Ticarcillin

Last updated
Ticarcillin
Ticarcillin.svg
Clinical data
AHFS/Drugs.com Monograph
MedlinePlus a685037
Pregnancy
category
  • AU:B2
Routes of
administration
Intravenous
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Protein binding 45%
Elimination half-life 1.1 hours
Excretion Renal
Identifiers
  • (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
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.047.451 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C15H16N2O6S2
Molar mass 384.42 g·mol−1
3D model (JSmol)
  • O=C(O)[C@@H]2N3C(=O)[C@@H](NC(=O)[C@@H](c1ccsc1)C(=O)O)[C@H]3SC2(C)C
  • 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 Yes check.svgY
  • Key:OHKOGUYZJXTSFX-KZFFXBSXSA-N Yes check.svgY
   (verify)

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.

Contents

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. [1]

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.[ 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).[ citation needed ]

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 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

However Timentin contains clavulanate unlike Ticar

Synthesis

Carbenicillin is used in the clinic primarily because of its low toxicity and its utility in treating urinary tract infections due to susceptible Pseudomonas 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: GEORGE BRAIN EDWARD, CHARLES NAYLER JOHN HERBERT;
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BE 646991  (1964 to Beecham). Ticarcillin synthesis.svg
Ticarcillin synthesis: GEORGE BRAIN EDWARD, CHARLES NAYLER JOHN HERBERT; BE 646991   (1964 to Beecham).

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.

Related Research Articles

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β-Lactamase inhibitor Family of enzymes

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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 action and restored efficacy against ticarcillin-resistant bacteria that produce certain β-lactamases.

References

  1. Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 491. ISBN   9783527607495.