Cefixime

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.

Cefixime
Clinical data
Trade namesSuprax, others
AHFS/Drugs.comMonograph
MedlinePlusa690007
License data
Routes of
administration		By mouth
ATC code
Legal status
Legal status
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US: ℞-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability30 to 50%
Protein bindingApproximately 60%
Elimination half-lifeVariable
Average 3 to 4 hours
ExcretionKidney and biliary
Identifiers
  • (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=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)

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

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

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