Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Ticarcillin: Difference between pages

{{Short description|Antibiotic medication}}

| Watchedfields = changed

| verifiedrevid = 470610157

| IUPAC_name = (2''S'',5''R'',6''R'')-6-{[(2''R'')-2-carboxy-2-(3-thienyl)acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

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| ATC_supplemental = {{ATC|J01|CR03}}

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| ChEBI_Ref = {{ebicite|correct|EBI}}

| C=15 | H=16 | N=2 | O=6 | S=2

'''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 [[beta-lactam|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.

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.

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It was patented in 1963.<ref name=Fis2006>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=491 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA491 |language=en}}</ref>

== 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 [[Binary fission|divide]], causing cell death.{{cn|date=March 2023}}

Ticarcillin, like [[penicillin]], contains a β-lactam ring that can be cleaved by [[beta-lactamase|β-lactamase]]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 [[beta-lactamase inhibitor|β-lactamase inhibitor]] such as [[clavulanic acid]] ([[co-ticarclav]]).{{cn|date=March 2023}}

==Other uses==

In [[molecular biology]], ticarcillin is used to as an alternative to [[ampicillin]] to test the uptake of [[marker gene]]s 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 (pharmaceutical company)|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.

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]] 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.).

[[File:Ticarcillin synthesis.svg|thumb|center|700px|Ticarcillin synthesis: GEORGE BRAIN EDWARD, CHARLES NAYLER JOHN HERBERT; {{Cite patent|country=BE|number=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.

==References==

{{reflist}}

{{PenicillinAntiBiotics}}

[[Category:Penicillins]]

[[Category:Thiophenes]]