Amoxicillin/clavulanic acid

Amoxicillin/clavulanic acid
Combination of
AmoxicillinPenicillin antibiotic
Clavulanic acidBeta-lactamase inhibitor
Clinical data
Trade namesAugmentin, Clavulin, Amoclan, others[1]
Other namesCo-amoxiclav; Amox-clav
AHFS/Drugs.comMonograph
MedlinePlusa685024
License data
Pregnancy
category
  • AU: B1
Routes of
administration		By mouth, intravenous[2]
ATC code
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
ChemSpider
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC24H27KN4O10S
Molar mass602.66 g·mol−1
3D model (JSmol)
  • CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=C(C=C3)O)N)C(=O)O)C.C1C2N(C1=O)C(C(=CCO)O2)C(=O)[O-].[K+]
  • InChI=DWHGNUUWCJZQHO-ZVDZYBSKSA-M
  • Key:1S/C16H19N3O5S.C8H9NO5.K/c1-16(2)11(15(23)24)19-13(22)10(14(19)25-16)18-12(21)9(17)7-3-5-8(20)6-4-7;10-2-1-4-7(8(12)13)9-5(11)3-6(9)14-4;/h3-6,9-11,14,20H,17H2,1-2H3,(H,18,21)(H,23,24);1,6-7,10H,2-3H2,(H,12,13);/q;;+1/p-1/b;4-1-;/t9-,10-,11+,14-;6-,7-;/m11./s1
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Amoxicillin/clavulanic acid, also known as co-amoxiclav or amox-clav, sold under the brand name Augmentin, among others, is an antibiotic medication used for the treatment of a number of bacterial infections.[5] It is a combination consisting of amoxicillin, a β-lactam antibiotic, and potassium clavulanate, a β-lactamase inhibitor.[5] It is specifically used for otitis media, streptococcal pharyngitis, pneumonia, cellulitis, urinary tract infections, and animal bites.[5] It is taken by mouth or by injection into a vein.[2]

Common side effects include diarrhea, vomiting, and allergic reactions.[5] It also increases the risk of yeast infections, headaches, and blood clotting problems.[2][6] It is not recommended in people with a history of a penicillin allergy.[2] It is relatively safe for use during pregnancy.[5]

Amoxicillin/clavulanic acid was approved for medical use in the United States in 1984.[5] It is on the World Health Organization's List of Essential Medicines.[7][8] The World Health Organization classifies amoxicillin/clavulanic-acid as critically important for human medicine.[9] It is available as a generic medication.[5] In 2022, it was the 96th most commonly prescribed medication in the United States, with more than 6 million prescriptions.[10][11]

  1. ^ Hamilton R (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 97. ISBN 9781284057560.
  2. ^ a b c d World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. p. 102. hdl:10665/44053. ISBN 9789241547659.
  3. ^ "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Archived from the original on 6 July 2023. Retrieved 30 March 2024.
  4. ^ "Regulatory Decision Summary - Amoxicillin Sodium And Potassium Clavulanate For Injection". Health Canada. 23 October 2014. Archived from the original on 5 June 2022. Retrieved 4 June 2022.
  5. ^ a b c d e f g "Amoxicillin and Clavulanate Potassium". The American Society of Health-System Pharmacists. Archived from the original on 29 November 2016. Retrieved 8 December 2016.
  6. ^ Gillies M, Ranakusuma A, Hoffmann T, Thorning S, McGuire T, Glasziou P, et al. (January 2015). "Common harms from amoxicillin: a systematic review and meta-analysis of randomized placebo-controlled trials for any indication". CMAJ. 187 (1): E21–E31. doi:10.1503/cmaj.140848. PMC 4284189. PMID 25404399.
  7. ^ 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.
  8. ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
  9. ^ World Health Organization (2019). Critically important antimicrobials for human medicine (6th revision ed.). Geneva: World Health Organization. hdl:10665/312266. ISBN 9789241515528.
  10. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  11. ^ "Amoxicillin; Clavulanate Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.