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Chemical Compound Review

Azetamid     ethanamide

Synonyms: acetamid, Ethanamid, acetamide, Ethanamide, acetoamide, ...
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Disease relevance of acetamide

  • 2-oxopyrollidine acetamide (piracetam) is said to protect the cerebral cortex against hypoxia [1].
  • Inducible expression of the aliphatic amidase operon in Pseudomonas aeruginosa is controlled by an antitermination mechanism which allows production of the full-length transcript only in the presence of small-molecule inducers, such as acetamide [2].
  • Long-term feeding of relatively high levels of acetamide produces liver cancer in rats [3].
  • We investigated whether increasing levels of tissue hypoxia, measured by the binding of EF5 [2-(2-nitro-1-H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl) acetamide] or by Eppendorf needle electrodes, were associated with tumor aggressiveness in patients with previously untreated glial brain tumors [4].
  • Two highly bioactive analogs, (+/-)-2-(3-dodecylisoxazol-5-yl)-2-phenyl-N-(2,4,6-trimethoxypheny l) acetamide (13a) and (+/-)-2-(5-dodecylisoxazol-3-yl)-2-phenyl-N-(2,4,6-trimethoxypheny l) acetamide (16a), were selected for further study and were found to be nontoxic in a guinea pig model of adrenal toxicity [5].

Psychiatry related information on acetamide

  • Therefore, we investigated the effects of nefiracetam (N-(2, 6-dimethyl-phenyl)-2(2-oxo-1-pyrrolidinyl) acetamide), which increases intracellular cAMP and Ca(2+) levels, on the development of morphine dependence and tolerance [6].
  • Oxiracetam (4-hydroxy-2-oxo-1-pyrrolidine acetamide) is a novel compound effective in improving learning and memory in normal animals as well as in animals with acute cerebral impairment induced by a variety of noxious stimuli (i.e., electroshock, neurodepressants, metabolic inhibitors, hypoxia) [7].
  • The effects of N-(2,6-dimethyl-phenyl)-2-(2-oxo-1-pyrrolidinyl) acetamide (DM-9384), a new pyrrolidone derivative, were investigated on ethanol- and chlordiazepoxide (CDP)-induced amnesia animal model using the passive avoidance task in comparison with aniracetam, another pyrrolidone derivative [8].
  • Low doses of the selective kappa agonist (+/-)-trans-U-50-trans-3,4-dichloro-N-methyl-N[2-(1-pyrrodinyl)-cyclohexyl]benzene acetamide methasulphonate (U50, 488) and bremazocine-HCl increased motor activity leading to C-like position (CLP) and screw-like hyperkinesia (SLH) [9].

High impact information on acetamide

  • These are the same as those found for total catalase, in normal and treated rats, after allyl isopropyl acetamide: about 1.3 days, a result compatible with peroxisome degradation by autophagy [10].
  • The latter revealed PDT-protected tumor regions distant from vessels in the high fluence rate conditions, confirming regional tumor hypoxia shown by 2-(2-nitroimidazol-1[H]-yl)-N-(3,3,3-trifluoropropyl) acetamide staining [11].
  • Hypoxia was assessed using two 2-nitroimidazole markers, [(125)I]iodoazomycin arabinodise and 2-(2-nitro-1H-imidazol-l-yl)-N-(2,2,3,3,3,-pentafluoropropyl) acetamide (EF5), with binding in the rat spinal cord measured using gamma counting and immunohistochemistry, respectively [12].
  • Feeding a 4-chloro-6-(2,3 xylidino)-2-pyrimidinylthio (N-beta-hydroxyethyl) acetamide diet for 3 days and 2 wk induced marked enhancement of liver cell proliferation as judged by hepatocyte 5-bromo-2-deoxyuridine incorporation.(ABSTRACT TRUNCATED AT 250 WORDS)[13]
  • Male F344 rats were fed a choline-deficient diet or 0.16% 4-chloro-6-(2,3 xylidino)-2-pyrimidinylthio (N-beta-hydroxyethyl) acetamide diet for 6 and 4 wk, respectively [13].

Chemical compound and disease context of acetamide

  • Male rats were fed diets containing DEHP or clofibrate (CLF) for 3-60 days (hyperplasia) and 4-chloro-6-(2,3 xylidino)-2-pyrimidinyl-thio(N-beta-hydroxyethyl) acetamide for 10 months (HCC) [14].
  • The recovery of Pseudomonas aeruginosa was enhanced by incubating specimens in acetamide broth before subculture on cetrimide agar [15].
  • One hundred twenty seven human isolates of Nocardia asteroides complex were identified to the species level by drug susceptibility testing, acetamide utilization, thermotolerance studies, studies of arylsulfatase activity, and studies of acid production from rhamnose [16].
  • Our recent study demonstrated that nefiracetam, N-(2,6-dimethylphenyl)-2-(2-oxo-1-pyrrolidinyl) acetamide, prevented impairment of the cyclic AMP (cAMP)/cAMP-responsive element binding (CREB) protein signaling pathway in sustained cerebral ischemia [17].
  • Unlike other cellular systems, the presence of amides, specifically acetamide or formamide, did not reduce the toxicity of Me(2)SO in zebrafish embryos (P > 0.05) [18].

Biological context of acetamide

  • The occurrence of these acetyl transferases in the target organ of the human bladder carcinogen ABP suggests that metabolic activation of some proximate metabolites of ABP could occur directly in HUC and could play a pivotal role in susceptibility to aryl-amine/acetamide induced human bladder cancers [19].
  • Since the presence of a bond joining the A and C rings seems to be the determining factor in the suppression of alkylation, it is likely that inhibition by colchicine of the reaction with iodo[14C] acetamide is due largely to a conformational change induced by colchicine [20].
  • The EF-Tu fraction which is not methylated is still able to accept methyl groups, as shown by methylation of approximately 10% of the EF-Tu after addition of chloramphenicol (D-(-)-threo-2,2-dichloro-N-[beta-hydroxy-alpha-(hydroxymethyl)-o-nitrophenethyl] acetamide) to inhibit further protein synthesis [21].
  • This response was not observed when acetamide was used as a source of ammonia; therefore, it is specific for urea hydrolysis [22].
  • The substrate specificity was analysed with crude extracts from H. pylori cells grown in vitro; the best substrates were propionamide, acrylamide and acetamide [23].

Anatomical context of acetamide

  • We show that injected oocytes: (i) acidify the medium due to ammonia uptake, (ii) take up [(14)C]methylamine and [(14)C]formamide, (iii) swell in solution with formamide and acetamide and (iv) display an ammonia-induced NH(4) (+)-dependent clamp current [24].
  • The most potent of these, 2-(3,4-dichlorophenyl)-N-methyl-N-[(1S)-1-phenyl-2-(1-pyrrolidinyl)ethyl] acetamide (8), was 146-fold more active than U-50488 in vitro in the mouse vas deferens model and exhibited potent naloxone-reversible analgesic effects (ED50 = 0.004 mg/kg sc) in an abdominal constriction model [25].
  • The dissociation constants (KD values) and relative efficacies of seven acetamide analogues of oxotremorine, including two enantiomeric pairs, at muscarinic receptors in the guinea-pig isolated ileum were determined [26].
  • The ligand-binding affinity for [3H]5alpha,7alpha, 8beta(-)-N-methyl-N-(7-Cl-pyrrolidinyl)-1-oxaspiro(4, 5)dec-8-yl)benzene acetamide (U69593) was similar to that observed in monkey brain membranes and was 10-fold lower in the presence of sodium and GDP [27].
  • CL 259,763, N-[4-[(4-fluorophenyl)sulfonyl]phenyl] acetamide, is an orally active compound capable of modifying the reactivity of certain lymphoid cell populations affected by the growth of a tumor [28].

Associations of acetamide with other chemical compounds


Gene context of acetamide

  • In that case, both proteins Hap2p and NF-YA complemented, at least in part, the hap phenotype of A.nidulans with respect to lack of growth on acetamide [34].
  • Antiangiogenic effect of 2-benzoyl-phenoxy acetamide in EAT cell is mediated by HIF-1alpha and down regulation of VEGF of in-vivo [35].
  • The acetamide derivative 4b produced a noticeable reduction of GTPgammaS binding at MT2 receptor, thus being among the few inverse agonists described [36].
  • In the absence of thiol reducing agents such as DTT, cPLA2 takes up only 2.8 equiv of [1-14C]iodoacetamide at pH 8.03/37 degrees C. With DTT present, cPLA2 is in its fully reduced form, and 4-5 equiv of acetamide are taken up without altering enzyme activity to give IA-cPLA2 [37].
  • Inhibitors of iNOS [N-(3-aminomethyl)benzyl acetamide 2HCl] and nNOS [1-[2-(trifluoromethylphenyl)imidazole]] had no effect on this relaxation [38].

Analytical, diagnostic and therapeutic context of acetamide


  1. Effect of piracetam on level of consciousness after neurosurgery. Richardson, A.E., Bereen, F.J. Lancet (1977) [Pubmed]
  2. Crystal structure and induction mechanism of AmiC-AmiR: a ligand-regulated transcription antitermination complex. O'Hara, B.P., Norman, R.A., Wan, P.T., Roe, S.M., Barrett, T.E., Drew, R.E., Pearl, L.H. EMBO J. (1999) [Pubmed]
  3. Biological effects of acetamide, formamide, and their monomethyl and dimethyl derivatives. Kennedy, G.L. Crit. Rev. Toxicol. (1986) [Pubmed]
  4. Hypoxia is important in the biology and aggression of human glial brain tumors. Evans, S.M., Judy, K.D., Dunphy, I., Jenkins, W.T., Hwang, W.T., Nelson, P.T., Lustig, R.A., Jenkins, K., Magarelli, D.P., Hahn, S.M., Collins, R.A., Grady, M.S., Koch, C.J. Clin. Cancer Res. (2004) [Pubmed]
  5. Heterocyclic amides: inhibitors of acyl-CoA:cholesterol O-acyl transferase with hypocholesterolemic activity in several species and antiatherosclerotic activity in the rabbit. White, A.D., Purchase, C.F., Picard, J.A., Anderson, M.K., Mueller, S.B., Bocan, T.M., Bousley, R.F., Hamelehle, K.L., Krause, B.R., Lee, P., Stanfield, R.L., Reindel, J.F. J. Med. Chem. (1996) [Pubmed]
  6. Attenuation of the development of morphine dependence/tolerance by nefiracetam: involvement of adenosine 3':5'-cyclic monophosphate system. Itoh, A., Shiotani, T., Nakayama, S., Mamiya, T., Hasegawa, T., Noda, Y., Nabeshima, T. Behav. Brain Res. (2000) [Pubmed]
  7. Experimental behavioral studies with oxiracetam on different types of chronic cerebral impairment. Banfi, S., Dorigotti, L. Clinical neuropharmacology. (1986) [Pubmed]
  8. Effects of DM-9384, a pyrrolidone derivative, on alcohol- and chlordiazepoxide-induced amnesia in mice. Nabeshima, T., Tohyama, K., Kameyama, T. Pharmacol. Biochem. Behav. (1990) [Pubmed]
  9. Opioid-dopamine interaction in planaria: a behavioral study. Passarelli, F., Merante, A., Pontieri, F.E., Margotta, V., Venturini, G., Palladini, G. Comp. Biochem. Physiol. C, Pharmacol. Toxicol. Endocrinol. (1999) [Pubmed]
  10. Structure, composition, physical properties, and turnover of proliferated peroxisomes. A study of the trophic effects of Su-13437 on rat liver. Leighton, F., Coloma, L., Koenig, C. J. Cell Biol. (1975) [Pubmed]
  11. Choice of oxygen-conserving treatment regimen determines the inflammatory response and outcome of photodynamic therapy of tumors. Henderson, B.W., Gollnick, S.O., Snyder, J.W., Busch, T.M., Kousis, P.C., Cheney, R.T., Morgan, J. Cancer Res. (2004) [Pubmed]
  12. Hypoxia in radiation-induced blood-spinal cord barrier breakdown. Li, Y.Q., Ballinger, J.R., Nordal, R.A., Su, Z.F., Wong, C.S. Cancer Res. (2001) [Pubmed]
  13. Differential expression of hepatocyte growth factor, transforming growth factor-alpha and transforming growth factor-beta 1 messenger RNAs in two experimental models of liver cell proliferation. Masuhara, M., Katyal, S.L., Nakamura, T., Shinozuka, H. Hepatology (1992) [Pubmed]
  14. Hepatic hyperplasia and cancer in rats: alterations in copper metabolism. Eagon, P.K., Teepe, A.G., Elm, M.S., Tadic, S.D., Epley, M.J., Beiler, B.E., Shinozuka, H., Rao, K.N. Carcinogenesis (1999) [Pubmed]
  15. Acetamide broth for isolation of Pseudomonas aeruginosa from patients with cystic fibrosis. Kelly, N.M., Falkiner, F.R., Keane, C.T. J. Clin. Microbiol. (1983) [Pubmed]
  16. Opacification of Middlebrook agar as an aid in identification of Nocardia farcinica. Flores, M., Desmond, E. J. Clin. Microbiol. (1993) [Pubmed]
  17. Effects of nefiracetam on the levels of brain-derived neurotrophic factor and synapsin I mRNA and protein in the hippocampus of microsphere-embolized rats. Ando, T., Takagi, N., Takagi, K., Kago, T., Takeo, S. Eur. J. Pharmacol. (2005) [Pubmed]
  18. Overcoming a permeability barrier by microinjecting cryoprotectants into zebrafish embryos (Brachydanio rerio). Janik, M., Kleinhans, F.W., Hagedorn, M. Cryobiology (2000) [Pubmed]
  19. Metabolism and nucleic acid binding of N-hydroxy-4-acetylaminobiphenyl and N-acetoxy-4-acetylaminobiphenyl by cultured human uroepithelial cells. Swaminathan, S., Reznikoff, C.A. Cancer Res. (1992) [Pubmed]
  20. The effects of colchicine analogues on the reaction of tubulin with iodo[14C]acetamide and N,N'-ethylenebis(iodoacetamide). Roach, M.C., Bane, S., Ludueña, R.F. J. Biol. Chem. (1985) [Pubmed]
  21. In vivo methylation of prokaryotic elongation factor Tu. Ames, G.F., Niakido, K. J. Biol. Chem. (1979) [Pubmed]
  22. The Helicobacter pylori UreI protein: role in adaptation to acidity and identification of residues essential for its activity and for acid activation. Bury-Moné, S., Skouloubris, S., Labigne, A., De Reuse, H. Mol. Microbiol. (2001) [Pubmed]
  23. Identification and characterization of an aliphatic amidase in Helicobacter pylori. Skouloubris, S., Labigne, A., De Reuse, H. Mol. Microbiol. (1997) [Pubmed]
  24. Ammonia permeability of the aquaglyceroporins from Plasmodium falciparum, Toxoplasma gondii and Trypansoma brucei. Zeuthen, T., Wu, B., Pavlovic-Djuranovic, S., Holm, L.M., Uzcategui, N.L., Duszenko, M., Kun, J.F., Schultz, J.E., Beitz, E. Mol. Microbiol. (2006) [Pubmed]
  25. 2-(3,4-Dichlorophenyl)-N-methyl-N-[2-(1-pyrrolidinyl)-1-substituted- ethyl]-acetamides: the use of conformational analysis in the development of a novel series of potent opioid kappa agonists. Costello, G.F., James, R., Shaw, J.S., Slater, A.M., Stutchbury, N.C. J. Med. Chem. (1991) [Pubmed]
  26. Muscarinic receptor occupation and receptor activation in the guinea-pig ileum by some acetamides related to oxotremorine. Ringdahl, B. Br. J. Pharmacol. (1984) [Pubmed]
  27. Opioid efficacy in a C6 glioma cell line stably expressing the human kappa opioid receptor. Remmers, A.E., Clark, M.J., Mansour, A., Akil, H., Woods, J.H., Medzihradsky, F. J. Pharmacol. Exp. Ther. (1999) [Pubmed]
  28. Modulation of the immune response to tumors by a novel synthetic compound, N-[4-[(4-fluorophenyl)sulfonyl]phenyl] acetamide (CL 259,763). Wang, B.S., Ruszala-Mallon, V., Wallace, R.E., Citarella, R.V., Lin, Y.I., Durr, F.E. Cancer Immunol. Immunother. (1986) [Pubmed]
  29. Involvement of the Glu724-Pro760 region of the dihydropyridine receptor II-III loop in skeletal muscle-type excitation-contraction coupling. Saiki, Y., El-Hayek, R., Ikemoto, N. J. Biol. Chem. (1999) [Pubmed]
  30. Solution structure and acetyl-lysine binding activity of the GCN5 bromodomain. Hudson, B.P., Martinez-Yamout, M.A., Dyson, H.J., Wright, P.E. J. Mol. Biol. (2000) [Pubmed]
  31. Internal protein motions, concentrated glycerol, and hydrogen exchange studied in myoglobin. Calhoun, D.B., Englander, S.W. Biochemistry (1985) [Pubmed]
  32. The biochemical pathway for the breakdown of methyl cyanide (acetonitrile) in bacteria. Firmin, J.L., Gray, D.O. Biochem. J. (1976) [Pubmed]
  33. Oligomerization of the amide sensor protein AmiC by x-ray and neutron scattering and molecular modeling. Chamberlain, D., O'Hara, B.P., Wilson, S.A., Pearl, L.H., Perkins, S.J. Biochemistry (1997) [Pubmed]
  34. The CCAAT-binding complex of eukaryotes: evolution of a second NLS in the HapB subunit of the filamentous fungus Aspergillus nidulans despite functional conservation at the molecular level between yeast, A.nidulans and human. Tüncher, A., Spröte, P., Gehrke, A., Brakhage, A.A. J. Mol. Biol. (2005) [Pubmed]
  35. Antiangiogenic effect of 2-benzoyl-phenoxy acetamide in EAT cell is mediated by HIF-1alpha and down regulation of VEGF of in-vivo. Prabhakar, B.T., Khanum, S.A., Shashikanth, S., Salimath, B.P. Investigational new drugs. (2006) [Pubmed]
  36. Tricyclic alkylamides as melatonin receptor ligands with antagonist or inverse agonist activity. Lucini, V., Pannacci, M., Scaglione, F., Fraschini, F., Rivara, S., Mor, M., Bordi, F., Plazzi, P.V., Spadoni, G., Bedini, A., Piersanti, G., Diamantini, G., Tarzia, G. J. Med. Chem. (2004) [Pubmed]
  37. Inactivation of a cytosolic phospholipase A2 by thiol-modifying reagents: cysteine residues as potential targets of phospholipase A2. Li, B., Copp, L., Castelhano, A.L., Feng, R., Stahl, M., Yuan, Z., Krantz, A. Biochemistry (1994) [Pubmed]
  38. Role of nitric oxide in beta3-adrenoceptor activation on basal tone of internal anal sphincter. Banwait, K.S., Rattan, S. Am. J. Physiol. Gastrointest. Liver Physiol. (2003) [Pubmed]
  39. Sugar-assisted glycopeptide ligation. Brik, A., Yang, Y.Y., Ficht, S., Wong, C.H. J. Am. Chem. Soc. (2006) [Pubmed]
  40. Bimolecular homolytic substitution (S(H)2) reactions with hydrogen atoms. time-resolved electron spin resonance detection in the pulse radiolysis of alpha-(methylthio)acetamide. Wisniowski, P., Bobrowski, K., Carmichael, I., Hug, G.L. J. Am. Chem. Soc. (2004) [Pubmed]
  41. Successful cryopreservation of mouse ovaries by vitrification. Migishima, F., Suzuki-Migishima, R., Song, S.Y., Kuramochi, T., Azuma, S., Nishijima, M., Yokoyama, M. Biol. Reprod. (2003) [Pubmed]
  42. Cloning and molecular characterization of the acetamidase-encoding gene (amdS) from Aspergillus oryzae. Gomi, K., Kitamoto, K., Kumagai, C. Gene (1991) [Pubmed]
  43. NMDA-dependent GABAA-mediated polysynaptic potentials in the neonatal rat hippocampal CA3 region. McLean, H.A., Rovira, C., Ben-Ari, Y., Gaiarsa, J.L. Eur. J. Neurosci. (1995) [Pubmed]
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