Chemistry:Cefixime

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Short description: A third generation cephalosporin antibiotic
Cefixime
Cefixime.svg
Clinical data
Trade namesSuprax, others[1]
AHFS/Drugs.comMonograph
MedlinePlusa690007
License data
Routes of
administration		By mouth
ATC code
Legal status
Legal status
  • UK: POM (Prescription only) [2]
  • US: ℞-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability30 to 50%[3]
Protein bindingApproximately 60%
Elimination half-lifeVariable
Average 3 to 4 hours
ExcretionKidney and biliary
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Chemical and physical data
FormulaC16H15N5O7S2
Molar mass453.44 g·mol−1
3D model (JSmol)
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Cefixime, sold under the brand name Suprax among others, is an antibiotic medication used to treat a number of bacterial infections.[3] These infections include otitis media, strep throat, pneumonia, urinary tract infections, gonorrhea, and Lyme disease.[3] For gonorrhea typically only one dose is required.[4] In the United States it is a second-line treatment to ceftriaxone for gonorrhea.[3] It is taken by mouth.[3]

Common side effects include diarrhea, abdominal pain, and nausea.[3] Serious side effects may include allergic reactions and Clostridium difficile diarrhea.[3] It is not recommended in people with a history of a severe penicillin allergy.[4] It appears to be relatively safe during pregnancy.[5] It is in the third-generation cephalosporin class of medications.[3] It works by disrupting the bacteria's cell wall resulting in its death.[3]

Cefixime was patented in 1979 and approved for medical use in the United States in 1989.[3][6] It is on the World Health Organization's List of Essential Medicines.[7] It is available as a generic medication in the United States.[8]

Medical uses

Cefixime treats infections of the:

It is also used to treat typhoid fever.[11][12][3]

Spectrum of bacterial susceptibility

Cefixime is a broad spectrum cephalosporin antibiotic and is commonly used to treat bacterial infections of the ear, urinary tract, and upper respiratory tract. The following represents MIC susceptibility data for a few medically significant microorganisms:[13]

  • Escherichia coli: 0.015 µg/mL – 4 µg/mL
  • Haemophilus influenzae: ≤0.004 µg/mL – >4 µg/mL
  • Proteus mirabilis: ≤0.008 µg/mL – 0.06 µg/mL
  • Streptococcus pneumoniae: 0.12 µg/mL[10]
  • Staphylococcus aureus: >128 µg/mL (Resistant)[10]
  • Enterobacter spp.: >128 µg/mL (Resistant) [10]

Mechanism of action

The bactericidal action of Cefixime is due to the inhibition of cell wall synthesis. It binds to one of the penicillin binding proteins (PBPs) which inhibits the final transpeptidation step of the peptidoglycan synthesis in the bacterial cell wall, thus inhibiting biosynthesis and arresting cell wall assembly resulting in bacterial cell death.

Absorption Only 40–50% is absorbed from the GI tract (oral bioavailability). Absorption may be slowed but not decreased when taken with food. Average peak concentration after administration of oral suspension is approximately 25–50% greater than the peak concentration following oral tablet or capsules administration.[9]

Distribution It has high concentrations in bile and urine. It can cross the placenta and its protein binding capacity is 65%.

Contraindications

Cefixime is contraindicated in patients with known sensitivity or allergies to cephalosporin class of antibiotics.[9][14] As Cefixime is a third generation cephalosporin, it is not contraindicated for patients with a true penicillin allergy.

Adverse effects

Adverse drug reactions include diarrhea, dyspepsia, nausea and vomiting.[3] Hypersensitivity reactions like skin rashes, urticaria and Stevens–Johnson syndrome have been reported. There is no specific antidote for cefixime overdosage.

Drug interactions

History

It was sold under the trade name Suprax 125 in the United States until 2003, when it was taken off the market by drug manufacturer Wyeth after its patent expired.[citation needed] Lupin started selling Suprax in the United States in 2007,[16] and it is available in different formulations and strengths.[16][17][18][19]

Marketing

Cefixime is marketed under many brand names worldwide; examples include Pancef, Caricef, Taxim o, Texit, Ofex, Ceftid, Cef-3, Denvar, 3-C, Cefim, Magnett, Oroken, Ofiken, Fix-A, and Zifi.[1][20] In India it is marketed as Zifi 200 and is commonly counterfeited.[21]

References

  1. ↑ 1.0 1.1 "Cefixime—Drugs.com". https://www.drugs.com/international/cefixime.html. 
  2. ↑ 2.0 2.1 2.2 2.3 2.4 2.5 "Suprax 200 mg Tablets - Summary of Product Characteristics (SmPC)". 20 August 2019. https://www.medicines.org.uk/emc/product/5534/smpc. 
  3. ↑ 3.00 3.01 3.02 3.03 3.04 3.05 3.06 3.07 3.08 3.09 3.10 3.11 3.12 3.13 3.14 3.15 3.16 "Cefixime". The American Society of Health—System Pharmacists. https://www.drugs.com/monograph/cefixime.html. 
  4. ↑ 4.0 4.1 WHO Model Formulary 2008. World Health Organization. 2009. p. 107. ISBN 9789241547659. 
  5. ↑ "Cefixime (Suprax) Use During Pregnancy". 29 March 2019. https://www.drugs.com/pregnancy/cefixime.html. 
  6. ↑ Analogue-based Drug Discovery. John Wiley & Sons. 2006. p. 495. ISBN 9783527607495. https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA495. 
  7. ↑ World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. 2019. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO. 
  8. ↑ "Generic Suprax Availability". https://www.drugs.com/availability/generic-suprax.html. 
  9. ↑ 9.0 9.1 9.2 9.3 9.4 9.5 9.6 "Suprax- cefixime tablet Suprax- cefixime capsule Suprax- cefixime tablet, chewable Suprax- cefixime powder, for suspension". 26 November 2019. https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=d0fd45bd-7d52-4fa6-a5f7-f46d5651ffa2. 
  10. ↑ 10.0 10.1 10.2 10.3 Kucers' the use of antibiotics : a clinical review of antibacterial, antifungal, antiparasitic and antiviral drugs (Seventh ed.). Boca Raton. 2017. ISBN 978-1-315-15211-0. OCLC 1011357224. https://www.worldcat.org/oclc/1011357224. 
  11. ↑ "Mechanism of therapeutic effectiveness of cefixime against typhoid fever". Antimicrobial Agents and Chemotherapy 45 (9): 2450–2454. September 2001. doi:10.1128/aac.45.9.2450-2454.2001. PMID 11502513. 
  12. ↑ "Therapy of multidrug-resistant typhoid fever with oral cefixime vs. intravenous ceftriaxone". The Pediatric Infectious Disease Journal 13 (11): 990–994. November 1994. doi:10.1097/00006454-199411000-00010. PMID 7845753. 
  13. ↑ "Cefixime trihydrate Susceptibility and Minimum Inhibitory Concentration (MIC) Data". www.toku-e.com. http://www.toku-e.com/Assets/MIC/Cefixime%20trihydrate.pdf. 
  14. ↑ "Suprax- cefixime powder, for suspension". 2 January 2020. https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=7e2462b2-bfed-4da4-8c47-46838d6153f8. 
  15. ↑ "Medicines information links". NHS Choices. UK National Health Service. http://www.nhs.uk/conditions/gonorrhoea/pages/MedicineOverview.aspx?condition=Bacterial%20infections&medicine=Cefixime&preparationCefixime%20100mg/5ml%20oral%20suspension. 
  16. ↑ 16.0 16.1 "Suprax: FDA-Approved Drugs". https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=065355. 
  17. ↑ "Suprax: FDA-Approved Drugs". https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=065380. 
  18. ↑ "Suprax: FDA-Approved Drugs". https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=202091. 
  19. ↑ "Suprax: FDA-Approved Drugs". https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=203195. 
  20. ↑ "FDC—Products—Formulations". http://www.fdcindia.com/formulations.php. 
  21. ↑ "Fake drugs: the global industry putting your life at risk". Mosaic. 30 October 2018. https://mosaicscience.com/story/fake-drugs-global-antibiotics-amr-counterfeit-meds/. 



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