147158-68-7Relevant academic research and scientific papers
Calcium antagonism and structure-affinity relationships of terfenadine, a histamine H1 antagonist and some related compounds
Zhang,Caldirola,Timmerman
, p. 63 - 66 (1993)
Calcium channel affinity of terfenadine and its optical isomers was determined by the displacement of [3H]nitrendipine on rat cerebral cortex membranes. Terfenadine showed a pK(d) of 6.36 ± 0.03 whereas its R(+)-isomer (VUF4567) had a pK(d) val
METHODS AND COMPOSITIONS FOR TREATING INFECTION
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Paragraph 0217, (2015/09/28)
Provided herein are compositions and methods for treating or preventing infection.
Repurposing the antihistamine terfenadine for antimicrobial activity against staphylococcus aureus
Perlmutter, Jessamyn I.,Forbes, Lauren T.,Krysan, Damian J.,Ebsworth-Mojica, Katherine,Colquhoun, Jennifer M.,Wang, Jenna L.,Dunman, Paul M.,Flaherty, Daniel P.
supporting information, p. 8540 - 8562 (2014/12/11)
Staphylococcus aureus is a rapidly growing health threat in the U.S., with resistance to several commonly prescribed treatments. A high-throughput screen identified the antihistamine terfenadine to possess, previously unreported, antimicrobial activity against S. aureus and other Gram-positive bacteria. In an effort to repurpose this drug, structure-activity relationship studies yielded 84 terfenadine-based analogues with several modifications providing increased activity versus S. aureus and other bacterial pathogens, including Mycobacterium tuberculosis. Mechanism of action studies revealed these compounds to exert their antibacterial effects, at least in part, through inhibition of the bacterial type II topoisomerases. This scaffold suffers from hERG liabilities which were not remedied through this round of optimization; however, given the overall improvement in activity of the set, terfenadine-based analogues provide a novel structural class of antimicrobial compounds with potential for further characterization as part of the continuing process to meet the current need for new antibiotics.
Structure-activity relationships within a series of analogues of the histamine H1-antagonist terfenadine
Zhang,Ter Laak,Timmerman
, p. 165 - 173 (2007/10/02)
A number of terfenadine derivatives including terfenadine enantiomers were synthesized and tested for histamine H1-receptor affinity. No significant differences in H1 activity were found between terfenadine enantiomers. Qualitative structure-activity relationship studies identified the α,α-diphenyl-4-piperidinomethanol moiety as the pharmacophore for the H1 activity of this group of compounds. The major role of the phenylbutanol moiety in terfenadine seems to be preventing the compound from crossing the blood-brain barrier.
