AHFS/Drugs.com Monograph Molar mass 384.429 g/mol | MedlinePlus a685037 CAS ID 34787-01-4 Protein binding 45% | |
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Pregnancycategory AU: B2US: B (No risk in non-human studies) ATC code J01CA13 (WHO) J01CR03 (WHO) Legal status In general: ℞ (Prescription only) | ||
Ticarcillin and clavulanic acid will treat various bacterial infections overview
Ticarcillin is a carboxypenicillin. It is almost invariably sold and used in combination with clavulanate as Timentin. Because it is a penicillin, it also falls within the larger class of beta-lactam antibiotics. Its main clinical use is as an injectable antibiotic for the treatment of Gram-negative bacteria, particularly Pseudomonas aeruginosa. It is also one of the few antibiotics capable of treating Stenotrophomonas maltophilia infections.
Contents
- Ticarcillin and clavulanic acid will treat various bacterial infections overview
- Ticarcillin and clavulanic acid medications overview
- Mechanism of action
- Other uses
- Dosing and administration
- Trade names and preparations
- Synthesis
- References
It is provided as a white or pale-yellow powder. It is highly soluble in water, but should be dissolved only immediately before use to prevent degradation.
Ticarcillin and clavulanic acid medications overview
Mechanism of action
Ticarcillin's antibiotic properties arise from its ability to prevent cross-linking of peptidoglycan during cell wall synthesis, when the bacteria try to divide, causing cell death.
Ticarcillin, like penicillin, contains a β-lactam ring that can be cleaved by beta-lactamases, resulting in inactivation of the antibiotic. Those bacteria that can express β-lactamases are, therefore, resistant to β-lactam antibiotics. Due, at least in part, to the common β-lactam ring, ticarcillin can cause reactions in patients allergic to penicillin. Ticarcillin is also often paired with a β-lactamase inhibitor such as clavulanic acid (co-ticarclav).
Other uses
In molecular biology, ticarcillin is used to as an alternative to ampicillin to test the uptake of marker genes into bacteria. It prevents the appearance of satellite colonies that occur when ampicillin breaks down in the medium. It is also used in plant molecular biology to kill Agrobacterium, which is used to deliver genes to plant cells.
Dosing and administration
Ticarcillin is not absorbed orally, so must be given by intravenous or intramuscular injection.
Trade names and preparations
Synthesis
Carbenicillin is used in the clinic primarily because of its low toxicity and its utility in treating urinary tract infections due to susceptible Pseudomonas species. Its low potency, low oral activity, and susceptibility to bacterial beta-lactamases make it vulnerable to replacement by agents without these deficits. One contender in this race is ticaricillin. Its origin depended on the well-known fact that a divalent sulfur is roughly equivalent to a vinyl group (cf methiopropamine, sufentanil, pizotyline etc.).
One synthesis began by making the monobenzyl ester of 3-Thienylmalonic acid, converting this to the acid chloride with SOCl2, and condensing it with 6-Aminopenicillanic acid (6-APA). Hydrogenolysis (Pd/C) completed the synthesis of ticarcillin.