Carbenicillin

Last updated
Carbenicillin
Carbenicillin.svg
Clinical data
Trade names Geocillin; Pyopen
Other namesCB [1]
AHFS/Drugs.com Monograph
Pregnancy
category
Routes of
administration
Oral, parenteral
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability 30 to 40%
Protein binding 30 to 60%
Metabolism Minimal
Elimination half-life 1 hour
Excretion Renal (30 to 40%)
Identifiers
  • (2S,5R,6R)-6-{[carboxy(phenyl)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 100.022.882 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C17H18N2O6S
Molar mass 378.40 g·mol−1
3D model (JSmol)
  • O=C(O)[C@@H]2N3C(=O)[C@@H](NC(=O)C(c1ccccc1)C(=O)O)[C@H]3SC2(C)C
  • InChI=1S/C17H18N2O6S/c1-17(2)11(16(24)25)19-13(21)10(14(19)26-17)18-12(20)9(15(22)23)8-6-4-3-5-7-8/h3-7,9-11,14H,1-2H3,(H,18,20)(H,22,23)(H,24,25)/t9?,10-,11+,14-/m1/s1 Yes check.svgY
  • Key:FPPNZSSZRUTDAP-UWFZAAFLSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Carbenicillin is a bactericidal antibiotic belonging to the carboxypenicillin subgroup of the penicillins. [2] It was discovered by scientists at Beecham and marketed as Pyopen. It has Gram-negative coverage which includes Pseudomonas aeruginosa but limited Gram-positive coverage. The carboxypenicillins are susceptible to degradation by beta-lactamase enzymes, although they are more resistant than ampicillin to degradation. Carbenicillin is also more stable at lower pH than ampicillin.

Contents

Pharmacology

The antibiotic is highly soluble in water and is acid-labile. A typical lab working concentration is 50 to 100 μg per mL.[ citation needed ]

It is a semi-synthetic analogue of the naturally occurring benzylpenicillin. Carbenicillin at high doses can cause bleeding. Use of carbenicillin can cause hypokalemia by promoting potassium loss at the distal convoluted tubule of the kidney.[ citation needed ]

In molecular biology, carbenicillin may be preferred as a selecting agent (see plasmid stabilisation technology) because its breakdown results in byproducts with a lower toxicity than analogous antibiotics like ampicillin. Carbenicillin is more stable than ampicillin and results in fewer satellite colonies on selection plates. However, in most situations this is not a significant problem so ampicillin is sometimes used due to its lower cost.[ citation needed ]

Spectrum of bacterial susceptibility and resistance

Carbenicillin has been shown to be effective against bacteria responsible for causing urinary tract infections including Pseudomonas aeruginosa, Escherichia coli, and some Proteus species. The following represents carbenicillin susceptibility data for a few medically significant organisms. [3] This is not representative of all species of bacteria susceptible to carbenicillin exposure.

Related Research Articles

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Gram-negative bacteria are bacteria that unlike gram-positive bacteria do not retain the crystal violet stain used in the Gram staining method of bacterial differentiation. Their defining characteristic is their cell envelope, which consists of a thin peptidoglycan cell wall sandwiched between an inner (cytoplasmic) membrane and an outer membrane. These bacteria are found in all environments that support life on Earth.

<span class="mw-page-title-main">Aztreonam</span> Chemical compound

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<span class="mw-page-title-main">Ceftazidime</span> Antibiotic medication

Ceftazidime, sold under the brand name Fortaz among others, is a third-generation cephalosporin antibiotic useful for the treatment of a number of bacterial infections. Specifically it is used for joint infections, meningitis, pneumonia, sepsis, urinary tract infections, malignant otitis externa, Pseudomonas aeruginosa infection, and vibrio infection. It is given by injection into a vein, muscle, or eye.

<span class="mw-page-title-main">Tobramycin</span> Chemical compound

Tobramycin is an aminoglycoside antibiotic derived from Streptomyces tenebrarius that is used to treat various types of bacterial infections, particularly Gram-negative infections. It is especially effective against species of Pseudomonas.

<span class="mw-page-title-main">Ticarcillin</span> Antibiotic medication

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.

<span class="mw-page-title-main">Cefepime</span> Fourth-generation Cephalosporin Antibiotic

Cefepime is a fourth-generation cephalosporin antibiotic. Cefepime has an extended spectrum of activity against Gram-positive and Gram-negative bacteria, with greater activity against both types of organism than third-generation agents. A 2007 meta-analysis suggested when data of trials were combined, mortality was increased in people treated with cefepime compared with other β-lactam antibiotics. In response, the U.S. Food and Drug Administration (FDA) performed their own meta-analysis which found no mortality difference.

<span class="mw-page-title-main">Cefotaxime</span> Chemical compound

Cefotaxime is an antibiotic used to treat a number of bacterial infections in human, other animals and plant tissue culture. Specifically in humans it is used to treat joint infections, pelvic inflammatory disease, meningitis, pneumonia, urinary tract infections, sepsis, gonorrhea, and cellulitis. It is given either by injection into a vein or muscle.

<span class="mw-page-title-main">Cefadroxil</span> Antibiotic

Cefadroxil is a broad-spectrum antibiotic of the cephalosporin type, effective in Gram-positive and Gram-negative bacterial infections. It is a bactericidal antibiotic.

Ampicillin/sulbactam is a fixed-dose combination medication 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 brand name Unasyn, generic only outside the United States, is an intravenous antibiotic. The second, an oral form called sultamicillin, is marketed under the brand 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.

<span class="mw-page-title-main">Azlocillin</span> Antibiotic

Azlocillin is an acyl ampicillin antibiotic with an extended spectrum of activity and greater in vitro potency than the carboxy penicillins. Azlocillin is similar to mezlocillin and piperacillin. It demonstrates antibacterial activity against a broad spectrum of bacteria, including Pseudomonas aeruginosa and, in contrast to most cephalosporins, exhibits activity against enterococci.

<span class="mw-page-title-main">Apramycin</span> Chemical compound

Apramycin is an aminoglycoside antibiotic used in veterinary medicine. It is produced by Streptomyces tenebrarius.

<span class="mw-page-title-main">Carboxypenicillin</span> Drug class

The carboxypenicillins are a group of antibiotics. They belong to the penicillin family and comprise the members carbenicillin and ticarcillin.

<span class="mw-page-title-main">Mezlocillin</span> Chemical compound

Mezlocillin is a broad-spectrum penicillin antibiotic. It is active against both Gram-negative and some Gram-positive bacteria. Unlike most other extended spectrum penicillins, it is excreted by the liver, therefore it is useful for biliary tract infections, such as ascending cholangitis.

<span class="mw-page-title-main">Cefotiam</span> Chemical compound

Cefotiam is a parenteral third-generation cephalosporin antibiotic. It has broad-spectrum activity against Gram-positive and Gram-negative bacteria. As a beta-lactam, its bactericidal activity results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins.

<span class="mw-page-title-main">Enrofloxacin</span> Chemical compound

Enrofloxacin, sold under the brand name Baytril, among others, is a fluoroquinolone antibiotic used for the treatment of animals. It is a bactericidal agent.

<span class="mw-page-title-main">Cefoxitin</span> Chemical compound

Cefoxitin is a second-generation cephamycin antibiotic developed by Merck & Co., Inc. from Cephamycin C in the year following its discovery, 1972. It was synthesized in order to create an antibiotic with a broader spectrum. It is often grouped with the second-generation cephalosporins. Cefoxitin requires a prescription and as of 2010 is sold under the brand name Mefoxin by Bioniche Pharma, LLC. The generic version of cefoxitin is known as cefoxitin sodium.

<span class="mw-page-title-main">Cefminox</span> Chemical compound

Cefminox (INN) is a second-generation cephalosporin antibiotic.

<span class="mw-page-title-main">Carindacillin</span> Chemical compound

Carindacillin (INN), also known as carbenicillin indanyl (USAN), is a penicillin antibiotic. It is a prodrug of carbenicillin.

Infections caused by exposure to ionizing radiation can be extremely dangerous, and are of public and government concern. Numerous studies have demonstrated that the susceptibility of organisms to systemic infection increased following exposure to ionizing radiation. The risk of systemic infection is higher when the organism has a combined injury, such as a conventional blast, thermal burn, or radiation burn. There is a direct quantitative relationship between the magnitude of the neutropenia that develops after exposure to radiation and the increased risk of developing infection. Because no controlled studies of therapeutic intervention in humans are available, almost all of the current information is based on animal research.

<span class="mw-page-title-main">Ceftolozane/tazobactam</span> Antibiotic

Ceftolozane/tazobactam, sold under the brand name Zerbaxa, is a fixed-dose combination antibiotic medication used for the treatment of complicated urinary tract infections and complicated intra-abdominal infections in adults. Ceftolozane is a cephalosporin antibiotic, developed for the treatment of infections with gram-negative bacteria that are resistant to conventional antibiotics. It was studied for urinary tract infections, intra-abdominal infections and ventilator-associated bacterial pneumonia.

References

  1. "Antibiotic abbreviations list" . Retrieved 22 June 2023.
  2. Basker MJ, Comber KR, Sutherland R, Valler GH (1977). "Carfecillin: antibacterial activity in vitro and in vivo". Chemotherapy. 23 (6): 424–35. doi:10.1159/000222012. PMID   21771.
  3. "Carbenicillin Disodium, USP Susceptibility and Minimum Inhibitory Concentration (MIC) Data" (PDF). January 6, 2020.

Further reading