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a_zed24

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Hello, there!
Sorry if this is not the right place to ask this, but our Prof. was explaining the Beta-lactamase inhibitors and he mentioned the following:
-Clavulanic acid
-Sulbactam
-Tazobactam

-Avibactam
-Vaboractam
-Relebactam

And then he said that the last three are structurally different from the first three. He asked us why's that...
I've searched on Google and my answer would be that the last three do not have a Beta-lactam ring in their structure... do you think this is correct? Is there anything else I'm missing out?
Thanks a lot in advance!
 

Lucca

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mechanistically, the first set differs from the second set in that the first set of b-lac inhibitors forms a stable intermediate with the enzyme because of the b-lactam ring in their structure you mentioned (b-lactam ring-->looks like penicilin-->b-lac-ases bind penicilin); the second set forms transient, reversible interactions which inhibit the action of the enzyme (and therefore the p.kinetics and p.dynamics are very different from the first set) albeit in slightly different ways.

so, by my estimation anyway, b-lactam ring is probably what your prof was thinking of for the reason that it gives away the diff b/w the mechanism of action of the first set vs the second set.

sources for more info:
(clavulanic acid + sulbactam + tazobactam)
(avibactam + vaboractam + relebactam)
 
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a_zed24

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mechanistically, the first set differs from the second set in that the first set of b-lac inhibitors forms a stable intermediate with the enzyme because of the b-lactam ring in their structure you mentioned (b-lactam ring-->looks like penicilin-->b-lac-ases bind penicilin); the second set forms transient, reversible interactions which inhibit the action of the enzyme (and therefore the p.kinetics and p.dynamics are very different from the first set) albeit in slightly different ways.

so, by my estimation anyway, b-lactam ring is probably what your prof was thinking of for the reason that it gives away the diff b/w the mechanism of action of the first set vs the second set.

sources for more info:
(clavulanic acid + sulbactam + tazobactam)
(avibactam + vaboractam + relebactam)

Makes sense... thank you so much for your reply and for the references as well!
 
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