Showing metabocard for Amoxicillin (BMDB0063637)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2018-12-04 20:29:09 UTC
Update Date2020-06-04 20:42:45 UTC
BMDB IDBMDB0063637
Secondary Accession Numbers
  • BMDB63637
Metabolite Identification
Common NameAmoxicillin
DescriptionAmoxicillin (International Nonproprietary Name), or amoxycillin (British Approved Name), is a moderate-spectrum, bacteriolytic, -lactam antibiotic used to treat bacterial infections caused by susceptible microorganisms. It is a broad-spectrum semisynthetic antibiotic similar to ampicillin except that its resistance to gastric acid permits higher serum levels with oral administration (PubChem). Amoxicillin is active against a wide range of Gram-positive and a limited range of Gram-negative organisms. It is susceptible to degradation by beta-lactamase-producing bacteria, and so may be given with clavulanic acid to increase its susceptibility. The incidence of beta-lactamase-producing resistant organisms, including E. coli, appears to be increasing. Amoxicillin binds to penicillin-binding protein 1A (PBP-1A) located inside the bacterial cell wall. 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 amoxicillin interferes with an autolysin inhibitor. Amoxicillin is usually the drug of choice within the class because it is better absorbed, following oral administration, than other -lactam antibiotics. Amoxicillin in trihydrate form is available as capsules, chewable and dispersible tablets, syrup and pediatric suspension for oral use, and as the sodium salt for intravenous administration. It is one of the most common antibiotics prescribed for children, and the liquid forms are helpful in cases where the patient might find it difficult to take tablets or capsules. It has three ionizable groups. Amoxicillin as a once-daily dosing form (Moxatag) was approved by the American FDA in January 2008. Amoxicillin is one of the semi-synthetic penicillins discovered by Beecham scientists. The patent for amoxicillin has expired, thus amoxicillin is marketed under many trade names, including Actimoxi, Alphamox, AMK, Amoksibos, Amoxiclav Sandoz, Amoxidal, Amoxil, Amoxin, Amoksiklav, Amoxibiotic, Amoxicilina, Apo-Amoxi, Augmentin, Bactox, Betalaktam, Cilamox, Curam, Dedoxil, Dispermox, Duomox, E-Mox (250mg and 500 mg), Enhancin, Gimalxina, Geramox, Hiconcil, Isimoxin, Klavox, Lamoxy, Moxatag, Moxilen, Moxypen, Moxyvit, Nobactam, Novamoxin, Ospamox, Panklav, Pamoxicillin, Panamox, Polymox, Samthongcillin, Clamoxyl, Senox, Sinacilin, Trimox, Tolodina, Wymox, Yucla, Zerrsox, and Zimox. Amoxicillin is found in milk and milk products. It is a potential contaminant in cow's milk arising from its veterinary use.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(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 acidChEBI
6-(p-Hydroxy-alpha-aminophenylacetamido)penicillanic acidChEBI
alpha-Amino-p-hydroxybenzylpenicillinChEBI
AmolinChEBI
AmopenixinChEBI
AmoxicilinaChEBI
Amoxicillin anhydrousChEBI
AmoxicillineChEBI
AmoxicillinumChEBI
AmoxycilinChEBI
AmoxycillinChEBI
AMPCChEBI
AXChEBI
ClamoxylChEBI
MoxalChEBI
p-HydroxyampicillinChEBI
(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-carboxylateGenerator
6-(p-Hydroxy-a-aminophenylacetamido)penicillanateGenerator
6-(p-Hydroxy-a-aminophenylacetamido)penicillanic acidGenerator
6-(p-Hydroxy-alpha-aminophenylacetamido)penicillanateGenerator
6-(p-Hydroxy-α-aminophenylacetamido)penicillanateGenerator
6-(p-Hydroxy-α-aminophenylacetamido)penicillanic acidGenerator
a-Amino-p-hydroxybenzylpenicillinGenerator
Α-amino-p-hydroxybenzylpenicillinGenerator
Amoxicillin trihydrateHMDB
Amoxycillin trihydrateHMDB
D-AmoxicillinHMDB
ActimoxiHMDB
Amoxicillin monopotassium saltHMDB
Amoxicillin monosodium saltHMDB
Clariana brand OF amoxicillinHMDB
PolymoxHMDB
Amoxicillin sodiumHMDB
Clamoxyl parenteralHMDB
Trihydrate, amoxicillinHMDB
Anhydrous, amoxicillinHMDB
Clamoxyl g.a.HMDB
HydroxyampicillinHMDB
Pfizer brand OF amoxicillin sodium saltHMDB
TrimoxHMDB
WymoxHMDB
Amoxicillin clariana brandHMDB
Amoxicillin, (r*)-isomerHMDB
AmoxilHMDB
G.A., clamoxylHMDB
PenamoxHMDB
SmithKline beecham brand OF amoxicillin sodium saltHMDB
Sodium, amoxicillinHMDB
Parenteral, clamoxylHMDB
6-(a-Amino-4-hydroxyphenylacetamido)penicillanic acidHMDB
6-(D-(-)-p-Hydroxy-alpha-aminobenzyl)penicillinHMDB
6-[[Amino(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 9ciHMDB
AlmodanHMDB
AmixHMDB
AmoclenHMDB
AmopenHMDB
AmoramHMDB
Amox 250 cap 250MGHMDB
Amox 500 cap 500MGHMDB
Amox S 125 sus 125mg/5MLHMDB
Amox S 250 sus 250mg/5MLHMDB
AmoxiHMDB
Amoxi-mastHMDB
AmoxicapsHMDB
Amoxicillin (anhydrous)HMDB
Amoxicillin and clavulanate potassiumHMDB
Amoxicillin pediatricHMDB
Amoxicillin(usan)HMDB
AmoxidHMDB
AmoxidenHMDB
AmoxivetHMDB
Amoxycillin, banHMDB
AmoxymedHMDB
AmritHMDB
AnemolinHMDB
Apo-amoxiHMDB
Apo-amoxi cap 250MGHMDB
Apo-amoxi cap 500MGHMDB
Apo-amoxi PWR for susp 125mg/5MLHMDB
Apo-amoxi PWR for susp 250mg/5MLHMDB
Apo-amoxi sugar freeHMDB
AspenilHMDB
AUGMENTIN '125'HMDB
AUGMENTIN '200'HMDB
AUGMENTIN '250'HMDB
AUGMENTIN '400'HMDB
AUGMENTIN '500'HMDB
AUGMENTIN '875'HMDB
AUGMENTIN es-600HMDB
BiomoxHMDB
BristamoxHMDB
BRL 2333HMDB
CemoxinHMDB
Clamoxyl (SKB)HMDB
D-(-)-alpha-Amino-p-hydroxybenzyl penicillinHMDB
D-(-)-alpha-Amino-p-hydroxybenzylpenicillinHMDB
D-(alpha-Amino-p-hydroxybenzyl)penicillinHMDB
D-2-Amino-2-(4-hydroxyphenyl)acetamidopenicillanic acidHMDB
DelacillinHMDB
DispermoxHMDB
EfpenixHMDB
FlemoxinHMDB
GalenamoxHMDB
Gen-amoxicillin 250MGHMDB
Gen-amoxicillin 500MGHMDB
HiconcilHMDB
HistocillinHMDB
IbiamoxHMDB
ImacillinHMDB
LarotidHMDB
Metafarma capsulesHMDB
Metifarma capsulesHMDB
MoxacinHMDB
MoxatagHMDB
Novamoxin cap 250MGHMDB
Novamoxin cap 500MGHMDB
Novamoxin sus 125mg/5MLHMDB
Novamoxin sus 250mg/5MLHMDB
Nu-amoxi cap 250MGHMDB
Nu-amoxi cap 500MGHMDB
Nu-amoxi sus 125/5MLHMDB
Nu-amoxi sus 250mg/5MLHMDB
OspamoxHMDB
PHL-AmoxicillinHMDB
PiramoxHMDB
PMS-AmoxicillinHMDB
PrevpacHMDB
Pro amox PWR for oral susp 125mg/5MLHMDB
Pro amox-250 cap 250MGHMDB
Pro amox-500 cap 500MGHMDB
Pro-amox-250 orl sus 250mg/5MLHMDB
R-HydroxyampicillinHMDB
RimoxallinHMDB
RobamoxHMDB
SauracillinHMDB
Sawamox PMHMDB
SumoxHMDB
UnicillinHMDB
UtimoxHMDB
VetramoxHMDB
AmoxicillinHMDB
Chemical FormulaC16H19N3O5S
Average Molecular Weight365.404
Monoisotopic Molecular Weight365.104541423
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
Traditional Nameamoxicillin
CAS Registry Number26787-78-0
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
InChI Identifier
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
InChI KeyLSQZJLSUYDQPKJ-NJBDSQKTSA-N
Chemical Taxonomy
Description 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].
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactams
Sub ClassBeta lactams
Direct ParentPenicillins
Alternative Parents
Substituents
  • Penicillin
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Phenylacetamide
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Benzenoid
  • Monocyclic benzene moiety
  • Thiazolidine
  • Tertiary carboxylic acid amide
  • Azetidine
  • Amino acid or derivatives
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Amino acid
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Dialkylthioether
  • Hemithioaminal
  • Thioether
  • Primary aliphatic amine
  • Amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point194 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility9.58e-01 g/LNot Available
LogP0.0Not Available
Predicted Properties
PropertyValueSource
logP0.75ALOGPS
logP-2.3ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)3.23ChemAxon
pKa (Strongest Basic)7.22ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area132.96 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity89.5 m³·mol⁻¹ChemAxon
Polarizability35.52 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-1900000000-1c2ac124e627e76a25cdView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0006-0900000000-f1dcbada55dfb975b85fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-03xs-0859000000-8225987d1a20c14acc00View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00di-0190000000-febb22de5b7f210e4a46View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-056u-4960000000-f3c347843d63d99418c5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0036-8900000000-eca01f197da058161684View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-007o-9800000000-cec182c5a522a2979385View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00ec-9700000000-dc767a962e9f2608b083View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00dl-9600000000-b831842a45369bb2b48cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-06r2-0589000000-9c90c12d4fbef3a04a14View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-0910000000-e26fa392674b2a230233View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-1900000000-9e60140bfff56767dbecView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-1900000000-f3065ce1009dda06cf72View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03e9-2900000000-5516c0723837b4149a68View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-06s9-5900000000-cd377b53cefaa4b23c6fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03xs-0859000000-8225987d1a20c14acc00View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-0036-8900000000-62bd26570eb8aae7a515View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-056u-5960000000-d19d44c39e4481d0e1b2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-03e9-2900000000-f6e458dd9ce3de4c0c25View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-00di-0190000000-9c79deb14e40c1956190View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-03di-0910000000-26e374b1aeae888b2869View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-096r-1942000000-113f344b62fa2da12fa2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08mi-2920000000-1af60e30ced839146281View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0abc-9800000000-8bfef7a27c2a9bdb662cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0091000000-5a11ce4f38e4518c703cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0391000000-55921977de48ce477471View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dl-9520000000-9f116d1f75d12afd48bfView in MoNA
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Milk
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
MilkDetected and Quantified0.052 uMNot SpecifiedNot Specified
Normal
    • Nina Bilandžić, B...
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0015193
DrugBank IDDB01060
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID31006
KEGG Compound IDC06827
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAmoxicillin
METLIN IDNot Available
PubChem Compound33613
PDB IDNot Available
ChEBI ID2676
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Nina Bilandžić, Božica Solomun Kolanović, Ivana Varenina, Giampiero Scortichini, Loredana Annunziata, Matko Brstilo, Nevenka Rudan (2011). Nina Bilandžić, Božica Solomun Kolanović, Ivana Varenina, Giampiero Scortichini, Loredana Annunziata, Matko Brstilo, Nevenka Rudan. Veterinary drug residues determination in raw milk in Croatia. Food Control. Volume 22, Issue 12, December 2011, Pages 1941-1948. Food Control.