Record Information
Version1.0
Creation date2010-04-08 22:05:21 UTC
Update date2019-11-26 02:57:22 UTC
Primary IDFDB002369
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAmoxycillin
DescriptionPotential contaminant in cow's milk arising from its veterinary use Amoxicillin (INN), formerly amoxycillin (BAN), is a moderate-spectrum, bacteriolytic, ?-lactam antibiotic used to treat bacterial infections caused by susceptible microorganisms. It 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 dispersable tablets plus 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 where the patient might find it difficult to take tablets or capsules. It has three ionizable groups. A once daily dosing form (Moxatag) was approved by the American FDA in January 2008.; 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.; 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. Amoxycillin is found in milk and milk products.
CAS Number26787-78-0
Structure
Thumb
Synonyms
SynonymSource
6-(a-amino-4-hydroxyphenylacetamido)Penicillanic acidHMDB
6-(D-(-)-P-Hydroxy-alpha-aminobenzyl)penicillinHMDB
6-(P-Hydroxy-alpha-aminophenylacetamido)penicillanic acidHMDB
6-[[amino(4-Hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 9ciHMDB
AlmodanHMDB
alpha-amino-P-HydroxybenzylpenicillinHMDB
AmixHMDB
AmoclenHMDB
AmolinHMDB
AmopenHMDB
AmopenixinHMDB
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
AmoxicilinaHMDB
Amoxicillin (anhydrous)HMDB
AmoxicillinHMDB
Amoxicillin and clavulanate potassiumHMDB
Amoxicillin anhydrousHMDB
Amoxicillin pediatricHMDB
Amoxicillin trihydrateHMDB
Amoxicillin(usan)HMDB
AmoxicillineHMDB
AmoxicillinumHMDB
AmoxidHMDB
AmoxidenHMDB
AmoxilHMDB
AmoxivetHMDB
Amoxycillin trihydrateHMDB
Amoxycillin, banHMDB
AmoxymedHMDB
AMPCHMDB
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
ClamoxylHMDB
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
D-AmoxicillinHMDB
DelacillinHMDB
DispermoxHMDB
EfpenixHMDB
FlemoxinHMDB
GalenamoxHMDB
Gen-amoxicillin 250MGHMDB
Gen-amoxicillin 500MGHMDB
HiconcilHMDB
HistocillinHMDB
HydroxyampicillinHMDB
IbiamoxHMDB
ImacillinHMDB
LarotidHMDB
Metafarma capsulesHMDB
Metifarma capsulesHMDB
MoxacinHMDB
MoxalHMDB
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
P-HydroxyampicillinHMDB
PHL-AmoxicillinHMDB
PiramoxHMDB
PMS-AmoxicillinHMDB
PolymoxHMDB
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
TrimoxHMDB
UnicillinHMDB
UtimoxHMDB
VetramoxHMDB
WymoxHMDB
α-amino-p-hydroxybenzylpenicillinbiospider
6-(a-Amino-4-hydroxyphenylacetamido)penicillanic aciddb_source
6-(D-(-)-p-Hydroxy-alpha-aminobenzyl)penicillinbiospider
6-(p-hydroxy-alpha-aminophenylacetamido)penicillanic acidbiospider
6-[[Amino(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 9CIdb_source
Alpha-amino-p-hydroxybenzylpenicillinbiospider
Amox 250 Cap 250mgbiospider
Amox 500 Cap 500mgbiospider
Amox S 125 Sus 125mg/5mlbiospider
Amox S 250 Sus 250mg/5mlbiospider
Amoxicillin (inn)biospider
Amoxicillin (TN)biospider
Amoxicilline [inn]biospider
Amoxycillinbiospider
Amoxycillin, BANdb_source
Apo-amoxibiospider
Apo-Amoxi Cap 250mgbiospider
Apo-Amoxi Cap 500mgbiospider
Apo-Amoxi Pwr for Susp 125mg/5mlbiospider
Apo-Amoxi Pwr for Susp 250mg/5mlbiospider
Apo-amoxi sugar freebiospider
AUGMENTIN ES-600biospider
D-(-)-α-amino-p-hydroxybenzyl penicillinbiospider
D-(-)-α-amino-p-hydroxybenzylpenicillinbiospider
D-(-)-alpha-amino-p-hydroxybenzylpenicillinbiospider
D-(α-amino-p-hydroxybenzyl)penicillinbiospider
D-2-Amino-2-(4-hydroxyphenyl)acetamidopenicillanic acidbiospider
D-amoxicillinbiospider
Gen-Amoxicillin 250mgbiospider
Gen-Amoxicillin 500mgbiospider
Novamoxin Cap 250mgbiospider
Novamoxin Cap 500mgbiospider
Novamoxin Sus 125mg/5mlbiospider
Novamoxin Sus 250mg/5mlbiospider
Nu-Amoxi Cap 250mgbiospider
Nu-Amoxi Cap 500mgbiospider
Nu-Amoxi Sus 125/5mlbiospider
Nu-Amoxi Sus 250mg/5mlbiospider
P-hydroxyampicillinbiospider
PHL-amoxicillinbiospider
PMS-amoxicillinbiospider
Pro Amox Pwr for Oral Susp 125mg/5mlbiospider
Pro Amox-250 Cap 250mgbiospider
Pro Amox-500 Cap 500mgbiospider
Pro-Amox-250 Orl Sus 250mg/5mlbiospider
r-Hydroxyampicillindb_source
Predicted Properties
PropertyValueSource
Water Solubility0.96 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 Area132.96 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity89.5 m³·mol⁻¹ChemAxon
Polarizability35.22 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC16H19N3O5S
IUPAC name6-[2-amino-2-(4-hydroxyphenyl)acetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
InChI IdentifierInChI=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)
InChI KeyLSQZJLSUYDQPKJ-UHFFFAOYSA-N
Isomeric SMILESCC1(C)SC2C(NC(=O)C(N)C3=CC=C(O)C=C3)C(=O)N2C1C(O)=O
Average Molecular Weight365.404
Monoisotopic Molecular Weight365.104541423
Classification
Description Belongs to the class of organic compounds known as heteroaromatic compounds. Heteroaromatic compounds are compounds containing an aromatic ring where a carbon atom is linked to an hetero atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassHeteroaromatic compounds
Sub ClassNot Available
Direct ParentHeteroaromatic compounds
Alternative Parents
Substituents
  • Heteroaromatic compound
  • Furan
  • Organic disulfide
  • Oxacycle
  • Sulfenyl compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 52.59%; H 5.24%; N 11.50%; O 21.89%; S 8.78%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logP0.87SANGSTER (1994)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D +246 (c, 0.1 in H2O)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSAmoxycillin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-1900000000-44b45136a61943a5e0bcSpectrum
Predicted GC-MSAmoxycillin, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-1900000000-777d301a2b18fa62778eSpectrum
Predicted GC-MSAmoxycillin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAmoxycillin, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAmoxycillin, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAmoxycillin, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAmoxycillin, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAmoxycillin, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAmoxycillin, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAmoxycillin, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAmoxycillin, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAmoxycillin, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAmoxycillin, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAmoxycillin, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAmoxycillin, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAmoxycillin, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAmoxycillin, TBDMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAmoxycillin, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAmoxycillin, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAmoxycillin, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAmoxycillin, TBDMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAmoxycillin, TBDMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAmoxycillin, TBDMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAmoxycillin, TBDMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-07or-0933000000-9af2dae1c5cfc1494354Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-074i-1910000000-051f75154192e44a1170Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-6900000000-4c7f062558feb0f63590Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0091000000-3e424bc98e953e5d676eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-1291000000-114c3c45e8a14ae9cd45Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dl-9530000000-acd4df5a50a561a0e029Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dj-0904000000-cc66823c49c2eb56d067Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03k9-0901000000-17f3473a562b61aac479Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08mi-3900000000-02eeb34bd5613939a30cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0079-0090000000-cab4a7b69a27f76726faSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-3369000000-ff827401f965b208ded4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9710000000-3bfdc4b6a54c60a47c5bSpectrum
NMRNot Available
ChemSpider ID2086
ChEMBL IDNot Available
KEGG Compound IDC06827
Pubchem Compound ID2171
Pubchem Substance IDNot Available
ChEBI ID2676
Phenol-Explorer IDNot Available
DrugBank IDDB01060
HMDB IDHMDB30500
CRC / DFC (Dictionary of Food Compounds) IDCKX85-Z:CKX85-Z
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDAmoxicillin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference