Cefoxitin

Last updated
Cefoxitin
Cefoxitin.svg
Clinical data
Trade names Mefoxin, Renoxitin, others [1]
AHFS/Drugs.com Monograph
MedlinePlus a682737
License data
Pregnancy
category
  • AU:B1
Routes of
administration 		Intravenous
ATC code
Legal status
Legal status
Pharmacokinetic data
Metabolism minimal
Elimination half-life 41-59 min
Excretion 85% urine
Identifiers
  • (6R,7S)-3-(carbamoyloxymethyl)-7-methoxy-
    8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-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 100.047.841 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C16H17N3O7S2
Molar mass 427.45 g·mol−1
3D model (JSmol)
Melting point 149 to 150 °C (300 to 302 °F) (dec.)
  • O=C2N1/C(=C(\CS[C@@H]1[C@]2(OC)NC(=O)Cc3sccc3)COC(=O)N)C(=O)O
  • InChI=1S/C16H17N3O7S2/c1-25-16(18-10(20)5-9-3-2-4-27-9)13(23)19-11(12(21)22)8(6-26-15(17)24)7-28-14(16)19/h2-4,14H,5-7H2,1H3,(H2,17,24)(H,18,20)(H,21,22)/t14-,16+/m1/s1 Yes check.svgY
  • Key:WZOZEZRFJCJXNZ-ZBFHGGJFSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

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. [4] It is often grouped with the second-generation cephalosporins. [5] 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. [6] [7]

Contents

History and discovery

Groups of researchers at Merck and Lilly discovered Cephamycin C while looking at penicillin-producing bacteria. This followed their discovery of erythromycin, another antibiotic. [8] Cephamycin C was the first cephem discovered but while it was highly resistant to several beta-lactamases, as is its derivative cefoxitin, it was almost only effective against Gram negative bacteria. [8] The scientists used chemically modified the compound to give cefoxitin, so titled due to its semi-synthetic nature. This new modification broadened its spectrum to include Gram positive bacteria. More than 300 modifications were made to it and tested on the cephalosporin base with methoxy groups at the 7-alpha position. Yet only cefoxitin retained its previous effectiveness against Gram negative bacteria, developed effectiveness against Gram positive bacteria, and resisted breakdown by beta-lactamase. [9]

Cefoxitin, and the cephamycin family as a whole, served as a branching point and impulsed the discovery of more classes of beta-lactams. This is in part due to their primary and early discovery in the broths studied. [8]

Mechanism

Cefoxitin is a beta-lactam antibiotic which binds to penicillin binding proteins, or transpeptidases. By binding to PBPs, cefoxitin prevents the PBPs from forming the cross-linkages between the peptidoglycan layers that make up the bacterial cell wall, thereby interfering with cell wall synthesis. It is a strong beta-lactamase inducer, as are certain other antibiotics (such as imipenem). However, cefoxitin is a better substrate than imipenem for beta-lactamases. [10]

Microbiological resistance

In the presence of cefoxitin, bacteria that make beta-lactamases will increase their production and secretion to cleave the beta lactam ring. As a cephamycin, cefoxitin is highly resistant to hydrolysis by some beta-lactamases, in part due to the presence of the 7-alpha-methoxy functional group (see skeletal formula above). [11] [12] [13] [14]

Another more efficient form of resistance to cefoxitin is provided by the mecA gene in bacteria. This gene codes for an alternative penicillin binding protein, PBP2a. This PBP has a lower binding affinity for penicillin-based antibiotics such as cefoxitin and will continue to cross-link the peptidoglycan layers of the cell wall even in the presence of the beta-lactam antibiotics. MRSA, or methicillin-resistant Staphylococcus aureus is a strain that has acquired resistance to cefoxitin via this gene. [15] For the purposes of detecting bacterial strains with the mecC gene, which like mecA codes for a different PBP, cefoxitin is more reliable than oxacillin because mecC does not correlate as strongly with oxacillin resistance. [16]

Spectrum of bacterial susceptibility

Cefoxitin's spectrum of in vitro antimicrobial activity includes a broad range of gram-negative and gram-positive bacteria, including anaerobes. It is inactive against most strains of Pseudomonas aeruginosa and many strains of Enterobacter cloacae . Staphylococci that are resistant to methicillin and oxacillin should also be considered clinically resistant to cefoxitin even if they test susceptible by in vitro methods. [3]

Major bacterial strains susceptible to cefoxitin include: [11]

Major bacteria resistant to cefoxitin include: [11]

Replacement and substitution

In a 2005 study, Fernandes et al. determined that cefoxitin serves as an appropriate replacement for methicillin in determining if some bacteria display methicillin resistance. [17] Likewise, Funsun et al. found in a 2009 study that cefoxitin disk assays correctly identified all 60 mecA-positive Staphylococcus aureus, or MRSA isolates, to be resistant to cefoxitin. [18]

Due, in part, to the unavailability of methicillin in the United States, cefoxitin has replaced methicillin for disk diffusion tests, which determine the sensitivity of a bacterial specimen to a given antibiotic. [19] Cefoxitin also yields more accurate results for disk diffusion tests. [19] Interpretive criteria for determining susceptibility to cefoxitin via disk diffusion are greater than or equal to 22mm resulting in a "susceptible" result for Staphylococcus aureus and greater than or equal to 25mm for coagulase-negative staphylococci to be considered susceptible. [19]

The following are susceptibility data for several medically significant microorganisms, measured by minimum inhibitory concentration, which is an alternative, liquid medium test for susceptibility.

Uses in medicine

Cefoxitin is sold in three major IV doses, 1g, 2g, and 10g. [21] It is usually given to adults every six to eight hours in 1g or 2g doses. [22] Cefoxitin may interfere with tests detecting urine glucose and result in a false positive. [23] As with any antibiotic, it should not be given to patients who are allergic to it. [23]

Cefoxitin is used to treat: [24] [25] [26] [27]

Cefoxitin has many other uses; it may be given prior to surgery to prevent the development of surgical wound infections, [28] and when used in third and fourth degree perineal injuries in women after giving vaginal birth, cefoxitin decreases infection rate at two and six weeks. [29] However, the earlier and more times a child is exposed to cefoxitin, as with early and multiple exposure to many antibiotics, the greater the likelihood of developing inflammatory bowel disease later in life. This may be due in part to a decreased variety of microorganisms in the digestive system. [30]

It is also used to treat pelvic inflammatory disease, because it is a broad spectrum antibiotic. For outpatient treatment, oral antibiotics or those with less frequent dosing may be prescribed. [31] As an effective alternative to penicillin and spectinomycin, and replacement for methicillin, cefoxitin is used to treat gonorrhea in both men and women with few side effects. [32]

Side effects

Side effects for cefoxitin are regarded as mild. [32] Common side effects include:

While cefoxitin has not been associated with alcohol incompatibility like other members of the second generation cephalosporins class, it has been with a higher risk of coagulopathy, a bleeding disorder. [8]

This is not a comprehensive list and not intended to provide medical advice. If any of the previous side effects are severe, or if an allergic reaction takes place immediately contact your doctor.

Notable drug interactions

Contraindications

A contraindication means that the drug in question should not be used under particular circumstances. For cefoxitin, this includes patients who are hypersensitive to cephalosporin antibiotics. [34] [35]

Patients with colitis, kidney disease, or liver disease are also advised not to take cefoxitin. [36] However, some drug databases will considers the diseases means for caution rather than contraindications. [37]

Major or Severe

Aside from the above-mentioned contraindications and diseases which require monitoring by a doctor, the live cholera and live typhoid vaccines are known to have a severe interaction with cefoxitin. [38] [39]

Individuals on a low sodium diet, undergoing dialysis, or who have experienced seizures, particularly following antibiotic therapy, should also consult their physician prior to taking cefoxitin. [40]

Moderate

Only take additional antibiotics, anticoagulants and blood thinners under doctor supervision. [39] Cefoxitin may decrease the effectiveness of hormonal birth control. This increases the risk for pregnancy and a medical consult will help determine whether backup birth control methods should be used. [41]

Minor

Minor drug interactions do not usually require a change in treatment. Your doctor may monitor specific events, such as bleeding, while taking cefoxitin. Two such minor interactions occur between cefoxitin and heparin [42] as well as genistein. [43]

Pharmacodynamic and pharmacokinetic data

Pharmocokinetic and pharmacodynamic data for cefoxitin are, as of 2013, considered limited and outdated. A few relatively recent studies have attempted to remedy that.

One such study was by the Hôpitaux de Paris in collaboration with the French Ministry of Health. [44] However, while the clinical trials were completed in 2015, no study data have been published. [45] The expected results from using cefoxitin over carbapenems, another type of antibiotic with a wider bacterial spectrum, included effective treatment of E. coli produce extended spectrum beta-lactamase, less selective pressure on the GI tract which better maintains balanced flora, and a lower treatment cost. [44]

This followed a 2012 French study on the same E. coli strain with CTX-M-15 extended release beta-lactamase. [46] Lepeule et al. determined that in mice, the ideal pharmacodynamic target of fT>MIC=33%, where MIC is the minimum inhibitory concentration, was obtained with 200 mg/kg every four hours. [46] The fT>MIC (%) was increased by 11% when the administration frequency was increased from every four hours to every three hours. [46] This implied that increasing the frequency might yield similar results in humans. The study also found no significant difference between the effectiveness of carbapenems and cefoxitin and suggested that cefoxitin can be used as an alternative treatment for CTX-M producing E. coli to carbapenems such as imipenem and ertapenem. [46]

Related Research Articles

<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.

<i>Staphylococcus aureus</i> Species of Gram-positive bacterium

Staphylococcus aureus is a Gram-positive spherically shaped bacterium, a member of the Bacillota, and is a usual member of the microbiota of the body, frequently found in the upper respiratory tract and on the skin. It is often positive for catalase and nitrate reduction and is a facultative anaerobe that can grow without the need for oxygen. Although S. aureus usually acts as a commensal of the human microbiota, it can also become an opportunistic pathogen, being a common cause of skin infections including abscesses, respiratory infections such as sinusitis, and food poisoning. Pathogenic strains often promote infections by producing virulence factors such as potent protein toxins, and the expression of a cell-surface protein that binds and inactivates antibodies. S. aureus is one of the leading pathogens for deaths associated with antimicrobial resistance and the emergence of antibiotic-resistant strains, such as methicillin-resistant S. aureus (MRSA), is a worldwide problem in clinical medicine. Despite much research and development, no vaccine for S. aureus has been approved.

Methicillin-resistant <i>Staphylococcus aureus</i> Bacterium responsible for difficult-to-treat infections in humans

Methicillin-resistant Staphylococcus aureus (MRSA) is a group of gram-positive bacteria that are genetically distinct from other strains of Staphylococcus aureus. MRSA is responsible for several difficult-to-treat infections in humans. It caused more than 100,000 deaths worldwide attributable to antimicrobial resistance in 2019.

<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.

Vancomycin-resistant <i>Staphylococcus aureus</i> Antibiotica resistant bacteria

Vancomycin-resistant Staphylococcus aureus (VRSA) are strains of Staphylococcus aureus that have acquired resistance to the glycopeptide antibiotic vancomycin. Bacteria can acquire resistant genes either by random mutation or through the transfer of DNA from one bacterium to another. Resistance genes interfere with the normal antibiotic function and allow a bacteria to grow in the presence of the antibiotic. Resistance in VRSA is conferred by the plasmid-mediated vanA gene and operon. Although VRSA infections are uncommon, VRSA is often resistant to other types of antibiotics and a potential threat to public health because treatment options are limited. VRSA is resistant to many of the standard drugs used to treat S. aureus infections. Furthermore, resistance can be transferred from one bacterium to another.

<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">Nafcillin</span> Chemical compound

Nafcillin sodium is a narrow-spectrum beta-lactam antibiotic of the penicillin class. As a beta-lactamase-resistant penicillin, it is used to treat infections caused by Gram-positive bacteria, in particular, species of staphylococci that are resistant to other penicillins.

<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">Antibiotic sensitivity testing</span> 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">Flucloxacillin</span> Penicillin

Flucloxacillin, also known as floxacillin, is an antibiotic used to treat skin infections, external ear infections, infections of leg ulcers, diabetic foot infections, and infection of bone. It may be used together with other medications to treat pneumonia, and endocarditis. It may also be used prior to surgery to prevent Staphylococcus infections. It is not effective against methicillin-resistant Staphylococcus aureus (MRSA). It is taken by mouth or given by injection into a vein or muscle.

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

Dicloxacillin is a narrow-spectrum β-lactam antibiotic of the penicillin class. It is used to treat infections caused by susceptible (non-resistant) Gram-positive bacteria. It is active against beta-lactamase-producing organisms such as Staphylococcus aureus, which would otherwise be resistant to most penicillins. Dicloxacillin is available under a variety of trade names including Diclocil (BMS).

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

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

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

Cefditoren, also known as cefditoren pivoxil is an antibiotic used to treat infections caused by Gram-positive and Gram-negative bacteria that are resistant to other antibiotics. It is mainly used for treatment of community acquired pneumonia. It is taken by mouth and is in the cephalosporin family of antibiotics, which is part of the broader beta-lactam group of antibiotics.

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.

mecA is a gene found in bacterial cells which allows them to be resistant to antibiotics such as methicillin, penicillin and other penicillin-like antibiotics.

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

Ceftaroline fosamil (INN), brand name Teflaro in the US and Zinforo in Europe, is a cephalosporin antibiotic with anti-MRSA activity. Ceftaroline fosamil is a prodrug of ceftaroline. It is active against methicillin-resistant Staphylococcus aureus (MRSA) and other Gram-positive bacteria. It retains some activity of later-generation cephalosporins having broad-spectrum activity against Gram-negative bacteria, but its effectiveness is relatively much weaker. It is currently being investigated for community-acquired pneumonia and complicated skin and skin structure infection.

Staphylococcus schleiferi is a Gram-positive, cocci-shaped bacterium of the family Staphylococcaceae. It is facultatively anaerobic, coagulase-variable, and can be readily cultured on blood agar where the bacterium tends to form opaque, non-pigmented colonies and beta (β) hemolysis. There exists two subspecies under the species S. schleiferi: Staphylococcus schleiferi subsp. schleiferi and Staphylococcus schleiferi subsp. coagulans.

References

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  39. 1 2 "Cefoxitin Vial Interactions with Other Medication". WebMD. Retrieved 2017-05-29.
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  41. ↑ "Camrese and cefoxitin Drug Interactions". Drugs.com. Retrieved 2017-05-29.
  42. ↑ "Cefoxitin and heparin Drug Interactions". Drugs.com. Retrieved 2017-05-29.
  43. ↑ "Cefoxitin and cholecalciferol / genistein / zinc chelazome Drug Interactions". Drugs.com. Retrieved 2017-05-29.
  44. 1 2 "Efficacy and Pharmacokinetic/Pharmacodynamic Parameters of Cefoxitin in Women With Acute Pyelonephritis Without Severity Symptoms Due to Extended-spectrum β-lactamase Producing Escherichia Coli". ICH GCP - Clinical Trials Registry. Retrieved 2017-05-29.
  45. ↑ Clinical trial number NCT01820793 for "Efficacy and Pharmacokinetic/Pharmacodynamic Parameters of Cefoxitin in Women With Acute Pyelonephritis Without Severity Symptoms Due to Extended-spectrum β-lactamase Producing Escherichia Coli" at ClinicalTrials.gov
  46. 1 2 3 4 Lepeule R, Ruppé E, Le P, Massias L, Chau F, Nucci A, et al. (March 2012). "Cefoxitin as an alternative to carbapenems in a murine model of urinary tract infection due to Escherichia coli harboring CTX-M-15-type extended-spectrum β-lactamase". Antimicrobial Agents and Chemotherapy. 56 (3): 1376–81. doi:10.1128/AAC.06233-11. PMC   3294923 . PMID   22214774.
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