User:LeiC CP133 G22/sandbox

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LeiC CP133 G22/sandbox
Clinical data
Trade namesAncef, Cefacidal, Cefamezin, Cefrina, Elzogram, Faxilen, Gramaxin, Kefzol, Kefol, Kefzolan, Kezolin, Novaporin, Reflin, Zinol Zolicef
AHFS/Drugs.comMonograph
Pregnancy
category
  • AU: B1
Routes of
administration		Intravenous, intramuscular
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
BioavailabilityNA
Metabolism?
Elimination half-life1.8 hours (given IV)
2 hours (given IM)
ExcretionRenal, 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
Chemical and physical data
FormulaC14H14N8O4S3
Molar mass454.51 g/mol g·mol−1
3D model (JSmol)
  • 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 checkY
  • Key:MLYYVTUWGNIJIB-BXKDBHETSA-N checkY
  (verify)

Cefazolin (INN), also known as cefazoline or cephazolin, is an antibiotic used for the treatment of a number of bacterial infections.[1] It is marketed by GlaxoSmithKline under the trade name Ancef, but is no longer available as brand name products.[2]

Cefazolin is a first-generation cephalosporin antibiotic with broad spectrum antibiotic with activity against both gram-negative and gram-positive bacteria. Due to cross-reactivity with penicillins, patients who have experienced anaphylaxis to penicillins are not advised to receive cephalosporins.[1] Common side effects include nausea, vomiting, diarrhea, and rash.[3] The drug is usually administered by either intramuscular injection (injection into a large muscle) or intravenous infusion (intravenous fluid into a vein).[2] It is on the World Health Organization's List of Essential Medicines for use in a basic health system.[4]

Medical uses[edit]

Cefazolin is used in a variety of infections provided that susceptible organisms are involved. It is indicated for use in the following infections:[3]

  • Respiratory tract infections
  • Urinary tract infections
  • Skin infections
  • Biliary tract infections
  • Bone and joint infections
  • Genital infections
  • Blood infections (sepsis)
  • Endocarditis

It can also be used peri-operatively to prevent infections post-surgery, and is often the preferred drug for surgical prophylaxis.[5]

There is no penetration into the central nervous system and therefore cefazolin is not effective in treating meningitis.[1]

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).[1] In many instances of staphylococcal infections, such as bacteremia, cefazolin is an alternative to penicillin in patients who are allergic to penicillin.[1] 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.[5] Cefazolin does not fight against Enterococcus, anaerobic bacteria or atypical bacteria among others.[5]

Bacterial susceptibility[edit]

As a first-generation cephalosporin antibiotic, Cefazolin and other first-generation antibiotics are very active against gram-positive bacteria and some gram-negative bacteria.[3] The spectrum of activity is as follows:

Gram-Positive Aerobes:

  • Staphylococcus aureus (including beta-lactamase producing strains)
  • Staphylococcus epidermidis
  • Streptococcus pyogenes, Streptococcus agalactiae, and other strains of streptococci
  • Streptococcus pneumoniae

Gram-Negative Aerobes:

  • Escherichia coli
  • Proteus mirabilis

Cefazolin is not effective against Methicillin-resistant staphylococci, enterococci, most strains of indole positive Proteus (Proteus vulgaris), Enterobacter spp., Morganella morganii, Providencia rettgeri, Serratia spp., or Pseudomonas spp.[3] Compared to penicillins, cephalosporins have a broader spectrum of activity due to their improved stability to many bacterial beta-lactamases.[1]

Uses in special populations[edit]

Pregnancy[edit]

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.[3] 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.[6]

Neonates[edit]

There has been no established safety and effectiveness for use in premature infants and neonates.[3]

Elderly[edit]

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.[3]

Additional considerations[edit]

People with kidney disease and those on hemodialysis should make sure their physician is aware of such conditions. Cefazolin is cleared by the kidneys and those with decreased kidney function will need their dosages adjusted[7]. Cefazolin levels are not significantly affected by liver disease. As with other antibiotics, cefazolin may interact with other medications being taken, such as phenytoin, probenecid and warfarin. All persons should inform the prescribing physician of all other medications (prescribed, over the counter, etc.) they are taking.[8]

Mechanism of action[edit]

Cefazolin inhibits cell wall biosynthesis by binding Penicillin Binding Proteins which stops peptidoglycan synthesis. 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. [1]

Adverse effects[edit]

Possible side effects associated with the use of cefazolin include diarrhea, stomach pain or upset stomach, vomiting, and rash.[3] Patients with penicillin allergies could experience a potential reaction to cefazolin and other cephalosporins. [1] As with other antibiotics, patients experiencing watery and/or bloody stools occurring two months or longer following therapy should contact their prescriber.[3] 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.[9]

References[edit]

  1. ^ a b c d e f g h Katzung, Bertram; et al. (2015). Basic & Clinical Pharmacology. New York: McGraw Hill Education. p. 778. ISBN 978-0-07-182505-4. {{cite book}}: Explicit use of et al. in: |last= (help)
  2. ^ a b "Cefazolin Sodium Injection: MedlinePlus Drug Information". www.nlm.nih.gov. Retrieved 2015-11-05.
  3. ^ a b c d e f g h i "DailyMed - CEFAZOLIN - cefazolin sodium injection, powder, for solution". dailymed.nlm.nih.gov. Retrieved 2015-11-05.
  4. ^ "WHO Model List of Essential Medicines" (PDF). WHO Model List of Essential Medicines. August 2015. Retrieved November 4, 2015.
  5. ^ a b c "The Cephalosporins - Mayo Clinic Proceedings". www.mayoclinicproceedings.org. Retrieved 2015-11-05.
  6. ^ "Prevention of Perinatal Group B Streptococcal Disease". www.cdc.gov. Retrieved 2015-11-05.
  7. ^ Trotman, Rbin (2005). "Antibiotic Dosing in Critically Ill Adult Patients Receiving Continuous Renal Replacement Therapy". Clinical Infectious Diseases. 41 (8): 1159–1166. doi:10.1086/444500. PMID 16163635. Retrieved 2015-11-04.
  8. ^ "Kefzol (cefazolin) dosing, indications, interactions, adverse effects, and more". reference.medscape.com. Retrieved 2015-11-05.
  9. ^ Stork, CM (2006). Antibiotics, antifungals, and antivirals. New York: New York: McGraw-Hill. p. 847. ISBN 0-07-143763-0.

External links[edit]

Category:Cephalosporin antibiotics Category:World Health Organization essential medicines Category:Tetrazoles Category:Thiadiazoles

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