Cefixime

Cefixime

File:Cefixime.svg
Systematic (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
Clinical data
Trade names	Suprax, Trixon-O
AHFS/Drugs.com	monograph
MedlinePlus	a690007
Pregnancy category	B
Legal status	℞ (Prescription only)
Routes of administration	Oral capsule/suspension
Pharmacokinetic data
Bioavailability	40% to 50%
Protein binding	Approximately 60%
Biological half-life	Variable Average 3 to 4 hours
Excretion	Renal and biliary
Identifiers
CAS Number	79350-37-1 Y
ATC code	J01DD08 (WHO)
PubChem	CID: 5362065
DrugBank	DB00671 Y
ChemSpider	4514923 Y
UNII	97I1C92E55 Y
KEGG	D00258 Y
ChEBI	CHEBI:472657 Y
ChEMBL	CHEMBL1541 Y
Chemical data
Formula	C16H15N5O7S2
Molecular mass	453.452 g/mol
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
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Cefixime 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.

Medical uses

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

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:

• 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

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). Rate may be decreased if taken with food. Absorption from oral suspensions than tablet is more.

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

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.

Adverse effects

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

Drug Interactions

• Alcohol - No major interaction has been observed between cefixime and alcohol.

History

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.

Trade Names

Trade names include:

• Setic (Sandoz, Bangladesh)
• Afix (Aristopharma, Bangladesh)
• Tocef (General Pharmaceuticals, Bangladesh)
• Ofex (Delta Pharma, Bangladesh)
• Taxim-O (Alkem Laboratories Limited, India)
• C-3 (Astra Biopharmaceuticals, Bangladesh)
• CEXIM (Vijayadee Laboratories, Nepal)
• Taxone-O (Mapra Laboratories, India)
• Caricef (Sami Pharmaceutical, Pakistan)
• Trixon-O (Lincoln Pharmaceuticals, India)
• Emixef (Incepta Pharmaceuticals, Bangladesh)
• Verixim (Veritas Pharmaceuticals, Bangladesh)