Cefixime

Cefixime

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, Hebixime, Zenicef, Posicef, Cefacef or Eficef
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 Y
ATC code	J01DD08
PubChem	CID 5362065
DrugBank	DB00671
ChemSpider	4514923 Y
UNII	97I1C92E55 Y
KEGG	D00258 Y
ChEBI	CHEBI:472657 Y
ChEMBL	CHEMBL1541 Y
Chemical data
Formula	C16H15N5O7S2
Mol. 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
Y (what is this?)  (verify)

Cefixime (under the brand name of Suprax in the USA, Zenicef by Zenith Pharmaceuticals Ltd. in Bangladesh, Posicef by Positive Medicare Pvt. Ltd. in India, Hebixime by atm Pharmaceuticals in Egypt and Eficef by Antibiotice Iaşi in Romania) is a cephalosporin antibiotic used to treat infections caused by bacteria.

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.
Urinary system and genital organs: Uncomplicated gonorrhea caused by Neisseria gonorrhoeae.

Mechanism of action

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. Greater 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

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. There is no specific antidote for Cefixime overdosage. Gastric lavage may performed. Dialysis will not remove Cefixime in significant quantities.

History

It was sold under the trade name Suprax 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 was re-launched by Lupin in the USA. In Bangladesh, it is sold as Roxim by Eskayef Bangladesh Limited. Suprax is still manufactured in Europe by Sanofi.

Cefixime API is manufactured by many pharmaceutical companies all over the world. The major manufacturers are based in India.