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Identification
NameAmoxicillin
Accession NumberDB01060  (APRD00248)
Typesmall molecule
Groupsapproved
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
Synonyms
SynonymLanguageCode
6-(p-hydroxy-α-aminophenylacetamido)penicillanic acidNot AvailableNot Available
AmoxNot AvailableNot Available
AmoxicilinaSpanishINN
Amoxicillin anhydrousNot AvailableNot Available
AmoxicillineFrenchINN
AmoxicillinumLatinINN
AmoxycillinNot AvailableBAN
AMPCNot AvailableNot Available
p-HydroxyampicillinNot AvailableNot Available
α-amino-p-hydroxybenzylpenicillinNot AvailableNot Available
Salts
Name/CAS Structure Properties
Amoxicillin sodium
Thumb Not applicable DBSALT000868
Amoxycillin trihydrate
Thumb Not applicable DBSALT000867
Brand names
NameCompany
ActimoxiNot Available
AmoclenNot Available
AmolinNot Available
AmopenNot Available
AmopenixinNot Available
AmoxibioticNot Available
AmoxilGlaxoSmithKline
AMPCNot Available
Apo-AmoxiNot Available
AugmentinXRNot Available
ClamoxylNot Available
DispermoxNot Available
EfpenixNot Available
FlemoxinNot Available
HiconcilNot Available
IbiamoxNot Available
ImacillinNot Available
LarotidRoche
MoxacinNot Available
MoxalNot Available
MoxatagNot Available
OspamoxNot Available
PamoxicillinNot Available
PolymoxNot Available
TrimoxNot Available
WymoxNot Available
Brand mixtures
Brand NameIngredients
Augmentinamoxicillin + clavulanic acid
Co-amoxiclavamoxicillin + clavulanic acid
Prevpacamoxicillin + clarithromycin + lansoprazole
Categories
CAS number26787-78-0
WeightAverage: 365.404
Monoisotopic: 365.104541423
Chemical FormulaC16H19N3O5S
InChI KeyLSQZJLSUYDQPKJ-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][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CC=C(O)C=C1)C(O)=O
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassLactams
SubclassBeta Lactams
Direct parentPenicillins
Alternative parentsN-acyl-alpha Amino Acids and Derivatives; Alpha Amino Acid Amides; Phenols and Derivatives; Tertiary Carboxylic Acid Amides; Thiazolidines; Polyols; Hemiaminals; Secondary Carboxylic Acid Amides; Tertiary Amines; Azetidines; Polyamines; Enols; Enolates; Carboxylic Acids; Aminals; Thioethers; Monoalkylamines
Substituentsn-acyl-alpha amino acid or derivative; alpha-amino acid amide; alpha-amino acid or derivative; phenol derivative; benzene; thiazolidine; tertiary carboxylic acid amide; carboxamide group; tertiary amine; polyol; hemiaminal; azetidine; secondary carboxylic acid amide; polyamine; aminal; carboxylic acid derivative; enolate; thioether; enol; carboxylic acid; primary amine; primary aliphatic amine; amine; organonitrogen compound
Classification descriptionThis compound belongs to the 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].
Pharmacology
IndicationFor 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).
PharmacodynamicsAmoxicillin 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 actionAmoxicillin 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.
AbsorptionRapidly absorbed after oral administration.
Volume of distributionNot Available
Protein bindingIn blood serum, amoxicillin is approximately 20% protein-bound
Metabolism

Hepatic metabolism accounts for less than 30% of the biotransformation of most penicillins

Route of eliminationMost of the amoxicillin is excreted unchanged in the urine; its excretion can be delayed by concurrent administration of probenecid.
Half life61.3 minutes
ClearanceNot Available
ToxicitySerious 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrate Non-inhibitor 0.907
CYP450 2D6 substrate Non-inhibitor 0.9231
CYP450 2C19 substrate Non-inhibitor 0.915
CYP450 3A4 substrate 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
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
FormRouteStrength
CapsuleOral
Powder, for solutionOral
Powder, for suspensionOral
SuspensionOral
TabletOral
Prices
Unit descriptionCostUnit
Amoxil 400 mg/5ml Suspension 100ml Bottle19.99USDbottle
Amoxil 400 mg/5ml Suspension 75ml Bottle17.99USDbottle
Amoxicillin 400 mg/5ml Suspension 100ml Bottle16.99USDbottle
Amoxil 400 mg/5ml Suspension 50ml Bottle15.99USDbottle
Amoxicillin 250 mg/5ml Suspension 150ml Bottle14.0USDbottle
Amoxil 50 mg/ml Suspension 30ml Bottle13.99USDbottle
Amoxil 250 mg/5ml Suspension 100ml Bottle12.99USDbottle
Amoxil 250 mg/5ml Suspension 150ml Bottle12.99USDbottle
Amoxil 200 mg/5ml Suspension 100ml Bottle11.99USDbottle
Trimox 125 mg/5ml Suspension 100ml Bottle11.99USDbottle
Trimox 125 mg/5ml Suspension 150ml Bottle11.99USDbottle
Trimox 250 mg/5ml Suspension 80ml Bottle11.99USDbottle
Amoxil 875 mg tablet1.13USDtablet
Amoxil 400 mg Chew Tabs1.05USDtab
Amoxicillin 875 mg tablet0.89USDtablet
Amoxil 500 mg tablet0.77USDtablet
Novamoxin 250 mg Chewable Tablet0.64USDtablet
Amoxicillin 125 mg Chew Tabs0.57USDtab
Amoxil 500 mg capsule0.53USDcapsule
Amoxicillin 500 mg tablet0.5USDtablet
Amoxicillin 250 mg Chew Tabs0.47USDtab
Amoxicillin 500 mg capsule0.47USDcapsule
Novamoxin 125 mg Chewable Tablet0.44USDtablet
Apo-Amoxi 500 mg Capsule0.36USDcapsule
Mylan-Amoxillin 500 mg Capsule0.36USDcapsule
Novamoxin 500 mg Capsule0.36USDcapsule
Nu-Amoxi 500 mg Capsule0.36USDcapsule
Pms-Amoxicillin 500 mg Capsule0.36USDcapsule
Amoxicillin 250 mg capsule0.25USDcapsule
Apo-Amoxi 250 mg Capsule0.18USDcapsule
Mylan-Amoxillin 250 mg Capsule0.18USDcapsule
Novamoxin 250 mg Capsule0.18USDcapsule
Nu-Amoxi 250 mg Capsule0.18USDcapsule
Pms-Amoxicillin 250 mg Capsule0.18USDcapsule
Apo-Amoxi 50 mg/ml Suspension0.06USDml
Novamoxin 50 mg/ml Suspension0.06USDml
Novamoxin Sugar-Reduced 50 mg/ml Suspension0.06USDml
Nu-Amoxi 50 mg/ml Suspension0.06USDml
Pms-Amoxicillin 50 mg/ml Suspension0.06USDml
Apo-Amoxi 25 mg/ml Suspension0.04USDml
Novamoxin 25 mg/ml Suspension0.04USDml
Novamoxin Sugar-Reduced 25 mg/ml Suspension0.04USDml
Nu-Amoxi 25 mg/ml Suspension0.04USDml
Pms-Amoxicillin 25 mg/ml Suspension0.04USDml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
CountryPatent NumberApprovedExpires (estimated)
United States65445552000-10-132020-10-13
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point194 °CNot Available
water solubility3430 mg/LNot Available
logP0.87SANGSTER (1994)
Caco2 permeability-6.1ADME Research, USCD
Predicted Properties
PropertyValueSource
water solubility9.58e-01 g/lALOGPS
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 area132.96ChemAxon
rotatable bond count4ChemAxon
refractivity89.5ChemAxon
polarizability35.53ChemAxon
number of rings3ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
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 Reference
  1. Drawz SM, Bonomo RA: Three decades of beta-lactamase inhibitors. Clin Microbiol Rev. 2010 Jan;23(1):160-201. Pubmed
External Links
ResourceLink
KEGG CompoundC06827
PubChem Compound33613
PubChem Substance46507578
ChemSpider31006
ChEBI2676
ChEMBLCHEMBL1082
Therapeutic Targets DatabaseDAP000443
PharmGKBPA448406
Drug Product Database2262886
RxListhttp://www.rxlist.com/cgi/generic/amox.htm
Drugs.comhttp://www.drugs.com/amoxicillin.html
WikipediaAmoxicillin
ATC CodesJ01CA04
AHFS Codes
  • 08:12.16.08
PDB EntriesNot Available
FDA labelshow(49.6 KB)
MSDSshow(38.1 KB)
Interactions
Drug Interactions
Drug
DemeclocyclinePossible antagonism of action
DoxycyclinePossible antagonism of action
Ethinyl EstradiolThis anti-infectious agent could decrease the effect of the oral contraceptive
MestranolThis anti-infectious agent could decrease the effect of the oral contraceptive
MethacyclinePossible antagonism of action
MethotrexateThe penicillin increases the effect and toxicity of methotrexate
MinocyclinePossible antagonism of action
OxytetracyclinePossible antagonism of action
RolitetracyclinePossible antagonism of action
TetracyclinePossible antagonism of action
Food Interactions
  • Take without regard to meals.

Targets

1. Penicillin-binding protein 1A

Kind: protein

Organism: Clostridium perfringens (strain 13 / Type A)

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Penicillin-binding protein 1A Q8XJ01 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2C19 P33261 Details

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. Solute carrier family 15 member 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 15 member 1 P46059 Details

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. Solute carrier family 15 member 2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 15 member 2 Q16348 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 6 Q4U2R8 Details

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

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:13