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Identification
NameAmpicillin
Accession NumberDB00415  (APRD00320)
TypeSmall Molecule
GroupsApproved
Description

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

Structure
Thumb
Synonyms
SynonymLanguageCode
(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 acidNot AvailableNot Available
(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 acidNot AvailableNot Available
6-(D-(2-amino-2-Phenylacetamido))-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acidNot AvailableNot Available
ABPCNot AvailableNot Available
AminobenzylpenicillinNot AvailableNot Available
AMPNot AvailableNot Available
AmpicilinaSpanishINN
AmpicillinNot AvailableINN, BAN, USAN, JAN
Ampicillin AcidNot AvailableNot Available
Ampicillin AnhydrousNot AvailableNot Available
AmpicillineFrenchINN
AmpicillinumLatinINN
Anhydrous ampicillinNot AvailableNot Available
APNot AvailableNot Available
D-(-)-6-(alpha-Aminophenylacetamido)penicillanic acidNot AvailableNot Available
D-(-)-AmpicillinNot AvailableNot Available
D-(−)-6-(α-aminophenylacetamido)penicillanic acidNot AvailableNot Available
D-(−)-ampicillinNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ampicillininjection, powder, for solution1 gintramuscular; intravenousC.O. Truxton, Inc.2009-12-28Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillincapsule250 mgoralSandoz Inc1995-08-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillincapsule500 mgoralSandoz Inc1995-08-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution125 mgintramuscular; intravenousSandoz Inc1971-03-03Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution250 mgintramuscular; intravenousSandoz Inc1971-03-03Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution1 gintramuscular; intravenousSandoz Inc1971-03-03Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution500 mgintramuscular; intravenousSandoz Inc1971-03-03Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution2 gintravenousSandoz Inc1971-03-03Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution10 gintravenousSandoz Inc1971-03-03Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution1 gintravenousSandoz Inc1987-02-19Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution2 gintravenousSandoz Inc1987-02-19Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution125 mgintramuscular; intravenousSandoz Inc1971-03-03Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution250 mgintramuscular; intravenousSandoz Inc1971-03-03Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution1 gintramuscular; intravenousSandoz Inc1971-03-03Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution500 mgintramuscular; intravenousSandoz Inc1971-03-03Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution2 gintravenousSandoz Inc1971-03-03Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution10 gintravenousSandoz Inc1971-03-03Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution1 gintravenousSandoz Inc1987-02-19Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution2 gintravenousSandoz Inc1987-02-19Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution2 gintramuscular; intravenousGC Hanford Manufacturing Company2008-02-15Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution10 gintravenousGC Hanford Manufacturing Company2008-02-15Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution250 mgintramuscular; intravenousGC Hanford Manufacturing Company2010-09-17Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution500 mgintramuscular; intravenousGC Hanford Manufacturing Company2008-02-15Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution1 gintramuscular; intravenousGC Hanford Manufacturing Company2008-02-15Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution250 mgintramuscular; intravenousSagent Pharmaceuticals2014-07-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution500 mgintramuscular; intravenousSagent Pharmaceuticals2014-07-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution1 gintramuscular; intravenousSagent Pharmaceuticals2014-07-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution2 gintravenousSagent Pharmaceuticals2014-07-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution10 g/100mLintravenousSagent Pharmaceuticals2010-07-07Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution1 gintramuscular; intravenousPutney Inc1971-03-03Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution250 mgintramuscular; intravenousClaris Lifesciences, Inc.2010-04-25Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution500 mgintramuscular; intravenousClaris Lifesciences, Inc.2010-04-25Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution1 gintramuscular; intravenousClaris Lifesciences, Inc.2010-04-25Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution2 gintravenousClaris Lifesciences, Inc.2010-04-25Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution250 mgintramuscular; intravenousWG Critical Care, LLC2012-05-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution500 mgintramuscular; intravenousWG Critical Care, LLC2012-05-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution1 gintramuscular; intravenousWG Critical Care, LLC2012-05-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution2 gintramuscular; intravenousWG Critical Care, LLC2012-05-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution10 g/100mLintravenousWG Critical Care, LLC2012-05-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution500 mg/500mgintramuscular; intravenousGeneral Injectables & Vaccines, Inc2011-09-02Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution1 g/gintramuscular; intravenousGeneral Injectables & Vaccines, Inc2011-09-07Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution500 mg/500mgintramuscular; intravenousGeneral Injectables & Vaccines, Inc2013-03-13Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution1 g/gintramuscular; intravenousGeneral Injectables & Vaccines, Inc2013-03-14Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution1 g/gintravenousGeneral Injectables & Vaccines, Inc2010-04-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillincapsule500 mgoralH.J. Harkins Company, Inc.1988-02-25Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillincapsule500 mgoralA S Medication Solutions Llc1988-02-25Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillincapsule500 mgoralPhysicians Total Care, Inc.2011-03-22Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution250 mgintramuscular; intravenousAuro Medics Pharma Llc2012-02-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution500 mgintramuscular; intravenousAuro Medics Pharma Llc2012-02-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution1 gintramuscular; intravenousAuro Medics Pharma Llc2012-02-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution2 gintramuscular; intravenousAuro Medics Pharma Llc2012-02-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution10 g/100mLintravenousAuro Medics Pharma Llc2012-02-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution250 mgintramuscular; intravenousCardinal Health1971-03-03Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution250 mgintramuscular; intravenousCardinal Health1987-05-12Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution2 gintramuscular; intravenousCardinal Health1993-07-12Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution1 gintramuscular; intravenousCardinal Health1987-05-12Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillincapsule250 mgoralPd Rx Pharmaceuticals, Inc.1995-08-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillincapsule500 mgoralPd Rx Pharmaceuticals, Inc.1988-02-25Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution250 mgintramuscular; intravenousAPP Pharmaceuticals, Inc.1987-05-12Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution500 mgintramuscular; intravenousAPP Pharmaceuticals, Inc.1987-05-12Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution1 gintramuscular; intravenousAPP Pharmaceuticals, Inc.1987-05-12Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution2 gintramuscular; intravenousAPP Pharmaceuticals, Inc.1993-07-12Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution10 gintravenousAPP Pharmaceuticals, LLC2013-12-20Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillincapsule250 mgoralDAVA Pharmaceuticals, Inc.1988-02-25Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillincapsule500 mgoralDAVA Pharmaceuticals, Inc.1988-02-25Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillinsuspension25 mg/mLoralDAVA Pharmaceuticals, Inc.1989-02-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillinsuspension50 mg/mLoralDAVA Pharmaceuticals, Inc.1989-02-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution250 mg/mLintramuscular; intravenousAGILA SPECIALTIES PRIVATE LIMITED2014-04-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution500 mg/mLintramuscular; intravenousAGILA SPECIALTIES PRIVATE LIMITED2014-04-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution1 g/mLintramuscular; intravenousAGILA SPECIALTIES PRIVATE LIMITED2014-04-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillininjection, powder, for solution2 g/mLintravenousAGILA SPECIALTIES PRIVATE LIMITED2014-04-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ampicillin Sodiuminjection, powder, for solution10 g/100mLintravenousAGILA SPECIALTIES PRIVATE LIMITED2014-04-08Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Over the Counter ProductsNot Available
International Brands
NameCompany
AustrapenLennon Healthcare
BinotalBayer
PenbritinGlaxoSmithKline
PrincipenNot Available
ViccillinMeiji
Brand mixtures
Brand NameIngredients
Pro Biosan KitAmpicillin + Probenecid
Synergistin Injectable SuspensionAmpicillin + Sulbactam (Sulbactam Benzathine)
Salts
Name/CASStructureProperties
Ampicillin sodium
69-52-3
Thumb
  • InChI Key: KLOHDWPABZXLGI-YWUHCJSESA-M
  • Monoisotopic Mass: 371.091571444
  • Average Mass: 371.387
DBSALT000533
Categories
CAS number69-53-4
WeightAverage: 349.405
Monoisotopic: 349.109626801
Chemical FormulaC16H19N3O4S
InChI KeyAVKUERGKIZMTKX-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)[C@H]2NC(=O)[C@H](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.
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 substrateNon-inhibitor0.9402
CYP450 2D6 substrateNon-inhibitor0.9401
CYP450 2C19 substrateNon-inhibitor0.9399
CYP450 3A4 substrateNon-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
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
Capsuleoral250 mg
Capsuleoral500 mg
Injection, powder, for solutionintramuscular; intravenous1 g
Injection, powder, for solutionintramuscular; intravenous1 g/g
Injection, powder, for solutionintramuscular; intravenous1 g/mL
Injection, powder, for solutionintramuscular; intravenous125 mg
Injection, powder, for solutionintramuscular; intravenous2 g
Injection, powder, for solutionintramuscular; intravenous250 mg
Injection, powder, for solutionintramuscular; intravenous250 mg/mL
Injection, powder, for solutionintramuscular; intravenous500 mg
Injection, powder, for solutionintramuscular; intravenous500 mg/500mg
Injection, powder, for solutionintramuscular; intravenous500 mg/mL
Injection, powder, for solutionintravenous1 g
Injection, powder, for solutionintravenous1 g/g
Injection, powder, for solutionintravenous10 g
Injection, powder, for solutionintravenous10 g/100mL
Injection, powder, for solutionintravenous2 g
Injection, powder, for solutionintravenous2 g/mL
Suspensionoral25 mg/mL
Suspensionoral50 mg/mL
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 ReferenceNot Available
External Links
ATC CodesJ01CA01S01AA19
AHFS Codes
  • 08:12.16.08
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (71.8 KB)
Interactions
Drug Interactions
Drug
AcenocoumarolMay enhance the anticoagulant effect of Vitamin K Antagonists.
AllopurinolMay enhance the potential for allergic or hypersensitivity reactions to Ampicillin.
AmikacinMay decrease the serum concentration of Aminoglycosides. Primarily associated with extended spectrum penicillins, and patients with renal dysfunction. Exceptions: Amoxicillin; Ampicillin; Cloxacillin; Dicloxacillin; Nafcillin; Oxacillin; Penicillin G (Parenteral/Aqueous); Penicillin G Benzathine; Penicillin G Procaine; Penicillin V Potassium.
AtenololMay decrease the bioavailability of Atenolol.
BiotinTetracycline Derivatives may diminish the therapeutic effect of Penicillins.
ChloroquineMay decrease the serum concentration of Ampicillin.
DoxycyclineTetracycline Derivatives may diminish the therapeutic effect of Penicillins.
KanamycinMay decrease the serum concentration of Aminoglycosides. Primarily associated with extended spectrum penicillins, and patients with renal dysfunction. Exceptions: Amoxicillin; Ampicillin; Cloxacillin; Dicloxacillin; Nafcillin; Oxacillin; Penicillin G (Parenteral/Aqueous); Penicillin G Benzathine; Penicillin G Procaine; Penicillin V Potassium.
Lanthanum carbonateLanthanum may decrease the serum concentration of Ampicillin.
MethotrexatePenicillins may increase the serum concentration of Methotrexate.
MinocyclineTetracycline Derivatives may diminish the therapeutic effect of Penicillins.
Mycophenolate mofetilMay decrease serum concentrations of the active metabolite(s) of Mycophenolate. This effect appears to be the result of impaired enterohepatic recirculation.
Mycophenolic acidMay decrease serum concentrations of the active metabolite(s) of Mycophenolate. This effect appears to be the result of impaired enterohepatic recirculation.
NeomycinMay decrease the serum concentration of Aminoglycosides. Primarily associated with extended spectrum penicillins, and patients with renal dysfunction. Exceptions: Amoxicillin; Ampicillin; Cloxacillin; Dicloxacillin; Nafcillin; Oxacillin; Penicillin G (Parenteral/Aqueous); Penicillin G Benzathine; Penicillin G Procaine; Penicillin V Potassium.
ProbenecidMay increase the serum concentration of Penicillins.
StreptomycinMay decrease the serum concentration of Aminoglycosides. Primarily associated with extended spectrum penicillins, and patients with renal dysfunction. Exceptions: Amoxicillin; Ampicillin; Cloxacillin; Dicloxacillin; Nafcillin; Oxacillin; Penicillin G (Parenteral/Aqueous); Penicillin G Benzathine; Penicillin G Procaine; Penicillin V Potassium.
TetracyclineTetracycline Derivatives may diminish the therapeutic effect of Penicillins.
Food Interactions
  • Take on an empty stomach.

Targets

1. Penicillin-binding protein 2a

Kind: protein

Organism: Streptococcus pneumoniae (strain ATCC BAA-255 / R6)

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Penicillin-binding protein 2a Q8DNB6 Details

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

2. Penicillin-binding protein 1b

Kind: protein

Organism: Streptococcus pneumoniae (strain ATCC BAA-255 / R6)

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Penicillin-binding protein 1b Q7CRA4 Details

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
  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
  3. 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
  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. 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
  6. 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
  7. 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

3. Penicillin-binding protein 3

Kind: protein

Organism: Streptococcus pneumoniae

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Penicillin-binding protein 3 Q75Y35 Details

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
  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

4. Penicillin-binding protein 1A

Kind: protein

Organism: Streptococcus pneumoniae (strain ATCC BAA-255 / R6)

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Penicillin-binding protein 1A Q8DR59 Details

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

5. Penicillin-binding protein 2B

Kind: protein

Organism: Streptococcus pneumoniae (strain ATCC BAA-255 / R6)

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Penicillin-binding protein 2B P0A3M6 Details

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

6. Solute carrier family 15 member 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

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

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

7. Solute carrier family 15 member 2

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

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

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

8. Angiopoietin-1 receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Angiopoietin-1 receptor Q02763 Details

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

Carriers

1. Serum albumin

Kind: protein

Organism: Human

Pharmacological action: no

Actions: other/unknown

Components

Name UniProt ID Details
Serum albumin P02768 Details

References:

  1. Bratlid D, Bergan T: Displacement of albumin-bound antimicrobial agents by bilirubin. Pharmacology. 1976;14(5):464-72. Pubmed

Transporters

1. Solute carrier family 22 member 5

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 5 O76082 Details

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

2. 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. 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
  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
  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
  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
  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

3. 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

4. Monocarboxylate transporter 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Monocarboxylate transporter 1 P53985 Details

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

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:10