N-Acetylarylamine (BioDeep_00000001437)

 

Secondary id: BioDeep_00000405741

human metabolite Endogenous


代谢物信息卡片


N-Acetylaminobenzene

化学式: C8H9NO (135.0684104)
中文名称: 乙酰苯胺-15N, N-乙酰苯胺
谱图信息: 最多检出来源 Homo sapiens(bile_acids) 1.25%

分子结构信息

SMILES: CC(=O)Nc(c1)cccc1
InChI: InChI=1S/C8H9NO/c1-7(10)9-8-5-3-2-4-6-8/h2-6H,1H3,(H,9,10)

描述信息

N-Acetylarylamine is an odourless solid chemical of leaf or flake-like appearance. It is also known as acetanilide, N-phenylacetamide, acetanil, or acetanilid, and was formerly known by the trade name Antifebrin. N-Acetylarylamine has analgesic and fever-reducing properties; it is in the same class of drugs as acetaminophen (paracetamol). Under the name acetanilid it formerly figured in the formula of a number of patent medicines and over the counter drugs. In 1948, Julius Axelrod and Bernard Brodie discovered that acetanilide is much more toxic in these applications than other drugs, causing methemoglobinemia and ultimately doing damage to the liver and kidneys. As such, acetanilide has largely been replaced by less toxic drugs, in particular acetaminophen, which is a metabolite of acetanilide and whose use Axelrod and Brodie suggested in the same study.
Acetanilide has analgesic and fever-reducing properties; it is in the same class of drugs as acetaminophen (paracetamol). Under the name acetanilid it formerly figured in the formula of a number of patent medicines and over the counter drugs. In 1948, Julius Axelrod and Bernard Brodie discovered that acetanilide is much more toxic in these applications than other drugs, causing methemoglobinemia and ultimately doing damage to the liver and kidneys. As such, acetanilide has largely been replaced by less toxic drugs, in particular acetaminophen, which is a metabolite of acetanilide and whose use Axelrod and Brodie suggested in the same study.
KEIO_ID A130

同义名列表

10 个代谢物同义名

N-Acetylaminobenzene; Acetic acid anilide; N-phenylacetamide; N-Acetylarylamine; Acetamidobenzene; Acetate anilide; acetanilide; Antifebrin; Acetanilid; Acetanil



数据库引用编号

27 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

2 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(2)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

5 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

  • Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
  • Tian Li, Zhi F Zhou, Ping Zhang, Kun Qian, Tian C Zhang. Enhancing nitrobenzene biodegradation in aquatic systems: Feasibility of using plain soil as an inoculant and effects of adding ascorbic acid and peptone. Chemosphere. 2020 Jan; 239(?):124806. doi: 10.1016/j.chemosphere.2019.124806. [PMID: 31726521]
  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
  • Chenxi Zhang, Liyuan Zhang, Runzhong Yu. Extraction and separation of acetanilide herbicides in beans based on metal-organic framework MIL-101 (Zn) as sorbent. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment. 2019 Nov; 36(11):1677-1687. doi: 10.1080/19440049.2019.1657966. [PMID: 31479387]
  • Jessica L Counihan, Megan Duckering, Esha Dalvie, Wan-Min Ku, Leslie A Bateman, Karl J Fisher, Daniel K Nomura. Chemoproteomic Profiling of Acetanilide Herbicides Reveals Their Role in Inhibiting Fatty Acid Oxidation. ACS chemical biology. 2017 03; 12(3):635-642. doi: 10.1021/acschembio.6b01001. [PMID: 28094496]
  • Georg Dierkes, Tobias Weiss, Hendrik Modick, Heiko Udo Käfferlein, Thomas Brüning, Holger M Koch. N-Acetyl-4-aminophenol (paracetamol), N-acetyl-2-aminophenol and acetanilide in urine samples from the general population, individuals exposed to aniline and paracetamol users. International journal of hygiene and environmental health. 2014 Apr; 217(4-5):592-9. doi: 10.1016/j.ijheh.2013.11.005. [PMID: 24370547]
  • Daniel J Warner, Hongming Chen, Louis-David Cantin, J Gerry Kenna, Simone Stahl, Clare L Walker, Tobias Noeske. Mitigating the inhibition of human bile salt export pump by drugs: opportunities provided by physicochemical property modulation, in silico modeling, and structural modification. Drug metabolism and disposition: the biological fate of chemicals. 2012 Dec; 40(12):2332-41. doi: 10.1124/dmd.112.047068. [PMID: 22961681]
  • Sumio Hirata. [Appropriate pharmacotherapy in patients with chronic kidney disease - new approach - ]. Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan. 2012; 132(4):461-70. doi: 10.1248/yakushi.132.461. [PMID: 22465923]
  • Xiaowei Shi, Zhi Zhou, Lingling Wang, Feng Yue, Mengqiang Wang, Chuanyan Yang, Linsheng Song. The immunomodulation of acetylcholinesterase in zhikong scallop Chlamys farreri. PloS one. 2012; 7(1):e30828. doi: 10.1371/journal.pone.0030828. [PMID: 22292052]
  • Yunlan Li, Zhuyan Gao, Pu Guo, Qingshan Li. Pharmacokinetic Study of Di-Phenyl-Di-(2,4-Difluobenzohydroxamato)Tin(IV): Novel Metal-Based Complex with Promising Antitumor Potential. Bioinorganic chemistry and applications. 2012; 2012(?):210682. doi: 10.1155/2012/210682. [PMID: 22400014]
  • Alan Wayne Jones. Early drug discovery and the rise of pharmaceutical chemistry. Drug testing and analysis. 2011 Jun; 3(6):337-44. doi: 10.1002/dta.301. [PMID: 21698778]
  • Deepika Gupta, Rajinder K Gupta. Bioprotective properties of Dragon's blood resin: in vitro evaluation of antioxidant activity and antimicrobial activity. BMC complementary and alternative medicine. 2011 Feb; 11(?):13. doi: 10.1186/1472-6882-11-13. [PMID: 21329518]
  • Wataru Tamura, Soichi Kojima, Ayako Toyokawa, Hideo Watanabe, Mayumi Tabuchi-Kobayashi, Toshihiko Hayakawa, Tomoyuki Yamaya. Disruption of a Novel NADH-Glutamate Synthase2 Gene Caused Marked Reduction in Spikelet Number of Rice. Frontiers in plant science. 2011; 2(?):57. doi: 10.3389/fpls.2011.00057. [PMID: 22645542]
  • Lei Ma, Jiangli Dong, Yongsheng Jin, Mingliang Chen, Xiaoye Shen, Tao Wang. RMDAP: a versatile, ready-to-use toolbox for multigene genetic transformation. PloS one. 2011; 6(5):e19883. doi: 10.1371/journal.pone.0019883. [PMID: 21603635]
  • 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]
  • Taigang Liang, Wenyan Yue, Qingshan Li. Comparison of the phenolic content and antioxidant activities of Apocynum venetum L. (Luo-Bu-Ma) and two of its alternative species. International journal of molecular sciences. 2010 Nov; 11(11):4452-64. doi: 10.3390/ijms11114452. [PMID: 21151449]
  • Barbara M Fischer, Heinrich Schatz, Mark Maraun. Community structure, trophic position and reproductive mode of soil and bark-living oribatid mites in an alpine grassland ecosystem. Experimental & applied acarology. 2010 Nov; 52(3):221-37. doi: 10.1007/s10493-010-9366-8. [PMID: 20490626]
  • Fars Alanazi. Pravastatin provides antioxidant activity and protection of erythrocytes loaded Primaquine. International journal of medical sciences. 2010 Oct; 7(6):358-65. doi: 10.7150/ijms.7.358. [PMID: 21060723]
  • Choimaa Dulamsuren, Markus Hauck, Mookhor Khishigjargal, Hanns Hubert Leuschner, Christoph Leuschner. Diverging climate trends in Mongolian taiga forests influence growth and regeneration of Larix sibirica. Oecologia. 2010 Aug; 163(4):1091-102. doi: 10.1007/s00442-010-1689-y. [PMID: 20571829]
  • Chia-Chuan Chang, Angela Fay Ku, Yun-Yu Tseng, Wen-Bin Yang, Jim-Min Fang, Chi-Huey Wong. 6,8-Di-C-glycosyl flavonoids from Dendrobium huoshanense. Journal of natural products. 2010 Feb; 73(2):229-32. doi: 10.1021/np900252f. [PMID: 20055483]
  • 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]
  • Mu Li, Lin-Chuan Liao, You-Yi Yan, Lin Yang, Xiao-Min Liu, Jin Dai, Xiao-Na Ma, Xin Sheng, Hong Huang, Gui Su. [Analysis of multiple cephalosporins in blood and urine by HPLC]. Fa yi xue za zhi. 2009 Dec; 25(6):437-9. doi: NULL. [PMID: 20225621]
  • Amanda C Spivak, Elizabeth A Canuel, J Emmett Duffy, J Paul Richardson. Nutrient enrichment and food web composition affect ecosystem metabolism in an experimental seagrass habitat. PloS one. 2009 Oct; 4(10):e7473. doi: 10.1371/journal.pone.0007473. [PMID: 19829713]
  • Yunlan Li, Jinjie Liu, Yong Li, Qingshan Li. Determination and pharmacokinetics of a new diorganotin(IV) complex dibutyldi(4-chlorobenzohydroxamato)tin(IV) in rat plasma by a high performance liquid chromatographic method. Analytical sciences : the international journal of the Japan Society for Analytical Chemistry. 2009 May; 25(5):699-703. doi: 10.2116/analsci.25.699. [PMID: 19430156]
  • Maité Lohmann, Stefan Scheu, Caroline Müller. Decomposers and root feeders interactively affect plant defence in Sinapis alba. Oecologia. 2009 May; 160(2):289-98. doi: 10.1007/s00442-009-1306-0. [PMID: 19252930]
  • A Messina, V Chirulli, P G Gervasi, V Longo. Purification, molecular cloning, heterologous expression and characterization of pig CYP1A2. Xenobiotica; the fate of foreign compounds in biological systems. 2008 Dec; 38(12):1453-70. doi: 10.1080/00498250802474437. [PMID: 18949657]
  • G Hendriks, D R A Uges, J P Franke. New practical algorithm for modelling analyte recovery in bioanalytical reversed phase and mixed-mode solid phase extraction. Journal of pharmaceutical and biomedical analysis. 2008 Sep; 48(1):158-70. doi: 10.1016/j.jpba.2008.05.005. [PMID: 18579329]
  • Venkatesan Radhika, Christian Kost, Stefan Bartram, Martin Heil, Wilhelm Boland. Testing the optimal defence hypothesis for two indirect defences: extrafloral nectar and volatile organic compounds. Planta. 2008 Aug; 228(3):449-57. doi: 10.1007/s00425-008-0749-6. [PMID: 18493790]
  • Eric L Kendig, Scott N Schneider, Deborah J Clegg, Mary Beth Genter, Howard G Shertzer. Over-the-counter analgesics normalize blood glucose and body composition in mice fed a high fat diet. Biochemical pharmacology. 2008 Jul; 76(2):216-24. doi: 10.1016/j.bcp.2008.05.001. [PMID: 18554574]
  • Jui-Hung Yen, Pi-Wen Tsai, Wen-Ching Chen, Yei-Shung Wang. Fate of anilide and aniline herbicides in plant-materials-amended soils. Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes. 2008 Jun; 43(5):382-9. doi: 10.1080/10934520701795582. [PMID: 18576218]
  • Vera Chirulli, Luigi Marvasi, Anna Zaghini, Roberto Fiorio, Vincenzo Longo, P Giovanni Gervasi. Inducibility of AhR-regulated CYP genes by beta-naphthoflavone in the liver, lung, kidney and heart of the pig. Toxicology. 2007 Oct; 240(1-2):25-37. doi: 10.1016/j.tox.2007.07.015. [PMID: 17804143]
  • K Brune, U Niederweis. [From willow bark to the coxibs. Development of antiphlogistic analgesics]. Schmerz (Berlin, Germany). 2007 Aug; 21(4):318, 320-8, 330. doi: 10.1007/s00482-007-0564-1. [PMID: 17674056]
  • Patrick Masson, Marie-Thérèse Froment, Sultan Darvesh, Lawrence M Schopfer, Oksana Lockridge. Aryl acylamidase activity of human serum albumin with o-nitrotrifluoroacetanilide as the substrate. Journal of enzyme inhibition and medicinal chemistry. 2007 Aug; 22(4):463-9. doi: 10.1080/14756360701383932. [PMID: 17847714]
  • N Vitelli, A Chiodini, C Colosio, G De Paschale, C Somaruga, R Turci, C Minoia, G Brambilla, A Colombi. [Occupational and environmental exposure to anilide and dicarboximide pesticides]. Giornale italiano di medicina del lavoro ed ergonomia. 2007 Jul; 29(3 Suppl):276-7. doi: . [PMID: 18409684]
  • F Karatas, A Cansiz, H Kara, M Karatepe, M Koparir. [Synthesis of two new acetanilide derivatives and their effect on the serum antioxidant vitamins (A, E, and C) and the MDA level in rats]. Bioorganicheskaia khimiia. 2005 Sep; 31(5):553-6. doi: 10.1007/s11171-005-0068-7. [PMID: 16245699]
  • Yumin Li, Guangtao Min, Qunji Xue, Liren Chen, Weimin Liu, Hao Chen. High-performance liquid chromatographic method for simultaneous determination of sophoridine and matrine in rat plasma. Biomedical chromatography : BMC. 2004 Nov; 18(9):619-24. doi: 10.1002/bmc.348. [PMID: 15484226]
  • Atmakuru Ramesh, Sinthalapadi Thulasiramaraja Maheswari. Dissipation of alachlor in cotton plant, soil and water and its bioaccumulation in fish. Chemosphere. 2004 Feb; 54(5):647-52. doi: 10.1016/j.chemosphere.2003.08.008. [PMID: 14599510]
  • S O Kachula, O O Pentiuk. [Effect of starvation and acetone on the enzyme systems of biotransformation and toxicity of xenobiotics--CYP2E1 substrates in rats]. Ukrains'kyi biokhimichnyi zhurnal (1999 ). 2004 Jan; 76(1):114-22. doi: . [PMID: 15909426]
  • Dong June Ahn, Eun-Hyuk Chae, Gil Sun Lee, Hee-Yong Shim, Tae-Eun Chang, Kwang-Duk Ahn, Jong-Man Kim. Colorimetric reversibility of polydiacetylene supramolecules having enhanced hydrogen-bonding under thermal and pH stimuli. Journal of the American Chemical Society. 2003 Jul; 125(30):8976-7. doi: 10.1021/ja0299001. [PMID: 15369329]
  • 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]
  • M Tugnait, E M Lenz, M Hofmann, M Spraul, I D Wilson, J C Lindon, J K Nicholson. The metabolism of 2-trifluormethylaniline and its acetanilide in the rat by 19F NMR monitored enzyme hydrolysis and 1H/19F HPLC-NMR spectroscopy. Journal of pharmaceutical and biomedical analysis. 2003 Jan; 30(5):1561-74. doi: 10.1016/s0731-7085(02)00546-0. [PMID: 12467928]
  • Noriko Takahashi, Toshihiro Ohba, Shin-ichi Togashi, Tetsuya Fukui. Biological activity of p-methylaminophenol, an essential structural component of N-(4-hydroxyphenyl)retinamide, fenretinide. Journal of biochemistry. 2002 Nov; 132(5):767-74. doi: 10.1093/oxfordjournals.jbchem.a003285. [PMID: 12417027]
  • M Tugnait, E M Lenz, P Phillips, M Hofmann, M Spraul, J C Lindon, J K Nicholson, I D Wilson. The metabolism of 4-trifluoromethoxyaniline and [13C]-4-trifluoromethoxyacetanilide in the rat: detection and identification of metabolites excreted in the urine by NMR and HPLC-NMR. Journal of pharmaceutical and biomedical analysis. 2002 Jun; 28(5):875-85. doi: 10.1016/s0731-7085(01)00699-9. [PMID: 12039629]
  • G B Scarfe, J K Nicholson, J C Lindon, I D Wilson, S Taylor, E Clayton, B Wright. Identification of the urinary metabolites of 4-bromoaniline and 4-bromo-[carbonyl-13C]-acetanilide in rat. Xenobiotica; the fate of foreign compounds in biological systems. 2002 Apr; 32(4):325-37. doi: 10.1080/00498250110079806. [PMID: 12028665]
  • Nancy J Thiex, Harold Manson, Shirley Andersson, Jan-Ake Persson. Determination of crude protein in animal feed, forage, grain, and oilseeds by using block digestion with a copper catalyst and steam distillation into boric acid: collaborative study. Journal of AOAC International. 2002 Mar; 85(2):309-17. doi: . [PMID: 11990013]
  • A Ménard, R Castonguay, C Lherbet, C Rivard, Y Roupioz, J W Keillor. Nonlinear free energy relationship in the general-acid-catalyzed acylation of rat kidney gamma-glutamyl transpeptidase by a series of gamma-glutamyl anilide substrate analogues. Biochemistry. 2001 Oct; 40(42):12678-85. doi: 10.1021/bi011234d. [PMID: 11601992]
  • A A Pentiuk, A P Petrovskaia, D V Dmitriev, E Iu Dmitrieva, A N Iavorskiĭ, A D Durnev. [Various mechanisms of the depriming effect of bacterial endotoxin on drug metabolism]. Eksperimental'naia i klinicheskaia farmakologiia. 2001 Sep; 64(5):56-9. doi: . [PMID: 11764504]
  • H Kowalska-Pyłka, B Majer-Dziedzic, A Niewiadomy, J Matysiak. Evaluation of the toxicity of substituted benzthioanilides by using in vitro tests. Alternatives to laboratory animals : ATLA. 2001 Sep; 29(5):547-56. doi: 10.1177/026119290102900508. [PMID: 11604098]
  • 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]
  • T Matsumoto, A Ohashi, N Ito, H Fujiwara, T Matsumoto. A long-term lifetime amperometric glucose sensor with a perfluorocarbon polymer coating. Biosensors & bioelectronics. 2001 Jun; 16(4-5):271-6. doi: 10.1016/s0956-5663(01)00139-7. [PMID: 11390214]
  • R A Scherrer, S M Howard. Use of distribution coefficients in quantitative structure-activity relationships. Journal of medicinal chemistry. 1977 Jan; 20(1):53-8. doi: 10.1021/jm00211a010. [PMID: 13215]
  • J L Cunningham, M J Leyland, I W Delamore, D A Evans. Acetanilide oxidation in phenylbutazone-associated hypoplastic anaemia. British medical journal. 1974 Aug; 3(5926):313-7. doi: 10.1136/bmj.3.5926.313. [PMID: 4411815]
  • B SCHNITZER, E B SMITH, A GOLDEN. THE EFFECTS OF PHENACETIN AND ITS CONTAMINANT ON THE KIDNEY OF THE RAT. The American journal of pathology. 1965 Jun; 46(?):917-27. doi: NULL. [PMID: 14328021]
  • M F VEST, R ROSSIER. DETOXIFICATION IN THE NEWBORN: THE ABILITY OF THE NEWBORN INFANT TO FORM CONJUGATES WITH GLUCURONIC ACID, GLYCINE, ACETATE AND GLUTATHIONE. Annals of the New York Academy of Sciences. 1963 Dec; 111(?):183-98. doi: 10.1111/j.1749-6632.1963.tb36958.x. [PMID: 14085842]
  • E LOZINSKI. THE COMPARATIVE PHARMACOLOGY. Applied therapeutics. 1963 Nov; 5(?):963-9. doi: NULL. [PMID: 14073464]
  • P CAREDDU, T APOLLONIO, L PICENI-SERENI, T MEREU. [Research on the urinary elimination of N-acetyl-p-aminophenol (NAPA) in newborn infants. II. Renal factors influencing the elimination of free NAPA and its conjugates]. Minerva pediatrica. 1962 Oct; 14(?):1047-9. doi: NULL. [PMID: 14018621]
  • A EISALO, S TALANTI. Observations on the effect of phenacetin and N-acetyl-p-aminophenol on rat kidneys. Acta medica Scandinavica. 1961 Jun; 169(?):655-60. doi: 10.1111/j.0954-6820.1961.tb07876.x. [PMID: 13726160]
  • P CAREDDU, T MEREU, T APOLLONIO. [Urinary elimination of N-acetyl-p-aminophenol after loading with acetanilid in the newborn infant]. Bollettino della Societa italiana di biologia sperimentale. 1961 Apr; 37(?):359-63. doi: NULL. [PMID: 13690750]
  • M F VEST, R R STREIFF. Studies on glucoronide formation in newborn infants and older children. Measurement of paminophenol glucuronide levels in the serum after an oral dose of acetanilid. A.M.A. journal of diseases of children. 1959 Dec; 98(?):688-93. doi: 10.1001/archpedi.1959.02070020690003. [PMID: 13841991]
  • J H WEIKEL. A comparison of human serum levels of acetylsalicylic acid, salicylamide and N-acetyl-p-aminophenol following oral administration. Journal of the American Pharmaceutical Association. American Pharmaceutical Association. 1958 Jul; 47(7):477-9. doi: 10.1002/jps.3030470705. [PMID: 13563248]
  • G CORTE, W JOHNSON. Effect of N-acetyl-para-aminophenol on plasma levels of 17-hydroxycorticosteroids. Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine (New York, N.Y.). 1958 Apr; 97(4):751-5. doi: 10.3181/00379727-97-23869. [PMID: 13554471]
  • P E CARLO, N M CAMBOSOS, G C FEENEY, P K SMITH. Plasma levels after the oral administration of acetylsalicylic acid and N-acetyl-p-aminophenol in different forms to human subjects. Journal of the American Pharmaceutical Association. American Pharmaceutical Association. 1955 Jul; 44(7):396-9. doi: 10.1002/jps.3030440703. [PMID: 13242422]
  • L A GREENBERG, D LESTER. The metabolic fate of acetanilid and other aniline derivatives; major metabolites of acetanilid appearing in the urine. The Journal of pharmacology and experimental therapeutics. 1946 Sep; 88(1):87-98. doi: NULL. [PMID: 20274530]