Cefixime

Cefixime
Clinical data
Trade namesSuprax, others[1]
AHFS/Drugs.comMonograph
MedlinePlusa690007
License data
Routes of
administration		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability30 to 50%[5]
Protein bindingApproximately 60%
Elimination half-lifeVariable
Average 3 to 4 hours
ExcretionKidney and biliary
Identifiers
IUPAC name
  • (6R,7R)-7-{[2-(2-Amino-1,3-thiazol-4-yl)-2-(carboxymethoxyimino)acetyl]amino}-3-ethenyl-8-oxo-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 InfoCard100.119.331
Chemical and physical data
FormulaC16H15N5O7S2
Molar mass453.44 g·mol−1
3D model (JSmol)
SMILES
  • O=C2N1/C(=C(/C=C)CS[C@@H]1[C@@H]2NC(=O)C(=N\OCC(=O)O)/c3nc(sc3)N)C(=O)O
InChI
  • InChI=1S/C16H15N5O7S2/c1-2-6-4-29-14-10(13(25)21(14)11(6)15(26)27)19-12(24)9(20-28-3-8(22)23)7-5-30-16(17)18-7/h2,5,10,14H,1,3-4H2,(H2,17,18)(H,19,24)(H,22,23)(H,26,27)/b20-9-/t10-,14-/m1/s1 Y
  • Key:OKBVVJOGVLARMR-QSWIMTSFSA-N Y
 NY (what is this?)  (verify)

Cefixime, sold under the brand name Suprax among others, is an antibiotic medication used to treat a number of bacterial infections.[5] These infections include otitis media, strep throat, pneumonia, urinary tract infections, gonorrhea, and Lyme disease.[5] For gonorrhea typically only one dose is required.[6] In the United States it is a second-line treatment to ceftriaxone for gonorrhea.[5] It is taken by mouth.[5]

Common side effects include diarrhea, abdominal pain, and nausea.[5] Serious side effects may include allergic reactions and Clostridioides difficile diarrhea.[5] It is not recommended in people with a history of a severe penicillin allergy.[6] It appears to be relatively safe during pregnancy.[7] It is in the third-generation cephalosporin class of medications.[5] It works by disrupting the bacteria's cell wall resulting in its death.[5]

Cefixime was patented in 1979 and approved for medical use in the United States in 1989.[5][8] It is on the World Health Organization's List of Essential Medicines.[9] It is available as a generic medication in the United States.[10]

  1. ^ Cite error: The named reference genericnames was invoked but never defined (see the help page).
  2. ^ "Antibiotics". Health Canada. 8 May 2018. Retrieved 13 April 2024.
  3. ^ "Regulatory Decision Summary for Auro-Cefixime". Drug and Health Products Portal. 9 November 2016. Retrieved 13 April 2024.
  4. ^ "Suprax 200 mg Tablets - Summary of Product Characteristics (SmPC)". (emc). 20 August 2019. Archived from the original on 22 September 2020. Retrieved 23 April 2020.
  5. ^ a b c d e f g h i j "Cefixime". The American Society of Health—System Pharmacists. Archived from the original on 27 November 2016. Retrieved 8 December 2016.
  6. ^ a b World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. p. 107. hdl:10665/44053. ISBN 9789241547659.
  7. ^ "Cefixime (Suprax) Use During Pregnancy". Drugs.com. 29 March 2019. Retrieved 24 December 2019.
  8. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 495. ISBN 9783527607495.
  9. ^ 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.
  10. ^ "Generic Suprax Availability". Drugs.com. Retrieved 23 April 2020.
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