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Quantitative structure-activity relationships and carminative activity.

B K Evans, K C James, D K Luscombe

    Journal of Pharmaceutical Sciences
    |February 1, 1978
    PubMed
    Summary
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    Carminative compounds, including alcohols and esters, were tested for their ability to inhibit muscle contractions. Activity was primarily linked to solubility and steric factors, suggesting a nonspecific mechanism similar to anesthetics.

    Area of Science:

    • Pharmacology
    • Medicinal Chemistry

    Background:

    • Carminative agents are used to relieve flatulence.
    • The precise mechanism of action for many carminatives is not fully understood.
    • Previous research suggested nonspecific biological activity for certain compounds.

    Purpose of the Study:

    • To investigate the carminative activities of various chemical compounds.
    • To determine the relationship between chemical structure, solubility, and carminative effect.
    • To elucidate the mechanism of action for carminative compounds.

    Main Methods:

    • Tested 34 compounds (alcohols, esters, ethers, phenols, carbonyls) for carminative activity.
    • Used guinea pig isolated ileum preparation to measure 50% inhibition dose (ID50) against carbachol.

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  • Measured aqueous solubilities at 37°C using UV absorption or gas-liquid chromatography (GLC).
  • Performed Hansch analysis using octanol-water distribution coefficients.

    • Main Results:

    • Carminative activity (ID50) was determined for 34 compounds.
    • Solubility-to-ID50 ratios were relatively constant across compounds.
    • Hansch analysis showed solubility (octanol-water partition coefficient) as the primary determinant of activity.
    • Steric availability of the functional group's oxygen atom was a secondary factor.

    Conclusions:

    • Carminative activity appears to be mediated by a nonspecific mechanism, similar to general anesthetics.
    • Lipophilicity (solubility) and steric accessibility of the functional group significantly influence carminative potency.
    • Further research could explore structure-activity relationships for developing more effective carminative agents.