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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
(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 acidNot AvailableNot Available
6-(P-Hydroxy-alpha-aminophenylacetamido)penicillanic acidNot AvailableNot Available
6-(p-hydroxy-α-aminophenylacetamido)penicillanic acidNot AvailableNot Available
alpha-amino-P-HydroxybenzylpenicillinNot AvailableNot Available
AmolinNot AvailableNot Available
AmopenixinNot AvailableNot Available
AmoxNot AvailableNot Available
AmoxicilinaSpanishINN
AmoxicillinNot AvailableNot Available
Amoxicillin anhydrousNot AvailableNot Available
AmoxicillineFrenchINN
AmoxicillinumLatinINN
AmoxycillinNot AvailableBAN
AMPCNot AvailableNot Available
AXNot AvailableNot Available
ClamoxylNot AvailableNot Available
MoxalNot AvailableNot Available
p-HydroxyampicillinNot AvailableNot Available
α-amino-p-hydroxybenzylpenicillinNot AvailableNot Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Amoxicillinpowder, for suspension400 mg/5mLoralDr Reddys Laboratories Inc1999-04-15Not AvailableUs
Amoxicillintablet, film coated875 mgoralDr Reddys Laboratories Inc1978-07-10Not AvailableUs
Amoxicillinpowder, for suspension200 mg/5mLoralDr Reddys Laboratories Inc1999-04-15Not AvailableUs
Amoxicillintablet, film coated500 mgoralDr Reddys Laboratories Inc1978-07-10Not AvailableUs
Amoxicillin Extended-releasetablet, film coated, extended release775 mgoralFera Pharmaceuticals, LLC2014-07-28Not AvailableUs
Amoxicillintablet, film coated875 mgoralUnit Dose Services1978-07-10Not AvailableUs
Augmentinxrtablet, film coated, extended release1000; 62.5 mg/1; mgoralPhysicians Total Care, Inc.2003-01-30Not AvailableUs
Amoxicillinpowder, for suspension200 mg/5mLoralClinical Solutions Wholesale1999-04-15Not AvailableUs
Amoxicillinpowder, for suspension400 mg/5mLoralClinical Solutions Wholesale1999-04-15Not AvailableUs
Amoxicillintablet, film coated875 mgoralClinical Solutions Wholesale1978-07-10Not AvailableUs
Moxatagtablet, film coated, extended release775 mgoralPragma Pharmaceuticals, LLC2014-07-28Not AvailableUs
Moxatagtablet, film coated, extended release775 mgoralShionogi Inc.2011-08-26Not AvailableUs
Amoxicillintablet, film coated875 mgoralDIRECT RX2014-01-01Not AvailableUs
Amoxicillintablet, film coated875 mgoralProficient Rx LP1978-07-10Not AvailableUs
Amoxicillinpowder, for suspension400 mg/5mLoralProficient Rx LP1999-04-15Not AvailableUs
Amoxicillintablet, film coated875 mgoralReady Meds1978-07-10Not AvailableUs
Amoxicillintablet, film coated500 mgoralReady Meds1978-07-10Not AvailableUs
Novamoxintablet (chewable)125 mgoralTeva Canada LimitedNot AvailableNot AvailableCanada
Novamoxintablet (chewable)250 mgoralTeva Canada LimitedNot AvailableNot AvailableCanada
Novamoxincapsule250 mgoralTeva Canada LimitedNot AvailableNot AvailableCanada
Novamoxincapsule500 mgoralTeva Canada LimitedNot AvailableNot AvailableCanada
Novamoxingranules for suspension50 mgoralTeva Canada LimitedNot AvailableNot AvailableCanada
Novamoxingranules for suspension25 mgoralTeva Canada LimitedNot AvailableNot AvailableCanada
Novamoxingranules for suspension250 mgoralTeva Canada LimitedNot AvailableNot AvailableCanada
Novamoxingranules for suspension125 mgoralTeva Canada LimitedNot AvailableNot AvailableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Amoxicillintablet, film coated500 mgoralTeva Pharmaceuticals USA Inc2000-11-21Not AvailableUs
Amoxicillintablet, film coated875 mgoralTeva Pharmaceuticals USA Inc2000-09-26Not AvailableUs
Amoxicillintablet, chewable125 mgoralTeva Pharmaceuticals USA Inc1995-10-01Not AvailableUs
Amoxicillintablet, chewable250 mgoralTeva Pharmaceuticals USA Inc1993-01-01Not AvailableUs
Amoxicillincapsule250 mgoralTeva Pharmaceuticals USA Inc1990-09-30Not AvailableUs
Amoxicillincapsule500 mgoralTeva Pharmaceuticals USA Inc1990-09-30Not AvailableUs
Amoxicillinpowder, for suspension125 mg/5mLoralTeva Pharmaceuticals USA Inc1990-09-30Not AvailableUs
Amoxicillinpowder, for suspension250 mg/5mLoralTeva Pharmaceuticals USA Inc1990-09-30Not AvailableUs
Amoxicillinpowder, for suspension200 mg/5mLoralTeva Pharmaceuticals USA Inc2003-04-02Not AvailableUs
Amoxicillinpowder, for suspension400 mg/5mLoralTeva Pharmaceuticals USA Inc2003-02-26Not AvailableUs
Amoxicillinpowder, for suspension200 mg/5mLoralWest ward Pharmaceutical Corp2006-06-19Not AvailableUs
Amoxicillinpowder, for suspension400 mg/5mLoralWest ward Pharmaceutical Corp2006-06-19Not AvailableUs
Amoxicillinpowder, for suspension125 mg/5mLoralWest ward Pharmaceutical Corp2006-06-19Not AvailableUs
Amoxicillinpowder, for suspension250 mg/5mLoralWest ward Pharmaceutical Corp2006-06-19Not AvailableUs
Amoxicillincapsule250 mgoralWest ward Pharmaceutical Corp2007-03-01Not AvailableUs
Amoxicillincapsule500 mgoralWest ward Pharmaceutical Corp2007-03-01Not AvailableUs
Amoxicillintablet, coated875 mgoralWest ward Pharmaceutical Corp2006-03-29Not AvailableUs
Amoxicillincapsule250 mgoralLiberty Pharmaceuticals, Inc.1988-02-25Not AvailableUs
Amoxicillincapsule250 mgoralSandoz Inc1994-09-30Not AvailableUs
Amoxicillincapsule500 mgoralSandoz Inc1994-09-30Not AvailableUs
Amoxicillintablet, film coated500 mgoralSandoz Inc2005-07-13Not AvailableUs
Amoxicillintablet, film coated875 mgoralSandoz Inc2005-07-13Not AvailableUs
Amoxicillinpowder, for suspension125 mg/5mLoralSandoz Inc2007-03-26Not AvailableUs
Amoxicillinpowder, for suspension250 mg/5mLoralSandoz Inc2007-03-26Not AvailableUs
Amoxicillinpowder, for suspension200 mg/5mLoralSandoz Inc2007-03-26Not AvailableUs
Amoxicillinpowder, for suspension400 mg/5mLoralSandoz Inc2007-03-26Not AvailableUs
Amoxicillincapsule500 mgoralBlenheim Pharmacal, Inc.2010-07-20Not AvailableUs
Amoxicillincapsule500 mgoralBlenheim Pharmacal, Inc.2013-01-16Not AvailableUs
Amoxicillincapsule250 mgoralBlenheim Pharmacal, Inc.2012-04-23Not AvailableUs
Amoxicillincapsule500 mgoralBlenheim Pharmacal, Inc.2009-12-14Not AvailableUs
Amoxicillincapsule500 mgoralBlenheim Pharmacal, Inc.2010-05-17Not AvailableUs
Amoxicillincapsule250 mgoralApotheca Inc.2005-03-08Not AvailableUs
Amoxicillincapsule500 mgoralApotheca Inc.2005-03-08Not AvailableUs
Amoxicillincapsule250 mgoralAmerican Antibiotics,Inc2011-07-01Not AvailableUs
Amoxicillincapsule500 mgoralAmerican Antibiotics,Inc2011-07-01Not AvailableUs
Amoxicillincapsule250 mgoralSTAT Rx USA LLC2005-09-11Not AvailableUs
Amoxicillinpowder, for suspension250 mg/5mLoralSTAT Rx USA LLC2012-04-13Not AvailableUs
Amoxicillincapsule500 mgoralSTAT Rx USA LLC2005-09-11Not AvailableUs
Amoxicillintablet, film coated875 mgoralSTAT Rx USA LLC2005-11-09Not AvailableUs
Amoxicillinpowder, for suspension125 mg/5mLoralSTAT Rx USA LLC2012-04-13Not AvailableUs
Amoxicillinpowder, for suspension400 mg/5mLoralSTAT Rx USA LLC2006-12-28Not AvailableUs
Amoxicillintablet, chewable125 mgoralSTAT Rx USA LLC2010-01-28Not AvailableUs
Amoxicillincapsule250 mgoralNorth Star Rx Llc2005-11-09Not AvailableUs
Amoxicillincapsule500 mgoralNorth Star Rx Llc2005-11-09Not AvailableUs
Amoxicillinpowder, for suspension400 mg/5mLoralRebel Distributors Corp.2006-12-28Not AvailableUs
Amoxicillincapsule250 mgoralRebel Distributors Corp.2005-09-11Not AvailableUs
Amoxicillincapsule500 mgoralRebel Distributors Corp.2005-09-11Not AvailableUs
Amoxicillinpowder, for suspension125 mg/5mLoralRebel Distributors Corp.2010-02-01Not AvailableUs
Amoxicillinpowder, for suspension250 mg/5mLoralRebel Distributors Corp.2010-02-01Not AvailableUs
Amoxicillintablet250 mgoralRebel Distributors Corp.2010-01-28Not AvailableUs
Amoxicillintablet, film coated875 mgoralRebel Distributors Corp.2005-07-13Not AvailableUs
Amoxicillincapsule250 mgoralPutney Inc1994-09-30Not AvailableUs
Amoxicillincapsule500 mgoralPutney Inc1994-09-30Not AvailableUs
Amoxicillincapsule500 mgoralAidarex Pharmaceuticals LLC2005-09-11Not AvailableUs
Amoxicillincapsule250 mgoralAidarex Pharmaceuticals LLC2005-09-11Not AvailableUs
Amoxicillinpowder, for suspension250 mg/5mLoralAidarex Pharmaceuticals LLC2006-06-19Not AvailableUs
Amoxicillinpowder, for suspension400 mg/5mLoralAidarex Pharmaceuticals LLC2006-12-28Not AvailableUs
Amoxicillintablet, film coated875 mgoralAidarex Pharmaceuticals LLC2005-11-09Not AvailableUs
Amoxicillinpowder, for suspension125 mg/5mLoralAidarex Pharmaceuticals LLC2006-06-19Not AvailableUs
Amoxicillinpowder, for suspension250 mg/5mLoralAidarex Pharmaceuticals LLC2006-06-19Not AvailableUs
Amoxicillinpowder, for suspension200 mg/5mLoralAidarex Pharmaceuticals LLC2006-12-28Not AvailableUs
Amoxicillintablet, coated875 mgoralLake Erie Medical DBA Quality Care Products LLC2006-03-29Not AvailableUs
Amoxicillintablet, film coated875 mgoralLake Erie Medical DBA Quality Care Products LLC2005-11-09Not AvailableUs
Amoxicillincapsule500 mgoralLake Erie Medical DBA Quality Care Products LLC1988-02-25Not AvailableUs
Amoxicillincapsule500 mgoralLake Erie Medical DBA Quality Care Products LLC2012-01-12Not AvailableUs
Amoxicillintablet, film coated875 mgoralLake Erie Medical DBA Quality Care Products LLC2005-07-13Not AvailableUs
Amoxicillinpowder, for suspension200 mg/5mLoralRebel Distributors Corp2006-06-19Not AvailableUs
Amoxicillincapsule250 mgoralAv Kare, Inc.2011-08-09Not AvailableUs
Amoxicillincapsule500 mgoralAv Kare, Inc.2011-08-09Not AvailableUs
Amoxicillincapsule250 mgoralPd Rx Pharmaceuticals, Inc.2007-03-01Not AvailableUs
Amoxicillincapsule500 mgoralPd Rx Pharmaceuticals, Inc.2007-03-01Not AvailableUs
Amoxicillintablet, chewable250 mgoralPd Rx Pharmaceuticals, Inc.2011-11-18Not AvailableUs
Amoxicillincapsule500 mgoralPd Rx Pharmaceuticals, Inc.1990-09-30Not AvailableUs
Amoxicillincapsule500 mgoralPd Rx Pharmaceuticals, Inc.2012-01-12Not AvailableUs
Amoxicillincapsule500 mgoralDr Reddys Laboratories Inc1979-08-02Not AvailableUs
Amoxicillinpowder, for suspension250 mg/5mLoralDr Reddys Laboratories Inc1979-09-19Not AvailableUs
Amoxicillinpowder, for suspension125 mg/5mLoralDr Reddys Laboratories Inc1979-09-19Not AvailableUs
Amoxicillincapsule250 mgoralDr Reddys Laboratories Inc1979-08-02Not AvailableUs
Amoxicillincapsule500 mgoralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2011-12-15Not AvailableUs
Amoxicillincapsule250 mgoralLake Erie Medical DBA Quality Care Products LLC2005-09-11Not AvailableUs
Amoxicillintablet, film coated875 mgoralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2011-12-15Not AvailableUs
Amoxicillincapsule500 mgoralUnit Dose Services1988-02-25Not AvailableUs
Amoxicillincapsule250 mgoralUnit Dose Services2007-03-01Not AvailableUs
Amoxicillincapsule500 mgoralNorthwind Pharmaceuticals, LLC2014-11-06Not AvailableUs
Amoxicillincapsule250 mgoralH.J. Harkins Company, Inc.2005-09-11Not AvailableUs
Amoxicillincapsule500 mgoralH.J. Harkins Company, Inc.2005-09-11Not AvailableUs
Amoxicillinpowder, for suspension400 mg/5mLoralH.J. Harkins Company, Inc.2006-12-28Not AvailableUs
Amoxicillinpowder, for suspension250 mg/5mLoralH.J. Harkins Company, Inc.2006-06-19Not AvailableUs
Amoxicillincapsule250 mgoralA S Medication Solutions Llc2005-09-11Not AvailableUs
Amoxicillincapsule500 mgoralA S Medication Solutions Llc2012-01-12Not AvailableUs
Amoxicillinpowder, for suspension125 mg/5mLoralA S Medication Solutions Llc2006-06-19Not AvailableUs
Amoxicillinpowder, for suspension250 mg/5mLoralA S Medication Solutions Llc1990-09-30Not AvailableUs
Amoxicillinpowder, for suspension125 mg/5mLoralA S Medication Solutions Llc2007-03-26Not AvailableUs
Amoxicillinpowder, for suspension250 mg/5mLoralA S Medication Solutions Llc1990-09-30Not AvailableUs
Amoxicillinpowder, for suspension250 mg/5mLoralA S Medication Solutions Llc1990-09-30Not AvailableUs
Amoxicillincapsule500 mgoralA S Medication Solutions Llc2012-01-12Not AvailableUs
Amoxicillintablet, chewable250 mgoralA S Medication Solutions Llc1993-01-01Not AvailableUs
Amoxicillintablet, film coated500 mgoralA S Medication Solutions Llc2005-07-13Not AvailableUs
Amoxicillintablet, film coated875 mgoralA S Medication Solutions Llc2005-11-09Not AvailableUs
Amoxicillinpowder, for suspension400 mg/5mLoralA S Medication Solutions Llc2003-02-26Not AvailableUs
Amoxicillincapsule500 mgoralA S Medication Solutions Llc2012-01-12Not AvailableUs
Amoxicillinpowder, for suspension400 mg/5mLoralA S Medication Solutions Llc2006-06-19Not AvailableUs
Amoxicillinpowder, for suspension400 mg/5mLoralA S Medication Solutions Llc2006-06-19Not AvailableUs
Amoxicillintablet, chewable250 mgoralPhysicians Total Care, Inc.2004-06-01Not AvailableUs
Amoxicillincapsule250 mgoralPhysicians Total Care, Inc.2003-10-29Not AvailableUs
Amoxicillincapsule500 mgoralPhysicians Total Care, Inc.1994-09-30Not AvailableUs
Amoxicillinpowder, for suspension125 mg/5mLoralPhysicians Total Care, Inc.2004-11-24Not AvailableUs
Amoxicillinpowder, for suspension250 mg/5mLoralPhysicians Total Care, Inc.2009-01-22Not AvailableUs
Amoxicillinpowder, for suspension200 mg/5mLoralPhysicians Total Care, Inc.2006-02-28Not AvailableUs
Amoxicillintablet, film coated875 mgoralPhysicians Total Care, Inc.2002-03-12Not AvailableUs
Amoxicillinpowder, for suspension400 mg/5mLoralPhysicians Total Care, Inc.2010-02-25Not AvailableUs
Amoxicillinpowder, for suspension400 mg/5mLoralDispensing Solutions Inc.2009-06-01Not AvailableUs
Amoxicillincapsule250 mgoralCardinal Health2011-11-18Not AvailableUs
Amoxicillincapsule500 mgoralCardinal Health2011-11-18Not AvailableUs
Amoxicillincapsule250 mgoralPd Rx Pharmaceuticals, Inc.2011-11-18Not AvailableUs
Amoxicillincapsule500 mgoralPd Rx Pharmaceuticals, Inc.1990-09-30Not AvailableUs
Amoxicillintablet, chewable250 mgoralPd Rx Pharmaceuticals, Inc.2010-01-28Not AvailableUs
Amoxicillintablet, coated875 mgoralPd Rx Pharmaceuticals, Inc.2006-03-29Not AvailableUs
Amoxicillincapsule500 mgoralLake Erie Medical DBA Quality Care Products LLC2005-11-09Not AvailableUs
Amoxicillintablet, film coated500 mgoralCitron Pharma LLC2005-11-09Not AvailableUs
Amoxicillintablet, film coated875 mgoralCitron Pharma LLC2005-11-09Not AvailableUs
Amoxicillincapsule250 mgoralCitron Pharma LLC2005-11-09Not AvailableUs
Amoxicillincapsule500 mgoralCitron Pharma LLC2005-11-09Not AvailableUs
Amoxicillinpowder, for suspension200 mg/5mLoralCitron Pharma LLC2006-12-28Not AvailableUs
Amoxicillinpowder, for suspension400 mg/5mLoralCitron Pharma LLC2006-12-28Not AvailableUs
Amoxicillintablet, film coated875 mgoralHikma Pharmaceutical2006-03-29Not AvailableUs
Amoxicillincapsule500 mgoralHikma Pharmaceutical2007-02-05Not AvailableUs
Amoxicillincapsule250 mgoralHikma Pharmaceutical2007-02-05Not AvailableUs
Amoxicillinpowder, for suspension400 mg/5mLoralHikma Pharmaceutical2006-06-19Not AvailableUs
Amoxicillinpowder, for suspension250 mg/5mLoralHikma Pharmaceutical2006-06-19Not AvailableUs
Amoxicillinpowder, for suspension200 mg/5mLoralHikma Pharmaceutical2006-06-19Not AvailableUs
Amoxicillinpowder, for suspension125 mg/5mLoralHikma Pharmaceutical2006-06-19Not AvailableUs
Amoxicillincapsule250 mgoralGreenstone LLC2005-09-112015-03-31Us
Amoxicillincapsule500 mgoralGreenstone LLC2005-09-112015-04-30Us
Amoxicillintablet, film coated875 mgoralGreenstone LLC2005-11-092015-05-31Us
Amoxicillincapsule250 mgoralGolden State Medical Supply, Inc.2009-07-15Not AvailableUs
Amoxicillincapsule500 mgoralGolden State Medical Supply, Inc.2009-07-15Not AvailableUs
Amoxicillinpowder, for suspension400 mg/5mLoralMorton Grove Pharmaceuticals, Inc.2007-06-18Not AvailableUs
Amoxicillincapsule500 mgoralREMEDYREPACK INC.2015-01-24Not AvailableUs
Amoxicillinpowder, for suspension250 mg/5mLoralDIRECT RX2014-01-01Not AvailableUs
Amoxicillincapsule500 mgoralDIRECT RX2014-01-01Not AvailableUs
Amoxicillinpowder, for suspension400 mg/5mLoralDIRECT RX2014-01-01Not AvailableUs
Amoxicillincapsule250 mgoralDIRECT RX2014-01-01Not AvailableUs
Amoxicillinpowder, for suspension250 mg/5mLoralProficient Rx LP2006-06-19Not AvailableUs
Amoxicillincapsule250 mgoralProficient Rx LP1988-02-25Not AvailableUs
Amoxicillincapsule500 mgoralProficient Rx LP2012-01-12Not AvailableUs
Amoxicillintablet, coated875 mgoralProficient Rx LP2006-03-29Not AvailableUs
Amoxicillinpowder, for suspension250 mg/5mLoralProficient Rx LP1990-09-30Not AvailableUs
Amoxicillinpowder, for suspension600 mg/5mLoralProficient Rx LP2006-06-19Not AvailableUs
Amoxicillincapsule250 mgoralAltura Pharmaceuticals, Inc.2010-01-01Not AvailableUs
Amoxicillincapsule500 mgoralAltura Pharmaceuticals, Inc.2010-01-01Not AvailableUs
Amoxicillincapsule500 mgoralReady Meds2012-01-12Not AvailableUs
Amoxicillincapsule500 mgoralTYA Pharmaceuticals2005-11-09Not AvailableUs
Amoxicillintablet, film coated500 mgoralAurobindo Pharma Limited2005-11-09Not AvailableUs
Amoxicillintablet, film coated875 mgoralAurobindo Pharma Limited2005-11-09Not AvailableUs
Amoxicillincapsule250 mgoralAurobindo Pharma Limited2005-11-09Not AvailableUs
Amoxicillincapsule500 mgoralAurobindo Pharma Limited2005-11-09Not AvailableUs
Amoxicillinpowder, for suspension200 mg/5mLoralAurobindo Pharma Limited2006-12-28Not AvailableUs
Amoxicillinpowder, for suspension400 mg/5mLoralAurobindo Pharma Limited2006-12-28Not AvailableUs
Amoxicillinpowder, for suspension125 mg/5mLoralAurobindo Pharma Limited2014-09-15Not AvailableUs
Amoxicillinpowder, for suspension250 mg/5mLoralAurobindo Pharma Limited2014-09-15Not AvailableUs
Amoxicillinpowder, for suspension250 mg/5mLoralMed Vantx, Inc.1990-09-30Not AvailableUs
Amoxicillincapsule500 mgoralMed Vantx, Inc.2005-09-11Not AvailableUs
Amoxicillintablet, film coated875 mgoralMed Vantx, Inc.2005-11-09Not AvailableUs
Amoxicillincapsule500 mgoralMed Vantx, Inc.1990-09-30Not AvailableUs
Amoxicillintablet, coated875 mgoralDispensing Solutions, Inc.2006-03-29Not AvailableUs
Amoxicillincapsule250 mgoralDAVA Pharmaceuticals, Inc.1988-02-25Not AvailableUs
Amoxicillincapsule500 mgoralDAVA Pharmaceuticals, Inc.1988-02-25Not AvailableUs
Amoxicillinfor suspension25 mg/mLoralDAVA Pharmaceuticals, Inc.1988-11-25Not AvailableUs
Amoxicillinfor suspension50 mg/mLoralDAVA Pharmaceuticals, Inc.1988-11-25Not AvailableUs
Amoxicillincapsule250 mgoralDAVA Pharmaceuticals Inc2014-08-01Not AvailableUs
Amoxicillintablet875 mgoralDAVA Pharmaceuticals, Inc.2009-07-15Not AvailableUs
Amoxicillinpowder, for suspension125 mg/5mLoralDAVA Pharmaceuticals Inc2014-08-01Not AvailableUs
Amoxicillinpowder, for suspension200 mg/5mLoralDAVA Pharmaceuticals Inc2014-08-01Not AvailableUs
Amoxicillinpowder, for suspension250 mg/5mLoralDAVA Pharmaceuticals Inc2014-08-01Not AvailableUs
Amoxicillinpowder, for suspension400 mg/5mLoralDAVA Pharmaceuticals Inc2014-08-01Not AvailableUs
Amoxicillincapsule500 mgoralDAVA Pharmaceuticals Inc2014-08-01Not AvailableUs
Amoxicillintablet, chewable125 mgoralDAVA Pharmaceuticals, Inc.1996-01-29Not AvailableUs
Amoxicillintablet, chewable250 mgoralDAVA Pharmaceuticals, Inc.1996-01-29Not AvailableUs
Amoxicillincapsule250 mgoralRed Pharm Drug Inc.2010-01-28Not AvailableUs
Amoxicillincapsule500 mgoralRed Pharm Drug Inc.2007-11-01Not AvailableUs
Amoxicillincapsule500 mgoralRed Pharm Drug Inc.2005-09-11Not AvailableUs
Amoxicillintablet, film coated875 mgoralRed Pharm Drug Inc.2005-11-09Not AvailableUs
Amoxicillintablet, coated875 mgoralRed Pharm Drug Inc.2006-03-29Not AvailableUs
Amoxicillintablet, coated875 mgoralPreferred Pharmaceuticals, Inc2011-05-18Not AvailableUs
Amoxicillinpowder, for suspension250 mg/5mLoralPreferred Pharmaceuticals, Inc.2011-06-15Not AvailableUs
Amoxicillinpowder, for suspension400 mg/5mLoralPreferred Pharmaceuticals, Inc.2011-06-15Not AvailableUs
Amoxicillinpowder, for suspension125 mg/5mLoralPreferred Pharmaceuticals, Inc.2011-06-15Not AvailableUs
Amoxicillincapsule250 mgoralPreferred Pharmaceuticals, Inc.2010-01-01Not AvailableUs
Amoxicillincapsule500 mgoralPreferred Pharmaceuticals, Inc.2010-01-01Not AvailableUs
Amoxicillinpowder, for suspension400 mg/5mLoralPreferred Pharmaceuticals, Inc2011-07-25Not AvailableUs
Amoxicillincapsule250 mgoralPreferred Pharmaceuticals, Inc.2013-01-30Not AvailableUs
Amoxicillincapsule500 mgoralPreferred Pharmaceuticals, Inc.2012-06-04Not AvailableUs
Amoxicillinpowder, for suspension250 mg/5mLoralPreferred Pharmaceuticals, Inc.2012-01-12Not AvailableUs
Amoxicillinpowder, for suspension125 mg/5mLoralPreferred Pharmaceuticals, Inc.2012-01-12Not AvailableUs
Amoxicillincapsule250 mgoralVirtus Pharmaceuticals, LLC2012-01-12Not AvailableUs
Amoxicillincapsule500 mgoralVirtus Pharmaceuticals, LLC2012-01-12Not AvailableUs
Amoxicillincapsule250 mgoralSanis Health IncNot AvailableNot AvailableCanada
Amoxicillincapsule500 mgoralSanis Health IncNot AvailableNot AvailableCanada
Amoxicillingranules for suspension125 mgoralSanis Health IncNot AvailableNot AvailableCanada
Amoxicillingranules for suspension250 mgoralSanis Health IncNot AvailableNot AvailableCanada
Amoxicillingranules for suspension125 mgoralSanis Health IncNot AvailableNot AvailableCanada
Amoxicillingranules for suspension250 mgoralSanis Health IncNot AvailableNot AvailableCanada
Over the Counter ProductsNot Available
International Brands
NameCompany
ActimoxiNot Available
AmoclenNot Available
AmolinNot Available
AmopenNot Available
AmopenixinNot Available
AmoxibioticNot Available
AmoxilGlaxoSmithKline
AMPCNot Available
Apo-AmoxiNot Available
ClamoxylNot Available
DispermoxNot Available
EfpenixNot Available
FlemoxinNot Available
HiconcilNot Available
IbiamoxNot Available
ImacillinNot Available
LarotidRoche
MoxacinNot Available
MoxalNot 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
Salts
Name/CASStructureProperties
Amoxicillin sodium
ThumbNot applicableDBSALT000868
Amoxycillin trihydrate
ThumbNot applicableDBSALT000867
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
Taxonomy
DescriptionThis 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].
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
  • Phenylacetamide
  • Alpha-amino acid or derivatives
  • Aralkylamine
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Thiazolidine
  • Tertiary carboxylic acid amide
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azetidine
  • Azacycle
  • Dialkylthioether
  • Hemithioaminal
  • Thioether
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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
PropertyValueProbability
Human Intestinal Absorption-0.9008
Blood Brain Barrier-0.9967
Caco-2 permeable-0.8722
P-glycoprotein substrateSubstrate0.5741
P-glycoprotein inhibitor INon-inhibitor0.9665
P-glycoprotein inhibitor IINon-inhibitor0.9968
Renal organic cation transporterNon-inhibitor0.9636
CYP450 2C9 substrateNon-substrate0.843
CYP450 2D6 substrateNon-substrate0.8446
CYP450 3A4 substrateNon-substrate0.5478
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 substrateNon-inhibitor0.907
CYP450 2D6 substrateNon-inhibitor0.9231
CYP450 2C19 substrateNon-inhibitor0.915
CYP450 3A4 substrateNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9767
Ames testNon AMES toxic0.9099
CarcinogenicityNon-carcinogens0.5439
BiodegradationNot ready biodegradable0.9606
Rat acute toxicity1.7036 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9996
hERG inhibition (predictor II)Non-inhibitor0.8761
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Capsuleoral250 mg
Capsuleoral500 mg
For suspensionoral25 mg/mL
For suspensionoral50 mg/mL
Granules for suspensionoral125 mg
Granules for suspensionoral25 mg
Granules for suspensionoral250 mg
Granules for suspensionoral50 mg
Powder, for suspensionoral125 mg/5mL
Powder, for suspensionoral200 mg/5mL
Powder, for suspensionoral250 mg/5mL
Powder, for suspensionoral400 mg/5mL
Powder, for suspensionoral600 mg/5mL
Tabletoral250 mg
Tabletoral875 mg
Tablet (chewable)oral125 mg
Tablet (chewable)oral250 mg
Tablet, chewableoral125 mg
Tablet, chewableoral250 mg
Tablet, coatedoral875 mg
Tablet, film coatedoral500 mg
Tablet, film coatedoral875 mg
Tablet, film coated, extended releaseoral1000; 62.5 mg/1; mg
Tablet, film coated, extended releaseoral775 mg
Prices
Unit descriptionCostUnit
Amoxil 400 mg/5ml Suspension 100ml Bottle19.99USD bottle
Amoxil 400 mg/5ml Suspension 75ml Bottle17.99USD bottle
Amoxicillin 400 mg/5ml Suspension 100ml Bottle16.99USD bottle
Amoxil 400 mg/5ml Suspension 50ml Bottle15.99USD bottle
Amoxicillin 250 mg/5ml Suspension 150ml Bottle14.0USD bottle
Amoxil 50 mg/ml Suspension 30ml Bottle13.99USD bottle
Amoxil 250 mg/5ml Suspension 100ml Bottle12.99USD bottle
Amoxil 250 mg/5ml Suspension 150ml Bottle12.99USD bottle
Amoxil 200 mg/5ml Suspension 100ml Bottle11.99USD bottle
Trimox 125 mg/5ml Suspension 100ml Bottle11.99USD bottle
Trimox 125 mg/5ml Suspension 150ml Bottle11.99USD bottle
Trimox 250 mg/5ml Suspension 80ml Bottle11.99USD bottle
Amoxil 875 mg tablet1.13USD tablet
Amoxil 400 mg Chew Tabs1.05USD tab
Amoxicillin 875 mg tablet0.89USD tablet
Amoxil 500 mg tablet0.77USD tablet
Novamoxin 250 mg Chewable Tablet0.64USD tablet
Amoxicillin 125 mg Chew Tabs0.57USD tab
Amoxil 500 mg capsule0.53USD capsule
Amoxicillin 500 mg tablet0.5USD tablet
Amoxicillin 250 mg Chew Tabs0.47USD tab
Amoxicillin 500 mg capsule0.47USD capsule
Novamoxin 125 mg Chewable Tablet0.44USD tablet
Apo-Amoxi 500 mg Capsule0.36USD capsule
Mylan-Amoxillin 500 mg Capsule0.36USD capsule
Novamoxin 500 mg Capsule0.36USD capsule
Nu-Amoxi 500 mg Capsule0.36USD capsule
Pms-Amoxicillin 500 mg Capsule0.36USD capsule
Amoxicillin 250 mg capsule0.25USD capsule
Apo-Amoxi 250 mg Capsule0.18USD capsule
Mylan-Amoxillin 250 mg Capsule0.18USD capsule
Novamoxin 250 mg Capsule0.18USD capsule
Nu-Amoxi 250 mg Capsule0.18USD capsule
Pms-Amoxicillin 250 mg Capsule0.18USD capsule
Apo-Amoxi 50 mg/ml Suspension0.06USD ml
Novamoxin 50 mg/ml Suspension0.06USD ml
Novamoxin Sugar-Reduced 50 mg/ml Suspension0.06USD ml
Nu-Amoxi 50 mg/ml Suspension0.06USD ml
Pms-Amoxicillin 50 mg/ml Suspension0.06USD ml
Apo-Amoxi 25 mg/ml Suspension0.04USD ml
Novamoxin 25 mg/ml Suspension0.04USD ml
Novamoxin Sugar-Reduced 25 mg/ml Suspension0.04USD ml
Nu-Amoxi 25 mg/ml Suspension0.04USD ml
Pms-Amoxicillin 25 mg/ml Suspension0.04USD ml
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 Solubility0.958 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity89.5 m3·mol-1ChemAxon
Polarizability35.53 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
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
ATC CodesJ01CA04
AHFS Codes
  • 08:12.16.08
PDB EntriesNot Available
FDA labelDownload (49.6 KB)
MSDSDownload (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