Cefixime

Cefixime, sold under the brand name Suprax among others, is an antibiotic medication used to treat a number of bacterial infections.[5] These infections include otitis media, strep throat, pneumonia, urinary tract infections, gonorrhea, and Lyme disease.[5] For gonorrhea typically only one dose is required.[6] In the United States it is a second-line treatment to ceftriaxone for gonorrhea.[5] It is taken by mouth.[5]

Cefixime

Clinical data
Trade names	Suprax, others[1]
AHFS/Drugs.com	Monograph
MedlinePlus	a690007
License data	US DailyMed: Cefixime
Pregnancy category	US: B (No risk in non-human studies) [2]
Routes of administration	By mouth (capsule, suspension, or tablet)[3]
ATC code	J01DD08 (WHO)
Legal status
Legal status	UK: POM (Prescription only) [4] US: ℞-only In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	30 to 50%[5]
Protein binding	Approximately 60%
Elimination half-life	Variable Average 3 to 4 hours
Excretion	Kidney and biliary
Identifiers
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
CAS Number	79350-37-1^Y
PubChem CID	5362065
DrugBank	DB00671^Y
ChemSpider	4514923^Y
UNII	XZ7BG04GJX
KEGG	D00258^Y
ChEBI	CHEBI:472657^Y
ChEMBL	ChEMBL1541^Y
CompTox Dashboard (EPA)	DTXSID7022754
ECHA InfoCard	100.119.331
Chemical and physical data
Formula	C16H15N5O7S2
Molar mass	453.44 g·mol^−1
3D model (JSmol)	Interactive image
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
^NY (what is this?)  (verify)

Common side effects include diarrhea, abdominal pain, and nausea.[5] Serious side effects may include allergic reactions and Clostridium difficile diarrhea.[5] It is not recommended in people with a history of a severe penicillin allergy.[6] It appears to be relatively safe during pregnancy.[2] It is in the third-generation cephalosporin class of medications.[5] It works by disrupting the bacteria's cell wall resulting in its death.[5]

Cefixime was patented in 1979 and approved for medical use in the United States in 1989.[5][7] It is on the World Health Organization's List of Essential Medicines, the safest and most effective medicines needed in a health system.[8] It is available as a generic medication in the United States.[9] The wholesale cost in the developing world is about US$0.26–2.09 per dose.[10] In the United States a course of treatment costs about $100–200 as of 2015.[11]

Medical uses

Cefixime treats infections of the:

• Urinary tract: Uncomplicated urinary tract infections caused by susceptible isolates of Escherichia coli and Proteus mirabilis.[3][4][5]
• Ear: Otitis media caused by Haemophilus influenzae, Moraxella catarrhalis and Streptococcus pyogenes.[3][4][5]
• Throat: Tonsillitis and pharyngitis caused by Streptococcus pyogenes.[3][4][5]
• Chest and lungs: Chronic bronchitis caused by Streptococcus pneumoniae and Haemophilus influenzae.[3][4][5]
• Cervix and urethra: Gonorrhea (cervical/urethral) caused by susceptible isolates of Neisseria gonorrhoeae (penicillinase-and non-penicillinase-producing isolates).[3][4][5]

It is also used to treat typhoid fever.[12][13][5]

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:[14]

• 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.[3]

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.[3][15] 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.[16]

History

It was sold under the trade name Suprax 125 in the United States until 2003, when it was taken off the market by drug manufacturer Wyeth after its patent expired. Lupin started selling Suprax in the United States in 2007,[17] and it is available in different formulations and strengths.[17][18][19][20]

Marketing

Cefixime is marketed under many trade names worldwide; examples include Caricef, Taxim o, Texit, Cef-3, Denvar, 3-C, Cefim, Magnett, Oroken, Ofiken, Fix-A, and Zifi.[1][21] In India it is marketed as Zifi 200 and is commonly counterfeited.[22]

References

1. "Cefixime—Drugs.com". www.drugs.com. Archived from the original on 30 May 2016. Retrieved 10 December 2016.
2. "Cefixime (Suprax) Use During Pregnancy". Drugs.com. 29 March 2019. Retrieved 24 December 2019.
3. "Suprax- cefixime tablet Suprax- cefixime capsule Suprax- cefixime tablet, chewable Suprax- cefixime powder, for suspension". DailyMed. 26 November 2019. Retrieved 23 April 2020.
4. "Suprax 200 mg Tablets - Summary of Product Characteristics (SmPC)". (emc). 20 August 2019. Retrieved 23 April 2020.
5. "Cefixime". The American Society of Health—System Pharmacists. Archived from the original on 27 November 2016. Retrieved 8 December 2016.
6. World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. p. 107. hdl:10665/44053. ISBN 9789241547659.
7. Fischer, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 495. ISBN 9783527607495.
8. World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
9. "Generic Suprax Availability". Drugs.com. Retrieved 23 April 2020.
10. "Cefixime". International Drug Price Indicator Guide. Retrieved 8 December 2016.
11. Hamilton, Richart (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 86. ISBN 9781284057560.
12. Matsumoto Y, Ikemoto A, Wakai Y, Ikeda F, Tawara S, Matsumoto K (September 2001). "Mechanism of therapeutic effectiveness of cefixime against typhoid fever". Antimicrob. Agents Chemother. 45 (9): 2450–4. doi:10.1128/aac.45.9.2450-2454.2001. PMC 90676. PMID 11502513.
13. Bhutta ZA, Khan IA, Molla AM (November 1994). "Therapy of multidrug-resistant typhoid fever with oral cefixime vs. intravenous ceftriaxone". Pediatr. Infect. Dis. J. 13 (11): 990–4. doi:10.1097/00006454-199411000-00010. PMID 7845753.
14. http://www.toku-e.com/Assets/MIC/Cefixime%20trihydrate.pdf
15. "Suprax- cefixime powder, for suspension". DailyMed. 2 January 2020. Retrieved 23 April 2020.
16. Choices, N. H. S. "Medicines information links". www.nhs.uk. NHS Choices. Archived from the original on 11 July 2015. Retrieved 22 August 2016.
17. "Suprax: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Retrieved 23 April 2020.
18. "Suprax: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Retrieved 23 April 2020.
19. "Suprax: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Retrieved 23 April 2020.
20. "Suprax: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Retrieved 23 April 2020.
21. "FDC—Products—Formulations". fdcindia.com. Retrieved 2 May 2018.
22. "Fake drugs: the global industry putting your life at risk". Mosaic. 30 October 2018. Retrieved 13 December 2018.

External links

• "Cefixime". Drug Information Portal. U.S. National Library of Medicine.