Ticarcillin

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Ticarcillin
Ticarcillin.svg
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
    Legal status
    Legal status
    • In general: ℞ (Prescription only)
    Pharmacokinetic data
    Protein binding 45%
    Elimination half-life 1.1 hours
    Excretion Renal
    Identifiers
    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)
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    Ticarcillin is a carboxypenicillin. It is almost always[ citation needed ] 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 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.

    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.

    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).

    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; 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

    Ampicillin Antibiotic

    Ampicillin is an antibiotic used to prevent and treat a number of bacterial infections, such as respiratory tract infections, urinary tract infections, meningitis, salmonellosis, and endocarditis. It may also be used to prevent group B streptococcal infection in newborns. It is used by mouth, by injection into a muscle, or intravenously. Like all antibiotics, it is not useful for the treatment of viral infections.

    Amoxicillin Antibiotic

    Amoxicillin is an antibiotic used to treat a number of bacterial infections. These include middle ear infection, strep throat, pneumonia, skin infections, and urinary tract infections among others. It is taken by mouth, or less commonly by injection.

    Beta-lactamase class of enzymes

    Beta-lactamases are enzymes produced by bacteria that provide multi-resistance to β-lactam antibiotics such as penicillins, cephalosporins, cephamycins, and carbapenems (ertapenem), although carbapenems are relatively resistant to beta-lactamase. Beta-lactamase provides antibiotic resistance by breaking the antibiotics' structure. These antibiotics all have a common element in their molecular structure: a four-atom ring known as a β-lactam. Through hydrolysis, the enzyme lactamase breaks the β-lactam ring open, deactivating the molecule's antibacterial properties.

    Penicillin group of antibiotics derived from Penicillium fungi

    Penicillin is a group of antibiotics, derived originally from common moulds known as Penicillium moulds; which includes penicillin G, penicillin V, procaine penicillin, and benzathine penicillin. Penicillin antibiotics were among the first medications to be effective against many bacterial infections caused by staphylococci and streptococci. They are still widely used today, though many types of bacteria have developed resistance following extensive use.

    β-lactam antibiotic class of broad-spectrum antibiotics, consisting of all antibiotic agents that contain a β-lactam ring in their molecular structures

    β-lactam antibiotics are antibiotics that contain a beta-lactam ring in their molecular structure. This includes penicillin derivatives (penams), cephalosporins (cephems), monobactams, carbapenems and carbacephems. Most β-lactam antibiotics work by inhibiting cell wall biosynthesis in the bacterial organism and are the most widely used group of antibiotics. Until 2003, when measured by sales, more than half of all commercially available antibiotics in use were β-lactam compounds. The first β-lactam antibiotic discovered, penicillin, was isolated from a rare variant of Penicillium notatum.

    Methicillin chemical compound

    Methicillin, also known as meticillin, is a narrow-spectrum β-lactam antibiotic of the penicillin class.

    Amoxicillin/clavulanic acid combination antibiotic drug

    Amoxicillin/clavulanic acid, also known as co-amoxiclav, is an antibiotic useful for the treatment of a number of bacterial infections. It is a combination consisting of amoxicillin, a β-lactam antibiotic, and potassium clavulanate, a β-lactamase inhibitor. It is specifically used for otitis media, strep throat, pneumonia, cellulitis, urinary tract infections, and animal bites. It is taken by mouth or by injection into a vein.

    Tazobactam chemical compound

    Tazobactam is a pharmaceutical drug that inhibits the action of bacterial β-lactamases, especially those belonging to the SHV-1 and TEM groups. It is commonly used as its sodium salt, tazobactam sodium. In simple terms, it is an ingredient that can be added to certain antibiotics to make them less vulnerable to bacteria's antimicrobial resistance.

    Clavulanic acid chemical compound

    Clavulanic acid is a β-lactam drug that functions as a mechanism-based β-lactamase inhibitor. While not effective by itself as an antibiotic, when combined with penicillin-group antibiotics, it can overcome antibiotic resistance in bacteria that secrete β-lactamase, which otherwise inactivates most penicillins.

    Cefuroxime axetil chemical compound

    Cefuroxime axetil, sold under the brand name Ceftin among others, is a second generation oral cephalosporin antibiotic.

    Carbapenem group of β-lactam antibiotics

    Carbapenems are a class of highly effective antibiotic agents commonly used for the treatment of severe or high-risk bacterial infections. This class of antibiotics is usually reserved for known or suspected multidrug-resistant (MDR) bacterial infections. Similar to penicillins and cephalosporins, carbapenems are members of the beta lactam class of antibiotics, which kill bacteria by binding to penicillin-binding proteins, thus inhibiting bacterial cell wall synthesis. However, these agents individually exhibit a broader spectrum of activity compared to most cephalosporins and penicillins. Furthermore, carbapenems are typically unaffected by emerging antibiotic resistance, even to other beta-lactams.

    Ampicillin/sulbactam is a combination of the common penicillin-derived antibiotic ampicillin and sulbactam, an inhibitor of bacterial beta-lactamase. Two different forms of the drug exist. The first, developed in 1987 and marketed in the United States under the tradename Unasyn, generic only outside the United States, is an intravenous antibiotic. The second, an oral form called sultamicillin, is marketed under the trade name Ampictam outside the United States. And generic only in the United States, ampicillin/sulbactam is used to treat infections caused by bacteria resistant to beta-lactam antibiotics. Sulbactam blocks the enzyme which breaks down ampicillin and thereby allows ampicillin to attack and kill the bacteria.

    Sulbactam chemical compound

    Sulbactam is a β-lactamase inhibitor. This drug is given in combination with β-lactam antibiotics to inhibit β-lactamase, an enzyme produced by bacteria that destroys the antibiotics.

    Flucloxacillin chemical compound

    Flucloxacillin, also known as floxacillin, is a narrow-spectrum beta-lactam antibiotic of the penicillin class. It is used to treat infections caused by susceptible Gram-positive bacteria. Unlike other penicillins, flucloxacillin has activity against beta-lactamase-producing organisms such as Staphylococcus aureus as it is beta-lactamase stable. However, it is ineffective against methicillin-resistant Staphylococcus aureus (MRSA). It is very similar to dicloxacillin; they are considered interchangeable.

    Oxacillin chemical compound

    Oxacillin is a narrow-spectrum beta-lactam antibiotic of the penicillin class developed by Beecham.

    Beecham Group British defunct pharmaceutical company

    The Beecham Group plc was a British pharmaceutical company. It was once a constituent of the FTSE 100 Index. Beecham, after having merged with SmithKline Beckman to become SmithKline Beecham, merged with Glaxo Wellcome to become GlaxoSmithKline (GSK). GSK still uses the Beechams brand name in the UK for its over-the-counter cold and flu relief products.

    Thienamycin chemical compound

    Thienamycin is one of the most potent naturally produced antibiotics known thus far, discovered in Streptomyces cattleya in 1976. Thienamycin has excellent activity against both Gram-positive and Gram-negative bacteria and is resistant to bacterial β-lactamase enzymes. Thienamycin is a zwitterion at pH 7.

    β-Lactamase inhibitor Endogenous substances and drugs that inhibit or block the activity of beta-lactamases

    Beta-lactamases are a family of enzymes involved in bacterial resistance to beta-lactam antibiotics. They act by breaking the beta-lactam ring that allows penicillin-like antibiotics to work. Strategies for combating this form of resistance have included the development of new beta-lactam antibiotics that are more resistant to cleavage and the development of the class of enzyme inhibitors called beta-lactamase inhibitors. Although β-lactamase inhibitors have little antibiotic activity of their own, they prevent bacterial degradation of beta-lactam antibiotics and thus extend the range of bacteria the drugs are effective against.

    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, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 491. ISBN   9783527607495.