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Chemical Compound Review

Acetanil     N-phenylethanamide

Synonyms: Phenalgin, Acetanilid, Antifebrin, Phenalgene, acetanilide, ...
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Disease relevance of Acetanilid


High impact information on Acetanilid

  • Urine samples were collected before and after work (i.e., pre-shift and post-shift, respectively) and stored at -70 degrees C. Base hydrolysis was used to convert acetanilide and N-acetyl-o-toluidine, metabolites of aniline and o-toluidine present in the urine, to the parent compounds [5].
  • Enzymatic analysis of the cell homogenates in vitro and of the dividing cells in situ showed very high acetanilide hydroxylase activity and very low aryl hydrocarbon hydroxylase activity, a diagnostic feature of the cytochrome P3-450 [6].
  • The antibody inhibits microsomal acetanilide hydroxylation (80%) [7].
  • When reconstituted, this cytochrome catalyzes acetanilide hydroxylation at a higher rate than microsomes or the minor fraction [7].
  • Reaction thermodynamics have been calculated for an oxene model for cytochrome P-450 oxidations of four related arylamines: aniline, p-hydroxyaniline, acetanilide, and acetaminophen, by both radical and nonradical mechanisms, using a semiempirical molecular orbital method (modified neglect of differential overlap) [8].

Chemical compound and disease context of Acetanilid


Biological context of Acetanilid


Anatomical context of Acetanilid


Associations of Acetanilid with other chemical compounds


Gene context of Acetanilid

  • CYP1A2 was more active than CYP1A1 for acetanilide hydroxylation and activation of aflatoxin B1 (AFB1) [28].
  • In contrast, hydroxylated flavonoids increased the 7-methoxyresorufin O-demethylation and acetanilide 4-hydroxylation activities of cDNA-expressed human CYP1A2 and in human liver microsomes [29].
  • The Ah locus in the C57BL/6N mouse regulates at least two cytochrome P-450 gene products, termed in the mouse P1-450 and P3-450; these two enzymes are so named because each is responsible for the highest turnover number for the substrates benzo[a]pyrene and acetanilide, respectively [30].
  • The strain AI3 is able to use acetanilide as a carbon source through a mutation (T103I) in the amiE gene that encodes an aliphatic amidase (EC [31].
  • Hepatic receptor levels, beta-naphthoflavone-inducible and control aryl hydrocarbon hydroxylase (EC and acetanilide 4-hydroxylase activities and total P-450 content were studied in the Sprague-Dawley rat, C57BL/6N mouse, New Zealand White rabbit and Sigmoden hispedis (cotton rat) as a function of age [32].

Analytical, diagnostic and therapeutic context of Acetanilid


  1. Pseudomonas aeruginosa mutants resistant to urea inhibition of growth on acetanilide. Gregoriou, M., Brown, P.R., Tata, R. J. Bacteriol. (1977) [Pubmed]
  2. Acetanilide pharmacokinetics in kwashiorkor. Buchanan, N., Davis, M.D., Henderson, D.B., Mucklow, J.C., Rawlins, M.D. British journal of clinical pharmacology. (1980) [Pubmed]
  3. The acute effects of ethanol on acetanilide disposition in normal subjects, and in patients with liver disease. McKay, J., Rawlings, M.D., Cobden, I., James, O.F. British journal of clinical pharmacology. (1982) [Pubmed]
  4. Research strategies for design and development of NSAIDs: clue to balance potency and toxicity of acetanilide compounds. Pal, A.K., Sen, S., Ghosh, S., Bera, A.K., Bhattacharya, S., Chakraborty, S., Banerjee, A. J. Biomol. Struct. Dyn. (2001) [Pubmed]
  5. Monitoring of aromatic amine exposures in workers at a chemical plant with a known bladder cancer excess. Ward, E.M., Sabbioni, G., DeBord, D.G., Teass, A.W., Brown, K.K., Talaska, G.G., Roberts, D.R., Ruder, A.M., Streicher, R.P. J. Natl. Cancer Inst. (1996) [Pubmed]
  6. Transduction of cytochrome P3-450 by retroviruses: constitutive expression of enzymatically active microsomal hemoprotein in animal cells. Battula, N. J. Biol. Chem. (1989) [Pubmed]
  7. Resolution of two forms of cytochrome P-450 from liver microsomes of rabbit treated with 2,3,7,8-tetrachlorodibenzo-p-dioxin. Johnson, E.F., Muller-Eberhard, U. J. Biol. Chem. (1977) [Pubmed]
  8. Metabolic activation and toxicity of acetaminophen and related analogs. A theoretical study. Loew, G.H., Goldblum, A. Mol. Pharmacol. (1985) [Pubmed]
  9. Adaptation to phenylacetamide as a growth substrate by an acetanilide-utilizing mutant of Pseudomonas aeruginosa. Gregoriou, M., Brown, P.R. Arch. Microbiol. (1980) [Pubmed]
  10. Relationship between mutant amidases of Pseudomonas aeruginosa and hydroxyurea as an inhibitor. Brown, P.R., Gregoriou, M., Tata, R. Mol. Gen. Genet. (1978) [Pubmed]
  11. Studies on lethal concentrations and toxicity stress of some xenobiotics on aquatic organisms. Farah, M.A., Ateeq, B., Ali, M.N., Sabir, R., Ahmad, W. Chemosphere (2004) [Pubmed]
  12. Quantitative analysis of rat activity in the home cage by infrared monitoring. Application to the acute toxicity testing of acetanilide and phenylmercuric acetate. Tamborini, P., Sigg, H., Zbinden, G. Arch. Toxicol. (1989) [Pubmed]
  13. Antipyretic therapy. Botting, R. Front. Biosci. (2004) [Pubmed]
  14. In vitro studies on the deacetylation-reacetylation of arylamides and the transacetylation of arylamines by human and rat whole blood. Lindsay, R.M., Fox, W.R., Baty, J.D., Willis, R.G. Biochem. Pharmacol. (1991) [Pubmed]
  15. Kinetic analysis of maize glutathione S-transferase I catalysing the detoxification from chloroacetanilide herbicides. Labrou, N.E., Karavangeli, M., Tsaftaris, A., Clonis, Y.D. Planta (2005) [Pubmed]
  16. In vivo hydroxylation of 3H-acetanilide--evaluation of a new radiospirometric method in the rat. Toutoungi, M., Bieri, H.U., Huguenin, P., Karlaganis, G., Zeng, T.T., Bircher, J. Biochem. Pharmacol. (1983) [Pubmed]
  17. Metabolic activation routes of arylamines and their genotoxic effects. Meerman, J.H., van de Poll, M.L. Environ. Health Perspect. (1994) [Pubmed]
  18. "Oxidative stress" response in liver of an untreated newborn mouse having a 1.2-centimorgan deletion on chromosome 7. Liang, H.C., Shertzer, H.G., Nebert, D.W. Biochem. Biophys. Res. Commun. (1992) [Pubmed]
  19. Comparison of aryl hydrocarbon hydroxylase and acetanilide 4-hydroxylase induction by polycyclic aromatic compounds in human and mouse cell lines. Jaiswal, A.K., Nebert, D.W., Eisen, H.W. Biochem. Pharmacol. (1985) [Pubmed]
  20. Changes in carboxylesterase isoenzymes of rat liver microsomes during hepatocarcinogenesis. Maki, T., Hosokawa, M., Satoh, T., Sato, K. Jpn. J. Cancer Res. (1991) [Pubmed]
  21. Cloning and sequencing of rat liver carboxylesterase ES-3 (egasyn). Robbi, M., Beaufay, H. Biochem. Biophys. Res. Commun. (1994) [Pubmed]
  22. The localization and some properties of the N-deacetylase of Ascaris lumbricoides var suum. Douch, P.G., Gahagan, H.M. Xenobiotica (1977) [Pubmed]
  23. Alterations in drug metabolising enzymes and lipid peroxidation in different rat tissues by fluoride. Soni, M.G., Kachole, M.S., Pawar, S.S. Toxicol. Lett. (1984) [Pubmed]
  24. Immunochemical analysis of a cytochrome P-450IA1 homologue in human lung microsomes. Wheeler, C.W., Park, S.S., Guenthner, T.M. Mol. Pharmacol. (1990) [Pubmed]
  25. Substrate specificity of the form of cytochrome P-450 catalyzing the 4-hydroxylation of debrisoquine in man. Boobis, A.R., Murray, S., Kahn, G.C., Robertz, G.M., Davies, D.S. Mol. Pharmacol. (1983) [Pubmed]
  26. Hydrolysis of ester- and amide-type drugs by the purified isoenzymes of nonspecific carboxylesterase from rat liver. Mentlein, R., Heymann, E. Biochem. Pharmacol. (1984) [Pubmed]
  27. Effect of isoniazid administration on selected rat and mouse hepatic microsomal mixed-function oxidases and in vitro [14C]acetylhydrazine-derived covalent binding. Powell-Jackson, P.R., Tredger, J.M., Smith, H.M., Davis, M., Williams, R. Biochem. Pharmacol. (1982) [Pubmed]
  28. Development of a human lymphoblastoid cell line constitutively expressing human CYP1A1 cDNA: substrate specificity with model substrates and promutagens. Penman, B.W., Chen, L., Gelboin, H.V., Gonzalez, F.J., Crespi, C.L. Carcinogenesis (1994) [Pubmed]
  29. Isozyme- and species-specific susceptibility of cDNA-expressed CYP1A P-450s to different flavonoids. Tsyrlov, I.B., Mikhailenko, V.M., Gelboin, H.V. Biochim. Biophys. Acta (1994) [Pubmed]
  30. Regulation of mouse cytochrome P3-450 by the Ah receptor. Studies with a P3-450 cDNA clone. Tukey, R.H., Nebert, D.W. Biochemistry (1984) [Pubmed]
  31. Substitutions of Thr-103-Ile and Trp-138-Gly in amidase from Pseudomonas aeruginosa are responsible for altered kinetic properties and enzyme instability. Karmali, A., Pacheco, R., Tata, R., Brown, P. Mol. Biotechnol. (2001) [Pubmed]
  32. Ontogenetic expression of regulatory and structural gene products associated with the Ah locus. Comparison of rat, mouse, rabbit and Sigmoden hispedis. Kahl, G.F., Friederici, D.E., Bigelow, S.W., Okey, A.B., Nebert, D.W. Developmental pharmacology and therapeutics. (1980) [Pubmed]
  33. Acetanilides: effects on invertebrate neurons correlated with analgesic activity in vertebrates. Barker, J.L., Levitan, H. J. Pharmacol. Exp. Ther. (1975) [Pubmed]
  34. Debenzoylating and deacetylating activities of rat liver and mammary gland microsomes. Effect of ovariectomy. Ritter, C.L., Malejka-Giganti, D. Biochem. Pharmacol. (1995) [Pubmed]
  35. Separation of acetanilide and its hydroxylated metabolites and quantitative determination of "acetanilide 4-hydroxylase activity" by high-pressure liquid chromatography. Guenthner, T.M., Negishi, M., Nebert, D.W. Anal. Biochem. (1979) [Pubmed]
  36. Clastogenicity of pentachlorophenol, 2,4-D and butachlor evaluated by Allium root tip test. Ateeq, B., Abul Farah, M., Niamat Ali, M., Ahmad, W. Mutat. Res. (2002) [Pubmed]
  37. Selective induction of xenobiotic metabolizing esterases/amidases of liver by methaqualone consumption. Kaur, S., Ali, B. Toxicol. Appl. Pharmacol. (1983) [Pubmed]
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