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Clavulanic acid is a β-lactam drug that functions as a mechanism-based β-lactamase inhibitor. While not effective by itself as an antibiotic , when combined with penicillin -group antibiotics, it can overcome antibiotic resistance in bacteria that secrete β-lactamase , which otherwise inactivates most penicillins.
For example, Augmentin (FGP) is made of amoxicillin (a β-lactam antibiotic) and clavulanic acid (a β-lactamase inhibitor). The clavulanic acid is designed to overwhelm all β-lactamase enzymes, and effectively serve as an antagonist so that the amoxicillin is not affected by the β-lactamase enzymes. Another β-lactam/β-lactamase inhibitor ...
Opening the active site to beta-lactam substrates also typically enhances the susceptibility of the enzyme to β-lactamase inhibitors, such as clavulanic acid. Single amino acid substitutions at positions 104, 164, 238, and 240 produce the ESBL phenotype, but ESBLs with the broadest spectrum usually have more than a single amino acid substitution.
Clavulanic acid is a broad-spectrum antibiotic and 5S clavams may have anti-fungal properties. They are similar to penams, but with an oxygen substituted for the sulfur. [3] Thus, they are also known as oxapenams. An example is clavulanic acid, [4] from which this compound class receives its name. Clavulanic acid, a type of clavam, has ...
The β-lactam core structures. (A) A penam.(B) A carbapenam.(C) An oxapenam.(D) A penem.(E) A carbapenem.(F) A monobactam.(G) A cephem.(H) A carbacephem.(I) An oxacephem. This is a list of common β-lactam antibiotics—both administered drugs and those not in clinical use—organized by structural class.
This is a favorable drug design over many clinically used competing agents, because most of them, such as clavulanic acid, become hydrolysed, and are therefore only useful for a finite period of time. This generally causes the need for a higher concentration of competitive inhibitor than would be necessary in an unhydrolyzable inhibitor.
Anti-seizure medications: Gabapentin, carbamazepine, and valproic acid. Antihistamines: Diphenhydramine (the active ingredient in Benadryl) Diabetes medications: Insulin and thiazolidinediones.
Streptomyces clavuligerus is a species of Gram-positive bacterium notable for producing clavulanic acid. [1]S. clavuligerus ATCC 27064 (NRRL 3585, DSM 738) was first described by Higgens and Kastner (1971), who isolated it from a South American soil sample. [2]