Cefixime

Cefixime
Names
Trade namesSuprax, others[1]
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
Drug classAntibiotic (3rd-generation cephalosporin)[2]
Main usesOtitis media, strep throat, pneumonia, urinary tract infections, gonorrhea, Lyme disease[2]
Side effectsDiarrhea, abdominal pain, nausea[2]
WHO AWaReUnlinkedWikibase error: ⧼unlinkedwikibase-error-statements-entity-not-set⧽
Pregnancy
category
  • US: B (No risk in non-human studies)[3]
    Routes of
    use    		By mouth (capsule, suspension, or tablet)[4]
    Defined daily dose400 mg[5]
    External links
    AHFS/Drugs.comMonograph
    MedlinePlusa690007
    Legal
    License data
    Legal status
    • UK: POM (Prescription only) [6]
    • US: ℞-only
    • In general: ℞ (Prescription only)
    Pharmacokinetics
    Bioavailability30 to 50%[2]
    Protein bindingApproximately 60%
    Elimination half-lifeVariable
    Average 3 to 4 hours
    ExcretionKidney and biliary
    Chemical and physical data
    FormulaC16H15N5O7S2
    Molar mass453.44 g·mol−1
    3D model (JSmol)
    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 checkY
    • Key:OKBVVJOGVLARMR-QSWIMTSFSA-N checkY

    Cefixime, sold under the brand name Suprax among others, is an antibiotic medication used to treat a number of bacterial infections.[2] These infections include otitis media, strep throat, pneumonia, urinary tract infections, gonorrhea, and Lyme disease.[2] For gonorrhea typically only one dose is required.[7] 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.[7] It appears to be relatively safe during pregnancy.[3] It is in the third-generation cephalosporin class of medications and works by disrupting the bacteria's cell wall resulting in its death.[2]

    Cefixime was patented in 1979 and approved for medical use in the United States in 1989.[2][8] It is on the World Health Organization's List of Essential Medicines.[9] It is available as a generic medication in the United States.[10] The wholesale cost in the developing world is about US$0.26–2.09 per dose.[11] In the United States a course of treatment costs about $100–200 as of 2015.[12]

    Medical uses

    It is in the 'watch' group of the WHO AWaRe Classification.[13]

    Cefixime treats infections of the:

    It is also used to treat typhoid fever.[14][15][2]

    Spectrum of activity

    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:[16]

    • 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

    Dosage

    For bladder or kidney infections it is used at a dose of 200 mg twice per day while for bladder infections in children it is used at a dose of 8 mg/kg once per day in those over the age of two.[17] For gonorrhea it is used as a single 400 mg dose or at 8 mg/kg in children.[17] Treatment of bladder infections are for 5 days in adults while treatment of kidney infections are for 10 to 14 days.[17] It may also be used for typhoid fever at a dose of 200 mg twice a day or 10 mg/kg twice a day for 7 days.[17]

    The defined daily dose is 400 mg (by mouth).[5]

    Contraindications

    Cefixime is contraindicated in patients with known sensitivity or allergies to cephalosporin class of antibiotics.[4][18] As Cefixime is a third generation cephalosporin, it is not contraindicated for patients with a true penicillin allergy.

    Side 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.

    Interactions

    • Alcohol – No major interaction has been observed between cefixime and alcohol.[19]

    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.[4]

    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.

    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,[20] and it is available in different formulations and strengths.[20][21][22][23]

    Society and culture

    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][24] In India it is marketed as Zifi 200 and is commonly counterfeited.[25]

    References

    1. 1 2 "Cefixime—Drugs.com". www.drugs.com. Archived from the original on 30 May 2016. Retrieved 10 December 2016.
    2. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 "Cefixime". The American Society of Health—System Pharmacists. Archived from the original on 27 November 2016. Retrieved 8 December 2016.
    3. 1 2 "Cefixime (Suprax) Use During Pregnancy". Drugs.com. 29 March 2019. Archived from the original on 19 September 2020. Retrieved 24 December 2019.
    4. 1 2 3 4 5 6 7 8 "Suprax- cefixime tablet Suprax- cefixime capsule Suprax- cefixime tablet, chewable Suprax- cefixime powder, for suspension". DailyMed. 26 November 2019. Archived from the original on 10 December 2020. Retrieved 23 April 2020.
    5. 1 2 "WHOCC - ATC/DDD Index". www.whocc.no. Archived from the original on 19 September 2020. Retrieved 21 September 2020.
    6. 1 2 3 4 5 6 "Suprax 200 mg Tablets - Summary of Product Characteristics (SmPC)". (emc). 20 August 2019. Archived from the original on 22 September 2020. Retrieved 23 April 2020.
    7. 1 2 World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. p. 107. hdl:10665/44053. ISBN 9789241547659.
    8. ↑ Fischer, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 495. ISBN 9783527607495. Archived from the original on 20 December 2016. Retrieved 2 March 2019.
    9. ↑ 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.
    10. ↑ "Generic Suprax Availability". Drugs.com. Archived from the original on 27 July 2020. Retrieved 23 April 2020.
    11. ↑ "Cefixime". International Drug Price Indicator Guide. Archived from the original on 22 January 2018. Retrieved 8 December 2016.
    12. ↑ Hamilton, Richart (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 86. ISBN 9781284057560.
    13. ↑ Zanichelli, Veronica; Sharland, Michael; Cappello, Bernadette; Moja, Lorenzo; Getahun, Haileyesus; Pessoa-Silva, Carmem; Sati, Hatim; van Weezenbeek, Catharina; Balkhy, Hanan; Simão, Mariângela; Gandra, Sumanth; Huttner, Benedikt (1 April 2023). "The WHO AWaRe (Access, Watch, Reserve) antibiotic book and prevention of antimicrobial resistance". Bulletin of the World Health Organization. 101 (4): 290–296. doi:10.2471/BLT.22.288614. ISSN 0042-9686. Archived from the original on 7 May 2023. Retrieved 17 November 2023.
    14. ↑ 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.
    15. ↑ 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.
    16. ↑ "Archive copy" (PDF). Archived (PDF) from the original on 4 March 2016. Retrieved 15 August 2013.{{cite web}}: CS1 maint: archived copy as title (link)
    17. 1 2 3 4 "CEFIXIME oral - Essential drugs". medicalguidelines.msf.org. Archived from the original on 28 August 2021. Retrieved 26 August 2020.
    18. ↑ "Suprax- cefixime powder, for suspension". DailyMed. 2 January 2020. Archived from the original on 28 July 2020. Retrieved 23 April 2020.
    19. ↑ Choices, N. H. S. "Medicines information links". www.nhs.uk. NHS Choices. Archived from the original on 11 July 2015. Retrieved 22 August 2016.
    20. 1 2 "Suprax: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Archived from the original on 27 July 2020. Retrieved 23 April 2020.
    21. ↑ "Suprax: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Archived from the original on 27 July 2020. Retrieved 23 April 2020.
    22. ↑ "Suprax: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Archived from the original on 27 July 2020. Retrieved 23 April 2020.
    23. ↑ "Suprax: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Archived from the original on 27 July 2020. Retrieved 23 April 2020.
    24. ↑ "FDC—Products—Formulations". fdcindia.com. Archived from the original on 26 April 2018. Retrieved 2 May 2018.
    25. ↑ "Fake drugs: the global industry putting your life at risk". Mosaic. 30 October 2018. Archived from the original on 11 April 2020. Retrieved 13 December 2018.
    • "Cefixime". Drug Information Portal. U.S. National Library of Medicine. Archived from the original on 27 July 2020. Retrieved 23 April 2020.
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