Cefixime

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Cefixime
Cefixime.svg
Systematic (IUPAC) name
(6R,7R)-7-{[2-(2-amino-1,3-thiazol-4-yl)-2-(carboxy
methoxyimino)acetyl]amino}-3-ethenyl-8-oxo-5-thia-
1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Clinical data
Trade names Suprax
AHFS/Drugs.com monograph
MedlinePlus a690007
Pregnancy cat. B
Legal status Prescription only
Routes Oral
Pharmacokinetic data
Bioavailability 40% to 50%
Protein binding Approximately 60%
Half-life Variable
Average 3 to 4 hours
Excretion Renal and biliary
Identifiers
CAS number 79350-37-1 YesY
ATC code J01DD08
PubChem CID 5362065
DrugBank DB00671
ChemSpider 4514923 YesY
UNII 97I1C92E55 YesY
KEGG D00258 YesY
ChEBI CHEBI:472657 YesY
ChEMBL CHEMBL1541 YesY
Chemical data
Formula C16H15N5O7S2 
Mol. mass 453.452 g/mol
 YesY (what is this?)  (verify)

Cefixime (under the brand name of Suprax in the USA, Setic in Bangladesh, ) is a third generation cephalosporin antibiotic used to treat bacterial infections.

Spectrum of bacterial susceptibility[edit]

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:[1]

  • 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

Medical uses[edit]

Cefixime treats infections of the:
Ear: Otitis caused by Haemophilus influenzae, Moraxella catarrhalis and Streptococcus pyogenes.
Sinuses: Sinusitis.
Throat: Tonsillitis, pharyngitis caused by Streptococcus pyogenes.
Chest and lungs: Bronchitis, pneumonia caused by Streptococcus pneumoniae and Haemophilus influenzae.

It is also used to treat typhoid fever

Mechanism of action[edit]

The bactericidal action of cephalosporin 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). Rate may be decreased if taken with food. Absorption from oral suspensions than tablet.

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

It is always better to perform appropriate cultures and susceptibility studies to determine the causative organism and its sensitivity to cefixime.

Contraindications[edit]

Cefixime is contraindicated in patients with known sensitivity or allergies to cephalosporin class of antibiotics. As Cefixime is a third generation cephalosporin, it is not contraindicated for patients with a true penicillin allergy.[2]

Adverse effects[edit]

Adverse drug reactions include diarrhea, dyspepsia, nausea and vomiting. Hypersensitivity reactions like skin rashes, urticaria and Stevens-Johnson syndrome have been reported. There is no specific antidote for Cefixime overdosage. Gastric lavage may performed. Dialysis will not remove Cefixime in significant quantities.

History[edit]

It was sold under the trade name Suprax 125 in the USA until 2003 when it was taken off the market by drug manufacturer Wyeth after its patent expired.

The oral suspension form of Suprax 125 was re-launched by Lupin in the USA..

References[edit]

  1. ^ http://www.toku-e.com/Assets/MIC/Cefixime%20trihydrate.pdf
  2. ^ http://www.cks.nhs.uk/gonorrhoea/prescribing_information/prescribing_information/cephalosporins_ceftriaxone_or_cefixime