Cefamandole

Last updated
Cefamandole
Cefamandole.svg
Clinical data
Trade names former Mandol
AHFS/Drugs.com Micromedex Detailed Consumer Information
MedlinePlus a601206
Pregnancy
category
  • AU:B1
Routes of
administration
Intramuscular, intravenous
ATC code
Legal status
Legal status
  • UK: POM (Prescription only)
  • US:Discontinued
Pharmacokinetic data
Protein binding 75%
Elimination half-life 48 minutes
Excretion Mostly renal, as unchanged drug
Identifiers
  • (6R,7R)-7-{[(2R)-2-hydroxy-2-phenylacetyl]amino}-
    3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-
    5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.047.285 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C18H18N6O5S2
Molar mass 462.50 g·mol−1
3D model (JSmol)
  • O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)[C@H](O)c3ccccc3)CSc4nnnn4C)C(=O)O
  • InChI=1S/C18H18N6O5S2/c1-23-18(20-21-22-23)31-8-10-7-30-16-11(15(27)24(16)12(10)17(28)29)19-14(26)13(25)9-5-3-2-4-6-9/h2-6,11,13,16,25H,7-8H2,1H3,(H,19,26)(H,28,29)/t11-,13-,16-/m1/s1 Yes check.svgY
  • Key:OLVCFLKTBJRLHI-AXAPSJFSSA-N Yes check.svgY
   (verify)

Cefamandole (INN, also known as cephamandole) is a second-generation broad-spectrum cephalosporin antibiotic. The clinically used form of cefamandole is the formate ester cefamandole nafate, a prodrug which is administered parenterally. Cefamandole is no longer available in the United States.

The chemical structure of cefamandole, like that of several other cephalosporins, contains an N-methylthiotetrazole (NMTT or 1-MTT) side chain. As the antibiotic is broken down in the body, it releases free NMTT, which can cause hypoprothrombinemia (likely due to inhibition of the enzyme vitamin K epoxide reductase)(vitamin K supplement is recommended during therapy) and a reaction with ethanol similar to that produced by disulfiram (Antabuse), due to inhibition of aldehyde dehydrogenase.

Cefamandole has a broad spectrum of activity and can be used to treat bacterial infections of the skin, bones and joints, urinary tract, and lower respiratory tract. The following represents cefamandole MIC susceptibility data for a few medically significant microorganisms.

CO2 is generated during the normal constitution of cefamandole and ceftazidime, potentially resulting in an explosive-like reaction in syringes. [2]

See also

Related Research Articles

<span class="mw-page-title-main">Cephalosporin</span> Class of pharmaceutical drugs

The cephalosporins are a class of β-lactam antibiotics originally derived from the fungus Acremonium, which was previously known as Cephalosporium.

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

Aztreonam, sold under the brand name Azactam among others, is an antibiotic used primarily to treat infections caused by gram-negative bacteria such as Pseudomonas aeruginosa. This may include bone infections, endometritis, intra abdominal infections, pneumonia, urinary tract infections, and sepsis. It is given by intravenous or intramuscular injection or by inhalation.

<span class="mw-page-title-main">Cefotetan</span> Pharmaceutical drug

Cefotetan is an injectable antibiotic of the cephamycin type for prophylaxis and treatment of bacterial infections. It is often grouped together with second-generation cephalosporins and has a similar antibacterial spectrum, but with additional anti-anaerobe coverage.

<span class="mw-page-title-main">Cefixime</span> Ofloxacin

Cefixime, sold under the brand name Suprax among others, is an antibiotic medication used to treat a number of bacterial infections. These infections include otitis media, strep throat, pneumonia, urinary tract infections, gonorrhea, and Lyme disease. For gonorrhea typically only one dose is required. In the United States it is a second-line treatment to ceftriaxone for gonorrhea. It is taken by mouth.

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

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">Cefaclor</span>

Cefaclor, sold under the trade name Ceclor among others, is a second-generation cephalosporin antibiotic used to treat certain bacterial infections such as pneumonia and infections of the ear, lung, skin, throat, and urinary tract. It is also available from other manufacturers as a generic.

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

Cefpodoxime is an oral, third-generation cephalosporin antibiotic. It is active against most Gram-positive and Gram-negative organisms. Notable exceptions include Pseudomonas aeruginosa, Enterococcus, and Bacteroides fragilis. Currently, it is only marketed as generic preparations in the US, according to the FDA Orange Book. It is commonly used to treat acute otitis media, pharyngitis, sinusitis, and gonorrhea. It also finds use as oral continuation therapy when intravenous cephalosporins are no longer necessary for continued treatment.

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

Cefepime is a fourth-generation cephalosporin antibiotic with the ability to cross the blood–brain barrier. 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.

Antibiotic sensitivity testing Microbiology test used in medicine

Antibiotic sensitivity testing or antibiotic susceptibility testing is the measurement of the susceptibility of bacteria to antibiotics. It is used because bacteria may have resistance to some antibiotics. Sensitivity testing results can allow a clinician to change the choice of antibiotics from empiric therapy, which is when an antibiotic is selected based on clinical suspicion about the site of an infection and common causative bacteria, to directed therapy, in which the choice of antibiotic is based on knowledge of the organism and its sensitivities.

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

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

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

Azlocillin is an acylampicillin 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">Cefdinir</span> Chemical compound

Cefdinir, sold under the brand name Omnicef among others, is an antibiotic used to treat pneumonia, otitis media, strep throat, and cellulitis. It is a less preferred option for pneumonia, otitis media, and strep throat which may be used in those with a severe allergy to penicillin. It is taken by mouth.

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

Cefotiam is a parenteral second-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">Cefoxitin</span>

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">Cefoperazone</span> Antibiotic

Cefoperazone is a third-generation cephalosporin antibiotic, marketed by Pfizer under the name Cefobid. It is one of few cephalosporin antibiotics effective in treating Pseudomonas bacterial infections which are otherwise resistant to these antibiotics.

<span class="mw-page-title-main">Ceftibuten</span> Chemical to treat chronic bronchitis

Ceftibuten is a third-generation cephalosporin antibiotic. It is an orally administered agent, with two dosage forms, capsule or oral suspension. It is marketed by Pernix Therapeutics under the trade name Cedax.

<span class="mw-page-title-main">Cefditoren</span> Chemical to treat skin infections

Cefditoren also known as cefditoren pivoxil is a broad-spectrum antibiotic, taken by mouth to treat pneumonia and other infections. It is a third-generation oral cephalosporin with a broad spectrum of activity against bacterial pathogens, including both Gram-positive and Gram-negative bacteria, and it is effective against some antibiotic-resistant bacteria because it is not susceptible to hydrolysis by many common beta-lactamases. The United States Food and Drug Administration approved cefditoren pivoxil for adults and adolescents in 2001. In 2018 Zuventus Healthcare received approval for cefditoren pivoxil dry powder for suspension for the treatment of mild to moderate infection in children which are caused by susceptible strains of the designated microorganisms.

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

Cefmetazole is a cephamycin antibiotic, usually grouped with the second-generation cephalosporins.

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

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

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

Ceftolozane/tazobactam, sold under the brand name Zerbaxa, is a 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. "Cefamandole sodium salt Susceptibility and 0.5 - 32 Minimum Inhibitory Concentration (MIC) Data" (PDF). The Antimicrobial Index. TOKU-E. 6 January 2020.
  2. Stork CM (2006). "Antibiotics, antifungals, and antivirals". In Nelson LH, Flomenbaum N, Goldfrank LR, Hoffman RL, Howland MD, Lewin NA (eds.). Goldfrank's toxicologic emergencies. New York: McGraw-Hill. p. 847. ISBN   0-07-143763-0 . Retrieved 2009-07-03.