Cefpodoxime

Cefpodoxime
Names
Trade namesVantin, others
Other namesCephpodoxime, cefpodoxime proxetil
IUPAC name
  • (6R,7R)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyimino-acetyl]amino}-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Clinical data
Drug classAntibiotic (3rd generation cephalosporin)[1]
Main usesMiddle ear infections, strep throat, sinusitis, urinary tract infections, gonorrhea[2]
Side effectsDiarrhea, nausea, vaginal yeast infections, abdominal pain, headache[3]
WHO AWaReUnlinkedWikibase error: ⧼unlinkedwikibase-error-statements-entity-not-set⧽
Pregnancy
category
  • AU: B1
  • US: B (No risk in non-human studies)
    Routes of
    use    		By mouth
    External links
    AHFS/Drugs.comMonograph
    MedlinePlusa698024
    Legal
    Legal status
    Pharmacokinetics
    Bioavailability50%
    Protein binding21% to 29%
    MetabolismNegligible. Cefpodoxime proxetil is metabolized to cefpodoxime by the liver
    Elimination half-life2 hours
    ExcretionKidney, unchanged
    Chemical and physical data
    FormulaC15H17N5O6S2
    Molar mass427.45 g·mol−1
    3D model (JSmol)
    SMILES
    • O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)C(=N\OC)/c3nc(sc3)N)COC)C(=O)O
    InChI
    • InChI=1S/C15H17N5O6S2/c1-25-3-6-4-27-13-9(12(22)20(13)10(6)14(23)24)18-11(21)8(19-26-2)7-5-28-15(16)17-7/h5,9,13H,3-4H2,1-2H3,(H2,16,17)(H,18,21)(H,23,24)/b19-8-/t9-,13-/m1/s1 checkY
    • Key:WYUSVOMTXWRGEK-HBWVYFAYSA-N checkY

    Cefpodoxime, sold under the brand name Vantin among others, is an antibiotic used to treat middle ear infections, strep throat, sinusitis, urinary tract infections, and gonorrhea.[2] It is taken by mouth.[2]

    Common side effects include diarrhea, nausea, vaginal yeast infections, abdominal pain, and headache.[3] Other side effects may include allergic reactions and Clostridioides difficile infection.[2] While there is no evidence of harm with use in pregnancy, such use has not been well studied.[4] It is a third-generation cephalosporin and works by interfering with the bacterial cell wall.[1]

    Cefpodoxime was patented in 1980 and approved for medical use in 1989.[5] It is available as a generic medication.[2] In the United States 20 tablets of 200 mg costs about 36 USD as of 2021.[6]

    Medical uses

    Spectrum of activity

    Cefpodoxime has been used to fight pathogenic bacteria responsible for causing gonorrhoea, tonsillitis, pneumonia, and bronchitis. Representative pathogenic genera include Streptococcus, Haemophilus, and Neisseria. The following represents MIC susceptibility data for a few medically significant microorganisms.[7]

    • Haemophilus influenzae: ≤0.03 - 1 μg/ml
    • Neisseria gonorrhoeae: 0.004 - 0.06 μg/ml
    • Streptococcus pyogenes: ≤0.004 - 2 μg/ml

    Dosage

    It is used at a dose of 200 to 800 mg per day.[3] This may be take as a single dose or divided into two doses.[3] Treatment may vary from 5 to 14 days.[3]

    Mechanism of action

    Cefpodoxime inhibits cell wall synthesis by inhibiting the final transpeptidation step of peptidoglycan synthesis in cell walls. It has well established pharmacokinetic profile with absorption of 50%.

    Society and culture

    Brand name

    Zoetis markets cefpodoxime proxetil under the trade name Simplicef for veterinary use. Finecure,[8] India markets the products under trade name Cefpo.[9]

    Vantin (by Pfizer)[10] in suspension or tablet form.

    Toraxim (by Delta Pharma Ltd. Bangladesh)

    Trucef (by Renata Limited, Bangladesh)

    Tricef (by Alkaloid Skopje, North Macedonia)

    Orelox (by Sanofi-Aventis)[11]

    MAPDOX-CV: Cefpodoxime and Clavulanic acid combination

    MONOTAX O (Cefpodoxime)/ MONOTAX CV (Cefpodoxime and Clavulanic acid combination) (by Zydus Healthcare Ltd.)

    POSTPOD-50 (Cefpodoxime 50mg/5ml) (by Laafon Galaxy Pharmaceuticals)[12]

    References

    1. 1 2 Beauduy, Camille E.; Winston, Lisa G. (2020). "43. Beta-lactam and other cell wall - & membrane - active antibiotics". In Katzung, Bertram G.; Trevor, Anthony J. (eds.). Basic and Clinical Pharmacology (15th ed.). New York: McGraw-Hill. p. 832. ISBN 978-1-260-45231-0. Archived from the original on 2021-10-10. Retrieved 2021-11-30.
    2. 1 2 3 4 5 "Cefpodoxime Monograph for Professionals". Drugs.com. Archived from the original on 28 January 2021. Retrieved 30 December 2021.
    3. 1 2 3 4 5 "DailyMed - CEFPODOXIME PROXETIL tablet, film coated". dailymed.nlm.nih.gov. Archived from the original on 28 December 2021. Retrieved 30 December 2021.
    4. ↑ "Cefpodoxime (Vantin) Use During Pregnancy". Drugs.com. Archived from the original on 29 November 2020. Retrieved 30 December 2021.
    5. ↑ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 495. ISBN 9783527607495. Archived from the original on 2016-12-20. Retrieved 2021-06-11.
    6. ↑ "Cefpodoxime Prices, Coupons & Savings Tips - GoodRx". GoodRx. Archived from the original on 9 November 2016. Retrieved 30 December 2021.
    7. ↑ "Cefpodoxime, Free Acid Susceptibility and Minimum Inhibitory Concentration (MIC) Data" (PDF). Archived (PDF) from the original on 2018-07-12. Retrieved 2021-06-11.
    8. ↑ "Pharmaceuticals Manufacturer, Marketer, Pharmaceutical Manufacturing Company India". www.finecurepharma.com. Archived from the original on 2019-05-26. Retrieved 2019-05-26.
    9. ↑ "Anti Biotics and Anti Bacterial". Finecurepharmaceuticalsltd. Archived from the original on 2012-03-06. Retrieved 2012-03-27.
    10. ↑ "Vantin - Drugs.com". www.drugs.com. Archived from the original on 2019-05-02. Retrieved 2019-05-02.
    11. ↑ "Orelox - Drugs.com". www.drugs.com. Archived from the original on 2015-12-08. Retrieved 2015-11-28.
    12. ↑ "Postpod dry syrup". Laafon Galaxy Pharmaceuticals Company in Karnal. Archived from the original on 2021-11-01. Retrieved 2020-09-16.
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