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Chemical Compound Review

Formamidine     methanimidamide

Synonyms: Formamidinium, formimidamide, imidoformamide, AG-L-18022, CHEBI:38477, ...
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Disease relevance of formamidine


High impact information on formamidine


Chemical compound and disease context of formamidine


Biological context of formamidine


Anatomical context of formamidine

  • These two proposed mechanisms of formamidine action were contrasted using electrical kindling of the amygdala [1].
  • Using a polarographic microsensor to measure real-time flux of nitric oxide release from RAW 264.7 macrophages, formamidine was found to require 30-90 min to inhibit enzyme activity, suggesting that cellular uptake of the drug may limit its biological activity [3].
  • Formamidine was 2- to 6-fold more effective in inhibiting nitric oxide production in cells expressing inducible nitric oxide synthase (NOS2) than in a cell line expressing calcium-dependent neuronal nitric oxide synthase (NOS1) [3].
  • Based on these findings we conclude that the formamidine pesticides act as partial agonists of presynaptic alpha(2D)-adrenergic receptors in the rat hypothalamus [18].
  • Formamidine pesticides enhance susceptibility to kindled seizures in amygdala and hippocampus of the rat [19].

Associations of formamidine with other chemical compounds


Gene context of formamidine


  1. Enhanced susceptibility to kindling by chlordimeform may be mediated by a local anesthetic action. Gilbert, M.E., Mack, C.M. Psychopharmacology (Berl.) (1989) [Pubmed]
  2. 9L gliosarcoma cell proliferation and tumor growth in rats are suppressed by N-hydroxy-N'-(4-butyl-2-methylphenol) formamidine (HET0016), a selective inhibitor of CYP4A. Guo, M., Roman, R.J., Fenstermacher, J.D., Brown, S.L., Falck, J.R., Arbab, A.S., Edwards, P.A., Scicli, A.G. J. Pharmacol. Exp. Ther. (2006) [Pubmed]
  3. Minimal amidine structure for inhibition of nitric oxide biosynthesis. Billack, B., Heck, D.E., Porterfield, D.M., Malchow, R.P., Smith, P.J., Gardner, C.R., Laskin, D.L., Laskin, J.D. Biochem. Pharmacol. (2001) [Pubmed]
  4. A randomized study comparing clinical efficacy and safety of thienamycin formamidine (MK0787)/renal dipeptidase inhibitor (MK0791) and cefazolin. Ribner, B.S., Raeder, R., Hollstein, M., Freimer, E.H. J. Antimicrob. Chemother. (1983) [Pubmed]
  5. Effect of amitraz and chlordimeform on heart rate and pupil diameter in rats: mediated by alpha 2-adrenoreceptors. Hsu, W.H., Kakuk, T.J. Toxicol. Appl. Pharmacol. (1984) [Pubmed]
  6. Inhibitors of cytochrome P450 4A suppress angiogenic responses. Chen, P., Guo, M., Wygle, D., Edwards, P.A., Falck, J.R., Roman, R.J., Scicli, A.G. Am. J. Pathol. (2005) [Pubmed]
  7. Potent nonclassical nucleoside antiviral drugs based on the N,N-diarylformamidine concept. Anastasi, C., Hantz, O., De Clercq, E., Pannecouque, C., Clayette, P., Dereuddre-Bosquet, N., Dormont, D., Gondois-Rey, F., Hirsch, I., Kraus, J.L. J. Med. Chem. (2004) [Pubmed]
  8. The permeability of the cGMP-activated channel to organic cations in retinal rods of the tiger salamander. Picco, C., Menini, A. J. Physiol. (Lond.) (1993) [Pubmed]
  9. Formamidinium-induced dimer stabilization and flicker block behavior in homo- and heterodimer channels formed by gramicidin A and N-acetyl gramicidin A. Seoh, S.A., Busath, D.D. Biophys. J. (1993) [Pubmed]
  10. The permeation properties of small organic cations in gramicidin A channels. Seoh, S.A., Busath, D. Biophys. J. (1993) [Pubmed]
  11. Potential neuromuscular toxicity of N'-(2,4-xylyl)-N-methyl formamidine HCl in rodents. Ravikumar, V.C., Rieger, J.A. Toxicology (1983) [Pubmed]
  12. Conformational studies of two histamine H2-receptor antagonistic phenylformamidines: mifentidine and its guanidinothiazole analogue DA 4643. Donetti, A., Trummlitz, G., Bietti, G., Cereda, E., Bazzano, C., Wagner, H.U. Arzneimittel-Forschung. (1985) [Pubmed]
  13. Synthesis and structure-activity relationship of C5-substituted analogues of (+-)-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imine [(+-)-desmethyl-MK801]: ligands for the NMDA receptor-coupled phencyclidine binding site. Monn, J.A., Thurkauf, A., Mattson, M.V., Jacobson, A.E., Rice, K.C. J. Med. Chem. (1990) [Pubmed]
  14. Monoamine oxidase inhibition cannot account for changes in visual evoked potentials produced by chlordimeform. Boyes, W.K., Moser, V.C., MacPhail, R.C., Dyer, R.S. Neuropharmacology (1985) [Pubmed]
  15. Influence of the formamidine pesticide chlordimeform on ovulation in the female hamster: dissociable shifts in the luteinizing hormone surge and oocyte release. Goldman, J.M., Stoker, T.E., Perreault, S.D., Cooper, R.L., Crider, M.A. Toxicol. Appl. Pharmacol. (1993) [Pubmed]
  16. Acute amitraz poisoning in adults: clinical features, laboratory findings, and management. Avsarogullari, L., Ikizceli, I., Sungur, M., Sözüer, E., Akdur, O., Yücei, M. Clinical toxicology (Philadelphia, Pa.) (2006) [Pubmed]
  17. Suppression of the antibody response by a formamidine pesticide: dependence on the route of exposure. Shopp, G.M., McCay, J.A., Holsapple, M.P. Journal of toxicology and environmental health. (1985) [Pubmed]
  18. Interaction of formamidine pesticides with the presynaptic alpha(2)-adrenoceptor regulating. Altobelli, D., Martire, M., Maurizi, S., Preziosi, P. Toxicol. Appl. Pharmacol. (2001) [Pubmed]
  19. Formamidine pesticides enhance susceptibility to kindled seizures in amygdala and hippocampus of the rat. Gilbert, M.E. Neurotoxicology and teratology. (1988) [Pubmed]
  20. Cation permeability ratios of sodium channels in normal and grayanotoxin-treated squid axon membranes. Hironaka, T., Narahashi, T. J. Membr. Biol. (1977) [Pubmed]
  21. Permeability to various cations of the voltage-dependent sodium channel of isolated rat hippocampal pyramidal neurons. Kaneda, M., Oomura, Y., Ishibashi, O., Akaike, N. Neurosci. Lett. (1988) [Pubmed]
  22. Inhibition of rat platelet 5-hydroxytryptamine uptake by chlordimeform. Johnson, T.L., Knowles, C.O. Toxicol. Lett. (1981) [Pubmed]
  23. Effects of amitraz on cytochrome P450-dependent monooxygenases and estrogenic activity in MCF-7 human breast cancer cells and immature female rats. Ueng, T.H., Hung, C.C., Wang, H.W., Chan, P.K. Food Chem. Toxicol. (2004) [Pubmed]
  24. Novel histamine H3 receptor antagonists: synthesis and evaluation of formamidine and S-methylisothiourea derivatives. Goto, T., Sakashita, H., Murakami, K., Sugiura, M., Kondo, T., Fukaya, C. Chem. Pharm. Bull. (1997) [Pubmed]
  25. The ability of new formamidine sugar-modified derivatives of daunorubicin to stimulate free radical formation in three enzymatic systems: NADH dehydrogenase, NADPH cytochrome P450 reductase and xanthine oxidase. Pawłowska, J., Tarasiuk, J., Borowski, E., Wasowska, M., Oszczapowicz, I., Wolf, C.R. Acta Biochim. Pol. (2000) [Pubmed]
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