Jump to content

Cefixime

From Wikipedia, the free encyclopedia

This is an old revision of this page, as edited by Donner60 (talk | contribs) at 02:49, 15 June 2018 (Reverted edits by 125.20.36.137 (talk): not adhering to manual of style (HG) (3.4.3)). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Cefixime
Clinical data
Trade namesmany[1]
AHFS/Drugs.comMonograph
MedlinePlusa690007
Pregnancy
category
  • B
Routes of
administration		by mouth (capsule or suspension)
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability30 to 50%[2]
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 Edit this at Wikidata
Chemical and physical data
FormulaC16H15N5O7S2
Molar mass453.452 g/mol g·mol−1
3D model (JSmol)
  • 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 checkY
  • Key:OKBVVJOGVLARMR-QSWIMTSFSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Cefixime is an antibiotic useful to treat a number of bacterial infections.[2] This includes otitis media, strep throat, pneumonia, urinary tract infections, gonorrhea, and Lyme disease.[2] For gonorrhea typically only one dose is required.[3] In the United States it is a second line treatment to ceftriaxone for gonorrhea.[2] It is taken by mouth.[2]

Common side effects include diarrhea, abdominal pain, and nausea.[2] Serious side effects may include allergic reactions and Clostridium difficile diarrhea.[2] It is not recommended in people with a history of a severe penicillin allergy.[3] It appears to be relatively safe during pregnancy.[4] It is in the third generation cephalosporin class of medications.[2] It works by disrupting the bacteria's cell wall resulting in its death.[2]

Cefixime was approved for medical use in the United States in 1989.[2] It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system.[5] It is not available as a generic medication in the United States.[6] The wholesale cost in the developing world is about 0.26 to 2.09 USD per dose.[7] In the United States a course of treatment costs about 100 to 200 USD as of 2015.[6]

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.[8]

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:[9]

  • 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 bioavailability). Absorption may be decreased when taken with food. Average peak concentration after administration of oral suspension is approximately 25–50% greater than the peak concentration following oral tablet or capsules administration.[10]

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

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.[11]

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

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

Cefixime is marketed under many trade names worldwide; examples include Taxim o, Texit, Cef-3, Denvar, 3-C, and Zifi.[1][13]

References

  1. ^ a b "Cefixime - Drugs.com". www.drugs.com. Archived from the original on 30 May 2016. Retrieved 10 December 2016. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  2. ^ a b c d e f g h i j "Cefixime". The American Society of Health—System Pharmacists. Archived from the original on 27 November 2016. Retrieved 8 December 2016. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  3. ^ a b WHO Model Formulary 2008 (PDF). World Health Organization. 2009. p. 107. ISBN 9789241547659. Archived from the original (PDF) on 13 December 2016. Retrieved 8 December 2016. {{cite book}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  4. ^ "Cefixime (Suprax) Use During Pregnancy". www.drugs.com. Archived from the original on 2016-12-20. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  5. ^ "WHO Model List of Essential Medicines (19th List)" (PDF). World Health Organization. April 2015. Archived from the original (PDF) on 13 December 2016. Retrieved 8 December 2016. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  6. ^ a b Hamilton, Richart (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 86. ISBN 9781284057560.
  7. ^ "Cefixime". International Drug Price Indicator Guide. Retrieved 8 December 2016.
  8. ^ "Mechanism of Therapeutic Effectiveness of Cefixime against Typhoid Fever". Antimicrobial Agents and Chemotherapy. September 2001. Archived from the original on 2 December 2015. Retrieved 7 April 2016. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  9. ^ http://www.toku-e.com/Assets/MIC/Cefixime%20trihydrate.pdf
  10. ^ "SUPRAX Package Insert" (PDF). Lupin Pharmaceuticals, Inc. March 2013. Archived from the original (PDF) on 23 February 2015. Retrieved 7 April 2016. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  11. ^ http://www.cks.nhs.uk/gonorrhoea/prescribing_information/prescribing_information/cephalosporins_ceftriaxone_or_cefixime[permanent dead link‍]
  12. ^ Choices, N. H. S. "Medicines information links". www.nhs.uk. NHS Choices. Archived from the original on 11 July 2015. Retrieved 22 August 2016. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  13. ^ "FDC - Products - Formulations". fdcindia.com. Retrieved 2018-05-02.
Retrieved from "https://en.wikipedia.org/w/index.php?title=Cefixime&oldid=845927662"