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 namesSuprax
AHFS/Drugs.commonograph
MedlinePlusa690007
Pregnancy cat.
  • B
Legal status
  • Prescription only
RoutesOral
Pharmacokinetic data
Bioavailability40% to 50%
Protein bindingApproximately 60%
Half-lifeVariable
Average 3 to 4 hours
ExcretionRenal and biliary
Identifiers
CAS number79350-37-1 YesY
ATC codeJ01DD08
PubChemCID 5362065
DrugBankDB00671
ChemSpider4514923 YesY
UNII97I1C92E55 YesY
KEGGD00258 YesY
ChEBICHEBI:472657 YesY
ChEMBLCHEMBL1541 YesY
Chemical data
FormulaC16H15N5O7S2 
Mol. mass453.452 g/mol
 YesY (what is this?)  (verify)
 
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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 namesSuprax
AHFS/Drugs.commonograph
MedlinePlusa690007
Pregnancy cat.
  • B
Legal status
  • Prescription only
RoutesOral
Pharmacokinetic data
Bioavailability40% to 50%
Protein bindingApproximately 60%
Half-lifeVariable
Average 3 to 4 hours
ExcretionRenal and biliary
Identifiers
CAS number79350-37-1 YesY
ATC codeJ01DD08
PubChemCID 5362065
DrugBankDB00671
ChemSpider4514923 YesY
UNII97I1C92E55 YesY
KEGGD00258 YesY
ChEBICHEBI:472657 YesY
ChEMBLCHEMBL1541 YesY
Chemical data
FormulaC16H15N5O7S2 
Mol. mass453.452 g/mol
 YesY (what is this?)  (verify)

Cefixime (under the brand name of Suprax in the USA, Setic in Bangladesh, Cefolac in India) is an antibiotic useful for the treatment of a number of bacterial infections. It is a third generation cephalosporin.

It is on the World Health Organization's List of Essential Medicines, a list of the most important medication needed in a basic health system.[1]

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

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:[2]

Mechanism of action[edit]

The bactericidal action of cephalosporin 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). 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.[3]

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.

Drug Interactions[edit]

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. The No.1 prescribed brand in India is Zifi, marketed by FDC Ltd.

References[edit]

  1. ^ "WHO Model List of EssentialMedicines". World Health Organization. October 2013. Retrieved 22 April 2014. 
  2. ^ http://www.toku-e.com/Assets/MIC/Cefixime%20trihydrate.pdf
  3. ^ http://www.cks.nhs.uk/gonorrhoea/prescribing_information/prescribing_information/cephalosporins_ceftriaxone_or_cefixime
  4. ^ http://www.nhs.uk/conditions/gonorrhoea/pages/MedicineOverview.aspx?condition=Bacterial%20infections&medicine=Cefixime&preparationCefixime%20100mg/5ml%20oral%20suspension