Ticarcillin

Ticarcillin

Clinical data
AHFS/Drugs.com	Monograph
MedlinePlus	a685037
Pregnancy category	AU: B2 US: B (No risk in non-human studies)
Routes of administration	Intravenous
ATC code	J01CA13 (WHO) J01CR03 (WHO)
Legal status
Legal status	℞ (Prescription only)
Pharmacokinetic data
Protein binding	45%
Biological half-life	1.1 hours
Excretion	Renal
Identifiers
IUPAC name (2S,5R,6R)-6-{[(2R)-2-carboxy-2-(3-thienyl)acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
CAS Number	34787-01-4 Y
PubChem (CID)	36921
DrugBank	DB01607 Y
ChemSpider	33876 Y
UNII	F93UJX4SWT Y
KEGG	D08593 Y
ChEBI	CHEBI:9587 Y
ChEMBL	CHEMBL1449 Y
ECHA InfoCard	100.047.451
Chemical and physical data
Formula	C15H16N2O6S2
Molar mass	384.429 g/mol
3D model (Jmol)	Interactive image
SMILES O=C(O)[C@@H]2N3C(=O)[C@@H](NC(=O)[C@@H](c1ccsc1)C(=O)O)[C@H]3SC2(C)C
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

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.

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'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).

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.