Ticarcillin Mechanism of action

Ticarcillin is a carboxypenicillin.It is sold and used together with clavulanate as ticarcillin/clavulanic acid.Because it is a penicillin, it also belongs to the larger class of beta-lactam antibiotics.Its main clinical use is as an injectable antibiotic for the treatment of Gram-negative bacteria, especially Pseudomonas aeruginosa and Proteus vulgaris.It is also one of the few antibiotics that can treat S. maltophilia infection.It is available as a white or light yellow powder.It is extremely soluble in water, but should only be dissolved immediately before use to prevent degradation.It was patented in 1963.

Mechanism of action

The antibiotic properties of ticarcillin stem from its ability to prevent cross-linking of peptidoglycan during cell wall synthesis, leading to cell death when the bacteria try to divide.Like penicillin, ticarcillin contains a β-lactam ring that is cleaved by β-lactamases, thereby inactivating the antibiotic.Therefore, those bacteria that can express β-lactamase are resistant to β-lactam antibiotics.Due to (at least in part) the common β-lactam ring, ticarcillin can cause reactions in patients allergic to penicillin.Ticarcillin is also commonly used in combination with beta-lactamase inhibitors such as clavulanic acid (co-ticarclav).

Other uses

• In molecular biology, ticarcillin is used as an alternative to ampicillin for testing marker gene uptake by bacteria.It prevents the formation of satellite colonies 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.

• Dosage and administration

• Ticarcillin is not absorbed orally and must be injected intravenously or intramuscularly.

• Trade names and formulations

• Ticarcillin: Ticar was formerly marketed by Beecham, then SmithKline Beecham until it merged with Glaxo in 1999 to form GlaxoSmithKline; it is no longer available in the UK.US distribution ceased in 2004.Ticar was replaced by Timentin.

• However,unlike Ticar, Timentin contains clavulanate

• Ticarcillin/clavulanic acid: In Australia, UK and US,Timentin is marketed by Beecham and GlaxoSmithKline.

• Marketed in India as TICANTROL (TICARCILLIN/clavulanate) by SCUTONIX LIFESCIENCES,Mumbai.

Synthesis

Carbenicillin is used clinically primarily because of its low toxicity and its utility in the treatment of urinary tract infections caused by susceptible Pseudomonas species.Its low potency, low oral activity, and susceptibility to bacterial β-lactamases make it susceptible to substitution by drugs that do not have these deficiencies.One contender in this race is Ticarcillin. Its origin rests on the well-known fact that divalent sulfur roughly corresponds to a vinyl group (see Methpropylamine, Sufentanil, Pyzotriptyline, etc.).One synthetic method is to prepare the monobenzyl ester of 3-thienylmalonic acid, convert it to the acid chloride with SOCl2, and condense it with 6-aminopenicillanic acid (6-APA).Hydrogenolysis (Pd/C) completes the synthesis of ticarcillin.