Cefazolin

Last updated
Cefazolin
Cefazolin.svg
Cefazolinate-from-xtal-3D-bs-17.png
Clinical data
Pronunciation /səˈfæzələn/ [1]
Trade names Ancef, Cefacidal, other
AHFS/Drugs.com Monograph
Pregnancy
category
  • AU:B1
Routes of
administration 		intravenous, intramuscular
Drug class First-generation cephalosporin
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability NA
Metabolism ?
Elimination half-life 1.8 hours (given IV)
2 hours (given IM)
Excretion kidney, unchanged
Identifiers
  • (6R,7R)-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl}-8-oxo-7-[(1H-tetrazol-1-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 100.043.042 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C14H14N8O4S3
Molar mass 454.50 g·mol−1
3D model (JSmol)
Melting point 198 to 200 °C (388 to 392 °F) (decompose.)
  • O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)Cn3nnnc3)CSc4nnc(s4)C)C(=O)O
  • InChI=1S/C14H14N8O4S3/c1-6-17-18-14(29-6)28-4-7-3-27-12-9(11(24)22(12)10(7)13(25)26)16-8(23)2-21-5-15-19-20-21/h5,9,12H,2-4H2,1H3,(H,16,23)(H,25,26)/t9-,12-/m1/s1 Yes check.svgY
  • Key:MLYYVTUWGNIJIB-BXKDBHETSA-N Yes check.svgY
   (verify)

Cefazolin, also known as cefazoline and cephazolin, is a first-generation cephalosporin antibiotic used for the treatment of a number of bacterial infections. [2] Specifically it is used to treat cellulitis, urinary tract infections, pneumonia, endocarditis, joint infection, and biliary tract infections. [2] It is also used to prevent group B streptococcal disease around the time of delivery and before surgery. [2] It is typically given by injection into a muscle or vein. [2]

Contents

Common side effects include diarrhea, vomiting, yeast infections, and allergic reactions. [2] Historically, it was thought to be contraindicated in patients with allergies to penicillin, although several recent studies have refuted this and it is proven to be safe in almost all patients, including those with known penicillin allergies. [3] It is relatively safe for use during pregnancy and breastfeeding. [2] [4] Cefazolin is in the first-generation cephalosporin class of medication and works by interfering with the bacteria's cell wall. [2]

Cefazolin was patented in 1967 and came into commercial use in 1971. [5] [6] It is on the World Health Organization's List of Essential Medicines. [7] It is available as a generic medication. [2]

Medical uses

Cefazolin is used in a variety of infections provided that susceptible organisms are involved. It is indicated for use in the following infections: [8]

It can also be used peri-operatively to prevent infections post-surgery, and is often the preferred drug for surgical prophylaxis. [8]

There is no penetration into the central nervous system and therefore cefazolin is not effective in treating meningitis. [9]

Cefazolin has been shown to be effective in treating methicillin-susceptible Staphylococcus aureus (MSSA) but does not work in cases of methicillin-resistant Staphylococcus aureus (MRSA). [8] In many instances of staphylococcal infections, such as bacteremia, cefazolin is an alternative to penicillin in patients who are allergic to penicillin. [9] However, there is still potential for a reaction to occur with cefazolin and other cephalosporins in patients allergic to penicillin. [8] Resistance to cefazolin is seen in several species of bacteria, such as Mycoplasma and Chlamydia , in which case different generations of cephalosporins may be more effective. [10] Cefazolin does not fight against Enterococcus , anaerobic bacteria, or atypical bacteria, among others. [9]

Bacterial susceptibility

As a first-generation cephalosporin antibiotic, cefazolin and other first-generation antibiotics are very active against gram-positive bacteria and some gram-negative bacteria. [8] Their broad spectrum of activity can be attributed to their improved stability to many bacterial beta-lactamases compared to penicillins. [9]

Spectrum of activity

Gram-positive aerobes: [8] [9]

Gram-Negative Aerobes: [11]

Non susceptible

The following are not susceptible: [8] [9]

Special populations

Pregnancy

Cefazolin is pregnancy category B, indicating general safety for use in pregnancy. Caution should be used in breastfeeding as a small amount of cefazolin enters the breast milk. [8] Cefazolin can be used prophylactically against perinatal Group B streptococcal infection (GBS). Although penicillin and ampicillin are the standard of care for GBS prophylaxis, penicillin-allergic women with no history of anaphylaxis can be given cefazolin instead. These patients should be closely monitored as there is a small chance of an allergic reaction due to the similar structure of the antibiotics. [12]

Newborns

There has been no established safety and effectiveness for use in premature infants and neonates. [8]

Elderly

No overall differences in safety or effectiveness were observed in clinical trials comparing elderly and younger subjects, however the trials could not eliminate the possibility that some older individuals may have a higher level of sensitivity. [8]

Additional considerations

People with kidney disease and those on hemodialysis may need the dose adjusted. [8] Cefazolin levels are not significantly affected by liver disease.

As with other antibiotics, cefazolin may interact with other medications being taken. Some important drugs that may interact with cefazolin such as probenecid. [9]

Side effects

Side effects associated with use of cefazolin therapy include: [8]

Patients with penicillin allergies could experience a potential reaction to cefazolin and other cephalosporins. [8] As with other antibiotics, patients experiencing watery and/or bloody stools occurring up to three months following therapy should contact their prescriber. [8]

Like those of several other cephalosporins, the chemical structure of cefazolin contains an N-methylthiodiazole (NMTD or 1-MTD) side-chain. As the antibiotic is broken down in the body, it releases free NMTD, which can cause hypoprothrombinemia (likely due to inhibition of the enzyme vitamin K epoxide reductase) and a reaction with ethanol similar to that produced by disulfiram (Antabuse), due to inhibition of aldehyde dehydrogenase. [14] Those with an allergy to penicillin may develop a cross sensitivity to cefazolin. [15] [16]

Mechanism of action

Cefazolin inhibits cell wall biosynthesis by binding penicillin-binding proteins which stops peptidoglycan synthesis. Penicillin-binding proteins are bacterial proteins that help to catalyze the last stages of peptidoglycan synthesis, which is needed to maintain the cell wall. They remove the D-alanine from the precursor of the peptidoglycan. The lack of synthesis causes the bacteria to lyse because they also continually break down their cell walls. Cefazolin is bactericidal, meaning it kills the bacteria rather than inhibiting their growth. [9]

Cost

Cefazolin is relatively inexpensive. [17]

Trade names

It was initially marketed by GlaxoSmithKline under the trade name Nostof. [18]

Other trade names include: Cefacidal, Cefamezin, Cefrina, Elzogram, Faxilen, Gramaxin, Kefol, Kefzol, Kefzolan, Kezolin, Novaporin, Reflin, Zinol, and Zolicef.

Related Research Articles

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

Ampicillin is an antibiotic belonging to the aminopenicillin class of the penicillin family. The drug is 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.

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

Ertapenem, sold under the brand name Invanz, is a carbapenem antibiotic medication used for the treatment of infections of the abdomen, the lungs, the upper part of the female reproductive system, and the diabetic foot.

<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">Ceftriaxone</span> Antibiotic medication

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">Cefalexin</span> Beta-lactam antibiotic

Cefalexin, also spelled cephalexin, is an antibiotic that can treat a number of bacterial infections. It kills gram-positive and some gram-negative bacteria by disrupting the growth of the bacterial cell wall. Cefalexin is a β-lactam antibiotic within the class of first-generation cephalosporins. It works similarly to other agents within this class, including intravenous cefazolin, but can be taken by mouth.

<span class="mw-page-title-main">Cefixime</span> A third generation cephalosporin antibiotic

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">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> 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">Imipenem/cilastatin</span> Combination antibiotic medication

Imipenem/cilastatin, sold under the brand name Primaxin among others, is an antibiotic useful for the treatment of a number of bacterial infections. It is made from a combination of imipenem and cilastatin. Specifically it is used for pneumonia, sepsis, endocarditis, joint infections, intra-abdominal infections, and urinary tract infections. It is given by injection into a vein or muscle.

<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.

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">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">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">Cefodizime</span> Chemical compound

Cefodizime is a 3rd generation cephalosporin antibiotic with broad spectrum activity against aerobic gram positive and gram negative bacteria. Clinically, it has been shown to be effective against upper and lower respiratory tract infections, urinary tract infections, and gonorrhea. Cefodizime is a bactericidal antibiotic that targets penicillin-binding proteins (PBPs) 1A/B, 2, and 3 resulting in the eventual death of the bacterial cell. In vivo experimental models of infection showed that bacterial clearance by this drug is at least as effective compared with other 3rd generation cephalosporins. It has similar adverse effect profile to other 3rd generation cephalosporins as well, mainly being limited to gastrointestinal or dermatological side effects.

<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.

The side effects of penicillin are bodily responses to penicillin and closely related antibiotics that do not relate directly to its effect on bacteria. A side effect is an effect that is not intended with normal dosing. Some of these reactions are visible and some occur in the body's organs or blood. Penicillins are a widely used group of medications that are effective for the treatment of a wide variety of bacterial infections in human adults and children as well as other species. Some side effects are predictable, of which some are common but not serious, some are uncommon and serious and others are rare. The route of administration of penicillin can have an effect on the development of side effects. An example of this is irritation and inflammation that develops at a peripheral infusion site when penicillin is administered intravenously. In addition, penicillin is available in different forms. There are different penicillin medications as well as a number of β-lactam antibiotics derived from penicillin.

References

  1. ↑ "Cefazolin". Merriam-Webster.com Dictionary . Retrieved 2016-01-21.
  2. 1 2 3 4 5 6 7 8 "Cefazolin Sodium". The American Society of Health-System Pharmacists. Retrieved 8 December 2016.
  3. ↑ "NEJM Journal Watch: Summaries of and commentary on original medical and scientific articles from key medical journals". www.jwatch.org. Retrieved 2023-01-20.
  4. ↑ Hamilton R (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 84. ISBN   9781284057560.
  5. ↑ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 493. ISBN   9783527607495. Archived from the original on 2017-09-10.
  6. ↑ USpatent 3516997,Takano T, Kurita M, Nikaido H, Mera M, Konishi N, Nakagawa R,"3,7-disubstituted cephalosporin compounds and preparation thereo",published 1970-06-23,issued 1970-06-23, assigned to Fujisawa Pharmaceutical Co Ltd
  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 6 7 8 9 10 11 12 13 14 "DailyMed - CEFAZOLIN - cefazolin sodium injection, powder, for solution". dailymed.nlm.nih.gov. Archived from the original on 2016-03-06. Retrieved 2015-11-05.
  9. 1 2 3 4 5 6 7 8 Trevor AJ, Katzung BG, Masters S (2015). Basic & Clinical Pharmacology. New York: McGraw Hill Education. pp. 776–778. ISBN   978-0-07-182505-4.
  10. ↑ "Cefazolin (Injection Route)". Mayo Clinic. 1 July 2015. Archived from the original on 19 April 2014.
  11. ↑ Beauduy C, Winston L (2021). Basic & Clinical Pharmacology (15 ed.). McGraw Hill.
  12. ↑ "Prevention of Perinatal Group B Streptococcal Disease". www.cdc.gov. Archived from the original on 2015-11-15. Retrieved 2015-11-05.
  13. ↑ "Cefazolin Prescribing Information" (PDF). FDA. 2004. Archived (PDF) from the original on 2016-03-04.
  14. ↑ Stork CM (2006). Antibiotics, antifungals, and antivirals. New York: McGraw-Hill. p. 847.
  15. ↑ "Pharmaceutical Sciences CSU Parenteral Antibiotic Allergy cross-sensitivity chart" (PDF). Vancouver Acute Pharmaceutical Sciences, Vancouver Hospital & Health Sciences Centre. 2016. Archived (PDF) from the original on April 17, 2016. Retrieved May 19, 2017.
  16. ↑ Gonzalez-Estrada A, Radojicic C (May 2015). "Penicillin allergy: A practical guide for clinicians". Cleveland Clinic Journal of Medicine. 82 (5): 295–300. doi: 10.3949/ccjm.82a.14111 . PMID   25973877. S2CID   6717270.
  17. ↑ Cunha BA (2009). Infectious Diseases in Critical Care Medicine. CRC Press. p. 506. ISBN   978-1-4200-9241-7.
  18. ↑ "Cefazolin Sodium Injection". MedlinePlus Drug Information. U.S. National Library of Medicine. Archived from the original on 2015-10-06. Retrieved 2015-11-05.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.