Identification

Name
Amoxicillin
Accession Number
DB01060
Description

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

Type
Small Molecule
Groups
Approved, Vet approved
Structure
Thumb
Weight
Average: 365.404
Monoisotopic: 365.104541423
Chemical Formula
C16H19N3O5S
Synonyms
  • (2S,5R,6R)-6-{[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
  • 6-(p-hydroxy-α-aminophenylacetamido)penicillanic acid
  • Amox
  • Amoxicilina
  • Amoxicillin
  • Amoxicillin (anhydrous)
  • Amoxicillin anhydrous
  • Amoxicilline
  • Amoxicillinum
  • Amoxycillin
  • AX
  • p-Hydroxyampicillin
  • α-amino-p-hydroxybenzylpenicillin
External IDs
  • NSC-277174

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.17,18 Amoxicillin is given with calvulanic acid to treat acute bacterial sinusitis, community acquired pneumonia, lower respiratory tract infections, acute bacterial otitis media, skin and skin structure infections, and urinary tract infections.14,15,16 Amoxicillin is given with omeprazole in the treatment of H. pylori.11,13

Associated Conditions
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More
Pharmacodynamics

Amoxicillin competitively inhibit penicillin binding proteins, leading to upregulation of autolytic enzymes and inhibition of cell wall synthesis.9,10,5 Amoxicillin has a long duration of action as it is usually given twice daily.15 Amoxicillin has a wide therapeutic range as mild overdoses are not associated with significant toxicity.14 Patients should be counselled regarding the risk of anaphylaxis, Clostridium difficile infections, and bacterial resistance.17

Mechanism of action

Amoxicillin competitively inhibits penicillin-binding protein 1 and other high molecular weight penicillin binding proteins.9,10 Penicillin bind proteins are responsible for glycosyltransferase and transpeptidase reactions that lead to cross-linking of D-alanine and D-aspartic acid in bacterial cell walls.10 Without the action of penicillin binding proteins, bacteria upregulate autolytic enzymes and are unable to build and repair the cell wall, leading to bacteriocidal action.5,10

TargetActionsOrganism
UPenicillin binding protein
inhibitor
Helicobacter pylori
Absorption

Amoxicillin is approximately 60% bioavailable.8 A 250mg dose of oral amoxicillin reaches a Cmax 3.93±1.13mg/L with a Tmax 1.31±0.33h and an AUC of 27.29±4.72mg*h/L.4 A 875mg dose of oral amoxicillin reaches a Cmax 11.21±3.42mg/L with a Tmax 1.52±0.40h and an AUC of 55.04±12.68mg*h/L.4

Volume of distribution

The central volume of distribution of amoxicillin is 27.7L.4

Protein binding

Amoxicillin is 17% protein bound in serum.3

Metabolism

Incubation with human liver microsomes has lead to the detection of 7 metabolites.1 The M1 metabolite has undergone hydroxylation, M2 has undergone oxidative deamination, M3 to M5 have undergone oxidation of the aliphatic chain, M6 has undergone decarboxylation, and M7 has undergone glucuronidation.1

Hover over products below to view reaction partners

Route of elimination

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

Half-life

The half life of amoxicillin is 61.3 minutes.8

Clearance

The mean clearance of amoxicillin is 21.3L/h.4

Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More
Toxicity

Patients experiencing an overdose may present with hematuria, oliguria, abdominal pain, acute renal failure, vomiting, diarrhea, rash, hyperactivity, and drowsiness.7,14 Treat overdose with symptomatic and supportive treatment, which may include emesis or hemodialysis.14

Affected organisms
  • Enteric bacteria and other eubacteria
  • Gram negative and gram positive bacteria
  • Streptococcus pyogenes
  • Streptococcus pneumoniae
  • Borrelia burgdorferi
  • Chlamydia pneumoniae
  • Salmonella typhi
  • Chlamydia psittaci
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirAbacavir may decrease the excretion rate of Amoxicillin which could result in a higher serum level.
AcarboseAcarbose may decrease the excretion rate of Amoxicillin which could result in a higher serum level.
AceclofenacAceclofenac may decrease the excretion rate of Amoxicillin which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Amoxicillin which could result in a higher serum level.
AcenocoumarolAmoxicillin may increase the anticoagulant activities of Acenocoumarol.
AcetaminophenAcetaminophen may decrease the excretion rate of Amoxicillin which could result in a higher serum level.
AcetazolamideAcetazolamide may increase the excretion rate of Amoxicillin which could result in a lower serum level and potentially a reduction in efficacy.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Amoxicillin which could result in a higher serum level.
AclidiniumAmoxicillin may decrease the excretion rate of Aclidinium which could result in a higher serum level.
AcrivastineAmoxicillin may decrease the excretion rate of Acrivastine which could result in a higher serum level.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

    Learn more
  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

    Learn more
  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

    Learn more
  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

    Learn more
Food Interactions
  • Take with food.

Products

Product Ingredients
IngredientUNIICASInChI Key
Amoxicillin sodium544Y3D6MYH34642-77-8BYHDFCISJXIVBV-YWUHCJSESA-M
Amoxycillin trihydrate804826J2HU61336-70-7MQXQVCLAUDMCEF-CWLIKTDRSA-N
Product Images
International/Other Brands
Actimoxi / Amoclen / Amolin / Amopen / Amopenixin / Amoxibiotic / AMPC / Apo-Amoxi / Clamoxyl / Efpenix / Flemoxin / Hiconcil / Ibiamox / Imacillin / Larotid (Roche) / Moxacin / Moxal / Ospamox / Pamoxicillin / Polymox / Trimox / Wymox
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Amox 250 Cap 250mgCapsuleOralJaapharm Canada Inc.1991-12-312002-04-02Canada flag
Amox 500 Cap 500mgCapsuleOralJaapharm Canada Inc.1991-12-312002-04-02Canada flag
Amox S 125 Sus 125mg/5mlSuspensionOralJaapharm Canada Inc.1991-12-312002-04-02Canada flag
Amox S 250 Sus 250mg/5mlSuspensionOralJaapharm Canada Inc.1991-12-312002-04-02Canada flag
AmoxicillinTablet, chewable125 mg/1OralRanbaxy Pharmaceutical Inc.2008-05-19Not applicableUS flag
AmoxicillinCapsule500 mgOralBgp Pharma UlcNot applicableNot applicableCanada flag
AmoxicillinGranule, for suspension125 mgOralSanis Health Inc2010-07-282017-07-31Canada flag
AmoxicillinTablet, film coated500 mg/1OralRanbaxy Pharmaceutical Inc.2008-05-19Not applicableUS flag
AmoxicillinTablet, film coated875 mg/1OralUnit Dose Services1978-07-10Not applicableUS flag50436 454320180907 15195 1wya70k
AmoxicillinGranule, for suspension250 mgOralSivem Pharmaceuticals Ulc2013-02-14Not applicableCanada flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

    Learn more
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Ag-amoxicillinCapsuleOralAngita Pharma Inc.2018-09-06Not applicableCanada flag
Ag-amoxicillinCapsuleOralAngita Pharma Inc.2018-09-06Not applicableCanada flag
AmoxicillanTablet500 mg/1OralNorthwind Pharmaceuticals2014-07-18Not applicableUS flag
AmoxicillanCapsule500 mg/1OralNorthwind Pharmaceuticals2014-06-01Not applicableUS flag67253 0141 50 nlmimage10 e215711b
AmoxicillinTablet, film coated875 mg/1OralProficient Rx LP2005-07-13Not applicableUS flag
AmoxicillinPowder, for suspension400 mg/5mLOralNucare Pharmaceuticals,inc.2006-06-19Not applicableUS flag
AmoxicillinCapsule500 mg/1OralA-S Medication Solutions2012-01-122016-09-30US flag
AmoxicillinTablet, film coated875 mg/1OralREMEDYREPACK INC.2018-04-242018-09-04US flag
AmoxicillinPowder, for suspension125 mg/5mLOralRebel Distributors2010-02-01Not applicableUS flag
AmoxicillinPowder, for suspension400 mg/5mLOralProficient Rx LP2006-12-28Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

    Learn more
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Amoxi-clavAmoxicillin (875 mg) + Clavulanate potassium (125 mg)TabletOralPro Doc Limitee2009-10-082018-04-26Canada flag
Amoxi-clavAmoxicillin (500 mg) + Clavulanate potassium (125 mg)TabletOralPro Doc Limitee2009-10-082018-01-23Canada flag
Amoxicillan and clavulanate potassiumAmoxycillin trihydrate (500 mg/1) + Clavulanate potassium (125 mg/1)Tablet, film coatedOralNorthwind Pharmaceuticals2014-07-18Not applicableUS flag
AmoxicillinAmoxycillin trihydrate (600 mg/5mL) + Clavulanate potassium (42.9 mg/5mL)Powder, for suspensionOralProficient Rx LP2006-06-19Not applicableUS flag
Amoxicillin and Calvulanate PotassiumAmoxycillin trihydrate (500 mg/1) + Clavulanate potassium (125 mg/1)TabletOralAmerincan Health Packaging2009-12-112010-05-31US flag
Amoxicillin and Calvulanate PotassiumAmoxycillin trihydrate (875 mg/1) + Clavulanate potassium (125 mg/1)TabletOralAmerincan Health Packaging2009-12-112010-03-31US flag
Amoxicillin and Clavulanate PotassiumAmoxycillin trihydrate (875 mg/1) + Clavulanate potassium (125 mg/1)Tablet, film coatedOralMicro Labs Limited2017-03-01Not applicableUS flag
Amoxicillin and Clavulanate PotassiumAmoxycillin trihydrate (200 mg/5mL) + Clavulanate potassium (28.5 mg/5mL)Powder, for suspensionOralPreferreed Pharmaceuticals Inc.2018-05-09Not applicableUS flag
Amoxicillin and Clavulanate PotassiumAmoxycillin trihydrate (600 mg/5mL) + Clavulanate potassium (42.9 mg/5mL)SuspensionOralRebel Distributors2007-08-13Not applicableUS flag
Amoxicillin and Clavulanate PotassiumAmoxycillin trihydrate (200 mg/5mL) + Clavulanate potassium (28.5 mg/5mL)Powder, for suspensionOralNorthStar Rx LLC2011-12-20Not applicableUS flag

Categories

ATC Codes
A02BD12 — Rabeprazole, amoxicillin and clarithromycinA02BD14 — Vonoprazan, amoxicillin and clarithromycinJ01CR50 — Combinations of penicillinsA02BD04 — Pantoprazole, amoxicillin and clarithromycinA02BD07 — Lansoprazole, amoxicillin and clarithromycinA02BD13 — Rabeprazole, amoxicillin and metronidazoleA02BD10 — Lansoprazole, amoxicillin and levofloxacinA02BD05 — Omeprazole, amoxicillin and clarithromycinA02BD03 — Lansoprazole, amoxicillin and metronidazoleA02BD01 — Omeprazole, amoxicillin and metronidazoleA02BD15 — Vonoprazan, amoxicillin and metronidazoleA02BD06 — Esomeprazole, amoxicillin and clarithromycinJ01CA04 — AmoxicillinA02BD11 — Pantoprazole, amoxicillin, clarithromycin and metronidazole
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as penicillins. These are organic compounds containing the penicillin core structure, which is structurally characterized by a penam ring bearing two methyl groups at position 2, and an amide group at position 6 [starting from the sulfur atom at position 1].
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Lactams
Sub Class
Beta lactams
Direct Parent
Penicillins
Alternative Parents
N-acyl-alpha amino acids and derivatives / Alpha amino acid amides / Phenylacetamides / 1-hydroxy-2-unsubstituted benzenoids / Aralkylamines / Thiazolidines / Tertiary carboxylic acid amides / Secondary carboxylic acid amides / Amino acids / Azetidines
show 10 more
Substituents
1-hydroxy-2-unsubstituted benzenoid / Alpha-amino acid amide / Alpha-amino acid or derivatives / Amine / Amino acid / Amino acid or derivatives / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Azetidine
show 26 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
penicillin (CHEBI:2676)

Chemical Identifiers

UNII
9EM05410Q9
CAS number
26787-78-0
InChI Key
LSQZJLSUYDQPKJ-NJBDSQKTSA-N
InChI
InChI=1S/C16H19N3O5S/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/h3-6,9-11,14,20H,17H2,1-2H3,(H,18,21)(H,23,24)/t9-,10-,11+,14-/m1/s1
IUPAC Name
(2S,5R,6R)-6-[(2R)-2-amino-2-(4-hydroxyphenyl)acetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
SMILES
[H][[email protected]]12SC(C)(C)[[email protected]@H](N1C(=O)[[email protected]]2NC(=O)[[email protected]](N)C1=CC=C(O)C=C1)C(O)=O

References

Synthesis Reference

Joan Cabre, Jose Diago, Asuncion Esteve, Johannes Ludescher, "Production of a crystalline salt of amoxicillin." U.S. Patent US6103897, issued April, 1971.

US6103897
General References
  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. 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. 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. 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. Akhavan BJ, Vijhani P: Amoxicillin . [PubMed:29489203]
  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. 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. 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. 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. 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. FDA Approved Drug Products: Talicia Amoxicillin, Omeprazole, and Rifabutin Oral Delayed Release Capsules [Link]
  12. FDA Approved Drug Products: Amoxil Amoxicillin Oral Capsules (Discontinued) [Link]
  13. FDA Approved Drug Products: Omeclamox-Pak Oral Capsules and Tablets [Link]
  14. FDA Approved Drug Products: Augmentin XR Amoxicillin and Clavulanate Oral Extended Release Tablets [Link]
  15. FDA Approved Drug Products: Augmentin Amoxicillin and Clavulanate Oral Tablets and Suspension [Link]
  16. FDA Approved Drug Products: Amoxicillin and Clavulanate Oral Suspension [Link]
  17. FDA Approved Drug Products: Amoxicillin Oral Suspension [Link]
  18. FDA Approved Drug Products: Amoxicillin Oral Tablets [Link]
Human Metabolome Database
HMDB0015193
KEGG Drug
D07452
KEGG Compound
C06827
PubChem Compound
33613
PubChem Substance
46507578
ChemSpider
31006
BindingDB
50350464
RxNav
1297882
ChEBI
2676
ChEMBL
CHEMBL1082
ZINC
ZINC000003830215
Therapeutic Targets Database
DAP000443
PharmGKB
PA448406
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Amoxicillin
AHFS Codes
  • 08:12.16.08 — Aminopenicillins
FDA label
Download (49.6 KB)
MSDS
Download (38.1 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingPreventionBacterial Infection Due to Helicobacter Pylori (H. Pylori) / Obesity, Morbid1
4Active Not RecruitingTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)1
4Active Not RecruitingTreatmentExacerbation of Ulcerative Colitis / Granulomatous Colitis / Ulcerative Colitis, Active Severe1
4Active Not RecruitingTreatmentPeriodontitis, Chronic1
4Active Not RecruitingTreatmentPneumonia3
4CompletedNot AvailableHealthy Volunteers2
4CompletedBasic ScienceBioequivalence of Amoxicillin1
4CompletedBasic ScienceMicrobial Colonization1
4CompletedHealth Services ResearchAntibiotic Resistant Bacteria1
4CompletedPreventionFever / Pneumonia1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Altura Pharmaceuticals Inc.
  • American Antibiotics LLC
  • Apotheca Inc.
  • A-S Medication Solutions LLC
  • Aurobindo Pharma Ltd.
  • Blenheim Pharmacal
  • Bristol-Myers Squibb Co.
  • Bryant Ranch Prepack
  • C.O. Truxton Inc.
  • Cardinal Health
  • Carlisle Laboratories Inc.
  • Casa De Amigos Pharmacy
  • Clonmel Healthcare Ltd.
  • Comprehensive Consultant Services Inc.
  • Darby Dental Supply Co. Inc.
  • DAVA Pharmaceuticals
  • Dept Health Central Pharmacy
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • DNA Pharmaceuticals
  • E.R. Squibb and Sons LLC
  • GlaxoSmithKline Inc.
  • Golden State Medical Supply Inc.
  • Greenstone LLC
  • H.J. Harkins Co. Inc.
  • Hikma Pharmaceuticals
  • Innoviant Pharmacy Inc.
  • International Ethical Labs Inc.
  • Keltman Pharmaceuticals Inc.
  • Laboratorios Atral Sarl
  • Lake Erie Medical and Surgical Supply
  • Liberty Pharmaceuticals
  • Major Pharmaceuticals
  • Medpharm Inc.
  • Medvantx Inc.
  • Middlebrook Pharmaceuticals
  • Mississippi State Dept Health
  • Murfreesboro Pharmaceutical Nursing Supply
  • Novopharm Ltd.
  • Nucare Pharmaceuticals Inc.
  • Okasa Pvt Ltd.
  • Palmetto Pharmaceuticals Inc.
  • Par Pharmaceuticals
  • Patient First Corp.
  • PCA LLC
  • PD-Rx Pharmaceuticals Inc.
  • Pharmedix
  • Physicians Total Care Inc.
  • Poli Industria Chimica SPA
  • Preferred Pharmaceuticals Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Prescription Dispensing Service Inc.
  • Putney Inc.
  • Qualitest
  • Ranbaxy Laboratories
  • Rebel Distributors Corp.
  • Redpharm Drug
  • Reid Provident Laboratories Inc.
  • Sandhills Packaging Inc.
  • Sandoz
  • Signal Health Ltd.
  • Southwood Pharmaceuticals
  • St Mary's Medical Park Pharmacy
  • Stat Rx Usa
  • Stat Scripts LLC
  • Talbert Medical Management Corp.
  • Teva Pharmaceutical Industries Ltd.
  • Tya Pharmaceuticals
  • UDL Laboratories
  • Veratex Corp.
  • West-Ward Pharmaceuticals
Dosage Forms
FormRouteStrength
Powder, for suspensionOral12 g
Tablet1 gr
SuspensionOral125 mg/5mL
Injection, powder, for solutionIntramuscular; Intravenous250 mg
Injection, powder, for solutionIntramuscular; Intravenous500 mg
Tablet500 mg
Tablet, coatedOral250 mg
Tablet, film coatedOral875 mg
InjectionIntravenous1000 mg
Powder, for suspensionOral400 mg
SuspensionOral600 mg
Tablet, orally disintegratingOral875 mg
Tablet, orally disintegratingOral500 mg
Suspension125 mg/5ml
Suspension250 mg/5ml
Tablet, orally disintegratingOral1 G
Capsule500 MG
TabletOral100 MG
GranuleOral
GranuleOral250 mg
PowderParenteral500 mg
Tablet100 mg
TabletOral
TabletOral750 mg
SuspensionOral250 mg/5ml
Powder, for suspensionOral57 mg
Powder, for suspensionOral8.2397 g
Capsule, coatedOral574 mg
Tablet, coatedOral125 mg
Tablet, coatedOral500 mg
Powder, for suspensionOral2.5 g
Powder, for suspensionOral5 g
TabletOral500 mg/1
CapsuleOral250 mg/1
CapsuleOral500 mg/1
For suspensionOral125 mg/5mL
For suspensionOral25 mg/1mL
For suspensionOral50 mg/1mL
Granule, for suspensionOral125 mg
Granule, for suspensionOral250 mg
Powder, for suspensionOral125 mg/5mL
Powder, for suspensionOral200 mg/5mL
Powder, for suspensionOral250 mg/5mL
Powder, for suspensionOral400 mg/5mL
SuspensionOral200 mg/5mL
SuspensionOral400 mg/5mL
TabletOral250 mg/1
TabletOral875 mg/1
Tablet, chewableOral125 mg/1
Tablet, chewableOral200 mg/1
Tablet, chewableOral250 mg
Tablet, chewableOral250 mg/1
Tablet, chewableOral400 mg/1
Tablet, coatedOral875 mg/1
Tablet, film coatedOral500 mg/1
Tablet, film coatedOral875 mg/1
Tablet, for suspensionOral200 mg/1
Tablet, for suspensionOral400 mg/1
Powder, for suspensionOral500 mg/5ml
Tablet, film coatedOral1000 MG
Tablet, film coatedOral500 MG
PowderParenteral50 mg/mL
Powder, for suspensionOral
SuspensionOral
Tablet, chewableOral
Tablet, film coatedOral
Tablet, multilayer, extended releaseOral
Tablet, film coatedOral750 MG
Tablet1000 MG
Powder, for suspensionOral
PowderParenteral500 MG/5ML
PowderParenteral125 mg
PowderParenteral250 mg
Tablet, film coatedOral250 MG
GranuleOral250 MG/5ML
GranuleOral500 MG/5ML
Injection, powder, for solution
Powder, for solutionIntravenous
Tablet, solubleOral1 G
Injection, powder, for solutionIntravenous; Parenteral1000 MG
Injection, powder, for solutionIntravenous; Parenteral2000 MG
Powder, for suspensionOral500 MG/10ML
Granule, for suspensionOral1 G
SuspensionOral5 %
Powder, for suspensionOral5 G/100ML
Granule1 G
Granule, for suspensionOral5 %
Tablet, for suspensionOral1000 MG
Tablet, for suspensionOral500 MG
CapsuleOral375 mg
Injection, powder, for solution1000 MG/5ML
Syrup60 ML
TabletOral1000 MG
TabletOral125 mg
Powder, for suspensionOral80 MG/ML
Granule, for suspensionOral875 MG
Granule, for suspensionOral3.75 %
Powder, for suspensionOral5 %
Tablet, coatedOral1000 MG
Tablet1 G
Injection, powder, for solutionParenteral1 G
Injection, powder, for solutionParenteral500 MG
Tablet, film coatedOral800 mg
TabletOral1 g
Powder, for suspensionOral10 g
Tablet, film coatedOral1006.205 mg
Powder, for suspensionOral15 g
Powder, for suspensionOral1.14 g
PowderParenteral100 mg/mL
Powder, for suspensionOral50 mg/1mL
Powder, for solutionOral
Powder, for solutionOral250 mg/5ml
CapsuleOral500 mg
Powder, for solutionOral500 mg/5ml
Tablet125 mg
Capsule250 MG
Solution / drops; suspension / drops
Tablet, solubleOral
Tablet250 mg
Tablet, film coatedOral
SuspensionOral250 mg/100ml
Injection, powder, for solutionIntravenous2 g
Injection, powder, for solutionIntravenous2000 MG
Injection, powder, for solutionIntravenous500 MG/10ML
Powder, for suspensionOral875 MG
TabletOral
PowderOral400 mg
SuspensionOral200 mg
SuspensionOral400 mg
Powder, for suspensionOral600 mg/5mL
Tablet, extended releaseOral1 g
Tablet, film coated500 mg
Tablet, film coated, extended releaseOral
Powder, for suspensionOral5.739 g
Tablet
Syrup
Granule
Suspension250 mg
TabletOral500 mg
Powder, for suspensionOral8 g
Capsule
Injection, powder, for solution1 g
Injection, powder, for solutionIntravenous1000 MG/120ML
Powder, for solutionIntravenous2000 MG
PowderIntravenous1 g
Tablet875 mg
Tablet, film coated875 mg
Tablet, film coatedOral125 mg
Powder, for suspensionOral600 mg
Tablet, solubleOral200 mg/1
Tablet, solubleOral400 mg/1
Tablet, solubleOral600 mg/1
Suspension
Powder, for suspensionOral50 g
TabletOral370 mg
Injection
Capsule; capsule, delayed release; kit; tabletOral
PowderParenteral750 mg
SuspensionOral125 mg
SuspensionOral250 mg
Powder, for suspensionOral200 mg
SuspensionOral500 mg
Injection1 g
Suspension125 mg
InjectionIntramuscular; Intravenous500 mg
PowderOral600 mg
Tablet, extended releaseOral775 mg/1
Tablet, film coated, extended releaseOral775 mg/1
Injection, powder, for solution500 mg
CapsuleOral
InjectionIntramuscular; Intravenous1 gr
TabletOral875 mg
Granule, for suspensionOral
Tablet, chewableOral
Injection, solution200 mg/1mL
Tablet400 mg
PowderOral5 %
Tablet, solubleOral1000 mg
CapsuleOral250 mg
Tablet, solubleOral250 mg
Tablet, solubleOral500 mg
Tablet, solubleOral750 mg
Powder, for solutionOral
KitOral
InjectionIntramuscular1 g
InjectionIntramuscular250 mg
InjectionIntramuscular500 mg
PowderOral
Powder; syrupOral250 mg/5mL
Powder, for suspensionOral250 mg
Powder, for suspensionOral11.482 g
CapsuleOral150 MG
Granule, for suspensionOral250 MG/5ML
TabletOral250 MG
TabletOral375 MG
Capsule, coatedOral500 mg
Powder, for suspensionOral80 MG
Tablet, coatedOral875 mg
Injection, powder, for solutionIntravenous1000 mg
Injection, powder, for solutionIntravenous500 mg
Powder
SuspensionOral
Capsule, delayed releaseOral
Tablet, film coated1000 mg
Tablet, chewableOral875 mg
Powder, for suspensionOral20 g
Capsule; tabletOral1000 mg
Granule, for suspensionOral2.5 %
Powder, for suspensionOral250 MG/7ML
Tablet, for suspensionOral1 G
Capsule375 MG
Granule, for suspensionOral250 mg/ml
Granule, for suspensionOral500 mg/ml
Solution / dropsOral10 G/100ML
Solution / dropsOral100 MG/ML
Tablet, soluble1 G
Tablet, soluble500 MG
Prices
Unit descriptionCostUnit
Amoxil 400 mg/5ml Suspension 100ml Bottle19.99USD bottle
Amoxil 400 mg/5ml Suspension 75ml Bottle17.99USD bottle
Amoxicillin 400 mg/5ml Suspension 100ml Bottle16.99USD bottle
Amoxil 400 mg/5ml Suspension 50ml Bottle15.99USD bottle
Amoxicillin 250 mg/5ml Suspension 150ml Bottle14.0USD bottle
Amoxil 50 mg/ml Suspension 30ml Bottle13.99USD bottle
Amoxil 250 mg/5ml Suspension 100ml Bottle12.99USD bottle
Amoxil 250 mg/5ml Suspension 150ml Bottle12.99USD bottle
Amoxil 200 mg/5ml Suspension 100ml Bottle11.99USD bottle
Trimox 125 mg/5ml Suspension 100ml Bottle11.99USD bottle
Trimox 125 mg/5ml Suspension 150ml Bottle11.99USD bottle
Trimox 250 mg/5ml Suspension 80ml Bottle11.99USD bottle
Amoxil 875 mg tablet1.13USD tablet
Amoxil 400 mg Chew Tabs1.05USD tab
Amoxicillin 875 mg tablet0.89USD tablet
Amoxil 500 mg tablet0.77USD tablet
Novamoxin 250 mg Chewable Tablet0.64USD tablet
Amoxicillin 125 mg Chew Tabs0.57USD tab
Amoxil 500 mg capsule0.53USD capsule
Amoxicillin 500 mg tablet0.5USD tablet
Amoxicillin 250 mg Chew Tabs0.47USD tab
Amoxicillin 500 mg capsule0.47USD capsule
Novamoxin 125 mg Chewable Tablet0.44USD tablet
Apo-Amoxi 500 mg Capsule0.36USD capsule
Mylan-Amoxillin 500 mg Capsule0.36USD capsule
Novamoxin 500 mg Capsule0.36USD capsule
Nu-Amoxi 500 mg Capsule0.36USD capsule
Pms-Amoxicillin 500 mg Capsule0.36USD capsule
Amoxicillin 250 mg capsule0.25USD capsule
Apo-Amoxi 250 mg Capsule0.18USD capsule
Mylan-Amoxillin 250 mg Capsule0.18USD capsule
Novamoxin 250 mg Capsule0.18USD capsule
Nu-Amoxi 250 mg Capsule0.18USD capsule
Pms-Amoxicillin 250 mg Capsule0.18USD capsule
Apo-Amoxi 50 mg/ml Suspension0.06USD ml
Novamoxin 50 mg/ml Suspension0.06USD ml
Novamoxin Sugar-Reduced 50 mg/ml Suspension0.06USD ml
Nu-Amoxi 50 mg/ml Suspension0.06USD ml
Pms-Amoxicillin 50 mg/ml Suspension0.06USD ml
Apo-Amoxi 25 mg/ml Suspension0.04USD ml
Novamoxin 25 mg/ml Suspension0.04USD ml
Novamoxin Sugar-Reduced 25 mg/ml Suspension0.04USD ml
Nu-Amoxi 25 mg/ml Suspension0.04USD ml
Pms-Amoxicillin 25 mg/ml Suspension0.04USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US6544555No2003-04-082020-10-13US flag
US6669948No2003-12-302020-10-13US flag
US6723341No2004-04-202020-10-13US flag
US8299052No2012-10-302027-05-07US flag
US8778924No2014-07-152026-12-08US flag
US8357394No2013-01-222026-12-08US flag
US6878386No2005-04-122020-04-04US flag
US7217430No2007-05-152020-04-04US flag
US7250176No2007-07-312020-04-04US flag
US6783773No2004-08-312020-04-04US flag
US6746692No2004-06-082020-04-04US flag
US9603806No2017-03-282034-02-12US flag
US9498445No2016-11-222034-02-12US flag
US9050263No2015-06-092034-02-12US flag
US10238606No2019-03-262034-02-12US flag
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)194 °CChemSpider
boiling point (°C)743.2ChemSpider
logP0.87SANGSTER (1994)
Caco2 permeability-6.1ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility0.958 mg/mLALOGPS
logP0.75ALOGPS
logP-2.3ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)3.23ChemAxon
pKa (Strongest Basic)7.43ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area132.96 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity89.5 m3·mol-1ChemAxon
Polarizability35.53 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.9008
Blood Brain Barrier-0.9967
Caco-2 permeable-0.8722
P-glycoprotein substrateSubstrate0.5741
P-glycoprotein inhibitor INon-inhibitor0.9665
P-glycoprotein inhibitor IINon-inhibitor0.9968
Renal organic cation transporterNon-inhibitor0.9636
CYP450 2C9 substrateNon-substrate0.843
CYP450 2D6 substrateNon-substrate0.8446
CYP450 3A4 substrateNon-substrate0.5478
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.915
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9767
Ames testNon AMES toxic0.9099
CarcinogenicityNon-carcinogens0.5439
BiodegradationNot ready biodegradable0.9606
Rat acute toxicity1.7036 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9996
hERG inhibition (predictor II)Non-inhibitor0.8761
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-00di-0190000000-febb22de5b7f210e4a46
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-056u-4960000000-f3c347843d63d99418c5
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0036-8900000000-eca01f197da058161684
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-007o-9800000000-cec182c5a522a2979385
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-00ec-9700000000-dc767a962e9f2608b083
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-00dl-9600000000-b831842a45369bb2b48c
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-06r2-0589000000-9c90c12d4fbef3a04a14
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-0910000000-e26fa392674b2a230233
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-1900000000-9e60140bfff56767dbec
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-1900000000-f3065ce1009dda06cf72
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03e9-2900000000-5516c0723837b4149a68
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-06s9-5900000000-cd377b53cefaa4b23c6f
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03xs-0859000000-8225987d1a20c14acc00

Targets

Kind
Protein
Organism
Helicobacter pylori
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Not Available
Specific Function
Penicillin binding
Gene Name
PBP1
Uniprot ID
Q8L103
Uniprot Name
Penicillin binding protein
Molecular Weight
74084.53 Da
References
  1. 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]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Curator comments
Amoxicillin inhibition of CYP2C8 is not expected to be clinically significant.
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Niwa T, Morimoto M, Hirai T, Hata T, Hayashi M, Imagawa Y: Effect of penicillin-based antibiotics, amoxicillin, ampicillin, and piperacillin, on drug-metabolizing activities of human hepatic cytochromes P450. J Toxicol Sci. 2016 Feb;41(1):143-6. doi: 10.2131/jts.41.143. [PubMed:26763401]
Kind
Protein
Organism
Bacillus cereus
Pharmacological action
Unknown
Actions
Substrate
General Function
Zinc ion binding
Specific Function
Can hydrolyze carbapenem compounds.
Gene Name
blm
Uniprot ID
P04190
Uniprot Name
Beta-lactamase 2
Molecular Weight
28092.24 Da
References
  1. FDA Approved Drug Products: Talicia Amoxicillin, Omeprazole, and Rifabutin Oral Delayed Release Capsules [Link]
  2. FDA Approved Drug Products: Augmentin XR Amoxicillin and Clavulanate Oral Extended Release Tablets [Link]
  3. FDA Approved Drug Products: Augmentin Amoxicillin and Clavulanate Oral Tablets and Suspension [Link]
  4. FDA Approved Drug Products: Amoxicillin and Clavulanate Oral Suspension [Link]
  5. FDA Approved Drug Products: Amoxicillin Oral Suspension [Link]
  6. FDA Approved Drug Products: Amoxicillin Oral Tablets [Link]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Garzon D, Ariza A, Regazzoni L, Clerici R, Altomare A, Sirtori FR, Carini M, Torres MJ, Perez-Sala D, Aldini G: Mass spectrometric strategies for the identification and characterization of human serum albumin covalently adducted by amoxicillin: ex vivo studies. Chem Res Toxicol. 2014 Sep 15;27(9):1566-74. doi: 10.1021/tx500210e. Epub 2014 Aug 13. [PubMed:25088930]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Proton-dependent oligopeptide secondary active transmembrane transporter activity
Specific Function
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products.
Gene Name
SLC15A1
Uniprot ID
P46059
Uniprot Name
Solute carrier family 15 member 1
Molecular Weight
78805.265 Da
References
  1. Wenzel U, Gebert I, Weintraut H, Weber WM, Clauss W, Daniel H: Transport characteristics of differently charged cephalosporin antibiotics in oocytes expressing the cloned intestinal peptide transporter PepT1 and in human intestinal Caco-2 cells. J Pharmacol Exp Ther. 1996 May;277(2):831-9. [PubMed:8627565]
  2. Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [PubMed:15567297]
  3. Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. [PubMed:9374833]
  4. Sala-Rabanal M, Loo DD, Hirayama BA, Turk E, Wright EM: Molecular interactions between dipeptides, drugs and the human intestinal H+ -oligopeptide cotransporter hPEPT1. J Physiol. 2006 Jul 1;574(Pt 1):149-66. Epub 2006 Apr 20. [PubMed:16627568]
  5. 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]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Peptide:proton symporter activity
Specific Function
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides.
Gene Name
SLC15A2
Uniprot ID
Q16348
Uniprot Name
Solute carrier family 15 member 2
Molecular Weight
81782.77 Da
References
  1. Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. [PubMed:9374833]
  2. Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [PubMed:15567297]
  3. 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]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
Gene Name
SLC22A6
Uniprot ID
Q4U2R8
Uniprot Name
Solute carrier family 22 member 6
Molecular Weight
61815.78 Da
References
  1. Jariyawat S, Sekine T, Takeda M, Apiwattanakul N, Kanai Y, Sophasan S, Endou H: The interaction and transport of beta-lactam antibiotics with the cloned rat renal organic anion transporter 1. J Pharmacol Exp Ther. 1999 Aug;290(2):672-7. [PubMed:10411577]
  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]

Drug created on June 13, 2005 07:24 / Updated on October 25, 2020 09:16

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