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Chemical Compound Review

Butyramid     butanamide

Synonyms: Butanamide, Butyramide, butyroamide, butyrylamide, N-BUTYLAMIDE, ...
 
 
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Disease relevance of butyramide

 

High impact information on butyramide

  • The amide binding site is extremely specific for acetamide and would not allow a closed conformation in the presence of the anti-inducer molecule butyramide [2].
  • In artificial lipid bilayer membranes, the ratio of the water permeability coefficient (Pd(water)) to the permeability coefficient of an arbitrary nonelectrolyte such as n-butyramide (Pd(n-butyramide)) remains relatively constant with changes in lipid composition and temperature, even though the individual Pd's increase more than 100-fold [3].
  • It is concluded that AmiC exhibits novel ligand-dependent oligomerization properties in solution when these are compared to other members of the periplasmic binding protein superfamily, where AmiC exists in monomeric and trimeric forms, the proportions of which depend on the presence of acetamide or butyramide [4].
  • A series containing a P1' butyramide group resulted in a nanomolar potent and selective HNC inhibitor as well as a dual HFS/HNC inhibitor [5].
  • In particular, the amino butyramide 21a exhibited potent NEP inhibitory activity (IC50 = 5.0 nM) in vitro and in vivo [6].
 

Biological context of butyramide

  • The molecular basis for the butyramide inducible phenotype of P.aeruginosa PAC181 has now been determined, and results from a Thr-->Asn mutation at position 106 in PAC181-AmiC [7].
  • In this investigation ADH-stimulated changes in urea and osmotic water permeability and luminal membrane aggregates at room temperature (24.8 +/- 0.4 degrees C) and in the cold 10.6 +/- 0.2 degrees) were compared with corresponding changes in membrane fluidity, as assessed by n-butyramide permeability [8].
 

Anatomical context of butyramide

  • Following intraperitoneal administration to rats of [14C]loperamide, [carbonyl-14] 4-(p-chlorophenyl)-4-hydroxy-N,N-dimethyl-alpha, alpha-diphenyl-1-piperidine butyramide, metabolites in feces and urine were separated, and identified by means of mass spectrometry [9].
 

Associations of butyramide with other chemical compounds

 

Gene context of butyramide

  • Although the mutation allows butyramide to be recognized as an inducer of amidase expression, the mutation is structurally sub-optimal, and produces a significant decrease in the stability of the mutant protein [7].
  • General pharmacology of the butanamide derivative S 19812, a new dual inhibitor of cyclooxygenase and lipoxygenase pathways [15].

References

  1. Butyramide and monobutyrin: growth inhibitory and differentiating agents. Lea, M.A., Xiao, Q., Sadhukhan, A., Sharma, S., Newmark, H.L. Anticancer Res. (1993) [Pubmed]
  2. Crystal structure of AmiC: the controller of transcription antitermination in the amidase operon of Pseudomonas aeruginosa. Pearl, L., O'Hara, B., Drew, R., Wilson, S. EMBO J. (1994) [Pubmed]
  3. Nature of the water permeability increase induced by antidiuretic hormone (ADH) in toad urinary bladder and related tissues. Finkelstein, A. J. Gen. Physiol. (1976) [Pubmed]
  4. 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]
  5. Inhibition of matrix metalloproteinases by hydroxamates containing heteroatom-based modifications of the P1' group. Gowravaram, M.R., Tomczuk, B.E., Johnson, J.S., Delecki, D., Cook, E.R., Ghose, A.K., Mathiowetz, A.M., Spurlino, J.C., Rubin, B., Smith, D.L. J. Med. Chem. (1995) [Pubmed]
  6. Dicarboxylic acid dipeptide neutral endopeptidase inhibitors. Ksander, G.M., Ghai, R.D., deJesus, R., Diefenbacher, C.G., Yuan, A., Berry, C., Sakane, Y., Trapani, A. J. Med. Chem. (1995) [Pubmed]
  7. Structural adaptation to selective pressure for altered ligand specificity in the Pseudomonas aeruginosa amide receptor, amiC. O'Hara, B.P., Wilson, S.A., Lee, A.W., Roe, S.M., Siligardi, G., Drew, R.E., Pearl, L.H. Protein Eng. (2000) [Pubmed]
  8. Relation of ADH effects to altered membrane fluidity in toad urinary bladder. Kachadorian, W.A., Muller, J., Rudich, S., DiScala, V.A. Am. J. Physiol. (1981) [Pubmed]
  9. Metabolites of loperamide in rats. Yoshida, K., Nambu, K., Arakawa, S., Miyazaki, H., Hashimoto, M. Biomed. Mass Spectrom. (1979) [Pubmed]
  10. Measurement of progabide and its deaminated metabolite in plasma by high-performance liquid chromatography and electrochemical detection. Yonekawa, W., Kupferberg, H.J., Lambert, T. J. Chromatogr. (1983) [Pubmed]
  11. Synthesis of the butanamide derivative S 19812, a new dual inhibitor of cyclooxygenase and lipoxygenase pathways. Tordjman, C., Sauveur, F., Droual, M., Briss, S., Andre, N., Bellot, I., Deschamps, C., Wierzbicki, M. Arzneimittel-Forschung. (2003) [Pubmed]
  12. Free radicals in U.V.-irradiated aqueous solutions of substituted amides: an e.s.r. and spin-trapping study. Rustgi, S., Riesz, P. Int. J. Radiat. Biol. Relat. Stud. Phys. Chem. Med. (1978) [Pubmed]
  13. Comparative studies on the dependence liability of morphine hydrochloride, codeine phosphate and two novel antitussive compounds vadocaine hydrochloride and N-(2',4'-dimethyl-6'-methoxyphenyl)-4-(diethylamine) butanamide hydrochloride in mice. Etemadzadeh, E., Ahtee, L., Männistö, P.T. Arzneimittel-Forschung. (1988) [Pubmed]
  14. Preparation and properties of glucagon analogs prepared by semi-synthesis from CNBr-glucagon. Wright, D.E., Hruby, V.J., Rodbell, M. Biochim. Biophys. Acta (1980) [Pubmed]
  15. General pharmacology of the butanamide derivative S 19812, a new dual inhibitor of cyclooxygenase and lipoxygenase pathways. Tordjman, C., Andre, N., Bresson, Y., Bellot, I., Deschamps, C., Pastoureau, P., Wierzbicki, M. Arzneimittel-Forschung. (2003) [Pubmed]
 
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