practice. 2019 Feb; 32(1):9-18. doi: 10.1177/0897190017735424. [PMID: 29017426]
  • Lu Song, Dan Gao, Shangfu Li, Yanwei Wang, Hongxia Liu, Yuyang Jiang. Simultaneous quantitation of hydrazine and acetylhydrazine in human plasma by high performance liquid chromatography-tandem mass spectrometry after derivatization with p-tolualdehyde. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2017 Sep; 1063(?):189-195. doi: 10.1016/j.jchromb.2017.08.036. [PMID: 28881295]
  • Getnet Yimer, Nobuhisa Ueda, Abiy Habtewold, Wondwossen Amogne, Akira Suda, Klaus-Dieter Riedel, Jürgen Burhenne, Getachew Aderaye, Lars Lindquist, Eyasu Makonnen, Eleni Aklillu. Pharmacogenetic & pharmacokinetic biomarker for efavirenz based ARV and rifampicin based anti-TB drug induced liver injury in TB-HIV infected patients. PloS one. 2011; 6(12):e27810. doi: 10.1371/journal.pone.0027810. [PMID: 22162992]
  • A H M Viswanatha Swamy, Rucha V Kulkarni, A H M Thippeswamy, B C Koti, Aparna Gore. Evaluation of hepatoprotective activity of Cissus quadrangularis stem extract against isoniazid-induced liver damage in rats. Indian journal of pharmacology. 2010 Dec; 42(6):397-400. doi: 10.4103/0253-7613.71920. [PMID: 21189914]
  • Masaaki Toyoda, Hisashi Narimatsu, Akihiko Kameyama. Enrichment method of sulfated glycopeptides by a sulfate emerging and ion exchange chromatography. Analytical chemistry. 2009 Aug; 81(15):6140-7. doi: 10.1021/ac900592t. [PMID: 19572564]
  • Mary E Bollard, Hector C Keun, Olaf Beckonert, Tim M D Ebbels, Henrik Antti, Andrew W Nicholls, John P Shockcor, Glenn H Cantor, Greg Stevens, John C Lindon, Elaine Holmes, Jeremy K Nicholson. Comparative metabonomics of differential hydrazine toxicity in the rat and mouse. Toxicology and applied pharmacology. 2005 Apr; 204(2):135-51. doi: 10.1016/j.taap.2004.06.031. [PMID: 15808519]
  • Victoria E Richards, Binh Chau, M Randy White, Charlene A McQueen. Hepatic gene expression and lipid homeostasis in C57BL/6 mice exposed to hydrazine or acetylhydrazine. Toxicological sciences : an official journal of the Society of Toxicology. 2004 Nov; 82(1):318-32. doi: 10.1093/toxsci/kfh232. [PMID: 15282401]
  • Abbas Afkhami, Ali Reza Zarei. Simultaneous kinetic-spectrophotometric determination of hydrazine and acetylhydrazine in micellar media using the H-point standard addition method. Analytical sciences : the international journal of the Japan Society for Analytical Chemistry. 2004 Aug; 20(8):1199-203. doi: 10.2116/analsci.20.1199. [PMID: 15352511]
  • Micaela Zonta, Annalisa Sebelin, Sara Gobbo, Tommaso Fellin, Tullio Pozzan, Giorgio Carmignoto. Glutamate-mediated cytosolic calcium oscillations regulate a pulsatile prostaglandin release from cultured rat astrocytes. The Journal of physiology. 2003 Dec; 553(Pt 2):407-14. doi: 10.1113/jphysiol.2003.046706. [PMID: 14500777]
  • Grazia Tamma, Burkhard Wiesner, Jens Furkert, Daniel Hahm, Alexander Oksche, Michael Schaefer, Giovanna Valenti, Walter Rosenthal, Enno Klussmann. The prostaglandin E2 analogue sulprostone antagonizes vasopressin-induced antidiuresis through activation of Rho. Journal of cell science. 2003 Aug; 116(Pt 16):3285-94. doi: 10.1242/jcs.00640. [PMID: 12829746]
  • A Walubo, P Smith, P I Folb. The role of oxygen free radicals in isoniazid-induced hepatotoxicity. Methods and findings in experimental and clinical pharmacology. 1998 Oct; 20(8):649-55. doi: 10.1358/mf.1998.20.8.487491. [PMID: 9922980]
  • T C Sarich, M Youssefi, T Zhou, S P Adams, R A Wall, J M Wright. Role of hydrazine in the mechanism of isoniazid hepatotoxicity in rabbits. Archives of toxicology. 1996; 70(12):835-40. doi: 10.1007/s002040050347. [PMID: 8911642]
  • R L Zhang, Z Y Wang, D Li, W B Cheng. Effects of rifampicin on pharmacokinetics of isoniazid and its metabolite acetylhydrazine in rats. Zhongguo yao li xue bao = Acta pharmacologica Sinica. 1992 Nov; 13(6):494-6. doi: . [PMID: 1302435]
  • N E Preece, S Forrow, S Ghatineh, G J Langley, J A Timbrell. Determination of hydrazine in biofluids by capillary gas chromatography with nitrogen-sensitive or mass spectrometric detection. Journal of chromatography. 1992 Jan; 573(2):227-34. doi: 10.1016/0378-4347(92)80123-8. [PMID: 1601955]
  • N E Preece, J K Nicholson, J A Timbrell. Identification of novel hydrazine metabolites by 15N-NMR. Biochemical pharmacology. 1991 May; 41(9):1319-24. doi: 10.1016/0006-2952(91)90103-c. [PMID: 2018564]
  • E Peretti, G Karlaganis, B H Lauterburg. Acetylation of acetylhydrazine, the toxic metabolite of isoniazid, in humans. Inhibition by concomitant administration of isoniazid. The Journal of pharmacology and experimental therapeutics. 1987 Nov; 243(2):686-9. doi: . [PMID: 3681700]
  • G Karlaganis, E Peretti, B H Lauterburg. Analysis of isoniazid, acetylhydrazine and [15N2]acetylhydrazine in serum by capillary gas chromatography-ammonia chemical ionization mass spectrometry. Journal of chromatography. 1987 Sep; 420(1):171-7. doi: 10.1016/0378-4347(87)80169-x. [PMID: 3667818]
  • P J Jenner, G A Ellard. Determination of the isoniazid metabolite monoacetylhydrazine in urine by high-performance liquid chromatography. Journal of chromatography. 1987 Mar; 415(1):188-96. doi: 10.1016/s0378-4347(00)83209-0. [PMID: 3584356]
  • B H Lauterburg, C V Smith, E L Todd, J R Mitchell. Pharmacokinetics of the toxic hydrazino metabolites formed from isoniazid in humans. The Journal of pharmacology and experimental therapeutics. 1985 Dec; 235(3):566-70. doi: NULL. [PMID: 4078724]
  • B H Lauterburg, C V Smith, E L Todd, J R Mitchell. Oxidation of hydrazine metabolites formed from isoniazid. Clinical pharmacology and therapeutics. 1985 Nov; 38(5):566-71. doi: 10.1038/clpt.1985.225. [PMID: 3931954]
  • J A Timbrell, B K Park, S J Harland. A study of the effects of rifampicin on isoniazid metabolism in human volunteer subjects. Human toxicology. 1985 May; 4(3):279-85. doi: 10.1177/096032718500400308. [PMID: 4007891]
  • E B Bhalerao, S V Bhide. Levels of acetyl hydrazines and rate of acetylation of isoniazid in adult tuberculosis patients. Indian journal of physiology and pharmacology. 1985 Apr; 29(2):83-8. doi: NULL. [PMID: 4093196]
  • W von Sassen, M Castro-Parra, E Musch, M Eichelbaum. Determination of isoniazid, acetylisoniazid, acetylhydrazine and diacetylhydrazine in biological fluids by high-performance liquid chromatography. Journal of chromatography. 1985 Feb; 338(1):113-22. doi: 10.1016/0378-4347(85)80075-x. [PMID: 4019638]
  • J A Timbrell, J M Wright. Urinary metabolic profile of isoniazid in patients who develop isoniazid-related liver damage. Human toxicology. 1984 Dec; 3(6):485-95. doi: 10.1177/096032718400300603. [PMID: 6526396]
  • Y Kaneo, S Iguchi, H Kubo, N Iwagiri, K Matsuyama. Tissue distribution of hydrazine and its metabolites in rats. Journal of pharmacobio-dynamics. 1984 Aug; 7(8):556-62. doi: 10.1248/bpb1978.7.556. [PMID: 6512678]
  • B H Thomas, L W Whitehouse, W Zeitz. Metabolism of [14C]acetylisoniazid and [14C]acetylhydrazine by the rat and rabbit. Fundamental and applied toxicology : official journal of the Society of Toxicology. 1984 Aug; 4(4):646-53. doi: . [PMID: 6479511]
  • T L Perry, J M Wright, S Hansen, S M Thomas, B M Allan, P A Baird, P A Diewold. A double-blind clinical trial of isoniazid in Huntington disease. Neurology. 1982 Apr; 32(4):354-8. doi: 10.1212/wnl.32.4.354. [PMID: 6460947]
  • A DEFRANCESCHI, V ZAMBONI. Identification of two metabolites of isoniazid (isonicotinoylglycine and 1-isonicotinoyl-2-acetylhydrazine) by paper chromatography in rat urine. Biochimica et biophysica acta. 1954 Feb; 13(2):304-5. doi: 10.1016/0006-3002(54)90326-1. [PMID: 13140337]