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Compound

Ticarcillin

Also called Tarcil

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Overview

Ticarcillin is a carboxypenicillin. 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 β-lactam antibiotics. Its main clinical use is as an injectable antibiotic for the treatment of Gram-negative bacteria, particularly Pseudomonas aeruginosa and Proteus vulgaris. It is also one of the few antibiotics capable of treating Stenotrophomonas maltophilia infections. WP

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. WP

It was patented in 1963.[1] WP

Pharmacology

Mechanism of action

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. WP⚠ Wikipedia itself has flagged this text: citation needed.

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 (co-ticarclav). WP⚠ Wikipedia itself has flagged this text: citation needed.

Chemistry

Formula
C15H16N2O6S2 PC
CAS number
34787-01-4 PC
Molar mass (g/mol)
384.4 PC
IUPAC name (computed by PubChem)
(2S,5R,6R)-6-[[(2R)-2-carboxy-2-thiophen-3-ylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid PC
SMILES
CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CSC=C3)C(=O)O)C(=O)O)C PC
InChIKey
OHKOGUYZJXTSFX-KZFFXBSXSA-N PC
PubChem CID
36921

Harm reduction information

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Sources

  1. Other Fischer J, Ganellin CR. Analogue-based Drug Discovery. 2006

Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.