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Chemical Compound Review

benzamidine     benzenecarboximidamide

Synonyms: Benzimidamide, Phenylamidine, AMIDINOBENZENE, Lopac-B-6506, SureCN9207, ...
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Disease relevance of benzenecarboximidamide

  • By means of reconstitution experiments with highly purified variants of P-450 IIC3 from rabbit liver and with purified variants of P-450 IIC expressed by recombinant Escherichia coli, the participation of the two variants P-450 IIC3 (6 beta H) and P-450 IIC3 (6 beta L) in the N-hydroxylation of benzamidine was unequivocally confirmed [1].
  • A series of benzamidine isoxazoline derivatives was evaluated for their inhibitory potency against purified human factor Xa (fXa) and in a rabbit model of arteriovenous shunt thrombosis for their antithrombotic activities, expressed as K(I) and IC(50), respectively [2].
  • Extraction from mastocytoma homogenates at high ionic strength, followed by gel filtration and benzamidine affinity chromatography yielded a product with several closely spaced bands (Mr 30,000-32,000) on gel electrophoresis and a single N-terminal sequence [3].
  • We assayed several benzamidine derivatives for inhibition potency with HRgpA and RgpB gingipains, enzymes which are involved in the pathogenesis of gingivitis and periodontal disease [4].
  • Comparison with benzamidine complement-inhibitory activity models and with benzene derivatives toxicity models from the literature favors our novel approach [5].

Psychiatry related information on benzenecarboximidamide


High impact information on benzenecarboximidamide

  • This conversion was also inhibited by pretreatment with the serine protease inhibitor benzamidine (10 mM) but not the cysteine protease inhibitor E64 (100 microM) [7].
  • In contrast, treating von Willebrand factor with neuraminidase and beta-galactosidase in the presence of protease inhibitors (20 mM benzamidine, 20 U/ml aprotonin, 15 micrograms/ml leupeptin) resulted in a comparable removal of carbohydrate with no change in ristocetin cofactor activity [8].
  • 2. The trypsin inhibitor benzamidine was found to inhibit the yolk proteinase in vivo [9].
  • The release of radioactivity was partially inhibited by protease inhibitors, including alpha 2-macroglobulin, leupeptin, and benzamidine, but the negative fluorescent spots appeared unaffected by any of these inhibitors [10].
  • (iii) Both cyclin A cleavage activity and OmpT activity are heat stable, resistant to denaturation, and inhibited by Zn(2+), Cu(2+), or benzamidine [11].

Biological context of benzenecarboximidamide


Anatomical context of benzenecarboximidamide

  • Both Ag-specific GEF and nonspecific GEF from the hybridoma bind to p-aminobenzamidine-agarose, and are recovered by elution with benzamidine [17].
  • Porcine ileal mucosa was homogenized and freeze-thawed in 0.05 M NH4HCO3 + 0.01 M EDTA + 1 mM benzamidine hydrochloride at pH 8 [18].
  • Leupeptin and benzamidine inhibited tryptase-induced fibroblast proliferation (P < 0.05), and SLIGKV mimicked tryptase's effect [19].
  • The addition of benzamidine, a noncompetitive synthetic trypsin inhibitor, to semen samples has kept a portion of the sperm phospholipase A2 (PA2) in its zymogen form and allowed its isolation after acid extraction [20].
  • In the present work, we have studied the membrane crystallization process of benzamidine inhibited trypsin from bovine pancreas (BPT), with ammonium sulphate (dissolved in Tris-HCl buffer, 0.1 M, pH 8.5), as precipitant agent [21].

Associations of benzenecarboximidamide with other chemical compounds

  • As demonstrated using the protease inhibitor benzamidine and by specific active site inhibition with 1,5-dansyl-Glu-Gly-Arg chloromethyl ketone, both FVIIa and FXa lost their ability to elicit a calcium response when devoid of their proteolytic activity [22].
  • The isolation method utilized benzamidine to inhibit the premeture activation of the zymogen and included pH precipitation, ammonium sulfate fractionation, and sodium chloride precipitation [23].
  • Pentamidine binds QacR in a novel fashion whereby one of its benzamidine groups interacts with residue Glu-63, and the other is neutralized by carbonyl and side chain oxygen atoms [24].
  • Conversion by the particulate enzyme was inhibited by benzamidine or chloroquine, but not by pancreatic trypsin inhibitor, indicating its dissimilarity to trypsin [25].
  • Refined 2.3 A X-ray crystal structure of bovine thrombin complexes formed with the benzamidine and arginine-based thrombin inhibitors NAPAP, 4-TAPAP and MQPA. A starting point for improving antithrombotics [26].

Gene context of benzenecarboximidamide


Analytical, diagnostic and therapeutic context of benzenecarboximidamide

  • A bound molecule of benzamidine, which was essential for crystallization and is also found in the hinge region, appears to reduce flexibility between the two domains [32].
  • Western blot analysis following SDS-PAGE of the proteins of the FE isolated in the presence of hMW-SBTI and benzamidine revealed the presence of the 350/320-kDa proteins which cross-reacted with anti-receptor antibody [33].
  • The two-way and three-way interactions among active-site-blocked bovine thrombin, bovine protein C, and the elastase fragment of rabbit thrombomodulin (elTM) were examined by analytical ultracentrifugation at 23.3 degrees C in 100 mM NaCl, 50 mM Tris (pH 7.65), and 1 mM benzamidine, in the presence of 0 to 5 mM calcium chloride [34].
  • However, NAPAP and other benzamidine derivatives do not show favorable pharmacological properties; above all, they have very low systemic bioavailability after oral administration [35].
  • The binding of a tetrazole to an N,N'-diethyl-substituted benzamidine has been studied for the first time by X-ray crystallography, solution NMR methods, and electrospray mass spectrometry [36].


  1. N-hydroxylation of benzamidine to benzamidoxime by a reconstituted cytochrome P-450 oxidase system from rabbit liver: involvement of cytochrome P-450 IIC3. Clement, B., Jung, F., Pfunder, H. Mol. Pharmacol. (1993) [Pubmed]
  2. Nonpeptide factor Xa inhibitors: I. Studies with SF303 and SK549, a new class of potent antithrombotics. Wong, P.C., Quan, M.L., Crain, E.J., Watson, C.A., Wexler, R.R., Knabb, R.M. J. Pharmacol. Exp. Ther. (2000) [Pubmed]
  3. Dog mastocytoma tryptase: affinity purification, characterization, and amino-terminal sequence. Caughey, G.H., Viro, N.F., Ramachandran, J., Lazarus, S.C., Borson, D.B., Nadel, J.A. Arch. Biochem. Biophys. (1987) [Pubmed]
  4. Inhibition of arginine gingipains (RgpB and HRgpA) with benzamidine inhibitors: zinc increases inhibitory potency. Krauser, J.A., Potempa, J., Travis, J., Powers, J.C. Biol. Chem. (2002) [Pubmed]
  5. A comparative QSAR study of benzamidines complement-inhibitory activity and benzene derivatives acute toxicity. Basak, S.C., Gute, B.D., Lucić, B., Nikolić, S., Trinajstić, N. Comput. Chem. (2000) [Pubmed]
  6. Enzyme-inhibitor association thermodynamics: explicit and continuum solvent studies. Resat, H., Marrone, T.J., McCammon, J.A. Biophys. J. (1997) [Pubmed]
  7. Intracellular activation of digestive zymogens in rat pancreatic acini. Stimulation by high doses of cholecystokinin. Leach, S.D., Modlin, I.M., Scheele, G.A., Gorelick, F.S. J. Clin. Invest. (1991) [Pubmed]
  8. Carbohydrate moiety of von Willebrand factor is not necessary for maintaining multimeric structure and ristocetin cofactor activity but protects from proteolytic degradation. Federici, A.B., Elder, J.H., De Marco, L., Ruggeri, Z.M., Zimmerman, T.S. J. Clin. Invest. (1984) [Pubmed]
  9. Proteolysis of the major yolk glycoproteins is regulated by acidification of the yolk platelets in sea urchin embryos. Mallya, S.K., Partin, J.S., Valdizan, M.C., Lennarz, W.J. J. Cell Biol. (1992) [Pubmed]
  10. Expression of transformation-associated protease(s) that degrade fibronectin at cell contact sites. Chen, W.T., Olden, K., Bernard, B.A., Chu, F.F. J. Cell Biol. (1984) [Pubmed]
  11. Cleavage of cyclin A at R70/R71 by the bacterial protease OmpT. Yam, C.H., Siu, W.Y., Kaganovich, D., Ruderman, J.V., Poon, R.Y. Proc. Natl. Acad. Sci. U.S.A. (2001) [Pubmed]
  12. Thrombospondin interaction with plasminogen. Evidence for binding to a specific region of the kringle structure of plasminogen. DePoli, P., Bacon-Baguley, T., Kendra-Franczak, S., Cederholm, M.T., Walz, D.A. Blood (1989) [Pubmed]
  13. Catalytic domain structures of MT-SP1/matriptase, a matrix-degrading transmembrane serine proteinase. Friedrich, R., Fuentes-Prior, P., Ong, E., Coombs, G., Hunter, M., Oehler, R., Pierson, D., Gonzalez, R., Huber, R., Bode, W., Madison, E.L. J. Biol. Chem. (2002) [Pubmed]
  14. The role of mast cell tryptase in regulating endothelial cell proliferation, cytokine release, and adhesion molecule expression: tryptase induces expression of mRNA for IL-1 beta and IL-8 and stimulates the selective release of IL-8 from human umbilical vein endothelial cells. Compton, S.J., Cairns, J.A., Holgate, S.T., Walls, A.F. J. Immunol. (1998) [Pubmed]
  15. Modulation of the biologic activities of IgE-binding factor. IV. Identification of glycosylation-enhancing factor as a kallikrein-like enzyme. Iwata, M., Munoz, J.J., Ishizaka, K. J. Immunol. (1983) [Pubmed]
  16. Interaction of human plasmin with human alpha 2-macroglobulin. Cummings, H.S., Castellino, F.J. Biochemistry (1984) [Pubmed]
  17. Antigen-specific T cells that form IgE-potentiating factor, IgG-potentiating factor, and antigen-specific glycosylation-enhancing factor on antigenic stimulation. Iwata, M., Adachi, M., Ishizaka, K. J. Immunol. (1988) [Pubmed]
  18. Isolation and partial characterization of an entero-oxyntin from porcine ileum. Wider, M.D., Vinik, A.I., Heldsinger, A. Endocrinology (1984) [Pubmed]
  19. Tryptase increases proliferative activity of human conjunctival fibroblasts through protease-activated receptor-2. Asano-Kato, N., Fukagawa, K., Okada, N., Dogru, M., Tsubota, K., Fujishima, H. Invest. Ophthalmol. Vis. Sci. (2005) [Pubmed]
  20. Detection of prophospholipase A2 in human spermatozoa. Antaki, P., Guérette, P., Chapdelaine, A., Roberts, K.D. Biol. Reprod. (1989) [Pubmed]
  21. Trypsin crystallization by membrane-based techniques. Di Profio, G., Curcio, E., Drioli, E. J. Struct. Biol. (2005) [Pubmed]
  22. Coagulation factors VII and X induce Ca2+ oscillations in Madin-Darby canine kidney cells only when proteolytically active. Camerer, E., Rottingen, J.A., Iversen, J.G., Prydz, H. J. Biol. Chem. (1996) [Pubmed]
  23. Boar proacrosin. Purification and preliminary activation studies of proacrosin isolated from ejaculated boar sperm. Polakoski, K.L., Parrish, R.F. J. Biol. Chem. (1977) [Pubmed]
  24. Crystal structures of QacR-diamidine complexes reveal additional multidrug-binding modes and a novel mechanism of drug charge neutralization. Murray, D.S., Schumacher, M.A., Brennan, R.G. J. Biol. Chem. (2004) [Pubmed]
  25. Conversion of proparathyroid hormone to parathyroid hormone by a particulate enzyme of the parathyroid gland. MacGregor, R.R., Chu, L.L., Cohn, D.V. J. Biol. Chem. (1976) [Pubmed]
  26. Refined 2.3 A X-ray crystal structure of bovine thrombin complexes formed with the benzamidine and arginine-based thrombin inhibitors NAPAP, 4-TAPAP and MQPA. A starting point for improving antithrombotics. Brandstetter, H., Turk, D., Hoeffken, H.W., Grosse, D., Stürzebecher, J., Martin, P.D., Edwards, B.F., Bode, W. J. Mol. Biol. (1992) [Pubmed]
  27. (4-aminomethyl)phenylguanidine derivatives as nonpeptidic highly selective inhibitors of human urokinase. Sperl, S., Jacob, U., Arroyo de Prada, N., Stürzebecher, J., Wilhelm, O.G., Bode, W., Magdolen, V., Huber, R., Moroder, L. Proc. Natl. Acad. Sci. U.S.A. (2000) [Pubmed]
  28. The refined crystal structure of bovine beta-trypsin at 1.8 A resolution. II. Crystallographic refinement, calcium binding site, benzamidine binding site and active site at pH 7.0. Bode, W., Schwager, P. J. Mol. Biol. (1975) [Pubmed]
  29. Crystal structure reveals basis for the inhibitor resistance of human brain trypsin. Katona, G., Berglund, G.I., Hajdu, J., Gráf, L., Szilágyi, L. J. Mol. Biol. (2002) [Pubmed]
  30. Amidolytic activity of prostatic acid phosphatase on human semenogelins and semenogelin-derived synthetic substrates. Brillard-Bourdet, M., Réhault, S., Juliano, L., Ferrer, M., Moreau, T., Gauthier, F. Eur. J. Biochem. (2002) [Pubmed]
  31. Specific conformational changes of plasminogen induced by chloride ions, 6-aminohexanoic acid and benzamidine, but not the overall openness of plasminogen regulate, production of biologically active angiostatins. Warejcka, D.J., Twining, S.S. Biochem. J. (2005) [Pubmed]
  32. The crystal structure of TrpD, a metabolic enzyme essential for lung colonization by Mycobacterium tuberculosis, in complex with its substrate phosphoribosylpyrophosphate. Lee, C.E., Goodfellow, C., Javid-Majd, F., Baker, E.N., Shaun Lott, J. J. Mol. Biol. (2006) [Pubmed]
  33. The 350-kDa sea urchin egg receptor for sperm is localized in the vitelline layer. Hirohashi, N., Lennarz, W.J. Dev. Biol. (1998) [Pubmed]
  34. Ca2+ dependence of the interactions between protein C, thrombin, and the elastase fragment of thrombomodulin. Analysis by ultracentrifugation. Olsen, P.H., Esmon, N.L., Esmon, C.T., Laue, T.M. Biochemistry (1992) [Pubmed]
  35. Synthesis and structure-activity relationships of potent thrombin inhibitors: piperazides of 3-amidinophenylalanine. Stürzebecher, J., Prasa, D., Hauptmann, J., Vieweg, H., Wikström, P. J. Med. Chem. (1997) [Pubmed]
  36. Noncovalent interactions between tetrazole and an N,N'-diethyl-substituted benzamidine. Peters, L., Fröhlich, R., Boyd, A.S., Kraft, A. J. Org. Chem. (2001) [Pubmed]
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