Identification

Name
Ampicillin
Accession Number
DB00415
Description

Ampicillin is a semi-synthetic derivative of penicillin that functions as an orally active broad-spectrum antibiotic.

Type
Small Molecule
Groups
Approved, Vet approved
Structure
Thumb
Weight
Average: 349.405
Monoisotopic: 349.109626801
Chemical Formula
C16H19N3O4S
Synonyms
  • ABPC
  • Aminobenzylpenicillin
  • Ampicilina
  • Ampicillin
  • Ampicillin (anhydrous)
  • Ampicillin acid
  • Ampicillin anhydrous
  • Ampicillin, anhydrous
  • Ampicilline
  • Ampicillinum
  • Anhydrous ampicillin
  • AP
  • D-(−)-6-(α-aminophenylacetamido)penicillanic acid
  • D-(−)-ampicillin
External IDs
  • AY-6108
  • Bayer 5427
  • BRL-1341
  • NSC-528986
  • P-50
  • WY 5103

Pharmacology

Indication

For 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

Associated Conditions
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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Pharmacodynamics

Ampicillin 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 action

By 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.

TargetActionsOrganism
APenicillin-binding protein 2a
inhibitor
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
APenicillin-binding protein 1b
inhibitor
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
APenicillin-binding protein 3
inhibitor
Streptococcus pneumoniae
APenicillin-binding protein 1A
inhibitor
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
APenicillin-binding protein 2B
inhibitor
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
USolute carrier family 15 member 1Not AvailableHumans
USolute carrier family 15 member 2Not AvailableHumans
UAngiopoietin-1 receptorNot AvailableHumans
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination

Ampicillin is excreted largely unchanged in the urine.

Half-life
Not Available
Clearance
Not Available
Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More
Toxicity
Not Available
Affected organisms
  • Enteric bacteria and other eubacteria
  • Gram-negative Bacteria
  • Gram-positive Bacteria
  • Streptococcus pyogenes
  • Streptococcus pneumoniae
  • Neisseria meningitidis
  • Listeria monocytogenes
  • Haemophilus influenzae
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirAmpicillin may decrease the excretion rate of Abacavir which could result in a higher serum level.
AcarboseAcarbose may decrease the excretion rate of Ampicillin which could result in a higher serum level.
AceclofenacAceclofenac may decrease the excretion rate of Ampicillin which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Ampicillin which could result in a higher serum level.
AcenocoumarolAmpicillin may increase the anticoagulant activities of Acenocoumarol.
AcetaminophenAcetaminophen may decrease the excretion rate of Ampicillin which could result in a higher serum level.
AcetazolamideAcetazolamide may increase the excretion rate of Ampicillin which could result in a lower serum level and potentially a reduction in efficacy.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Ampicillin which could result in a higher serum level.
AclidiniumAmpicillin may decrease the excretion rate of Aclidinium which could result in a higher serum level.
AcrivastineAmpicillin may decrease the excretion rate of Acrivastine which could result in a higher serum level.
Additional Data Available
  • Extended Description
    Extended Description
    Available for Purchase

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity
    Available for Purchase

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level
    Available for Purchase

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action
    Available for Purchase

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
  • Take on an empty stomach.

Products

Purchasing individual compounds or compound libraries for your research?
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Product Ingredients
IngredientUNIICASInChI Key
Ampicillin sodiumJFN36L5S8K69-52-3KLOHDWPABZXLGI-UHFFFAOYSA-M
Ampicillin trihydrateHXQ6A1N7R67177-48-2RXDALBZNGVATNY-CWLIKTDRSA-N
Product Images
International/Other Brands
Austrapen (Lennon Healthcare) / Binotal (Bayer) / Penbritin (GlaxoSmithKline) / Principen / Redicilin / Semicillin / Tokiocillin / Ultrabion / Viccillin (Meiji)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Ampicillin for InjectionPowder, for solutionIntramuscular; IntravenousFresenius KabiNot applicableNot applicableCanada flag
Ampicillin for Injection, USPPowder, for solutionIntramuscular; IntravenousSterimax IncNot applicableNot applicableCanada flag
Ampicillin for Injection, USPPowder, for solutionIntramuscular; IntravenousFresenius Kabi1998-08-14Not applicableCanada flag
Ampicillin for Injection, USPPowder, for solutionIntravenousFresenius Kabi1998-07-27Not applicableCanada flag
Ampicillin for Injection, USPPowder, for solutionIntramuscular; IntravenousSterimax IncNot applicableNot applicableCanada flag
Ampicillin for Injection, USPPowder, for solutionIntramuscular; IntravenousFresenius Kabi1998-08-14Not applicableCanada flag
Ampicillin for Injection, USPPowder, for solutionIntramuscular; IntravenousSterimax IncNot applicableNot applicableCanada flag
Ampicillin for Injection, USPPowder, for solutionIntramuscular; IntravenousSterimax IncNot applicableNot applicableCanada flag
Ampicillin for Injection, USPPowder, for solutionIntramuscular; IntravenousFresenius Kabi1998-08-14Not applicableCanada flag
Ampicillin for Injection, USPPowder, for solutionIntramuscular; IntravenousSterimax IncNot applicableNot applicableCanada flag
Additional Data Available
  • Application Number
    Application Number
    Available for Purchase

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code
    Available for Purchase

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AmpicillinInjection, powder, for solution2 g/1IntravenousAurobindo Pharma2010-08-172012-02-03US flag
AmpicillinPowder, for solution250 mg/250mgIntramuscular; IntravenousMethapharm Inc.2019-03-06Not applicableUS flag
AmpicillinCapsule250 mg/1OralAvera McKennan Hospital2015-07-152017-05-24US flag
AmpicillinInjection, powder, for solution500 mg/1Intramuscular; IntravenousAthenex Pharmaceutical Division, Llc.2018-08-01Not applicableUS flag
AmpicillinInjection, powder, for solution125 mg/1Intramuscular; IntravenousSandoz Inc1971-03-03Not applicableUS flag
AmpicillinInjection, powder, for solution2 g/1IntravenousSandoz Inc1987-02-19Not applicableUS flag
AmpicillinInjection, powder, for solution10 g/1IntravenousPiramal Critical Care Inc2020-03-09Not applicableUS flag
AmpicillinInjection, powder, for solution250 mg/1Intramuscular; IntravenousSandoz GmbH1971-03-03Not applicableUS flag
AmpicillinInjection, powder, for solution500 mg/1Intramuscular; IntravenousGC Hanford Manufacturing Company2008-02-15Not applicableUS flag
AmpicillinInjection, powder, for solution10 g/1IntravenousSandoz Inc1971-03-03Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number
    Available for Purchase

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code
    Available for Purchase

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Ampicillin and SulbactamAmpicillin sodium (250 mg/1mL) + Sulbactam sodium (125 mg/1mL)Injection, powder, for solutionIntramuscular; IntravenousBaxter Laboratories2010-02-242013-10-31US flag
Ampicillin and SulbactamAmpicillin sodium (1 g/1) + Sulbactam sodium (0.5 g/1)Injection, powder, for solutionIntravenousSandoz GmbH2006-07-25Not applicableUS flag
Ampicillin and SulbactamAmpicillin sodium (2 g/1) + Sulbactam sodium (1 g/1)Injection, powder, for solutionIntravenousAuroMedics Pharma LLC2012-09-13Not applicableUS flag
Ampicillin and SulbactamAmpicillin sodium (10 g/1) + Sulbactam sodium (5 g/1)Injection, powder, for solutionIntravenousMeitheal Pharmaceuticals Inc.2018-12-17Not applicableUS flag
Ampicillin and SulbactamAmpicillin sodium (250 mg/1mL) + Sulbactam sodium (125 mg/1mL)Injection, powder, for solutionIntramuscular; IntravenousBaxter Laboratories2010-02-242013-07-30US flag
Ampicillin and SulbactamAmpicillin sodium (2 g/20mL) + Sulbactam sodium (1 g/20mL)Injection, powder, for solutionIntramuscular; IntravenousWG Critical Care, LLC2005-11-30Not applicableUS flag
Ampicillin and SulbactamAmpicillin sodium (1 g/1) + Sulbactam sodium (0.5 g/1)Injection, powder, for solutionIntramuscular; IntravenousMeitheal Pharmaceuticals Inc.2018-12-17Not applicableUS flag
Ampicillin and SulbactamAmpicillin sodium (1 g/1) + Sulbactam sodium (0.5 g/1)Injection, powder, for solutionIntramuscular; IntravenousAuroMedics Pharma LLC2012-02-10Not applicableUS flag
Ampicillin and SulbactamAmpicillin sodium (250 mg/1mL) + Sulbactam sodium (125 mg/1mL)Injection, powder, for suspensionIntramuscular; IntravenousMylan Institutional2012-11-272014-03-31US flag
Ampicillin and SulbactamAmpicillin sodium (2 g/1) + Sulbactam sodium (1 g/1)Injection, powder, for solutionIntramuscular; IntravenousClaris Lifesciences, Inc.2015-12-14Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Ampicillin and SulbactamAmpicillin sodium (2 g/1) + Sulbactam sodium (1 g/1)Injection, powder, for suspensionIntramuscular; IntravenousCardinal Health2011-05-202014-02-28US flag

Categories

ATC Codes
J01CR50 — Combinations of penicillinsJ01CA51 — Ampicillin, combinationsJ01CA01 — AmpicillinS01AA19 — Ampicillin
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This 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].
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Lactams
Sub Class
Beta lactams
Direct Parent
Penicillins
Alternative Parents
N-acyl-alpha amino acids and derivatives / Alpha amino acid amides / Phenylacetamides / Aralkylamines / Thiazolidines / Tertiary carboxylic acid amides / Secondary carboxylic acid amides / Amino acids / Azetidines / Thiohemiaminal derivatives
show 9 more
Substituents
Alpha-amino acid amide / Alpha-amino acid or derivatives / Amine / Amino acid / Amino acid or derivatives / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Azetidine / Benzenoid
show 24 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
penicillin, beta-lactam antibiotic (CHEBI:28971) / penams (C06574)

Chemical Identifiers

UNII
7C782967RD
CAS number
69-53-4
InChI Key
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][[email protected]]12SC(C)(C)[[email protected]@H](N1C(=O)[[email protected]]2NC(=O)[[email protected]](N)C1=CC=CC=C1)C(O)=O

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 References
Not Available
Human Metabolome Database
HMDB0014559
KEGG Drug
D00204
KEGG Compound
C06574
PubChem Compound
6249
PubChem Substance
46505346
ChemSpider
6013
BindingDB
50350465
RxNav
221058
ChEBI
28971
ChEMBL
CHEMBL174
ZINC
ZINC000003830218
Therapeutic Targets Database
DAP000432
PharmGKB
PA448419
PDBe Ligand
AIC
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Ampicillin
AHFS Codes
  • 08:12.16.08 — Aminopenicillins
PDB Entries
1h8s / 1nx9 / 2rdd / 3ita / 3kp3 / 3ndv / 4gcp / 4kr4
MSDS
Download (71.8 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedPreventionBreast Cancer1
4CompletedPreventionCalcium Nephrolithiasis / Urinary Tract Infection1
4CompletedPreventionSurgical Site Infections1
4CompletedTreatmentComplicated Appendicitis1
4CompletedTreatmentIntra-Abdominal Infections2
4CompletedTreatmentPneumonia1
4CompletedTreatmentSkin Diseases, Bacterial1
4Enrolling by InvitationPreventionKidney Stones1
4Not Yet RecruitingTreatmentCholecystitis; Acute, With Cholelithiasis1
4Not Yet RecruitingTreatmentComplicated Appendicitis / Perforated Appendicitis1

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
  • American Antibiotics LLC
  • Apotheca Inc.
  • APP Pharmaceuticals
  • A-S Medication Solutions LLC
  • Bryant Ranch Prepack
  • C.O. Truxton Inc.
  • Cardinal Health
  • Carlisle Laboratories Inc.
  • Central Texas Community Health Centers
  • Claris Lifesciences Inc.
  • Clonmel Healthcare Ltd.
  • Comprehensive Consultant Services Inc.
  • Comptoir Francaise De Productores
  • Cura Pharmaceutical Co. Inc.
  • Darby Dental Supply Co. Inc.
  • DAVA Pharmaceuticals
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • E.R. Squibb and Sons LLC
  • GC Hanford Manufacturing Co.
  • H and H Laboratories
  • H.J. Harkins Co. Inc.
  • Ibi Istituto Biochimico Italiano Giovanni Lorenzini SPA
  • Major Pharmaceuticals
  • Marnel Pharmaceuticals Inc.
  • Mead Johnson and Co.
  • Medpharm Inc.
  • Nucare Pharmaceuticals Inc.
  • Palmetto Pharmaceuticals Inc.
  • Par Pharmaceuticals
  • PCA LLC
  • PD-Rx Pharmaceuticals Inc.
  • Pharmedix
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Prepackage Specialists
  • Prescript Pharmaceuticals
  • Putney Inc.
  • Sagent Pharmaceuticals
  • Sandhills Packaging Inc.
  • Sandoz
  • SC Antibiotice SA
  • Signal Health Ltd.
  • Southwood Pharmaceuticals
  • Teva Pharmaceutical Industries Ltd.
  • WG Critical Care LLC
Dosage Forms
FormRouteStrength
Injection, powder, for solutionIntramuscular; Intravenous1000 mg
Injection, powder, for solutionIntramuscular; Intravenous250 mg
Injection, powder, for solutionIntramuscular1000 mg
Injection, solutionIntravenous1 g/3mL
Tablet, film coatedOral
CapsuleOral
Capsule250 mg
CapsuleOral300 mg
Injection, powder, for solutionIntramuscular; Intravenous1.5 g
Injection, powder, for solutionIntravenous1 g
TabletOral200 mg
Powder, for suspensionOral2.5 g
Powder, for suspensionOral5 g
Injection, powder, for solutionIntramuscular; Intravenous500 mg
Capsule, coatedOral500 mg
TabletOral1 g
PowderOral12 5mg/5ml
CapsuleOral250 mg/1
CapsuleOral500 mg/1
Injection, powder, for solutionIntramuscular; Intravenous1 g/1
Injection, powder, for solutionIntramuscular; Intravenous1 g/1mL
Injection, powder, for solutionIntramuscular; Intravenous125 mg/1
Injection, powder, for solutionIntramuscular; Intravenous2 g/1
Injection, powder, for solutionIntramuscular; Intravenous250 mg/1mL
Injection, powder, for solutionIntramuscular; Intravenous250 mg/1
Injection, powder, for solutionIntramuscular; Intravenous500 mg/1mL
Injection, powder, for solutionIntramuscular; Intravenous500 mg/1
Injection, powder, for solutionIntravenous1 g/1
Injection, powder, for solutionIntravenous10 g/1
Injection, powder, for solutionIntravenous10 g/100mL
Injection, powder, for solutionIntravenous2 g/1mL
Injection, powder, for solutionIntravenous2 g/1
Powder, for solutionIntramuscular; Intravenous1 g/1g
Powder, for solutionIntramuscular; Intravenous2 g/2g
Powder, for solutionIntramuscular; Intravenous250 mg/250mg
Powder, for solutionIntramuscular; Intravenous500 mg/500mg
Powder, for suspensionOral125 mg/5mL
Powder; syrupOral125 mg/5mL
SuspensionOral125 mg/5mL
SuspensionOral25 mg/1mL
SuspensionOral250 mg/5mL
SuspensionOral50 mg/1mL
Syrup
Injection, powder, for solutionIntramuscular; Intravenous
Injection, powder, for solutionIntravenous
Injection, powder, for suspensionIntramuscular; Intravenous
Tablet, coatedOral125 mg
Injection, powder, for solution
Powder, for solutionIntramuscular; Intravenous
Injection, powder, for solution500 MG/2.5ML
Powder1000 MG
Powder250 MG
Injection, powder, for solutionIntramuscular1 g/3.2mL
Injection, powder, for solutionIntramuscular500 mg/1.6mL
TabletOral125 mg
Injection, powder, for solutionIntramuscular; Intravenous1 g
Powder; syrupOral250 mg/5mL
Tablet, chewableOral125 mg
InjectionIntramuscular; Intravenous1000 mg
InjectionIntramuscular; Intravenous2 g
Injection, powder, for solutionIntramuscular250 mg
InjectionIntramuscular; Intravenous250 mg
Injection, powder, for solutionIntramuscular500 mg
InjectionIntramuscular; Intravenous1 gr
TabletOral1 gr
TabletOral250 mg
Powder
CapsuleOral250 MG
CapsuleOral500 MG
Injection, powder, for solution1 G
Injection, powder, for solution500 MG
Powder, for suspensionOral250 MG/5ML
Solution / dropsOral2 g/20ml
SuspensionOral3 g
Solution / dropsOral100 mg/1mL
LiquidOral
InjectionIntramuscular1000 mg
InjectionIntramuscular500 mg
InjectionIntramuscular0.25 g
InjectionIntramuscular; Intravenous0.5 g
InjectionIntramuscular1 g
Powder, for suspensionOral5000 mg
TabletOral1000 mg
TabletOral500 mg
InjectionIntramuscular0.5 g
Injection, solutionIntramuscular1 g
Injection, solutionIntramuscular250 mg
Injection, solutionIntramuscular500 mg
SuspensionOral12 5MG/5ML
Injection, powder, for solution125 mg
TabletOral
Powder, for suspensionOral250 mg
Injection, powder, for solutionIntramuscular1 g
Powder, for solutionOral
SuspensionOral
InjectionIntramuscular; Intravenous1 G
LiquidIntramuscular; Intravenous
Powder, for solutionIntravenous
SuspensionOral80 ml
Solution / dropsOral30 ml
SuspensionOral8 ml
Capsule; tabletOral
Injection, powder, for solutionParenteral1 g
Injection, powder, for solutionParenteral2 g
Injection, powder, for solutionParenteral500 mg
InjectionIntramuscular; Intravenous500 MG
Injection, powder, for solution2 g
Injection, powder, for solution250 mg
Injection, solutionIntramuscular1000 mg
Injection, solutionIntramuscular; Intravenous1000 mg
Injection, solutionIntramuscular; Intravenous2 g
Injection, solutionIntramuscular; Intravenous250 mg
Injection, powder, for solutionIntramuscular500 mg/3.2ml
Injection, powder, for solutionIntramuscular; Intravenous2 g
Injection, powder, for solutionIntravenous125 mg/ml
Injection, powder, for solutionIntravenous250 mg/1.6ml
Injection, powder, for solutionIntravenous500 mg/3.2ml
Injection, powder, lyophilized, for solutionIntramuscular; Intravenous1000 mg
Tablet, coatedOral250 mg
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.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)208 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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0udi-1349000000-51be76a1d965184221c8
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0006-9810000000-75530784e97a116633e5
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0006-9600000000-0f235a2c675944bd7f8a
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-006x-9300000000-766d3a6fea596a3f18a8
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-9100000000-147bdc3aaa0be3d0b419

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
Uniprot Name
Penicillin-binding protein 2a
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
Uniprot Name
Penicillin-binding protein 1b
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
Uniprot Name
Penicillin-binding protein 3
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
Uniprot Name
Penicillin-binding protein 1A
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
Not Available
Specific Function
Penicillin binding
Gene Name
penA
Uniprot ID
P0A3M6
Uniprot Name
Penicillin-binding protein 2B
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
Humans
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
Uniprot Name
Solute carrier family 15 member 1
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
Humans
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
Uniprot Name
Solute carrier family 15 member 2
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]
Details
8. Angiopoietin-1 receptor
Kind
Protein
Organism
Humans
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...
Gene Name
TEK
Uniprot ID
Q02763
Uniprot Name
Angiopoietin-1 receptor
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
Humans
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 colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
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
Humans
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 cat...
Gene Name
SLC22A5
Uniprot ID
O76082
Uniprot Name
Solute carrier family 22 member 5
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
Humans
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
Uniprot Name
Solute carrier family 15 member 1
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
Humans
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
Uniprot Name
Solute carrier family 15 member 2
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
Humans
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 leucin...
Gene Name
SLC16A1
Uniprot ID
P53985
Uniprot Name
Monocarboxylate transporter 1
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]

Drug created on June 13, 2005 07:24 / Updated on October 31, 2020 10:29

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