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Identification
Name Amoxicillin
Accession Number DB01060 (APRD00248)
Type small molecule
Groups approved
Description

A broad-spectrum semisynthetic antibiotic similar to ampicillin except that its resistance to gastric acid permits higher serum levels with oral administration. Amoxicillin is commonly prescribed with clauvanic acid (a beta lactamase inhibitor) as it is susceptible to beta-lacatamase degradation. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Amoxicilina [INN-Spanish]
Amoxicillin anhydrous
Amoxicillin Trihydrate
Amoxicilline [INN-French]
Amoxicillinum [INN-Latin]
Amoxycillin
Amoxycillin Trihydrate
D-Amoxicillin
p-Hydroxyampicillin
Salts Not Available
Brand names
Name Company
Actimoxi
Amoclen
Amolin
Amopen
Amopenixin
Amoxi
Amoxi-Mast
Amoxibiotic
Amoxiden
Amoxil
Amoxivet
AMPC
Anemolin
Aspenil
Biomox
Bristamox
Cemoxin
Clamoxyl
Delacillin
Dispermox
Efpenix
Flemoxin
Hiconcil
Histocillin
Ibiamox
Imacillin
Lamoxy
Metafarma capsules
Metifarma capsules
Moxacin
Moxal
Ospamox
Pamoxicillin
Piramox
Polymox
Robamox
Sawamox PM
Sumox
Tolodina
Trimox
Unicillin
Utimox
Vetramox
Wymox
Zimox
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Brand mixtures
Brand Name Ingredients
Augmentin amoxicillin + clavulanic acid
Co-amoxiclav amoxicillin + clavulanic acid
Prevpac amoxicillin + clarithromycin + lansoprazole
Categories
  • Anti-Bacterial Agents
  • Penicillins
CAS number 26787-78-0
Weight Average: 365.404
Monoisotopic: 365.104541423
Chemical Formula C16H19N3O5S
InChI Key InChIKey=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
Plain Text
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][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CC=C(O)C=C1)C(O)=O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Phenols and Derivatives
  • Penicillins
  • Phenethylamines
Substructures
  • Hydroxy Compounds
  • Acetates
  • Phenols and Derivatives
  • Amino Ketones
  • Aliphatic and Aryl Amines
  • Benzene and Derivatives
  • Carboxylic Acids and Derivatives
  • Beta Lactams
  • Penicillins
  • Thiazoles
  • Phenethylamines
  • Heterocyclic compounds
  • Aromatic compounds
  • Carboxamides and Derivatives
  • Lactams
  • Azetidines
  • Thiazolidines
  • Phenyl Esters
Pharmacology
Indication For the treatment of infections of the ear, nose, and throat, the genitourinary tract, the skin and skin structure, and the lower respiratory tract due to susceptible (only b-lactamase-negative) strains of Streptococcus spp. (a- and b-hemolytic strains only), S. pneumoniae, Staphylococcus spp., H. influenzae, E. coli, P. mirabilis, or E. faecalis. Also for the treatment of acute, uncomplicated gonorrhea (ano-genital and urethral infections) due to N. gonorrhoeae (males and females).
Pharmacodynamics Amoxicillin is a moderate-spectrum antibiotic active against a wide range of Gram-positive, and a limited range of Gram-negative organisms. It is usually the drug of choice within the class because it is better absorbed, following oral administration, than other beta-lactam antibiotics. Amoxicillin is susceptible to degradation by β-lactamase-producing bacteria, and so may be given with clavulanic acid to increase its susceptability. The incidence of β-lactamase-producing resistant organisms, including E. coli, appears to be increasing. Amoxicillin is sometimes combined with clavulanic acid, a β-lactamase inhibitor, to increase the spectrum of action against Gram-negative organisms, and to overcome bacterial antibiotic resistance mediated through β-lactamase production.
Mechanism of action Amoxicillin binds to penicillin-binding protein 1A (PBP-1A) located inside the bacterial cell well. Penicillins acylate the penicillin-sensitive transpeptidase C-terminal domain by opening the lactam ring. This inactivation of the enzyme prevents the formation of a cross-link of two linear peptidoglycan strands, inhibiting the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that amoxicllin interferes with an autolysin inhibitor.
Absorption Rapidly absorbed after oral administration.
Volume of distribution Not Available
Protein binding In blood serum, amoxicillin is approximately 20% protein-bound
Metabolism Hepatic metabolism accounts for less than 30% of the biotransformation of most penicillins
Route of elimination Most of the amoxicillin is excreted unchanged in the urine; its excretion can be delayed by concurrent administration of probenecid.
Half life 61.3 minutes
Clearance Not Available
Toxicity Serious toxicity is unlikely following large doses of amoxicillin. Acute ingestion of large doses of amoxicillin may cause nausea, vomiting, diarrhea and abdominal pain. Acute oliguric renal failure and hematuria may occur following large doses.
Affected organisms
  • Enteric bacteria and other eubacteria
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • American antibiotics llc
  • Aurobindo pharma ltd
  • Dava pharmaceuticals inc
  • Hikma pharmaceuticals
  • Laboratorios atral sarl
  • Mylan pharmaceuticals inc
  • Ranbaxy pharmaceuticals inc
  • Sandoz inc
  • Teva pharmaceuticals usa inc
  • Glaxosmithkline
  • Apothecon inc div bristol myers squibb
  • Apothecon sub bristol myers squibb co
  • Parke davis div warner lambert co
  • Wyeth ayerst laboratories
  • Wockhardt eu operations (swiss) ag
  • Ranbaxy laboratories ltd
  • Middlebrook pharmaceuticals inc
  • Draximage inc
Packagers
Dosage forms
Form Route Strength
Capsule Oral
Powder, for solution Oral
Powder, for suspension Oral
Suspension Oral
Tablet Oral
Prices
Unit description Cost Unit
Amoxil 400 mg/5ml Suspension 100ml Bottle 19.99 USD bottle
Amoxil 400 mg/5ml Suspension 75ml Bottle 17.99 USD bottle
Amoxicillin 400 mg/5ml Suspension 100ml Bottle 16.99 USD bottle
Amoxil 400 mg/5ml Suspension 50ml Bottle 15.99 USD bottle
Amoxicillin 250 mg/5ml Suspension 150ml Bottle 14.0 USD bottle
Amoxil 50 mg/ml Suspension 30ml Bottle 13.99 USD bottle
Amoxil 250 mg/5ml Suspension 100ml Bottle 12.99 USD bottle
Amoxil 250 mg/5ml Suspension 150ml Bottle 12.99 USD bottle
Amoxil 200 mg/5ml Suspension 100ml Bottle 11.99 USD bottle
Trimox 125 mg/5ml Suspension 100ml Bottle 11.99 USD bottle
Trimox 125 mg/5ml Suspension 150ml Bottle 11.99 USD bottle
Trimox 250 mg/5ml Suspension 80ml Bottle 11.99 USD bottle
Amoxil 875 mg tablet 1.13 USD tablet
Amoxil 400 mg Chew Tabs 1.05 USD tab
Amoxicillin 875 mg tablet 0.89 USD tablet
Amoxil 500 mg tablet 0.77 USD tablet
Novamoxin 250 mg Chewable Tablet 0.64 USD tablet
Amoxicillin 125 mg Chew Tabs 0.57 USD tab
Amoxil 500 mg capsule 0.53 USD capsule
Amoxicillin 500 mg tablet 0.5 USD tablet
Amoxicillin 250 mg Chew Tabs 0.47 USD tab
Amoxicillin 500 mg capsule 0.47 USD capsule
Novamoxin 125 mg Chewable Tablet 0.44 USD tablet
Apo-Amoxi 500 mg Capsule 0.36 USD capsule
Mylan-Amoxillin 500 mg Capsule 0.36 USD capsule
Novamoxin 500 mg Capsule 0.36 USD capsule
Nu-Amoxi 500 mg Capsule 0.36 USD capsule
Pms-Amoxicillin 500 mg Capsule 0.36 USD capsule
Amoxicillin 250 mg capsule 0.25 USD capsule
Apo-Amoxi 250 mg Capsule 0.18 USD capsule
Mylan-Amoxillin 250 mg Capsule 0.18 USD capsule
Novamoxin 250 mg Capsule 0.18 USD capsule
Nu-Amoxi 250 mg Capsule 0.18 USD capsule
Pms-Amoxicillin 250 mg Capsule 0.18 USD capsule
Apo-Amoxi 50 mg/ml Suspension 0.06 USD ml
Novamoxin 50 mg/ml Suspension 0.06 USD ml
Novamoxin Sugar-Reduced 50 mg/ml Suspension 0.06 USD ml
Nu-Amoxi 50 mg/ml Suspension 0.06 USD ml
Pms-Amoxicillin 50 mg/ml Suspension 0.06 USD ml
Apo-Amoxi 25 mg/ml Suspension 0.04 USD ml
Novamoxin 25 mg/ml Suspension 0.04 USD ml
Novamoxin Sugar-Reduced 25 mg/ml Suspension 0.04 USD ml
Nu-Amoxi 25 mg/ml Suspension 0.04 USD ml
Pms-Amoxicillin 25 mg/ml Suspension 0.04 USD ml
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Patents
Country Patent Number Approved Expires (estimated)
United States 6544555 2000-10-13 2020-10-13
Properties
State solid
Experimental Properties
Property Value Source
melting point 194 °C Not Available
water solubility 3430 mg/L Not Available
logP 0.87 SANGSTER (1994)
Caco2 permeability -6.1 ADME Research, USCD
Predicted Properties
Property Value Source
water solubility 9.58e-01 g/l 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 ChemAxon
rotatable bond count 4 ChemAxon
refractivity 89.5 ChemAxon
polarizability 35.53 ChemAxon
References
Synthesis Reference Not Available
General Reference
  1. Drawz SM, Bonomo RA: Three decades of beta-lactamase inhibitors. Clin Microbiol Rev. 2010 Jan;23(1):160-201. Pubmed
External Links
Resource Link
KEGG Compound C06827 Link_out
PubChem Compound 33613 Link_out
PubChem Substance 46507578 Link_out
ChemSpider 31006 Link_out
ChEBI 2676 Link_out
ChEMBL 2676 Link_out
Therapeutic Targets Database DAP000443 Link_out
PharmGKB PA448406 Link_out
Drug Product Database 2262886 Link_out
RxList http://www.rxlist.com/cgi/generic/amox.htm Link_out
Drugs.com http://www.drugs.com/amoxicillin.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Amoxicillin Link_out
ATC Codes
  • J01CA04
AHFS Codes
  • 08:12.16.08
PDB Entries Not Available
FDA label show (49.6 KB)
MSDS show (38.1 KB)
Interactions
Drug Interactions
Drug Interaction
Demeclocycline Possible antagonism of action
Doxycycline Possible antagonism of action
Ethinyl Estradiol This anti-infectious agent could decrease the effect of the oral contraceptive
Mestranol This anti-infectious agent could decrease the effect of the oral contraceptive
Methacycline Possible antagonism of action
Methotrexate The penicillin increases the effect and toxicity of methotrexate
Minocycline Possible antagonism of action
Oxytetracycline Possible antagonism of action
Rolitetracycline Possible antagonism of action
Tetracycline Possible antagonism of action
Food Interactions
  • Take without regard to meals.
Targets

1. Penicillin-binding proteins 1A/1B

Pharmacological action: yes
Actions: inhibitor
Organism class: bacterial
UniProt ID: Q8XJ01 Link_out
Gene: pbpA
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. 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
Enzymes

1. Cytochrome P450 2C19

Actions: substrate

Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine

UniProt ID: P33261 Link_out
Gene: CYP2C19 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
Transporters

1. Oligopeptide transporter, small intestine isoform

Actions: inhibitor

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

UniProt ID: P46059 Link_out
Gene: SLC15A1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  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
  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
  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
  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

2. Oligopeptide transporter, kidney isoform

Actions: inhibitor

Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides

UniProt ID: Q16348 Link_out
Gene: SLC15A2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  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
  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

3. Solute carrier family 22 member 6

Actions: inhibitor
UniProt ID: Q4U2R8 Link_out
Gene: hROAT1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
Comments
Drug created on June 13, 2005 07:24 / Updated on February 19, 2013 16:46