Description

Simple

A penicillin antibiotic use to treat a wide variety of infections in the body.

Clinical

A penicillin derivative used for the treatment of infections caused by gram-positive bacteria, in particular streptococcal bacteria causing upper respiratory tract infections.

Overview

Amoxicillin, or BRL-2333, is a penicillin G derivative first described in the literature in 1972.[6] Amoxicillin has similar activity to [penicillin] and [ampicillin], but leads to higher serum concentrations than ampicillin.[6]

Amoxicillin was granted FDA approval on 18 January 1974.[12]

Pharmacology

Indication

Amoxicillin alone is indicated to treat susceptible bacterial infections of the ear, nose, throat, genitourinary tract, skin, skin structure, and lower respiratory tract.[17, Read more

Pharmacodynamic

Amoxicillin competitively inhibit penicillin binding proteins, leading to upregulation of autolytic enzymes and inhibition of cell wall synthesis.[ Read more

Mechanism of action

Amoxicillin competitively inhibits penicillin-binding protein 1 and other high molecular weight penicillin binding proteins.[ Read more

Absorption

Amoxicillin is approximately 60% bioavailable.[8 Read more

Protein binding

Amoxicillin is 17% protein bound in serum.[ Read more

Volume of distribution

The central volume of distribution of amoxicillin is 27.7L.[ Read more

Clearance

The mean clearance of amoxicillin is 21.3L/h.[ Read more

Half life

The half life of amoxicillin is 61.3 minutes.[8 Read more

Route of elimination

125mg to 1g doses of amoxicillin are 70-78% eliminated in the urine after 6 hours.[6]

Toxicity

Patients experiencing an overdose may present with hematuria, oliguria, abdominal pain, acute renal failure, vomiting, diarrhea, rash, hyperactivity, and drowsiness.[ Read more

Adverse Effects

Contraindications

  • Regions: US
  • Patient Conditions:
      • Name: Hepatic dysfunction
      • Drugbank Id: DBCOND0094733
  • With Drugs:
      • Name: Clavulanic acid
      • Drugbank Id: DB00766
  • Regions: US
  • Patient Conditions:
      • Name: Cholestatic jaundice
      • Drugbank Id: DBCOND0094562
  • With Drugs:
      • Name: Clavulanic acid
      • Drugbank Id: DB00766
  • Regions: US
  • Patient Conditions:
      • Name: Cholestatic jaundice
      • Drugbank Id: DBCOND0094562
  • Regions: US
  • Patient Conditions:
      • Name: Hepatic dysfunction
      • Drugbank Id: DBCOND0094733
  • Hypersensitivity:
    • beta-lactam antibiotics
  • Regions: US
  • Hypersensitivity:
    • true
  • Regions: US

Food Interactions

  • Take with food.

Interactions

Type in a drug name to check for interaction with Amoxicillin
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  • Paracetamol(acetaminophen)
  • Paxil(paroxetine)
  • Pamelor(nortriptyline)
  • Panadol(acetaminophen)
  • Patanol(olopatadine ophthalmic)
  • Pataday(olopatadine ophthalmic)
  • Parnate(tranylcypromine)
  • Pazeo(olopatadine ophthalmic)
(R)-warfarin
Amoxicillin may increase the anticoagulant activities of (R)-warfarin.
(S)-Warfarin
Amoxicillin may increase the anticoagulant activities of (S)-Warfarin.
4-hydroxycoumarin
Amoxicillin may increase the anticoagulant activities of 4-hydroxycoumarin.
Abacavir
Abacavir may decrease the excretion rate of Amoxicillin which could result in a higher serum level.
Acarbose
Acarbose may decrease the excretion rate of Amoxicillin which could result in a higher serum level.
Aceclofenac
Aceclofenac may decrease the excretion rate of Amoxicillin which could result in a higher serum level.
Acemetacin
Acemetacin may decrease the excretion rate of Amoxicillin which could result in a higher serum level.
Acenocoumarol
Amoxicillin may increase the anticoagulant activities of Acenocoumarol.
Acetaminophen
Acetaminophen may decrease the excretion rate of Amoxicillin which could result in a higher serum level.
Acetazolamide
Acetazolamide may increase the excretion rate of Amoxicillin which could result in a lower serum level and potentially a reduction in efficacy.
Acetylsalicylic acid
Acetylsalicylic acid may decrease the excretion rate of Amoxicillin which could result in a higher serum level.
Aclidinium
Amoxicillin may decrease the excretion rate of Aclidinium which could result in a higher serum level.
Acrivastine
Amoxicillin may decrease the excretion rate of Acrivastine which could result in a higher serum level.
Acyclovir
Acyclovir may decrease the excretion rate of Amoxicillin which could result in a higher serum level.
Adefovir
Adefovir may decrease the excretion rate of Amoxicillin which could result in a higher serum level.
Adefovir dipivoxil
Adefovir dipivoxil may decrease the excretion rate of Amoxicillin which could result in a higher serum level.
Albutrepenonacog alfa
Amoxicillin may decrease the excretion rate of Albutrepenonacog alfa which could result in a higher serum level.
Alclofenac
Alclofenac may decrease the excretion rate of Amoxicillin which could result in a higher serum level.
Alcuronium
The therapeutic efficacy of Alcuronium can be increased when used in combination with Amoxicillin.
Aldesleukin
Aldesleukin may decrease the excretion rate of Amoxicillin which could result in a higher serum level.
18 References
  1. 1 . Szultka M, Krzeminski R, Jackowski M, Buszewski B: Identification of In Vitro Metabolites of Amoxicillin in Human Liver Microsomes by LC-ESI/MS. Chromatographia. 2014;77:1027-1035. doi: 10.1007/s10337-014-2648-2. Epub 2014 Mar 22.PubMed: 25089048
  2. 2 . Li M, Anderson GD, Phillips BR, Kong W, Shen DD, Wang J: Interactions of amoxicillin and cefaclor with human renal organic anion and peptide transporters. Drug Metab Dispos. 2006 Apr;34(4):547-55. Epub 2006 Jan 24.PubMed: 16434549
  3. 3 . Carlier M, Noe M, De Waele JJ, Stove V, Verstraete AG, Lipman J, Roberts JA: Population pharmacokinetics and dosing simulations of amoxicillin/clavulanic acid in critically ill patients. J Antimicrob Chemother. 2013 Nov;68(11):2600-8. doi: 10.1093/jac/dkt240. Epub 2013 Jun 25.PubMed: 23800901
  4. 4 . de Velde F, de Winter BC, Koch BC, van Gelder T, Mouton JW: Non-linear absorption pharmacokinetics of amoxicillin: consequences for dosing regimens and clinical breakpoints. J Antimicrob Chemother. 2016 Oct;71(10):2909-17. doi: 10.1093/jac/dkw226. Epub 2016 Jun 20.PubMed: 27330071
  5. 5 . Akhavan BJ, Vijhani P: Amoxicillin .PubMed: 29489203
  6. 6 . Bodey GP, Nance J: Amoxicillin: in vitro and pharmacological studies. Antimicrob Agents Chemother. 1972 Apr;1(4):358-62. doi: 10.1128/aac.1.4.358.PubMed: 4598841
  7. 7 . Belko J, Urueta G, Emre U: Amoxicillin overdose manifested by hematuria and acute renal failure. Pediatr Infect Dis J. 1995 Oct;14(10):917-9.PubMed: 8584329
  8. 8 . Gordon C, Regamey C, Kirby WM: Comparative clinical pharmacology of amoxicillin and ampicillin administered orally. Antimicrob Agents Chemother. 1972 Jun;1(6):504-7. doi: 10.1128/aac.1.6.504.PubMed: 4680813
  9. 9 . Okamoto T, Yoshiyama H, Nakazawa T, Park ID, Chang MW, Yanai H, Okita K, Shirai M: A change in PBP1 is involved in amoxicillin resistance of clinical isolates of Helicobacter pylori. J Antimicrob Chemother. 2002 Dec;50(6):849-56.PubMed: 12461003
  10. 10 . Sauvage E, Terrak M: Glycosyltransferases and Transpeptidases/Penicillin-Binding Proteins: Valuable Targets for New Antibacterials. Antibiotics (Basel). 2016 Feb 17;5(1). pii: antibiotics5010012. doi: 10.3390/antibiotics5010012.PubMed: 27025527
  11. 11 . FDA Approved Drug Products: Talicia Amoxicillin, Omeprazole, and Rifabutin Oral Delayed Release Capsules Link
  12. 12 . FDA Approved Drug Products: Amoxil Amoxicillin Oral Capsules (Discontinued) Link
  13. 13 . FDA Approved Drug Products: Omeclamox-Pak Oral Capsules and Tablets Link
  14. 14 . FDA Approved Drug Products: Augmentin XR Amoxicillin and Clavulanate Oral Extended Release Tablets Link
  15. 15 . FDA Approved Drug Products: Augmentin Amoxicillin and Clavulanate Oral Tablets and Suspension Link
  16. 16 . FDA Approved Drug Products: Amoxicillin and Clavulanate Oral Suspension Link
  17. 17 . FDA Approved Drug Products: Amoxicillin Oral Suspension Link
  18. 18 . FDA Approved Drug Products: Amoxicillin Oral Tablets Link