Ticarcillin is a

carboxypenicillin The carboxypenicillins are a group of antibiotics. They belong to the penicillin family and comprise the members carbenicillin and ticarcillin. Chemical structure The carboxypenicillins feature the beta-lactam backbone of all penicillins b ...

. It can be sold and used in combination with clavulanate as

ticarcillin/clavulanic acid Ticarcillin/clavulanic acid, or co-ticarclav, is a combination antibiotic consisting of ticarcillin, a β-lactam antibiotic, and clavulanic acid, a β-lactamase inhibitor. This combination results in an antibiotic with an increased spectrum of a ...

. Because it is a penicillin, it also falls within the larger class of β-lactam antibiotics. Its main clinical use is as an injectable antibiotic for the treatment of

Gram-negative Gram-negative bacteria are bacteria that, unlike gram-positive bacteria, do not retain the crystal violet stain used in the Gram staining method of bacterial differentiation. Their defining characteristic is that their cell envelope consists ...

bacteria, particularly ''

Pseudomonas aeruginosa ''Pseudomonas aeruginosa'' is a common Bacterial capsule, encapsulated, Gram-negative bacteria, Gram-negative, Aerobic organism, aerobic–facultative anaerobe, facultatively anaerobic, Bacillus (shape), rod-shaped bacteria, bacterium that can c ...

'' and ''

Proteus vulgaris ''Proteus vulgaris'' is a rod-shaped, nitrate-reducing, indole-positive and catalase-positive, hydrogen sulfide-producing, Gram-negative bacterium that inhabits the intestinal tracts of humans and animals. It can be found in soil, water, and ...

''. It is also one of the few antibiotics capable of treating '' Stenotrophomonas maltophilia'' infections. 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. It was patented in 1963.

Mechanism of action

Ticarcillin's antibiotic properties arise from its ability to prevent cross-linking of

peptidoglycan Peptidoglycan or murein is a unique large macromolecule, a polysaccharide, consisting of sugars and amino acids that forms a mesh-like layer (sacculus) that surrounds the bacterial cytoplasmic membrane. The sugar component consists of alternating ...

during

cell wall A cell wall is a structural layer that surrounds some Cell type, cell types, found immediately outside the cell membrane. It can be tough, flexible, and sometimes rigid. Primarily, it provides the cell with structural support, shape, protection, ...

synthesis, when the bacteria try to divide, causing cell death. Ticarcillin, like

penicillin Penicillins (P, PCN or PEN) are a group of beta-lactam antibiotic, β-lactam antibiotics originally obtained from ''Penicillium'' Mold (fungus), moulds, principally ''Penicillium chrysogenum, P. chrysogenum'' and ''Penicillium rubens, P. ru ...

, contains a β-lactam ring that can be cleaved by

β-lactamase Beta-lactamases (β-lactamases) are enzymes () produced by bacteria that provide Multiple drug resistance, multi-resistance to beta-lactam antibiotics such as penicillins, cephalosporins, cephamycins, monobactams and carbapenems (ertapenem ...

s, 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 Beta-lactamases are a family of enzymes involved in bacterial antimicrobial resistance, resistance to β-lactam antibiotic, beta-lactam antibiotics. In bacterial resistance to beta-lactam antibiotics, the bacteria have beta-lactamase which degra ...

such as

clavulanic acid Clavulanic acid is a β-lactam antibiotic, β-lactam drug that functions as a Suicide inhibition, mechanism-based β-lactamase inhibitor. While not effective by itself as an antibiotic, when combined with penicillin-group antibiotics, it can ove ...

( co-ticarclav).

Other uses

molecular biology Molecular biology is a branch of biology that seeks to understand the molecule, molecular basis of biological activity in and between Cell (biology), cells, including biomolecule, biomolecular synthesis, modification, mechanisms, and interactio ...

, ticarcillin is used to as an alternative to

ampicillin Ampicillin is an antibiotic belonging to the aminopenicillin class of the penicillin family. The drug is used to prevent and treat several bacterial infections, such as respiratory tract infections, urinary tract infections, meningitis, s ...

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 ''Agrobacterium'' is a genus of Gram-negative bacteria established by Harold J. Conn, H. J. Conn that uses horizontal gene transfer to cause tumors in plants. ''Agrobacterium tumefaciens'' is the most commonly studied species in this genus. ''Agr ...

'', 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

* Ticarcillin: Ticar was formerly marketed by Beecham, then

SmithKline Beecham GSK plc (an acronym from its former name GlaxoSmithKline plc) is a British multinational pharmaceutical and biotechnology company with headquarters in London. It was established in 2000 by a merger of Glaxo Wellcome and SmithKline Beecham, w ...

until 1999, when it merged with Glaxo to form

GlaxoSmithKline GSK plc (an acronym from its former name GlaxoSmithKline plc) is a British Multinational corporation, multinational Pharmaceutics, pharmaceutical and biotechnology company with headquarters in London. It was established in 2000 by a Mergers an ...

; it is no longer available in the UK. US distribution ceased in 2004. Ticar was replaced by Timentin. However Timentin contains clavulanate unlike Ticar * Ticarcillin/clavulanate: Timentin, in Australia, the UK, and the US, was marketed by Beecham, then GlaxoSmithKline. * Available in India as TICANTROL (TICARCILLIN/ clavulanate) marketed by SCUTONIX LIFESCIENCES, Bombay

Synthesis

Carbenicillin Carbenicillin is a bactericidal antibiotic belonging to the carboxypenicillin subgroup of the penicillins. It was discovered by scientists at Beecham and marketed as Pyopen. It has Gram-negative coverage which includes ''Pseudomonas aeruginosa' ...

is used in the clinic primarily because of its low toxicity and its utility in treating

urinary tract infections A urinary tract infection (UTI) is an infection that affects a part of the urinary tract. Lower urinary tract infections may involve the bladder (cystitis) or urethra ( urethritis) while upper urinary tract infections affect the kidney (pye ...

due to susceptible

Pseudomonas ''Pseudomonas'' is a genus of Gram-negative bacteria belonging to the family Pseudomonadaceae in the class Gammaproteobacteria. The 348 members of the genus demonstrate a great deal of metabolic diversity and consequently are able to colonize a ...

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.). Ticarcillin synthesis

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.

References

{{PenicillinAntiBiotics Penicillins Thiophenes