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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
Structure for Amoxicillin (DB01060)
- 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
- Acute Bacterial Sinusitis (ABS)
- Acute Otitis Media
- Acute Otitis Media (AOM)
- Bacterial Infection Due to Helicobacter Pylori (H. Pylori)
- Bacterial Infections
- Community Acquired Pneumonia (CAP)
- Duodenal ulcer caused by helicobacter pylori
- Genitourinary infections
- Lower Respiratory Tract Infection (LRTI)
- Sinusitis
- Urinary Tract Infection
- Acute, uncomplicated Gonorrhea
- Bacterial skin and skin structure infections
- Ear, nose, and throat infections
- 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
Target Actions Organism UPenicillin binding protein inhibitorHelicobacter 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.
Drug Interaction Unlock Additional DataAbacavir 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. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
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
Ingredient UNII CAS InChI Key Amoxicillin sodium 544Y3D6MYH 34642-77-8 BYHDFCISJXIVBV-YWUHCJSESA-M Amoxycillin trihydrate 804826J2HU 61336-70-7 MQXQVCLAUDMCEF-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
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataAmox 250 Cap 250mg Capsule Oral Jaapharm Canada Inc. 1991-12-31 2002-04-02 Canada 
Amox 500 Cap 500mg Capsule Oral Jaapharm Canada Inc. 1991-12-31 2002-04-02 Canada Amox S 125 Sus 125mg/5ml Suspension Oral Jaapharm Canada Inc. 1991-12-31 2002-04-02 Canada Amox S 250 Sus 250mg/5ml Suspension Oral Jaapharm Canada Inc. 1991-12-31 2002-04-02 Canada Amoxicillin Powder, for suspension 200 mg/5mL Oral Clinical Solutions Wholsesale 1999-04-15 Not applicable US 
Amoxicillin Tablet, film coated 875 mg/1 Oral Ranbaxy Pharmaceutical Inc. 2008-05-19 Not applicable US Amoxicillin Tablet, film coated 875 mg/1 Oral Ready Meds 1978-07-10 Not applicable US 
Amoxicillin Capsule 250 mg/1 Oral Ranbaxy Pharmaceutical Inc. 2008-05-19 Not applicable US Amoxicillin Powder, for suspension 250 mg/5mL Oral Sandoz Inc. 2007-11-14 2007-11-14 US Amoxicillin Capsule 500 mg Oral Sanis Health Inc 2010-07-28 Not applicable Canada Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataAg-amoxicillin Capsule Oral Angita Pharma Inc. 2018-09-06 Not applicable Canada Ag-amoxicillin Capsule Oral Angita Pharma Inc. 2018-09-06 Not applicable Canada Amoxicillan Tablet 500 mg/1 Oral Northwind Pharmaceuticals 2014-07-18 Not applicable US Amoxicillan Capsule 500 mg/1 Oral Northwind Pharmaceuticals 2014-06-01 Not applicable US 
Amoxicillin Tablet, film coated 500 mg/1 Oral Denton Pharma, Inc. Dba Northwind Pharmaceuticals 2018-08-02 Not applicable US Amoxicillin Tablet, film coated 875 mg/1 Oral A-S Medication Solutions 2000-09-26 Not applicable US Amoxicillin Powder, for suspension 250 mg/5mL Oral A-S Medication Solutions 1990-09-30 2017-09-30 US Amoxicillin Capsule 500 mg/1 Oral QPharma Inc 2005-11-09 Not applicable US Amoxicillin Tablet, film coated 500 mg/1 Oral A S Medication Solutions 2005-07-13 Not applicable US Amoxicillin Tablet, chewable 250 mg/1 Oral Denton Pharma, Inc. Dba Northwind Pharmaceuticals 2018-06-25 Not applicable US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Amoxi-clav Amoxicillin (875 mg) + Clavulanate potassium (125 mg) Tablet Oral Pro Doc Limitee 2009-10-08 2018-04-26 Canada Amoxi-clav Amoxicillin (500 mg) + Clavulanate potassium (125 mg) Tablet Oral Pro Doc Limitee 2009-10-08 2018-01-23 Canada Amoxicillan and clavulanate potassium Amoxycillin trihydrate (500 mg/1) + Clavulanate potassium (125 mg/1) Tablet, film coated Oral Northwind Pharmaceuticals 2014-07-18 Not applicable US Amoxicillin Amoxycillin trihydrate (600 mg/5mL) + Clavulanate potassium (42.9 mg/5mL) Powder, for suspension Oral Proficient Rx LP 2006-06-19 Not applicable US Amoxicillin and Calvulanate Potassium Amoxycillin trihydrate (500 mg/1) + Clavulanate potassium (125 mg/1) Tablet Oral Amerincan Health Packaging 2009-12-11 2010-05-31 US Amoxicillin and Calvulanate Potassium Amoxycillin trihydrate (875 mg/1) + Clavulanate potassium (125 mg/1) Tablet Oral Amerincan Health Packaging 2009-12-11 2010-03-31 US Amoxicillin and Clavulanate Potassium Amoxycillin trihydrate (600 mg/5mL) + Clavulanate potassium (42.9 mg/5mL) Powder, for suspension Oral A-S Medication Solutions 2004-09-23 2019-07-31 US Amoxicillin and Clavulanate Potassium Amoxycillin trihydrate (875 mg/1) + Clavulanate potassium (125 mg/1) Tablet, film coated Oral NorthStar Rx LLC 2012-01-20 Not applicable US 
Amoxicillin and Clavulanate Potassium Amoxycillin trihydrate (400 mg/5mL) + Clavulanic acid (57 mg/5mL) Powder, for suspension Oral A S Medication Solutions 2007-12-01 Not applicable US Amoxicillin and Clavulanate Potassium Amoxycillin trihydrate (600 mg/5mL) + Clavulanate potassium (42.9 mg/5mL) Powder, for suspension Oral Nucare Pharmaceuticals,inc. 2011-12-20 Not applicable US
Categories
- ATC Codes
- A02BD12 — Rabeprazole, amoxicillin and clarithromycin
- A02BD — Combinations for eradication of Helicobacter pylori
- A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
- A02 — DRUGS FOR ACID RELATED DISORDERS
- A — ALIMENTARY TRACT AND METABOLISM
- A02BD — Combinations for eradication of Helicobacter pylori
- A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
- A02 — DRUGS FOR ACID RELATED DISORDERS
- A — ALIMENTARY TRACT AND METABOLISM
- J01CR — Combinations of penicillins, incl. beta-lactamase inhibitors
- J01C — BETA-LACTAM ANTIBACTERIALS, PENICILLINS
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- A02BD — Combinations for eradication of Helicobacter pylori
- A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
- A02 — DRUGS FOR ACID RELATED DISORDERS
- A — ALIMENTARY TRACT AND METABOLISM
- A02BD — Combinations for eradication of Helicobacter pylori
- A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
- A02 — DRUGS FOR ACID RELATED DISORDERS
- A — ALIMENTARY TRACT AND METABOLISM
- A02BD — Combinations for eradication of Helicobacter pylori
- A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
- A02 — DRUGS FOR ACID RELATED DISORDERS
- A — ALIMENTARY TRACT AND METABOLISM
- A02BD — Combinations for eradication of Helicobacter pylori
- A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
- A02 — DRUGS FOR ACID RELATED DISORDERS
- A — ALIMENTARY TRACT AND METABOLISM
- A02BD — Combinations for eradication of Helicobacter pylori
- A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
- A02 — DRUGS FOR ACID RELATED DISORDERS
- A — ALIMENTARY TRACT AND METABOLISM
- A02BD — Combinations for eradication of Helicobacter pylori
- A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
- A02 — DRUGS FOR ACID RELATED DISORDERS
- A — ALIMENTARY TRACT AND METABOLISM
- A02BD — Combinations for eradication of Helicobacter pylori
- A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
- A02 — DRUGS FOR ACID RELATED DISORDERS
- A — ALIMENTARY TRACT AND METABOLISM
- A02BD — Combinations for eradication of Helicobacter pylori
- A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
- A02 — DRUGS FOR ACID RELATED DISORDERS
- A — ALIMENTARY TRACT AND METABOLISM
- A02BD — Combinations for eradication of Helicobacter pylori
- A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
- A02 — DRUGS FOR ACID RELATED DISORDERS
- A — ALIMENTARY TRACT AND METABOLISM
- J01CA — Penicillins with extended spectrum
- J01C — BETA-LACTAM ANTIBACTERIALS, PENICILLINS
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- Drug Categories
- Alimentary Tract and Metabolism
- Amides
- Aminopenicillins
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antibacterials for Systemic Use
- Antiinfectives for Systemic Use
- Beta-Lactam Antibacterials
- beta-Lactams
- Cytochrome P-450 CYP2C8 Inhibitors
- Cytochrome P-450 CYP2C8 Inhibitors (weak)
- Cytochrome P-450 Enzyme Inhibitors
- Drugs for Acid Related Disorders
- Drugs for Peptic Ulcer and Gastro-Oesophageal Reflux Disease (Gord)
- Drugs that are Mainly Renally Excreted
- Heterocyclic Compounds, Fused-Ring
- Lactams
- OAT1/SLC22A6 inhibitors
- Penicillin G
- Penicillins
- Penicillins With Extended Spectrum
- Sulfur Compounds
- 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
- 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]
- 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]
- 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]
- 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]
- Akhavan BJ, Vijhani P: Amoxicillin . [PubMed:29489203]
- 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]
- 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]
- 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]
- 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]
- 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]
- FDA Approved Drug Products: Talicia Amoxicillin, Omeprazole, and Rifabutin Oral Delayed Release Capsules [Link]
- FDA Approved Drug Products: Amoxil Amoxicillin Oral Capsules (Discontinued) [Link]
- FDA Approved Drug Products: Omeclamox-Pak Oral Capsules and Tablets [Link]
- FDA Approved Drug Products: Augmentin XR Amoxicillin and Clavulanate Oral Extended Release Tablets [Link]
- FDA Approved Drug Products: Augmentin Amoxicillin and Clavulanate Oral Tablets and Suspension [Link]
- FDA Approved Drug Products: Amoxicillin and Clavulanate Oral Suspension [Link]
- FDA Approved Drug Products: Amoxicillin Oral Suspension [Link]
- FDA Approved Drug Products: Amoxicillin Oral Tablets [Link]
- External Links
- Human Metabolome Database
- HMDB0015193
- KEGG Drug
- D07452
- KEGG Compound
- C06827
- PubChem Compound
- 33613
- PubChem Substance
- 46507578
- ChemSpider
- 31006
- BindingDB
- 50350464
- 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
Phase Status Purpose Conditions Count 4 Active Not Recruiting Prevention Antibiotic Prophylaxis / Infection Control 1 4 Active Not Recruiting Prevention Bacterial Infection Due to Helicobacter Pylori (H. Pylori) / Obesity, Morbid 1 4 Active Not Recruiting Treatment Bacterial Infection Due to Helicobacter Pylori (H. Pylori) 1 4 Active Not Recruiting Treatment Exacerbation of Ulcerative Colitis / Granulomatous Colitis / Ulcerative Colitis, Active Severe 1 4 Active Not Recruiting Treatment Helicobacter Pylori Gastrointestinal Tract Infection 1 4 Active Not Recruiting Treatment Periodontitis, Chronic 1 4 Active Not Recruiting Treatment Pneumonia 4 4 Completed Not Available Healthy Volunteers 2 4 Completed Not Available Helicobacter Infections 1 4 Completed Basic Science Bioequivalence of Amoxicillin 1
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
Form Route Strength Powder, for suspension Oral 12 g Tablet 1 gr Suspension Oral 125 mg/5mL Injection, powder, for solution Intramuscular; Intravenous 250 mg Injection, powder, for solution Intramuscular; Intravenous 500 mg Tablet 500 mg Tablet, film coated Oral 875 mg Injection Intravenous 1000 mg Powder, for suspension Oral 400 mg Suspension Oral 600 mg Tablet, orally disintegrating Oral 875 mg Tablet, orally disintegrating Oral 500 mg Suspension 125 mg/5ml Suspension 250 mg/5ml Tablet, orally disintegrating Oral 1 G Capsule 500 MG Granule Oral 250 mg Powder Parenteral 500 mg Tablet 100 mg Tablet Oral 750 mg Suspension Oral 250 mg/5ml Powder, for suspension Oral 57 mg Powder, for suspension Oral 8.2397 g Capsule, coated Oral 574 mg Tablet, coated Oral 125 mg Tablet, coated Oral 500 mg Powder, for suspension Oral 2.5 g Powder, for suspension Oral 5 g Tablet Oral 500 mg/1 Capsule Oral 250 mg Capsule Oral 250 mg/1 Capsule Oral 500 mg/1 Capsule Oral 500 mg For suspension Oral 125 mg/5mL For suspension Oral 25 mg/1mL For suspension Oral 50 mg/1mL Granule, for suspension Oral 125 mg Granule, for suspension Oral 250 mg Powder, for suspension Oral 125 mg/5mL Powder, for suspension Oral 200 mg/5mL Powder, for suspension Oral 250 mg/5mL Powder, for suspension Oral 400 mg/5mL Suspension Oral 200 mg/5mL Suspension Oral 400 mg/5mL Tablet Oral 250 mg/1 Tablet Oral 875 mg/1 Tablet, chewable Oral 125 mg/1 Tablet, chewable Oral 200 mg/1 Tablet, chewable Oral 250 mg Tablet, chewable Oral 250 mg/1 Tablet, chewable Oral 400 mg/1 Tablet, coated Oral 875 mg/1 Tablet, film coated Oral 500 mg/1 Tablet, film coated Oral 875 mg/1 Tablet, for suspension Oral 200 mg/1 Tablet, for suspension Oral 400 mg/1 Tablet, film coated Oral 1000 MG Tablet, film coated Oral 500 MG Powder Parenteral 50 mg/mL Powder, for suspension Oral Suspension Oral Tablet, chewable Oral Tablet, film coated Oral Tablet, multilayer, extended release Oral Tablet, film coated Oral 750 MG Tablet 1000 MG Powder, for suspension Oral Powder Parenteral 500 MG/5ML Powder Parenteral 125 mg Powder Parenteral 250 mg Tablet, film coated Oral 250 MG Granule Oral 250 MG/5ML Granule Oral 500 MG/5ML Powder, for solution Intravenous Tablet, soluble Oral 1 G Powder, for suspension Oral 500 MG/10ML Granule, for suspension Oral 1 G Suspension Oral 5 % Powder, for suspension Oral 5 G/100ML Granule 1 G Granule, for suspension Oral 5 % Tablet, for suspension Oral 1000 MG Tablet, for suspension Oral 500 MG Injection, powder, for solution 1000 MG/5ML Syrup 60 ML Tablet Oral 1000 MG Granule, for suspension Oral 3.75 % Powder, for suspension Oral 5 % Tablet, coated Oral 1000 MG Tablet 1 G Injection, powder, for solution Parenteral 1 G Injection, powder, for solution Parenteral 500 MG Tablet, film coated Oral 800 mg Tablet Oral 1 g Powder, for suspension Oral 10 g Tablet, film coated Oral 1006.205 mg Powder, for suspension Oral 15 g Powder, for suspension Oral 1.14 g Powder Parenteral 100 mg/mL Powder, for suspension Oral 50 mg/1mL Tablet Oral Powder, for solution Oral Capsule 250 MG Suspension Oral 250 mg/100ml Tablet Oral Powder Oral 400 mg Suspension Oral 200 mg Suspension Oral 400 mg Tablet, film coated 500 mg Tablet, film coated, extended release Oral Powder, for suspension Oral 5.739 g Tablet Syrup Granule Suspension 250 mg Tablet Oral 500 mg Powder, for suspension Oral 8 g Powder Intravenous 1 g Tablet 875 mg Tablet, film coated 875 mg Tablet, film coated Oral 125 mg Powder, for suspension Oral 600 mg Tablet, soluble Oral 200 mg/1 Tablet, soluble Oral 400 mg/1 Tablet, soluble Oral 600 mg/1 Suspension Powder, for suspension Oral 50 g Tablet Oral 370 mg Injection Capsule; capsule, delayed release; kit; tablet Oral Powder Parenteral 750 mg Suspension Oral 125 mg Suspension Oral 250 mg Powder, for suspension Oral 200 mg Suspension Oral 500 mg Injection 1 g Suspension 125 mg Injection Intramuscular; Intravenous 500 mg Powder Oral 600 mg Tablet, extended release Oral 775 mg/1 Tablet, film coated, extended release Oral 775 mg/1 Capsule Oral Injection Intramuscular; Intravenous 1 gr Tablet Oral 875 mg Granule, for suspension Oral Tablet, chewable Oral Powder, for solution Oral Kit Oral Injection Intramuscular 1 g Injection Intramuscular 250 mg Injection Intramuscular 500 mg Powder Oral Powder, for suspension Oral 250 mg Powder, for suspension Oral 11.482 g Capsule, coated Oral 500 mg Tablet, coated Oral 875 mg Injection, powder, for solution Intravenous 1000 mg Injection, powder, for solution Intravenous 500 mg Powder Suspension Oral Capsule, delayed release Oral Tablet, film coated 1000 mg Tablet, chewable Oral 875 mg Powder, for suspension Oral 20 g Capsule; tablet Oral 1000 mg Capsule 375 MG Solution / drops Oral 10 G/100ML Solution / drops Oral 100 MG/ML Tablet, soluble 1 G Tablet, soluble 500 MG - Prices
Unit description Cost Unit Amoxil 400 mg/5ml Suspension 100ml Bottle 19.99USD bottle Amoxil 400 mg/5ml Suspension 75ml Bottle 17.99USD bottle Amoxicillin 400 mg/5ml Suspension 100ml Bottle 16.99USD bottle Amoxil 400 mg/5ml Suspension 50ml Bottle 15.99USD bottle Amoxicillin 250 mg/5ml Suspension 150ml Bottle 14.0USD bottle Amoxil 50 mg/ml Suspension 30ml Bottle 13.99USD bottle Amoxil 250 mg/5ml Suspension 100ml Bottle 12.99USD bottle Amoxil 250 mg/5ml Suspension 150ml Bottle 12.99USD bottle Amoxil 200 mg/5ml Suspension 100ml Bottle 11.99USD bottle Trimox 125 mg/5ml Suspension 100ml Bottle 11.99USD bottle Trimox 125 mg/5ml Suspension 150ml Bottle 11.99USD bottle Trimox 250 mg/5ml Suspension 80ml Bottle 11.99USD bottle Amoxil 875 mg tablet 1.13USD tablet Amoxil 400 mg Chew Tabs 1.05USD tab Amoxicillin 875 mg tablet 0.89USD tablet Amoxil 500 mg tablet 0.77USD tablet Novamoxin 250 mg Chewable Tablet 0.64USD tablet Amoxicillin 125 mg Chew Tabs 0.57USD tab Amoxil 500 mg capsule 0.53USD capsule Amoxicillin 500 mg tablet 0.5USD tablet Amoxicillin 250 mg Chew Tabs 0.47USD tab Amoxicillin 500 mg capsule 0.47USD capsule Novamoxin 125 mg Chewable Tablet 0.44USD tablet Apo-Amoxi 500 mg Capsule 0.36USD capsule Mylan-Amoxillin 500 mg Capsule 0.36USD capsule Novamoxin 500 mg Capsule 0.36USD capsule Nu-Amoxi 500 mg Capsule 0.36USD capsule Pms-Amoxicillin 500 mg Capsule 0.36USD capsule Amoxicillin 250 mg capsule 0.25USD capsule Apo-Amoxi 250 mg Capsule 0.18USD capsule Mylan-Amoxillin 250 mg Capsule 0.18USD capsule Novamoxin 250 mg Capsule 0.18USD capsule Nu-Amoxi 250 mg Capsule 0.18USD capsule Pms-Amoxicillin 250 mg Capsule 0.18USD capsule Apo-Amoxi 50 mg/ml Suspension 0.06USD ml Novamoxin 50 mg/ml Suspension 0.06USD ml Novamoxin Sugar-Reduced 50 mg/ml Suspension 0.06USD ml Nu-Amoxi 50 mg/ml Suspension 0.06USD ml Pms-Amoxicillin 50 mg/ml Suspension 0.06USD ml Apo-Amoxi 25 mg/ml Suspension 0.04USD ml Novamoxin 25 mg/ml Suspension 0.04USD ml Novamoxin Sugar-Reduced 25 mg/ml Suspension 0.04USD ml Nu-Amoxi 25 mg/ml Suspension 0.04USD ml Pms-Amoxicillin 25 mg/ml Suspension 0.04USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region Unlock Additional DataUS6544555 No 2003-04-08 2020-10-13 US US6669948 No 2003-12-30 2020-10-13 US US6723341 No 2004-04-20 2020-10-13 US US8299052 No 2012-10-30 2027-05-07 US US8778924 No 2014-07-15 2026-12-08 US US8357394 No 2013-01-22 2026-12-08 US US6878386 No 2005-04-12 2020-04-04 US US7217430 No 2007-05-15 2020-04-04 US US7250176 No 2007-07-31 2020-04-04 US US6783773 No 2004-08-31 2020-04-04 US US6746692 No 2004-06-08 2020-04-04 US US9603806 No 2017-03-28 2034-02-12 US US9498445 No 2016-11-22 2034-02-12 US US9050263 No 2015-06-09 2034-02-12 US US10238606 No 2019-03-26 2034-02-12 US Additional Data Available- Filed On
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 194 °C ChemSpider boiling point (°C) 743.2 ChemSpider logP 0.87 SANGSTER (1994) Caco2 permeability -6.1 ADME Research, USCD - Predicted Properties
Property Value Source Water Solubility 0.958 mg/mL ALOGPS logP 0.75 ALOGPS logP -2.3 ChemAxon logS -2.6 ALOGPS pKa (Strongest Acidic) 3.23 ChemAxon pKa (Strongest Basic) 7.43 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 6 ChemAxon Hydrogen Donor Count 4 ChemAxon Polar Surface Area 132.96 Å2 ChemAxon Rotatable Bond Count 4 ChemAxon Refractivity 89.5 m3·mol-1 ChemAxon Polarizability 35.53 Å3 ChemAxon Number of Rings 3 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.9008 Blood Brain Barrier - 0.9967 Caco-2 permeable - 0.8722 P-glycoprotein substrate Substrate 0.5741 P-glycoprotein inhibitor I Non-inhibitor 0.9665 P-glycoprotein inhibitor II Non-inhibitor 0.9968 Renal organic cation transporter Non-inhibitor 0.9636 CYP450 2C9 substrate Non-substrate 0.843 CYP450 2D6 substrate Non-substrate 0.8446 CYP450 3A4 substrate Non-substrate 0.5478 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.907 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.915 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9767 Ames test Non AMES toxic 0.9099 Carcinogenicity Non-carcinogens 0.5439 Biodegradation Not ready biodegradable 0.9606 Rat acute toxicity 1.7036 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9996 hERG inhibition (predictor II) Non-inhibitor 0.8761
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
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
- 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
- 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
- FDA Approved Drug Products: Talicia Amoxicillin, Omeprazole, and Rifabutin Oral Delayed Release Capsules [Link]
- FDA Approved Drug Products: Augmentin XR Amoxicillin and Clavulanate Oral Extended Release Tablets [Link]
- FDA Approved Drug Products: Augmentin Amoxicillin and Clavulanate Oral Tablets and Suspension [Link]
- FDA Approved Drug Products: Amoxicillin and Clavulanate Oral Suspension [Link]
- FDA Approved Drug Products: Amoxicillin Oral Suspension [Link]
- 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
- 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
- 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]
- 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]
- 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]
- 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]
- 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
- 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]
- 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]
- 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
- 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]
- 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 September 25, 2020 15:13
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