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Chemical Compound Review

Acephen     N-(4-hydroxyphenyl)ethanamide

Synonyms: Acetaco, Panadol, Tylenol, Acamol, Algotropyl, ...
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Disease relevance of Tylenol


Psychiatry related information on Tylenol


High impact information on Tylenol


Chemical compound and disease context of Tylenol


Biological context of Tylenol


Anatomical context of Tylenol


Associations of Tylenol with other chemical compounds


Gene context of Tylenol

  • One potential target of JNK is Bax translocation, which was enhanced by APAP and blocked by the JNK inhibitor [31].
  • COX-3, a cyclooxygenase-1 variant inhibited by acetaminophen and other analgesic/antipyretic drugs: cloning, structure, and expression [32].
  • Induction of an acetaminophen-sensitive cyclooxygenase with reduced sensitivity to nonsteroid antiinflammatory drugs [33].
  • CYP1A2 substrates include aflatoxin B1, acetaminophen, and a variety of environmental arylamines [34].
  • Protection against acetaminophen-induced liver injury and lethality by interleukin 10: role of inducible nitric oxide synthase [35].
  • We have identified a 2-signal requirement (Tlr9 and the Nalp3 inflammasome) for acetaminophen-induced hepatotoxicity and some potential therapeutic approaches [36].

Analytical, diagnostic and therapeutic context of Tylenol


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  2. Elevated brain concentrations of 1,4-benzodiazepines in fulminant hepatic failure. Basile, A.S., Hughes, R.D., Harrison, P.M., Murata, Y., Pannell, L., Jones, E.A., Williams, R., Skolnick, P. N. Engl. J. Med. (1991) [Pubmed]
  3. Acetaminophen toxicity in an urban county hospital. Schiødt, F.V., Rochling, F.A., Casey, D.L., Lee, W.M. N. Engl. J. Med. (1997) [Pubmed]
  4. Improvement by acetylcysteine of hemodynamics and oxygen transport in fulminant hepatic failure. Harrison, P.M., Wendon, J.A., Gimson, A.E., Alexander, G.J., Williams, R. N. Engl. J. Med. (1991) [Pubmed]
  5. Efficacy of oral N-acetylcysteine in the treatment of acetaminophen overdose. Analysis of the national multicenter study (1976 to 1985). Smilkstein, M.J., Knapp, G.L., Kulig, K.W., Rumack, B.H. N. Engl. J. Med. (1988) [Pubmed]
  6. Critical role of c-jun (NH2) terminal kinase in paracetamol- induced acute liver failure. Henderson, N.C., Pollock, K.J., Frew, J., Mackinnon, A.C., Flavell, R.A., Davis, R.J., Sethi, T., Simpson, K.J. Gut (2007) [Pubmed]
  7. Chronic excessive acetaminophen use and liver damage. Barker, J.D., de Carle, D.J., Anuras, S. Ann. Intern. Med. (1977) [Pubmed]
  8. Acute versus chronic alcohol consumption in acetaminophen-induced hepatotoxicity. Schmidt, L.E., Dalhoff, K., Poulsen, H.E. Hepatology (2002) [Pubmed]
  9. An improved model of acetaminophen-induced fulminant hepatic failure in dogs. Kelly, J.H., Koussayer, T., He, D.E., Chong, M.G., Shang, T.A., Whisennand, H.H., Sussman, N.L. Hepatology (1992) [Pubmed]
  10. Aspirin and nonsteroidal anti-inflammatory drug use and the risk of subsequent colorectal cancer. Peleg, I.I., Maibach, H.T., Brown, S.H., Wilcox, C.M. Arch. Intern. Med. (1994) [Pubmed]
  11. Acetaminophen sulfation in patients with Parkinson's disease or Huntington's disease is not impaired. Roos, R.A., Steenvoorden, J.M., Mulder, G.J., Van Kempen, G.M. Neurology (1993) [Pubmed]
  12. Acetaminophen, aspirin, and chronic renal failure. Fored, C.M., Ejerblad, E., Lindblad, P., Fryzek, J.P., Dickman, P.W., Signorello, L.B., Lipworth, L., Elinder, C.G., Blot, W.J., McLaughlin, J.K., Zack, M.M., Nyrén, O. N. Engl. J. Med. (2001) [Pubmed]
  13. Acetaminophen toxicity in an urban county hospital. Avorn, J. N. Engl. J. Med. (1998) [Pubmed]
  14. Effect on the duration of mechanical ventilation of identifying patients capable of breathing spontaneously. Ely, E.W., Baker, A.M., Dunagan, D.P., Burke, H.L., Smith, A.C., Kelly, P.T., Johnson, M.M., Browder, R.W., Bowton, D.L., Haponik, E.F. N. Engl. J. Med. (1996) [Pubmed]
  15. Risk of kidney failure associated with the use of acetaminophen, aspirin, and nonsteroidal antiinflammatory drugs. Perneger, T.V., Whelton, P.K., Klag, M.J. N. Engl. J. Med. (1994) [Pubmed]
  16. The treatment of acetaminophen poisoning. Prescott, L.F., Critchley, J.A. Annu. Rev. Pharmacol. Toxicol. (1983) [Pubmed]
  17. Migraine relief with acetaminophen, aspirin, and caffeine: abstract and commentary. Smith, R. JAMA (1998) [Pubmed]
  18. Selective inhibition of acetaminophen oxidation and toxicity by cimetidine and other histamine H2-receptor antagonists in vivo and in vitro in the rat and in man. Mitchell, M.C., Schenker, S., Speeg, K.V. J. Clin. Invest. (1984) [Pubmed]
  19. Over-the-counter analgesics and risk of ovarian cancer. Cramer, D.W., Harlow, B.L., Titus-Ernstoff, L., Bohlke, K., Welch, W.R., Greenberg, E.R. Lancet (1998) [Pubmed]
  20. Acetaminophen: potentially toxic metabolite formed by human fetal and adult liver microsomes and isolated fetal liver cells. Rollins, D.E., von Bahr, C., Glaumann, H., Moldéus, P., Rane, A. Science (1979) [Pubmed]
  21. Potentiation of acetaminophen hepatotoxicity by alcohol. McClain, C.J., Kromhout, J.P., Peterson, F.J., Holtzman, J.L. JAMA (1980) [Pubmed]
  22. Acetaminophen overdose in the third trimester of pregnancy. Byer, A.J., Traylor, T.R., Semmer, J.R. JAMA (1982) [Pubmed]
  23. Protective effect of acetaminophen against aspirin- and ethanol-induced damage to the human gastric mucosa. Stern, A.I., Hogan, D.L., Kahn, L.H., Isenberg, J.I. Gastroenterology (1984) [Pubmed]
  24. Infection and the progression of hepatic encephalopathy in acute liver failure. Vaquero, J., Polson, J., Chung, C., Helenowski, I., Schiodt, F.V., Reisch, J., Lee, W.M., Blei, A.T. Gastroenterology (2003) [Pubmed]
  25. Innate immune system plays a critical role in determining the progression and severity of acetaminophen hepatotoxicity. Liu, Z.X., Govindarajan, S., Kaplowitz, N. Gastroenterology (2004) [Pubmed]
  26. Heavy phenacetin use and bladder cancer in women aged 20 to 49 years. Piper, J.M., Tonascia, J., Matanoski, G.M. N. Engl. J. Med. (1985) [Pubmed]
  27. An assessment of the safety of pediatric ibuprofen. A practitioner-based randomized clinical trial. Lesko, S.M., Mitchell, A.A. JAMA (1995) [Pubmed]
  28. Diflunisal. A new oral analgesic with an unusually long duration of action. Forbes, J.A., Beaver, W.T., White, E.H., White, R.W., Neilson, G.B., Shackleford, R.W. JAMA (1982) [Pubmed]
  29. Gastrointestinal blood loss. Effect of aspirin, fenoprofen, and acetaminophen in rheumatoid arthritis as determined by sequential gastroscopy and radioactive fecal markers. Loebl, D.H., Craig, R.M., Culic, D.D., Ridolfo, A.S., Falk, J., Schmid, F.R. JAMA (1977) [Pubmed]
  30. Disposition of acetaminophen at 4, 6, and 8 g/day for 3 days in healthy young adults. Gelotte, C.K., Auiler, J.F., Lynch, J.M., Temple, A.R., Slattery, J.T. Clin. Pharmacol. Ther. (2007) [Pubmed]
  31. c-Jun N-terminal kinase plays a major role in murine acetaminophen hepatotoxicity. Gunawan, B.K., Liu, Z.X., Han, D., Hanawa, N., Gaarde, W.A., Kaplowitz, N. Gastroenterology (2006) [Pubmed]
  32. COX-3, a cyclooxygenase-1 variant inhibited by acetaminophen and other analgesic/antipyretic drugs: cloning, structure, and expression. Chandrasekharan, N.V., Dai, H., Roos, K.L., Evanson, N.K., Tomsik, J., Elton, T.S., Simmons, D.L. Proc. Natl. Acad. Sci. U.S.A. (2002) [Pubmed]
  33. Induction of an acetaminophen-sensitive cyclooxygenase with reduced sensitivity to nonsteroid antiinflammatory drugs. Simmons, D.L., Botting, R.M., Robertson, P.M., Madsen, M.L., Vane, J.R. Proc. Natl. Acad. Sci. U.S.A. (1999) [Pubmed]
  34. Cyp1a2(-/-) null mutant mice develop normally but show deficient drug metabolism. Liang, H.C., Li, H., McKinnon, R.A., Duffy, J.J., Potter, S.S., Puga, A., Nebert, D.W. Proc. Natl. Acad. Sci. U.S.A. (1996) [Pubmed]
  35. Protection against acetaminophen-induced liver injury and lethality by interleukin 10: role of inducible nitric oxide synthase. Bourdi, M., Masubuchi, Y., Reilly, T.P., Amouzadeh, H.R., Martin, J.L., George, J.W., Shah, A.G., Pohl, L.R. Hepatology (2002) [Pubmed]
  36. Acetaminophen-induced hepatotoxicity in mice is dependent on Tlr9 and the Nalp3 inflammasome. Imaeda, A.B., Watanabe, A., Sohail, M.A., Mahmood, S., Mohamadnejad, M., Sutterwala, F.S., Flavell, R.A., Mehal, W.Z. J. Clin. Invest. (2009) [Pubmed]
  37. Drug therapy. Acetaminophen. Koch-Weser, J. N. Engl. J. Med. (1976) [Pubmed]
  38. Acetaminophen and other risk factors for excessive warfarin anticoagulation. Hylek, E.M., Heiman, H., Skates, S.J., Sheehan, M.A., Singer, D.E. JAMA (1998) [Pubmed]
  39. Massive hemolysis caused by acetaminophen. Positive determination by direct Coombs test. Manor, E., Marmor, A., Kaufman, S., Leiba, H. JAMA (1976) [Pubmed]
  40. Measurement of serum acetaminophen-protein adducts in patients with acute liver failure. Davern, T.J., James, L.P., Hinson, J.A., Polson, J., Larson, A.M., Fontana, R.J., Lalani, E., Munoz, S., Shakil, A.O., Lee, W.M. Gastroenterology (2006) [Pubmed]
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