Abstract
BURIMAMIDE has been shown to antagonise the effects of histamine on isolated cardiac and uterine muscle in vitro, and to antagonise histamine-stimulated acid secretion in vivo in animals and in man1. This pattern of pharmacological effects is not achieved by conventional, tertiary amine, anti-histaminic drugs (of which mepyramine is typical) and has led to the definition of burimamide as an H2-receptor antagonist1 and mepyramine as an H1-receptor antagonist2. Although burimamide was pharmacologically sufficiently active to allow for definition of its properties in man3 it seemed to lack the combination of high specific activity with adequate oral bioavailability needed for exploring the therapeutic potential of this new type of drug action. Attempts to produce a more suitable drug were based on the observation that burimamide is a competitive antagonist to histamine and that both compounds possess imidazole rings, We therefore compared the relative species populations of the respective rings and modified the burimamide structure so as to increase the equilibrium concentration of imidazole species considered most likely to be active.
This is a preview of subscription content, access via your institution
Access options
Subscribe to this journal
Receive 51 print issues and online access
$199.00 per year
only $3.90 per issue
Rent or buy this article
Prices vary by article type
from$1.95
to$39.95
Prices may be subject to local taxes which are calculated during checkout
Similar content being viewed by others
References
Black, J. W., Duncan, W. A. M., Durant, G. J., Ganellin, C. R., and Parsons, M. E., Nature, 236, 385 (1972).
Ash, A. S. F., and Schild, H. O., Br. J. Pharmac. Chemother., 27, 427 (1966).
Wyllie, J. H., Hesselbo, T., and Black, J. W., Lancet, ii, 1117 (1972).
Barnett, R. E., Acc. Chem. Res., 6, 41 (1973); Ralph, E. K., and Grunwald, E., J. Am. chem. Soc., 91, 2422 (1969).
Katritzky, A. R., and Lagowski, J. M., Advances in Heterocyclic Chemistry, 2, 32 (Academic Press, New York, and London, 1963).
Albert, A., and Serjeant, E. P., The Determination of Ionisation Constants, 104 (Chapman and Hall, London, 1971).
Charton, M., J. org. Chem., 30, 3346 (1965).
Ganellin, C. R., J. Pharm. Pharmac., 25, 787 (1973).
Ganellin, C. R., J. med. Chem., 16, 620 (1973).
Black, J. W., Duncan, W. A. M., Emmett, J. C., Ganellin, C. R., Hesselbo, T., Parsons, M. E., and Wyllie, J. H., Agents and Actions, 3, 133 (1973).
Datta, S. P., and Grzybowski, A. K., J. Chem. Soc., B,136, (1966).
Paiva, T. B., Tominaga, M., and Paiva, A. C. M., J. med. Chem., 13, 689 (1970).
Pauling, L., The Nature of the Chemical Bond. (Cornell University, New York, 1960).
Exner, O., Coll. Czech. Chem. Commun., 32, 1 (1967).
Eliel, E. L., Stereochemistry of Carbon Compounds, 125 (McGraw-Hill, New York, 1962).
Pierce, L., and Hayashi, M., J. chem. Phys., 35, 479 (1961).
Hansch, C., Quinlan, J. E., and Lawrence, G. L., J. org. Chem., 33, 347 (1968).
Hansch, C., and Anderson, S. M., J. org. Chem., 32, 2583 (1967).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
BLACK, J., DURANT, G., EMMETT, J. et al. Sulphur-methylene isosterism in the developent of metiamide, a new histamine H2-receptor antagonist. Nature 248, 65–67 (1974). https://doi.org/10.1038/248065a0
Received:
Revised:
Published:
Issue Date:
DOI: https://doi.org/10.1038/248065a0
This article is cited by
-
Ag–TiO2 nanocomposite-catalyzed one-pot synthesis of 1,2,4,5-tetrasubstituted imidazoles: a green and benign approach
Journal of the Iranian Chemical Society (2021)
-
Development of novel and green NiFe2O4/geopolymer nanocatalyst based on bentonite for synthesis of imidazole heterocycles by ultrasonic irradiations
Scientific Reports (2020)
-
Nano-sized Cu/Zn-modified MCM-41 (Cu/Zn-MCM-41): preparation, characterization and catalytic application in a new more atom efficient synthesis of tetrasubstituted imidazoles
Journal of Porous Materials (2018)
-
Synthesis of polymer-supported Fe3O4 nanoparticles and their application as a novel route for the synthesis of imidazole derivatives
Research on Chemical Intermediates (2018)
-
2-(chromon-3-yl)imidazole derivatives as potential antimicrobial agents: synthesis, biological evaluation and molecular docking studies
Journal of Chemical Biology (2017)
Comments
By submitting a comment you agree to abide by our Terms and Community Guidelines. If you find something abusive or that does not comply with our terms or guidelines please flag it as inappropriate.