Cefotaxime

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Cefotaxime
Cefotaxime.svg
Cefotaxime ball-and-stick.png
Clinical data
Pronunciation /ˌsɛfəˈtækˌsiːm/ [1]
Trade names Claforan, others
Other namescefotaxime sodium
AHFS/Drugs.com Monograph
MedlinePlus a682765
License data
Pregnancy
category
Routes of
administration 		Intravenous and intramuscular
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
Pharmacokinetic data
Bioavailability n/a
Metabolism liver
Elimination half-life 0.8–1.4 hours
Excretion 50–85% kidney
Identifiers
  • (6R,7R,Z)-3-(Acetoxymethyl)-7-(2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.058.436 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C16H17N5O7S2
Molar mass 455.46 g·mol−1
3D model (JSmol)
  • O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)C(=N\OC)\c3nc(sc3)N)COC(=O)C)C(=O)O
  • InChI=1S/C16H17N5O7S2/c1-6(22)28-3-7-4-29-14-10(13(24)21(14)11(7)15(25)26)19-12(23)9(20-27-2)8-5-30-16(17)18-8/h5,10,14H,3-4H2,1-2H3,(H2,17,18)(H,19,23)(H,25,26)/b20-9+/t10-,14-/m1/s1 Yes check.svgY
  • Key:GPRBEKHLDVQUJE-VINNURBNSA-N Yes check.svgY
   (verify)

Cefotaxime is an antibiotic used to treat a number of bacterial infections in human, other animals and plant tissue culture. [3] Specifically in humans it is used to treat joint infections, pelvic inflammatory disease, meningitis, pneumonia, urinary tract infections, sepsis, gonorrhea, and cellulitis. [3] It is given either by injection into a vein or muscle. [3]

Contents

Common side effects include nausea, allergic reactions, and inflammation at the site of injection. [3] Another side effect may include Clostridium difficile diarrhea. [3] It is not recommended in people who have had previous anaphylaxis to a penicillin. [3] It is relatively safe for use during pregnancy and breastfeeding. [3] [4] It is in the third-generation cephalosporin family of medications and works by interfering with the bacteria's cell wall. [3]

Cefotaxime was discovered in 1976, and came into commercial use in 1980. [5] [6] It is on the World Health Organization's List of Essential Medicines. [7] It is available as a generic medication. [3]

Medical uses

It is a broad-spectrum antibiotic with activity against numerous gram-positive and gram-negative bacteria.[ citation needed ]

Given its broad spectrum of activity, cefotaxime is used for a variety of infections, including:

Although cefotaxime has demonstrated efficacy in these infections, it is not necessarily considered to be the first-line agent. In meningitis, cefotaxime crosses the blood–brain barrier better than cefuroxime.[ citation needed ]

Vial of cefotaxime Cefotaxima.jpg
Vial of cefotaxime

Spectrum of activity

As a β-lactam antibiotic in the third-generation class of cephalosporins, cefotaxime is active against numerous Gram-positive and Gram-negative bacteria, including several with resistance to classic β-lactams such as penicillin. These bacteria often manifest as infections of the lower respiratory tract, skin, central nervous system, bone, and intra-abdominal cavity. While regional susceptibilities must always be considered, cefotaxime typically is effective against these organisms (in addition to many others): [8]

Notable organisms against which cefotaxime is not active include Pseudomonas and Enterococcus . [9] As listed, it has modest activity against the anaerobic Bacteroides fragilis .

The following represents MIC susceptibility data for a few medically significant microorganisms:

[10] [11]

Historically, cefotaxime has been considered to be comparable to ceftriaxone (another third-generation cephalosporin) in safety and efficacy for the treatment of bacterial meningitis, lower respiratory tract infections, skin and soft tissue infections, genitourinary tract infections, and bloodstream infections, as well as prophylaxis for abdominal surgery. [12] [13] [14] The majority of these infections are caused by organisms traditionally sensitive to both cephalosporins. However, ceftriaxone has the advantage of once-daily dosing, whereas the shorter half-life of cefotaxime necessitates two or three daily doses for efficacy. Changing patterns in microbial resistance suggest cefotaxime may be suffering greater resistance than ceftriaxone, whereas the two were previously considered comparable. [15] Considering regional microbial sensitivities is also important when choosing any antimicrobial agent for the treatment of infection.[ citation needed ]

Adverse reactions

Cefotaxime is contraindicated in patients with a known hypersensitivity to cefotaxime or other cephalosporins. Caution should be used and risks weighed against potential benefits in patients with an allergy to penicillin, due to cross-reactivity between the classes.[ citation needed ]

The most common adverse reactions experienced are:

Mechanism of action

Cefotaxime is a β-lactam antibiotic (which refers to the structural components of the drug molecule itself). As a class, β-lactams inhibit bacterial cell wall synthesis by binding to one or more of the penicillin-binding proteins (PBPs). This inhibits the final transpeptidation step of peptidoglycan synthesis in bacterial cell walls, thus inhibiting cell wall biosynthesis. Bacteria eventually lyse due to ongoing activity of cell wall autolytic enzymes (autolysins and murein hydrolases) in the absence of cell wall assembly. [9] Due to the mechanism of their attack on bacterial cell wall synthesis, β-lactams are considered to be bactericidal. [8]

Unlike β-lactams such as penicillin and amoxicillin, which are highly susceptible to degradation by β-lactamase enzymes (produced, for example, nearly universally by S. aureus), cefotaxime boasts the additional benefit of resistance to β-lactamase degradation due to the structural configuration of the cefotaxime molecule. The syn-configuration of the methoxy imino moiety confers stability against β-lactamases. [16] Consequently, the spectrum of activity is broadened to include several β-lactamase-producing organisms (which would otherwise be resistant to β-lactam antibiotics), as outlined below.[ citation needed ]

Cefotaxime, like other β-lactam antibiotics, does not only block the division of bacteria, including cyanobacteria, but also the division of cyanelles, the photosynthetic organelles of the glaucophytes, and the division of chloroplasts of bryophytes. In contrast, it has no effect on the plastids of the vascular plants. This supports the endosymbiotic theory and indicates an evolution of plastid division in land plants. [17]

Administration

Cefotaxime is administered by intramuscular injection or intravenous infusion. As cefotaxime is metabolized to both active and inactive metabolites by the liver and largely excreted in the urine, dose adjustments may be appropriate in people with renal or hepatic impairment. [8] [18] [19]

Plant tissue culture

Cefotaxime is the only cephalosporin which has very low toxicity in plants, even at higher concentration (up to 500 mg/L). It is widely used to treat plant tissue infections with Gram-negative bacteria, [20] while vancomycin is used to treat the plant tissue infections with Gram-positive bacteria. [21] [22]

See also

Related Research Articles

<span class="mw-page-title-main">Ampicillin</span> 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. Common side effects include rash, nausea, and diarrhea. It should not be used in people who are allergic to penicillin. Serious side effects may include Clostridium difficile colitis or anaphylaxis. While usable in those with kidney problems, the dose may need to be decreased. Its use during pregnancy and breastfeeding appears to be generally safe.

<span class="mw-page-title-main">Beta-lactamase</span> Class of enzymes

Beta-lactamases, (β-lactamases) are enzymes produced by bacteria that provide multi-resistance to beta-lactam antibiotics such as penicillins, cephalosporins, cephamycins, monobactams 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 beta-lactam (β-lactam) ring. Through hydrolysis, the enzyme lactamase breaks the β-lactam ring open, deactivating the molecule's antibacterial properties.

<span class="mw-page-title-main">Penicillin</span> Group of antibiotics derived from Penicillium fungi

Penicillins are a group of β-lactam antibiotics originally obtained from Penicillium moulds, principally P. chrysogenum and P. rubens. Most penicillins in clinical use are synthesised by P. chrysogenum using deep tank fermentation and then purified. A number of natural penicillins have been discovered, but only two purified compounds are in clinical use: penicillin G and penicillin V. Penicillins were among the first medications to be effective against many bacterial infections caused by staphylococci and streptococci. They are still widely used today for different bacterial infections, though many types of bacteria have developed resistance following extensive use.

<span class="mw-page-title-main">Beta-lactam antibiotics</span> Class of broad-spectrum antibiotics

β-lactam antibiotics are antibiotics that contain a beta-lactam ring in their chemical structure. This includes penicillin derivatives (penams), cephalosporins and cephamycins (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 strain of Penicillium rubens.

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

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

<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> Chemical compound

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">Cefazolin</span> Chemical compound

Cefazolin, also known as cefazoline and cephazolin, is a first-generation cephalosporin antibiotic used for the treatment of a number of bacterial infections. Specifically it is used to treat cellulitis, urinary tract infections, pneumonia, endocarditis, joint infection, and biliary tract infections. It is also used to prevent group B streptococcal disease around the time of delivery and before surgery. It is typically given by injection into a muscle or vein.

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

Ceftriaxone, sold under the brand name Rocephin, is a third-generation cephalosporin antibiotic used for the treatment of a number of bacterial infections. These include middle ear infections, endocarditis, meningitis, pneumonia, bone and joint infections, intra-abdominal infections, skin infections, urinary tract infections, gonorrhea, and pelvic inflammatory disease. It is also sometimes used before surgery and following a bite wound to try to prevent infection. Ceftriaxone can be given by injection into a vein or into a muscle.

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

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

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

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> Chemical compound

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">Carbapenem</span> Class of highly effective antibiotic agents

Carbapenems are a class of very effective antibiotic agents most commonly used for the treatment of severe 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 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">Cefquinome</span> Chemical compound

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

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β-Lactamase inhibitor Family of enzymes

Beta-lactamases are a family of enzymes involved in bacterial resistance to beta-lactam antibiotics. In bacterial resistance to beta-lactam antibiotics, the bacteria have beta-lactamase which degrade the beta-lactam rings, rendering the antibiotic ineffective. However, with beta-lactamase inhibitors, these enzymes on the bacteria are inhibited, thus allowing the antibiotic to take effect. 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.

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

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Cephalosporins are a broad class of bactericidal antibiotics that include the β-lactam ring and share a structural similarity and mechanism of action with other β-lactam antibiotics. The cephalosporins have the ability to kill bacteria by inhibiting essential steps in the bacterial cell wall synthesis which in the end results in osmotic lysis and death of the bacterial cell. Cephalosporins are widely used antibiotics because of their clinical efficiency and desirable safety profile.

<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. ↑ "Cefotaxime". Merriam-Webster Dictionary . Retrieved 21 January 2016.
  2. ↑ "Cefotaxime (Claforan) Use During Pregnancy". Drugs.com. 5 April 2019. Retrieved 24 December 2019.
  3. 1 2 3 4 5 6 7 8 9 "Cefotaxime Sodium". The American Society of Health-System Pharmacists. Archived from the original on 20 December 2016. Retrieved 8 December 2016.
  4. ↑ Hamilton, Richart (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 87. ISBN   9781284057560.
  5. ↑ Walker, S. R. (2012). Trends and Changes in Drug Research and Development. Springer Science & Business Media. p. 109. ISBN   9789400926592. Archived from the original on 14 September 2016.
  6. ↑ Fischer, Janos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 494. ISBN   9783527607495. Archived from the original on 20 December 2016.
  7. ↑ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl: 10665/325771 . WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  8. 1 2 3 4 5 U.S. Food and Drug Administration. U.S. Department of Health and Human Services. Claforan Sterile (cefotaxime for injection, USP) and Injection (cefotaxime injection, USP). 19 June 2009. "Archived copy" (PDF). Archived (PDF) from the original on 4 March 2016. Retrieved 19 April 2014.{{cite web}}: CS1 maint: archived copy as title (link)
  9. 1 2 "Merck Manuals Professional Edition". Archived from the original on 15 September 2007.
  10. ↑ "Cefotaxime (Cephotaxime, Claforan) | the Antimicrobial Index Knowledgebase – TOKU-E". Archived from the original on 1 February 2014. Retrieved 24 January 2014.[ full citation needed ]
  11. ↑ http://www.toku-e.com/Assets/MIC/Cefotaxime%20sodium%20USP.pdf%5B%5D%5B%5D
  12. ↑ Scholz H, Hofmann T, Noack R, Edwards DJ, Stoeckel K (1998). "Prospective comparison of ceftriaxone and cefotaxime for the short-term treatment of bacterial meningitis in children". Chemotherapy. 44 (2): 142–7. doi:10.1159/000007106. PMID   9551246. S2CID   46826288.
  13. ↑ Woodfield JC, Van Rij AM, Pettigrew RA, van der Linden AJ, Solomon C, Bolt D (January 2003). "A comparison of the prophylactic efficacy of ceftriaxone and cefotaxime in abdominal surgery". American Journal of Surgery. 185 (1): 45–9. doi:10.1016/S0002-9610(02)01125-X. PMID   12531444.
  14. ↑ Simmons BP, Gelfand MS, Grogan J, Craft B (1995). "Cefotaxime twice daily versus ceftriaxone once daily. A randomized controlled study in patients with serious infections". Diagnostic Microbiology and Infectious Disease. 22 (1–2): 155–7. doi:10.1016/0732-8893(95)00080-T. PMID   7587031.
  15. ↑ Gums JG, Boatwright DW, Camblin M, Halstead DC, Jones ME, Sanderson R (January 2008). "Differences between ceftriaxone and cefotaxime: microbiological inconsistencies". The Annals of Pharmacotherapy. 42 (1): 71–9. doi:10.1345/aph.1H620. PMID   18094350. S2CID   44592925.
  16. ↑ Van TT, Nguyen HN, Smooker PM, Coloe PJ (March 2012). "The antibiotic resistance characteristics of non-typhoidal Salmonella enterica isolated from food-producing animals, retail meat and humans in South East Asia". International Journal of Food Microbiology. 154 (3): 98–106. doi:10.1016/j.ijfoodmicro.2011.12.032. PMID   22265849.
  17. ↑ Kasten B, Reski R (1997). "β-Lactam antibiotics inhibit chloroplast division in a moss (Physcomitrella patens) but not in tomato (Lycopersicon esculentum)". Journal of Plant Physiology. 150 (1–2): 137–40. doi:10.1016/S0176-1617(97)80193-9. INIST:2640663.
  18. ↑ Bertels RA, Semmekrot BA, Gerrits GP, Mouton JW (October 2008). "Serum concentrations of cefotaxime and its metabolite desacetyl-cefotaxime in infants and children during continuous infusion". Infection. 36 (5): 415–20. doi:10.1007/s15010-008-7274-1. PMID   18791659. S2CID   23502198.
  19. ↑ Coombes JD (1982). "Metabolism of cefotaxime in animals and humans". Reviews of Infectious Diseases. 4 (Suppl 2): S325–32. doi:10.1093/clinids/4.Supplement_2.S325. JSTOR   4452886. PMID   6294781.
  20. ↑ "cefotaxime for plant tissue culture" (PDF). Archived from the original (PDF) on 4 May 2012.
  21. ↑ "vancomycin for plant cell culture" (PDF). Archived from the original (PDF) on 4 May 2012.
  22. ↑ Pazuki, A; Asghari, J; Sohani, M; Pessarakli, M & Aflaki, F (2014). "Effects of Some Organic Nitrogen Sources and Antibiotics on Callus Growth of Indica Rice Cultivars" (PDF). Journal of Plant Nutrition. 38 (8): 1231–1240. doi:10.1080/01904167.2014.983118. S2CID   84495391 . Retrieved 17 November 2014.
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