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Identification
NameAmpicillin
Accession NumberDB00415  (APRD00320)
TypeSmall Molecule
GroupsApproved, Vet Approved
Description

Semi-synthetic derivative of penicillin that functions as an orally active broad-spectrum antibiotic. [PubChem]

Structure
Thumb
Synonyms
(2S,5R,6R)-6-{[(2R)-2-amino-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
(2S,5R,6R)-6-{[(2R)-2-amino-2-phenylethanoyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
6-(D-(2-amino-2-Phenylacetamido))-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
ABPC
Aminobenzylpenicillin
AMP
Ampicilina
Ampicillin
Ampicillin Acid
Ampicillin Anhydrous
Ampicilline
Ampicillinum
Anhydrous ampicillin
AP
D-(-)-6-(alpha-Aminophenylacetamido)penicillanic acid
D-(-)-Ampicillin
D-(−)-6-(α-aminophenylacetamido)penicillanic acid
D-(−)-ampicillin
External Identifiers
  • Bayer 5427
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ampicillin for Injectionpowder for solution2 gintravenousFresenius Kabi Canada Ltd1998-07-27Not applicableCanada
Ampicillin for Injectionpowder for solution125 mgintramuscular; intravenousFresenius Kabi Canada LtdNot applicableNot applicableCanada
Ampicillin for Injectionpowder for solution250 mgintramuscular; intravenousFresenius Kabi Canada Ltd1998-08-14Not applicableCanada
Ampicillin for Injectionpowder for solution500 mgintramuscular; intravenousFresenius Kabi Canada Ltd1998-08-14Not applicableCanada
Ampicillin for Injectionpowder for solution1 gintramuscular; intravenousFresenius Kabi Canada Ltd1998-08-14Not applicableCanada
Ampicillin for Injection, USPpowder for solution250 mgintramuscular; intravenousSterimax IncNot applicableNot applicableCanada
Ampicillin for Injection, USPpowder for solution10 gintramuscular; intravenousSterimax IncNot applicableNot applicableCanada
Ampicillin for Injection, USPpowder for solution2 gintramuscular; intravenousSterimax IncNot applicableNot applicableCanada
Ampicillin for Injection, USPpowder for solution1 gintramuscular; intravenousSterimax IncNot applicableNot applicableCanada
Ampicillin for Injection, USPpowder for solution500 mgintramuscular; intravenousSterimax IncNot applicableNot applicableCanada
Ampicillin Sodium for Injection, USPpowder for solution250 mgintramuscular; intravenousTeva Canada Limited1992-12-31Not applicableCanada
Ampicillin Sodium for Injection, USPpowder for solution2000 mgintramuscular; intravenousTeva Canada Limited1992-12-31Not applicableCanada
Ampicillin Sodium for Injection, USPpowder for solution1000 mgintramuscular; intravenousTeva Canada Limited1992-12-31Not applicableCanada
Ampicillin Sodium for Injection, USPpowder for solution500 mgintramuscular; intravenousTeva Canada Limited1992-12-31Not applicableCanada
Ampicin for Injection 250mgpowder for solution250 mgintramuscular; intravenousBristol Labs Division Of Bristol Myers Squibb1963-12-312002-07-11Canada
Ampicin Inj 125mg/vialpowder for solution125 mgintramuscular; intravenousBristol Labs Division Of Bristol Myers Squibb1984-12-312002-07-11Canada
Ampicin Inj 1gmpowder for solution1 gintramuscular; intravenousBristol Labs Division Of Bristol Myers Squibb1965-12-312002-07-11Canada
Ampicin Inj 2000mgpowder for solution2 gintravenousBristol Labs Division Of Bristol Myers Squibb1968-12-312002-07-11Canada
Ampicin Inj 500mgpowder for solution500 mgintramuscular; intravenousBristol Labs Division Of Bristol Myers Squibb1964-12-312002-07-11Canada
Jaa Amp Tab 125mgtablet125 mgoralJaapharm Canada Inc.1989-12-312010-08-06Canada
Novo-ampicillin Pws 500mg/5mlpowder for solution500 mgoralNovopharm Limited1972-12-312015-10-26Canada
Novo-ampicillin Sus 125mg/5mlpowder for solution125 mgoralNovopharm Limited1971-12-312005-08-10Canada
Novo-ampicillin Sus 250mg/5mlpowder for solution250 mgoralNovopharm Limited1971-12-312005-08-10Canada
Nu-ampi Capsules 250mgcapsule250 mgoralNu Pharm Inc1990-12-312012-09-04Canada
Nu-ampi Capsules 500mgcapsule500 mgoralNu Pharm Inc1990-12-312012-09-04Canada
Nu-ampi Sus 125mg/5mlsuspension125 mgoralNu Pharm Inc1990-12-312012-09-04Canada
Nu-ampi Suspension 250mg/5mlsuspension250 mgoralNu Pharm Inc1990-12-312012-09-04Canada
Penbritin Cap 250mgcapsule250 mgoralAyerst Laboratories1962-12-311996-09-10Canada
Penbritin Cap 500mgcapsule500 mgoralAyerst Laboratories1964-12-311996-09-10Canada
Penbritin Inj 1000mgpowder for solution1 gintramuscular; intravenousAyerst Laboratories1965-12-311996-09-10Canada
Penbritin Inj 2000mgliquid2 gintramuscular; intravenousAyerst Laboratories1963-12-311999-04-12Canada
Penbritin Inj 250mgpowder for solution250 mgintramuscular; intravenousAyerst Laboratories1964-12-311996-09-10Canada
Penbritin Inj 500mgpowder for solution500 mgintramuscular; intravenousAyerst Laboratories1964-12-311996-09-10Canada
Penbritin Pws 250mg/5mlpowder for solution250 mgoralAyerst Laboratories1965-12-311996-09-10Canada
Penbritin-1000 Pws 1000mg/vialpowder for solution1 gintravenousWyeth Ayerst Canada Inc.1995-12-311999-04-12Canada
Penbritin-125 Pws 125mg/vialpowder for solution125 mgintramuscular; intravenousWyeth Ayerst Canada Inc.1995-12-311996-09-10Canada
Penbritin-250 Pws Im/iv 250mg/vialpowder for solution250 mgintramuscular; intravenousWyeth Ayerst Canada Inc.1994-12-311996-09-10Canada
Pro Ampi 250 Cap 250mgcapsule250 mgoralPro Doc Limitee1985-12-312003-07-31Canada
Pro Ampi 500 Cap 500mgcapsule500 mgoralPro Doc Limitee1985-12-312003-07-31Canada
Sterile Ampicillin Sodium 250mg USPpowder for solution250 mgintramuscular; intravenousBioniche Pharma (Canada) Ltd1994-12-312014-11-24Canada
Taro-ampicillin Cap 250mgcapsule250 mgoralTaro Pharmaceuticals Inc1993-12-312000-08-31Canada
Taro-ampicillin Cap 500mgcapsule500 mgoralTaro Pharmaceuticals Inc1993-12-312000-08-31Canada
Teva-ampicillincapsule250 mgoralTeva Canada Limited1971-12-31Not applicableCanada
Teva-ampicillincapsule500 mgoralTeva Canada Limited1971-12-31Not applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ampicillininjection, powder, for solution1 g/gintravenousGeneral Injectables & Vaccines, Inc2010-04-01Not applicableUs
Ampicillininjection, powder, for solution500 mg/1intramuscular; intravenousWG Critical Care, LLC2012-05-10Not applicableUs
Ampicillininjection, powder, for solution2 g/1intravenousSagent Pharmaceuticals2014-07-01Not applicableUs
Ampicillininjection, powder, for solution1 g/1intramuscular; intravenousSandoz Inc1971-03-03Not applicableUs
Ampicillininjection, powder, for solution1 g/1intramuscular; intravenousSandoz Inc1971-03-03Not applicableUs
Ampicillininjection, powder, for solution2 g/1intravenousMylan Institutional LLC2014-04-10Not applicableUs
Ampicillininjection, powder, for solution250 mg/1intramuscular; intravenousHospira, Inc.2015-09-04Not applicableUs
Ampicillininjection, powder, for solution1 g/1intramuscular; intravenousCardinal Health1987-05-12Not applicableUs
Ampicillininjection, powder, for solution250 mg/1intramuscular; intravenousAuro Medics Pharma Llc2012-02-01Not applicableUs
Ampicillininjection, powder, for solution250 mg/1intramuscular; intravenousMylan Institutional LLC2014-04-10Not applicableUs
Ampicillininjection, powder, for solution1 g/1intramuscular; intravenousSagent Pharmaceuticals2014-07-01Not applicableUs
Ampicillininjection, powder, for solution2 g/1intravenousSandoz Inc1987-02-19Not applicableUs
Ampicillininjection, powder, for solution2 g/1intravenousSandoz Inc1971-03-03Not applicableUs
Ampicillininjection, powder, for solution500 mg/1intramuscular; intravenousSandoz Inc1971-03-03Not applicableUs
Ampicillininjection, powder, for solution250 mg/1intramuscular; intravenousSandoz Inc1971-03-03Not applicableUs
Ampicillininjection, powder, for solution1 g/1intramuscular; intravenousMylan Institutional LLC2014-04-10Not applicableUs
Ampicillininjection, powder, for solution2 g/1intramuscular; intravenousCardinal Health1993-07-12Not applicableUs
Ampicillininjection, powder, for solution500 mg/1intramuscular; intravenousSagent Pharmaceuticals2014-07-01Not applicableUs
Ampicillininjection, powder, for solution1 g/1intravenousSandoz Inc1987-02-19Not applicableUs
Ampicillininjection, powder, for solution1 g/gintramuscular; intravenousGeneral Injectables & Vaccines, Inc2013-03-14Not applicableUs
Ampicillininjection, powder, for solution250 mg/1intramuscular; intravenousWG Critical Care, LLC2012-05-10Not applicableUs
Ampicillininjection, powder, for solution250 mg/1intramuscular; intravenousSandoz Inc1971-03-03Not applicableUs
Ampicillininjection, powder, for solution125 mg/1intramuscular; intravenousSandoz Inc1971-03-03Not applicableUs
Ampicillininjection, powder, for solution500 mg/1intramuscular; intravenousMylan Institutional LLC2014-04-10Not applicableUs
Ampicillininjection, powder, for solution250 mg/1intramuscular; intravenousCardinal Health1987-05-12Not applicableUs
Ampicillininjection, powder, for solution250 mg/1intramuscular; intravenousSagent Pharmaceuticals2014-07-01Not applicableUs
Ampicillininjection, powder, for solution10 g/1intravenousSandoz Inc1971-03-03Not applicableUs
Ampicillininjection, powder, for solution500 mg/500mgintramuscular; intravenousGeneral Injectables & Vaccines, Inc2013-03-13Not applicableUs
Ampicillininjection, powder, for solution2 g/1intravenousClaris Lifesciences, Inc.2010-04-25Not applicableUs
Ampicillininjection, powder, for solution2 g/1intravenousSandoz Inc1987-02-19Not applicableUs
Ampicillininjection, powder, for solution1 g/1intramuscular; intravenousC.O. Truxton, Inc.2009-12-28Not applicableUs
Ampicillininjection, powder, for solution10 g/1intravenousAPP Pharmaceuticals, LLC2013-12-20Not applicableUs
Ampicillininjection, powder, for solution250 mg/1intramuscular; intravenousCardinal Health1971-03-03Not applicableUs
Ampicillininjection, powder, for solution2 g/mLintravenousAGILA SPECIALTIES PRIVATE LIMITED2014-04-10Not applicableUs
Ampicillininjection, powder, for solution1 g/1intramuscular; intravenousGC Hanford Manufacturing Company2008-02-15Not applicableUs
Ampicillininjection, powder, for solution2 g/1intravenousSandoz Inc1971-03-03Not applicableUs
Ampicillininjection, powder, for solution1 g/gintramuscular; intravenousGeneral Injectables & Vaccines, Inc2011-09-07Not applicableUs
Ampicillininjection, powder, for solution1 g/1intramuscular; intravenousClaris Lifesciences, Inc.2010-04-25Not applicableUs
Ampicillininjection, powder, for solution1 g/1intravenousSandoz Inc1987-02-19Not applicableUs
Ampicillininjection, powder, for solution10 g/1intravenousHospira, Inc.2015-09-04Not applicableUs
Ampicillininjection, powder, for solution2 g/1intramuscular; intravenousAPP Pharmaceuticals, Inc.1993-07-12Not applicableUs
Ampicillininjection, powder, for solution10 g/100mLintravenousAuro Medics Pharma Llc2012-02-01Not applicableUs
Ampicillininjection, powder, for solution1 g/mLintramuscular; intravenousAGILA SPECIALTIES PRIVATE LIMITED2014-04-10Not applicableUs
Ampicillininjection, powder, for solution500 mg/1intramuscular; intravenousGC Hanford Manufacturing Company2008-02-15Not applicableUs
Ampicillininjection, powder, for solution500 mg/1intramuscular; intravenousSandoz Inc1971-03-03Not applicableUs
Ampicillininjection, powder, for solution500 mg/500mgintramuscular; intravenousGeneral Injectables & Vaccines, Inc2011-09-02Not applicableUs
Ampicillininjection, powder, for solution500 mg/1intramuscular; intravenousClaris Lifesciences, Inc.2010-04-25Not applicableUs
Ampicillincapsule500 mg/1oralREMEDYREPACK INC.2016-02-10Not applicableUs
Ampicillininjection, powder, for solution500 mg/mLintramuscular; intravenousAGILA SPECIALTIES PRIVATE LIMITED2014-04-10Not applicableUs
Ampicillininjection, powder, for solution250 mg/1intramuscular; intravenousGC Hanford Manufacturing Company2010-09-17Not applicableUs
Ampicillininjection, powder, for solution1 g/1intramuscular; intravenousSandoz Inc1971-03-03Not applicableUs
Ampicillininjection, powder, for solution10 g/100mLintravenousWG Critical Care, LLC2012-05-10Not applicableUs
Ampicillininjection, powder, for solution250 mg/1intramuscular; intravenousClaris Lifesciences, Inc.2010-04-25Not applicableUs
Ampicillininjection, powder, for solution10 g/1intravenousSandoz Inc1971-03-03Not applicableUs
Ampicillininjection, powder, for solution2 g/1intramuscular; intravenousHospira, Inc.2015-09-04Not applicableUs
Ampicillininjection, powder, for solution1 g/1intramuscular; intravenousAPP Pharmaceuticals, Inc.1987-05-12Not applicableUs
Ampicillininjection, powder, for solution2 g/1intravenousAuro Medics Pharma Llc2012-02-01Not applicableUs
Ampicillininjection, powder, for solution10 g/1intravenousGC Hanford Manufacturing Company2008-02-15Not applicableUs
Ampicillininjection, powder, for solution250 mg/1intramuscular; intravenousSandoz Inc1971-03-03Not applicableUs
Ampicillininjection, powder, for solution2 g/1intramuscular; intravenousWG Critical Care, LLC2012-05-10Not applicableUs
Ampicillininjection, powder, for solution1 g/1intramuscular; intravenousPutney Inc1971-03-03Not applicableUs
Ampicillininjection, powder, for solution2 g/1intravenousSandoz Inc1971-03-03Not applicableUs
Ampicillininjection, powder, for solution1 g/1intramuscular; intravenousHospira, Inc.2015-09-04Not applicableUs
Ampicillininjection, powder, for solution500 mg/1intramuscular; intravenousAPP Pharmaceuticals, Inc.1987-05-12Not applicableUs
Ampicillininjection, powder, for solution1 g/1intramuscular; intravenousAuro Medics Pharma Llc2012-02-01Not applicableUs
Ampicillininjection, powder, for solution250 mg/mLintramuscular; intravenousAGILA SPECIALTIES PRIVATE LIMITED2014-04-10Not applicableUs
Ampicillininjection, powder, for solution2 g/1intramuscular; intravenousGC Hanford Manufacturing Company2008-02-15Not applicableUs
Ampicillininjection, powder, for solution125 mg/1intramuscular; intravenousSandoz Inc1971-03-03Not applicableUs
Ampicillininjection, powder, for solution1 g/1intramuscular; intravenousWG Critical Care, LLC2012-05-10Not applicableUs
Ampicillininjection, powder, for solution10 g/100mLintravenousSagent Pharmaceuticals2010-07-07Not applicableUs
Ampicillininjection, powder, for solution500 mg/1intramuscular; intravenousSandoz Inc1971-03-03Not applicableUs
Ampicillininjection, powder, for solution500 mg/1intramuscular; intravenousHospira, Inc.2015-09-04Not applicableUs
Ampicillininjection, powder, for solution250 mg/1intramuscular; intravenousAPP Pharmaceuticals, Inc.1987-05-12Not applicableUs
Ampicillininjection, powder, for solution500 mg/1intramuscular; intravenousAuro Medics Pharma Llc2012-02-01Not applicableUs
Ampicillin Sodiuminjection, powder, for solution10 g/100mLintravenousAGILA SPECIALTIES PRIVATE LIMITED2014-04-08Not applicableUs
Ampicillin Sodiuminjection, powder, for solution10 g/100mLintravenousMylan Institutional LLC2014-04-08Not applicableUs
Apo Ampi Capsules 250mgcapsule250 mgoralApotex Inc1984-12-31Not applicableCanada
Apo Ampi Capsules 500mgcapsule500 mgoralApotex Inc1984-12-31Not applicableCanada
Apo Ampi Liq 125mg/5mlliquid125 mgoralApotex Inc1984-12-31Not applicableCanada
Apo Ampi Liq 250mg/5mlliquid250 mgoralApotex Inc1984-12-31Not applicableCanada
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AustrapenLennon Healthcare
BinotalBayer
PenbritinGlaxoSmithKline
PrincipenNot Available
ViccillinMeiji
Brand mixtures
NameLabellerIngredients
Ampicillin and SulbactamHospira, Inc.
Ampicillin Sodium and Sulbactam SodiumMylan Institutional LLC
Pro Biosan KitIcn Canada Ltd.
UnasynRoerig
Salts
Name/CASStructureProperties
Ampicillin sodium
69-52-3
Thumb
  • InChI Key: KLOHDWPABZXLGI-YWUHCJSESA-M
  • Monoisotopic Mass: 371.091571444
  • Average Mass: 371.387
DBSALT000533
Ampicillin trihydrate
ThumbNot applicableDBSALT001206
Categories
UNII7C782967RD
CAS number69-53-4
WeightAverage: 349.405
Monoisotopic: 349.109626801
Chemical FormulaC16H19N3O4S
InChI KeyInChIKey=AVKUERGKIZMTKX-NJBDSQKTSA-N
InChI
InChI=1S/C16H19N3O4S/c1-16(2)11(15(22)23)19-13(21)10(14(19)24-16)18-12(20)9(17)8-6-4-3-5-7-8/h3-7,9-11,14H,17H2,1-2H3,(H,18,20)(H,22,23)/t9-,10-,11+,14-/m1/s1
IUPAC Name
(2S,5R,6R)-6-[(2R)-2-amino-2-phenylacetamido]-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)[[email protected]]2NC(=O)[[email protected]](N)C1=CC=CC=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
  • 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 treatment of infection (Respiratory, GI, UTI and meningitis) due to E. coli, P. mirabilis, enterococci, Shigella, S. typhosa and other Salmonella, nonpenicillinase-producing N. gononhoeae, H. influenzae, staphylococci, streptococci including streptoc
PharmacodynamicsAmpicillin is a penicillin beta-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms. The name "penicillin" can either refer to several variants of penicillin available, or to the group of antibiotics derived from the penicillins. Ampicillin has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of Ampicillin results from the inhibition of cell wall synthesis and is mediated through Ampicillin binding to penicillin binding proteins (PBPs). Ampicillin is stable against hydrolysis by a variety of beta-lactamases, including penicillinases, and cephalosporinases and extended spectrum beta-lactamases.
Mechanism of actionBy binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, Ampicillin inhibits 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 Ampicillin interferes with an autolysin inhibitor.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationAmpicillin is excreted largely unchanged in the urine.
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Enteric bacteria and other eubacteria
  • Gram-negative Bacteria
  • Gram-positive Bacteria
  • Streptococcus pyogenes
  • Streptococcus pneumoniae
  • Neisseria meningitidis
  • Listeria monocytogenes
  • Haemophilus influenzae
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.927
Blood Brain Barrier-0.9961
Caco-2 permeable-0.8956
P-glycoprotein substrateSubstrate0.5603
P-glycoprotein inhibitor INon-inhibitor0.9626
P-glycoprotein inhibitor IINon-inhibitor0.9971
Renal organic cation transporterNon-inhibitor0.9689
CYP450 2C9 substrateNon-substrate0.8297
CYP450 2D6 substrateNon-substrate0.8447
CYP450 3A4 substrateNon-substrate0.5825
CYP450 1A2 substrateNon-inhibitor0.9253
CYP450 2C9 inhibitorNon-inhibitor0.9402
CYP450 2D6 inhibitorNon-inhibitor0.9401
CYP450 2C19 inhibitorNon-inhibitor0.9399
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9884
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.5363
BiodegradationNot ready biodegradable0.9844
Rat acute toxicity1.5620 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9998
hERG inhibition (predictor II)Non-inhibitor0.9031
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Acic fine chemicals inc
  • Apothecon inc div bristol myers squibb
  • Baxter healthcare corp anesthesia and critical care
  • Consolidated pharmaceutical group inc
  • Gc hanford manufacturing co
  • Istituto biochimico italiano spa
  • Instituto biochemico italiano spa
  • International medication systems ltd
  • Eli lilly and co
  • Marsam pharmaceuticals llc
  • Sandoz inc
  • Wyeth ayerst laboratories
  • Bristol laboratories inc div bristol myers co
  • Glaxosmithkline
  • Parke davis div warner lambert co
  • American antibiotics llc
  • Dava pharmaceuticals inc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Lederle laboratories div american cyanamid co
  • Mylan pharmaceuticals inc
  • Purepac pharmaceutical co
  • Teva pharmaceuticals usa inc
  • Vitarine pharmaceuticals inc
  • Pfizer laboratories div pfizer inc
  • Bristol myers squibb co
  • Apothecon sub bristol myers squibb co
Packagers
Dosage forms
FormRouteStrength
Capsuleoral500 mg/1
Injection, powder, for solutionintramuscular; intravenous1 g/1
Injection, powder, for solutionintramuscular; intravenous1 g/mL
Injection, powder, for solutionintramuscular; intravenous1 g/g
Injection, powder, for solutionintramuscular; intravenous125 mg/1
Injection, powder, for solutionintramuscular; intravenous2 g/1
Injection, powder, for solutionintramuscular; intravenous250 mg/1
Injection, powder, for solutionintramuscular; intravenous250 mg/mL
Injection, powder, for solutionintramuscular; intravenous500 mg/1
Injection, powder, for solutionintramuscular; intravenous500 mg/mL
Injection, powder, for solutionintramuscular; intravenous500 mg/500mg
Injection, powder, for solutionintravenous1 g/g
Injection, powder, for solutionintravenous1 g/1
Injection, powder, for solutionintravenous10 g/100mL
Injection, powder, for solutionintravenous10 g/1
Injection, powder, for solutionintravenous2 g/1
Injection, powder, for solutionintravenous2 g/mL
Injection, powder, for solutionintravenous
Injection, powder, for suspensionintramuscular; intravenous
Powder for solutionintramuscular; intravenous10 g
Powder for solutionintramuscular; intravenous2 g
Powder for solutionintramuscular; intravenous1000 mg
Powder for solutionintramuscular; intravenous2000 mg
Powder for solutionintramuscular; intravenous250 mg
Powder for solutionintramuscular; intravenous500 mg
Powder for solutionintravenous2 g
Capsuleoral250 mg
Capsuleoral500 mg
Liquidoral125 mg
Liquidoral250 mg
Tabletoral125 mg
Powder for solutionoral500 mg
Powder for solutionoral125 mg
Powder for solutionoral250 mg
Suspensionoral125 mg
Suspensionoral250 mg
Powder for solutionintramuscular; intravenous1 g
Liquidintramuscular; intravenous2 g
Powder for solutionintravenous1 g
Powder for solutionintramuscular; intravenous125 mg
Capsule; tabletoral
Injection, powder, for solutionintramuscular; intravenous
Prices
Unit descriptionCostUnit
Ampicillin 10 gm vial107.77USD vial
Ampicillin 2 gm vial16.75USD vial
Principen 250 mg/5ml Suspension 200ml Bottle16.27USD bottle
Ampicillin 1 gm vial8.64USD vial
Principen 250 mg/5ml Suspension 100ml Bottle7.99USD bottle
Ampicillin Sodium 2 g/vial7.56USD vial
Ampicillin Sodium 1 g/vial3.78USD vial
Ampicillin tr 250 mg capsule3.53USD capsule
Ampicillin Sodium 500 mg/vial2.26USD vial
Ampicillin Sodium 250 mg/vial2.15USD vial
Ampicillin tr 500 mg capsule0.61USD capsule
Ampicillin 500 mg capsule0.5USD capsule
Ampicillin 250 mg capsule0.44USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point208 dec °CPhysProp
water solubility1.01E+004 mg/L (at 21 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP1.35SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.605 mg/mLALOGPS
logP0.88ALOGPS
logP-2ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)3.24ChemAxon
pKa (Strongest Basic)7.44ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area112.73 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity87.52 m3·mol-1ChemAxon
Polarizability34.54 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

Jean Bouchaudon, Pierre Le Roy, Mayer Naoum Messer, “Process for the preparation of ampicillin.” U.S. Patent US3978078, issued December, 1974.

US3978078
General ReferencesNot Available
External Links
ATC CodesJ01CA01J01CA51J01CR01S01AA19
AHFS Codes
  • 08:12.16.08
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (71.8 KB)
Interactions
Drug Interactions
Drug
AcenocoumarolAmpicillin may increase the anticoagulant activities of Acenocoumarol.
AllopurinolThe risk of a hypersensitivity reaction to Ampicillin is increased when it is combined with Allopurinol.
AmikacinThe serum concentration of Amikacin can be decreased when it is combined with Ampicillin.
AtenololThe bioavailability of Atenolol can be decreased when combined with Ampicillin.
BiotinThe therapeutic efficacy of Ampicillin can be decreased when used in combination with Biotin.
ChloroquineThe serum concentration of Ampicillin can be decreased when it is combined with Chloroquine.
DemeclocyclineThe therapeutic efficacy of Ampicillin can be decreased when used in combination with Demeclocycline.
DicoumarolAmpicillin may increase the anticoagulant activities of Dicoumarol.
DoxycyclineThe therapeutic efficacy of Ampicillin can be decreased when used in combination with Doxycycline.
GentamicinThe serum concentration of Gentamicin can be decreased when it is combined with Ampicillin.
KanamycinThe serum concentration of Kanamycin can be decreased when it is combined with Ampicillin.
LanthanumThe serum concentration of Ampicillin can be decreased when it is combined with Lanthanum.
Lanthanum carbonateThe serum concentration of Ampicillin can be decreased when it is combined with Lanthanum carbonate.
MethotrexateThe serum concentration of Methotrexate can be increased when it is combined with Ampicillin.
MinocyclineThe therapeutic efficacy of Ampicillin can be decreased when used in combination with Minocycline.
Mycophenolate mofetilThe serum concentration of the active metabolites of Mycophenolate mofetil can be reduced when Mycophenolate mofetil is used in combination with Ampicillin resulting in a loss in efficacy.
Mycophenolic acidThe serum concentration of the active metabolites of Mycophenolic acid can be reduced when Mycophenolic acid is used in combination with Ampicillin resulting in a loss in efficacy.
NeomycinThe serum concentration of Neomycin can be decreased when it is combined with Ampicillin.
OxytetracyclineThe therapeutic efficacy of Ampicillin can be decreased when used in combination with Oxytetracycline.
Picosulfuric acidThe therapeutic efficacy of Sodium picosulfate can be decreased when used in combination with Ampicillin.
ProbenecidThe serum concentration of Ampicillin can be increased when it is combined with Probenecid.
StreptomycinThe serum concentration of Streptomycin can be decreased when it is combined with Ampicillin.
TetracyclineThe therapeutic efficacy of Ampicillin can be decreased when used in combination with Tetracycline.
TobramycinThe serum concentration of Tobramycin can be decreased when it is combined with Ampicillin.
WarfarinAmpicillin may increase the anticoagulant activities of Warfarin.
Food Interactions
  • Take on an empty stomach.

Targets

Kind
Protein
Organism
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
Pharmacological action
yes
Actions
inhibitor
General Function:
Transferase activity, transferring acyl groups
Specific Function:
Not Available
Gene Name:
pbp2a
Uniprot ID:
Q8DNB6
Molecular Weight:
80797.94 Da
References
  1. Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [PubMed:7447421 ]
Kind
Protein
Organism
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
Pharmacological action
yes
Actions
inhibitor
General Function:
Transferase activity, transferring acyl groups
Specific Function:
Not Available
Gene Name:
pbp1b
Uniprot ID:
Q7CRA4
Molecular Weight:
89479.92 Da
References
  1. Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [PubMed:7447421 ]
  2. 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:16627568 ]
Kind
Protein
Organism
Streptococcus pneumoniae
Pharmacological action
yes
Actions
inhibitor
General Function:
Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function:
Not Available
Gene Name:
pbp3
Uniprot ID:
Q75Y35
Molecular Weight:
45209.84 Da
References
  1. Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [PubMed:7447421 ]
  2. Li YH, Tanno M, Itoh T, Yamada H: Role of the monocarboxylic acid transport system in the intestinal absorption of an orally active beta-lactam prodrug: carindacillin as a model. Int J Pharm. 1999 Nov 30;191(2):151-9. [PubMed:10564841 ]
Kind
Protein
Organism
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
Pharmacological action
yes
Actions
inhibitor
General Function:
Penicillin binding
Specific Function:
Cell wall formation.
Gene Name:
pbpA
Uniprot ID:
Q8DR59
Molecular Weight:
79700.9 Da
References
  1. Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [PubMed:7447421 ]
Kind
Protein
Organism
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
Pharmacological action
yes
Actions
inhibitor
General Function:
Penicillin binding
Specific Function:
Not Available
Gene Name:
penA
Uniprot ID:
P0A3M6
Molecular Weight:
73872.305 Da
References
  1. Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [PubMed:7447421 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Proton-dependent oligopeptide secondary active transmembrane transporter activity
Specific Function:
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.
Gene Name:
SLC15A1
Uniprot ID:
P46059
Molecular Weight:
78805.265 Da
References
  1. 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:15567297 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Peptide:proton symporter activity
Specific Function:
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides.
Gene Name:
SLC15A2
Uniprot ID:
Q16348
Molecular Weight:
81782.77 Da
References
  1. Pedretti A, De Luca L, Marconi C, Regazzoni L, Aldini G, Vistoli G: Fragmental modeling of hPepT2 and analysis of its binding features by docking studies and pharmacophore mapping. Bioorg Med Chem. 2011 Aug 1;19(15):4544-51. doi: 10.1016/j.bmc.2011.06.027. Epub 2011 Jun 16. [PubMed:21741846 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Transmembrane receptor protein tyrosine kinase activity
Specific Function:
Tyrosine-protein kinase that acts as cell-surface receptor for ANGPT1, ANGPT2 and ANGPT4 and regulates angiogenesis, endothelial cell survival, proliferation, migration, adhesion and cell spreading, reorganization of the actin cytoskeleton, but also maintenance of vascular quiescence. Has anti-inflammatory effects by preventing the leakage of proinflammatory plasma proteins and leukocytes from ...
Gene Name:
TEK
Uniprot ID:
Q02763
Molecular Weight:
125829.005 Da
References
  1. Gong XW, Mai JH, Xu YH: Discovery of loperamide as an antagonist of angiopoietin1 and angiopoietin2 by virtual screening. Bioorg Med Chem Lett. 2012 Apr 1;22(7):2388-92. doi: 10.1016/j.bmcl.2012.02.036. Epub 2012 Feb 22. [PubMed:22406116 ]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
no
Actions
other/unknown
General Function:
Toxic substance binding
Specific Function:
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloidal osmotic pressure of blood. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc.
Gene Name:
ALB
Uniprot ID:
P02768
Molecular Weight:
69365.94 Da
References
  1. Bratlid D, Bergan T: Displacement of albumin-bound antimicrobial agents by bilirubin. Pharmacology. 1976;14(5):464-72. [PubMed:1031216 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Symporter activity
Specific Function:
Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Also relative uptake activity ratio of carnitine to TEA is 11.3.
Gene Name:
SLC22A5
Uniprot ID:
O76082
Molecular Weight:
62751.08 Da
References
  1. Ganapathy ME, Huang W, Rajan DP, Carter AL, Sugawara M, Iseki K, Leibach FH, Ganapathy V: beta-lactam antibiotics as substrates for OCTN2, an organic cation/carnitine transporter. J Biol Chem. 2000 Jan 21;275(3):1699-707. [PubMed:10636865 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Proton-dependent oligopeptide secondary active transmembrane transporter activity
Specific Function:
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.
Gene Name:
SLC15A1
Uniprot ID:
P46059
Molecular Weight:
78805.265 Da
References
  1. Covitz KM, Amidon GL, Sadee W: Human dipeptide transporter, hPEPT1, stably transfected into Chinese hamster ovary cells. Pharm Res. 1996 Nov;13(11):1631-4. [PubMed:8956326 ]
  2. Guo A, Hu P, Balimane PV, Leibach FH, Sinko PJ: Interactions of a nonpeptidic drug, valacyclovir, with the human intestinal peptide transporter (hPEPT1) expressed in a mammalian cell line. J Pharmacol Exp Ther. 1999 Apr;289(1):448-54. [PubMed:10087037 ]
  3. 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:15567297 ]
  4. 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:9374833 ]
  5. 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:16627568 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Peptide:proton symporter activity
Specific Function:
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides.
Gene Name:
SLC15A2
Uniprot ID:
Q16348
Molecular Weight:
81782.77 Da
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:9374833 ]
  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:15567297 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Symporter activity
Specific Function:
Proton-coupled monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucine, valine and isoleucine, and the ketone bodies acetoacetate, beta-hydroxybutyrate and acetate. Depending on the tissue and on cicumstances, mediates the import or export of lactic acid and ketone bod...
Gene Name:
SLC16A1
Uniprot ID:
P53985
Molecular Weight:
53943.685 Da
References
  1. Li YH, Tanno M, Itoh T, Yamada H: Role of the monocarboxylic acid transport system in the intestinal absorption of an orally active beta-lactam prodrug: carindacillin as a model. Int J Pharm. 1999 Nov 30;191(2):151-9. [PubMed:10564841 ]
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:10