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. Because it is a penicillin, it also falls within the larger class of

beta-lactam A beta-lactam (β-lactam) ring is a four-membered lactam. A ''lactam'' is a cyclic amide, and ''beta''-lactams are named so because the nitrogen atom is attached to the β-carbon atom relative to the carbonyl. The simplest β-lactam possible i ...

antibiotics. Its main clinical use is as an injectable antibiotic for the treatment of

Gram-negative Gram-negative bacteria are bacteria that do not retain the crystal violet stain used in the Gram staining method of bacterial differentiation. They are characterized by their cell envelopes, which are composed of a thin peptidoglycan cell wa ...

bacteria, particularly ''

Pseudomonas aeruginosa ''Pseudomonas aeruginosa'' is a common encapsulated, gram-negative, aerobic–facultatively anaerobic, rod-shaped bacterium that can cause disease in plants and animals, including humans. A species of considerable medical importance, ''P. aerug ...

'' and Proteus vulgaris. 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 peptidoglycan layer outside the plasma membrane, the rigid cell wall (murein sacculus) characteristic of most ba ...

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

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 such as clavulanic acid (

co-ticarclav Ticarcillin/clavulanic acid, or co-ticarclav, is a combination antibiotic consisting of ticarcillin, a Β-Lactam antibiotic, β-lactam antibiotic, and clavulanic acid, a Β-Lactamase inhibitor, β-lactamase inhibitor. This combination results in ...

Other uses

molecular biology Molecular biology is the branch of biology that seeks to understand the molecular basis of biological activity in and between cells, including biomolecular synthesis, modification, mechanisms, and interactions. The study of chemical and physi ...

, ticarcillin is used to as an alternative to

ampicillin Ampicillin is an antibiotic used to prevent and treat a number of bacterial infections, such as respiratory tract infections, urinary tract infections, meningitis, salmonellosis, and endocarditis. It may also be used to prevent group B stre ...

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

* Ticarcillin: Ticar was formerly marketed by Beecham, then

SmithKline Beecham GSK plc, formerly GlaxoSmithKline plc, is a British multinational pharmaceutical and biotechnology company with global headquarters in London, England. Established in 2000 by a merger of Glaxo Wellcome and SmithKline Beecham. GSK is the tent ...

until 1999, when it merged with Glaxo to form GlaxoSmithKline; 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 part of the urinary tract. When it affects the lower urinary tract it is known as a bladder infection (cystitis) and when it affects the upper urinary tract it is known as a kidne ...

due to susceptible

Pseudomonas ''Pseudomonas'' is a genus of Gram-negative, Gammaproteobacteria, belonging to the family Pseudomonadaceae and containing 191 described species. The members of the genus demonstrate a great deal of metabolic diversity and consequently are able t ...

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 Sufentanil, sold under the brand names Dsuvia and Sufenta, is a synthetic opioid analgesic drug approximately 5 to 10 times as potent as its parent drug, fentanyl, and 500 times as potent as morphine. Structurally, sufentanil differs from fen ...

pizotyline Pizotifen ( INN) or pizotyline (USAN), trade name Sandomigran, is a benzocycloheptene-based drug used as a medicine, primarily as a preventive to reduce the frequency of recurrent migraine headaches. Uses The main medical use for pizotifen is ...

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 6-APA ((+)-6-aminopenicillanic acid) is a chemical compound used as an intermediate in the synthesis of β-lactam antibiotics. The major commercial source of 6-APA is still natural penicillin G: the semi-synthetic penicillins derived from 6-APA a ...

). Hydrogenolysis (Pd/C) completed the synthesis of ticarcillin.

References

{{PenicillinAntiBiotics Penicillins Thiophenes