Ticarcillin

Ticarcillin

Systematic (IUPAC) name
(2S,5R,6R)-6-{[(2S)-2-carboxy-2-(3-thienyl)acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Clinical data
AHFS/Drugs.com	monograph
MedlinePlus	a685037
Pregnancy cat.	B2(AU) B(US)
Legal status	℞ Prescription only
Routes	Intravenous
Pharmacokinetic data
Protein binding	45%
Half-life	1.1 hours
Excretion	Renal
Identifiers
CAS number	34787-01-4 Y
ATC code	J01CA13 J01CR03
PubChem	CID 36921
DrugBank	DB01607
ChemSpider	33876 Y
UNII	F93UJX4SWT Y
KEGG	D08593 Y
ChEBI	CHEBI:9587 Y
ChEMBL	CHEMBL1449 Y
Chemical data
Formula	C15H16N2O6S2
Mol. mass	384.429 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C15H16N2O6S2/c1-15(2)9(14(22)23)17-11(19)8(12(17)25-15)16-10(18)7(13(20)21)6-3-4-24-5-6/h3-5,7-9,12H,1-2H3,(H,16,18)(H,20,21)(H,22,23)/t7-,8-,9+,12-/m1/s1 Y Key:OHKOGUYZJXTSFX-KZFFXBSXSA-N Y
Y(what is this?)  (verify)

Ticarcillin is a carboxypenicillin. It is almost invariably^{[citation needed]} 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, in particular, Pseudomonas aeruginosa. 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.

Mechanism of action

Ticarcillin's antibiotic properties arise from its ability to prevent cross-linking of peptidoglycan during cell wall synthesis, when the bacteria tries to divide, causing cell death.

Ticarcillin, like penicillin, contains a β-lactam ring that can be cleaved by β-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.

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 media. It is also used in plant molecular biology to kill agrobacterium, which is used to deliver genes to plant cells.

Dosing and posology

Ticarcillin is not absorbed orally, and therefore must be given by intravenous or intramuscular injection

Trade names and preparations

• Ticarcillin: Ticar (Formerly marketed by Beecham, then SmithKline Beecham 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.)

• Ticarcillin/clavulanate: Timentin (Australia, UK and US, marketed by Beecham, then GlaxoSmithKline).

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