Identification

Name
Ampicillin
Accession Number
DB00415  (APRD00320)
Type
Small Molecule
Groups
Approved, Vet Approved
Description

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

Structure
Thumb
Synonyms
  • (2S,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
  • 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
Product Ingredients
IngredientUNIICASInChI Key
Ampicillin sodiumJFN36L5S8K69-52-3KLOHDWPABZXLGI-YWUHCJSESA-M
Ampicillin trihydrateHXQ6A1N7R67177-48-2RXDALBZNGVATNY-CWLIKTDRSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ampicillin for InjectionPowder, for solution1 gIntramuscular; IntravenousFresenius Kabi1998-08-14Not applicableCanada
Ampicillin for InjectionPowder, for solution500 mgIntramuscular; IntravenousFresenius Kabi1998-08-14Not applicableCanada
Ampicillin for InjectionPowder, for solution250 mgIntramuscular; IntravenousFresenius Kabi1998-08-14Not applicableCanada
Ampicillin for InjectionPowder, for solution125 mgIntramuscular; IntravenousFresenius KabiNot applicableNot applicableCanada
Ampicillin for InjectionPowder, for solution2 gIntravenousFresenius Kabi1998-07-27Not 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 solution500 mgIntramuscular; IntravenousSterimax IncNot applicableNot applicableCanada
Ampicillin for Injection, USPPowder, for solution1 gIntramuscular; IntravenousSterimax IncNot applicableNot applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AmpicillinCapsule500 mg/1OralSandoz1995-08-29Not applicableUs
AmpicillinInjection, powder, for solution500 mg/1Intramuscular; IntravenousFresenius Kabi1971-03-03Not applicableUs
AmpicillinInjection, powder, for solution2 g/1IntravenousSandoz1987-02-19Not applicableUs
AmpicillinInjection, powder, for solution2 g/1IntravenousSandoz1987-02-19Not applicableUs
AmpicillinInjection, powder, for solution10 g/1IntravenousHospira, Inc.2015-09-04Not applicableUs
AmpicillinInjection, powder, for solution250 mg/1Intramuscular; IntravenousClaris Lifesciences, Inc.2010-04-25Not applicableUs
AmpicillinInjection, powder, for solution250 mg/1Intramuscular; IntravenousCardinal Health1987-05-12Not applicableUs
AmpicillinInjection, powder, for solution10 g/100mLIntravenousAuro Medics Pharma Llc2012-02-01Not applicableUs
AmpicillinInjection, powder, for solution2 g/mLIntravenousAGILA SPECIALTIES PRIVATE LIMITED2014-04-10Not applicableUs
AmpicillinInjection, powder, for solution250 mg/1Intramuscular; IntravenousMylan Institutional2014-04-10Not applicableUs
International/Other Brands
Austrapen (Lennon Healthcare) / Binotal (Bayer) / Penbritin (GlaxoSmithKline) / Principen / Redicilin / Semicillin / Tokiocillin / Ultrabion / Viccillin (Meiji)
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Ampicillin and SulbactamAmpicillin sodium (1 g/4mL) + Sulbactam sodium (.5 g/4mL)Injection, powder, for solutionIntramuscular; IntravenousHospira, Inc.2006-07-25Not applicableUs
Ampicillin and SulbactamAmpicillin sodium (10 g/100mL) + Sulbactam sodium (5 g/100mL)Injection, powder, for solutionIntravenousWG Critical Care, LLC2005-11-25Not applicableUs
Ampicillin and SulbactamAmpicillin sodium (1 g/1) + Sulbactam sodium (.5 g/1)Injection, powder, for solutionIntravenousHospira, Inc.2006-07-25Not applicableUs
Ampicillin and SulbactamAmpicillin sodium (1 g/1) + Sulbactam sodium (.5 g/1)Injection, powder, for solutionIntramuscular; IntravenousClaris Lifesciences, Inc.2015-12-14Not applicableUs
Ampicillin and SulbactamAmpicillin sodium (250 mg/mL) + Sulbactam sodium (125 mg/mL)Injection, powder, for suspensionIntramuscular; IntravenousMylan Institutional2012-11-272017-02-18Us
Ampicillin and SulbactamAmpicillin sodium (1 g/1) + Sulbactam sodium (.5 g/1)Injection, powder, for solutionIntramuscular; IntravenousAuro Medics Pharma Llc2012-02-10Not applicableUs
Ampicillin and SulbactamAmpicillin sodium (100 mg/mL) + Sulbactam sodium (50 mg/mL)Injection, powder, for solutionIntravenousWest Ward Pharmaceutical2009-12-03Not applicableUs
Ampicillin and SulbactamAmpicillin sodium (2 g/1) + Sulbactam sodium (1 g/1)Injection, powder, for solutionIntramuscular; IntravenousSandoz2006-07-25Not applicableUs
Ampicillin and SulbactamAmpicillin sodium (2 g/20mL) + Sulbactam sodium (1 g/20mL)Injection, powder, for solutionIntramuscular; IntravenousWG Critical Care, LLC2005-11-30Not applicableUs
Ampicillin and SulbactamAmpicillin sodium (10 g/100mL) + Sulbactam sodium (5 g/100mL)Injection, powder, for solutionIntravenousSagent Pharmaceuticals2017-08-15Not applicableUs
Categories
UNII
7C782967RD
CAS number
69-53-4
Weight
Average: 349.405
Monoisotopic: 349.109626801
Chemical Formula
C16H19N3O4S
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

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

Structured Indications
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 AvailableHuman
USolute carrier family 15 member 2Not AvailableHuman
UAngiopoietin-1 receptorNot AvailableHuman
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
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
DrugInteractionDrug group
AcenocoumarolAmpicillin may increase the anticoagulant activities of Acenocoumarol.Approved
AclarubicinThe serum concentration of Aclarubicin can be decreased when it is combined with Ampicillin.Investigational
AllopurinolThe risk of a hypersensitivity reaction to Ampicillin is increased when it is combined with Allopurinol.Approved
AmikacinThe serum concentration of Amikacin can be decreased when it is combined with Ampicillin.Approved, Vet Approved
AmrubicinThe serum concentration of Amrubicin can be decreased when it is combined with Ampicillin.Approved, Investigational
annamycinThe serum concentration of annamycin can be decreased when it is combined with Ampicillin.Investigational
ApramycinThe serum concentration of Apramycin can be decreased when it is combined with Ampicillin.Experimental, Vet Approved
ArbekacinThe serum concentration of Arbekacin can be decreased when it is combined with Ampicillin.Approved
AtenololThe bioavailability of Atenolol can be decreased when combined with Ampicillin.Approved
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Ampicillin.Investigational
BekanamycinThe serum concentration of Bekanamycin can be decreased when it is combined with Ampicillin.Experimental
ChloroquineThe serum concentration of Ampicillin can be decreased when it is combined with Chloroquine.Approved, Vet Approved
ChlortetracyclineThe therapeutic efficacy of Ampicillin can be decreased when used in combination with Chlortetracycline.Approved, Vet Approved
ClorindioneAmpicillin may increase the anticoagulant activities of Clorindione.Experimental
DaunorubicinThe serum concentration of Daunorubicin can be decreased when it is combined with Ampicillin.Approved
DemeclocyclineThe therapeutic efficacy of Ampicillin can be decreased when used in combination with Demeclocycline.Approved
DibekacinThe serum concentration of Dibekacin can be decreased when it is combined with Ampicillin.Experimental
DicoumarolAmpicillin may increase the anticoagulant activities of Dicoumarol.Approved
DihydrostreptomycinThe serum concentration of Dihydrostreptomycin can be decreased when it is combined with Ampicillin.Vet Approved
DiphenadioneAmpicillin may increase the anticoagulant activities of Diphenadione.Experimental
DoxorubicinThe serum concentration of Doxorubicin can be decreased when it is combined with Ampicillin.Approved, Investigational
DoxycyclineThe therapeutic efficacy of Ampicillin can be decreased when used in combination with Doxycycline.Approved, Investigational, Vet Approved
EpirubicinThe serum concentration of Epirubicin can be decreased when it is combined with Ampicillin.Approved
Ethyl biscoumacetateAmpicillin may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
FluindioneAmpicillin may increase the anticoagulant activities of Fluindione.Investigational
FramycetinThe serum concentration of Framycetin can be decreased when it is combined with Ampicillin.Approved
GeneticinThe serum concentration of Geneticin can be decreased when it is combined with Ampicillin.Experimental
GentamicinThe serum concentration of Gentamicin can be decreased when it is combined with Ampicillin.Approved, Vet Approved
GENTAMICIN C1AThe serum concentration of GENTAMICIN C1A can be decreased when it is combined with Ampicillin.Experimental
GPX-150The serum concentration of GPX-150 can be decreased when it is combined with Ampicillin.Investigational
Hygromycin BThe serum concentration of Hygromycin B can be decreased when it is combined with Ampicillin.Vet Approved
IdarubicinThe serum concentration of Idarubicin can be decreased when it is combined with Ampicillin.Approved
INNO-206The serum concentration of INNO-206 can be decreased when it is combined with Ampicillin.Investigational
IsepamicinThe serum concentration of Isepamicin can be decreased when it is combined with Ampicillin.Experimental
KanamycinThe serum concentration of Kanamycin can be decreased when it is combined with Ampicillin.Approved, Vet Approved
Lanthanum carbonateThe serum concentration of Ampicillin can be decreased when it is combined with Lanthanum carbonate.Approved
MethotrexateThe serum concentration of Methotrexate can be increased when it is combined with Ampicillin.Approved
MetrizamideThe serum concentration of Metrizamide can be decreased when it is combined with Ampicillin.Approved
MicronomicinThe serum concentration of Micronomicin can be decreased when it is combined with Ampicillin.Experimental
MinocyclineThe therapeutic efficacy of Ampicillin can be decreased when used in combination with Minocycline.Approved, Investigational
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.Approved
NeamineThe serum concentration of Neamine can be decreased when it is combined with Ampicillin.Experimental
NeomycinThe serum concentration of Neomycin can be decreased when it is combined with Ampicillin.Approved, Vet Approved
NetilmicinThe serum concentration of Netilmicin can be decreased when it is combined with Ampicillin.Approved
ParomomycinThe serum concentration of Paromomycin can be decreased when it is combined with Ampicillin.Approved, Investigational
PhenindioneAmpicillin may increase the anticoagulant activities of Phenindione.Approved
PhenprocoumonAmpicillin may increase the anticoagulant activities of Phenprocoumon.Approved
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Ampicillin.Approved
PirarubicinThe serum concentration of Pirarubicin can be decreased when it is combined with Ampicillin.Investigational
PlazomicinThe serum concentration of Plazomicin can be decreased when it is combined with Ampicillin.Investigational
PlicamycinThe serum concentration of Plicamycin can be decreased when it is combined with Ampicillin.Approved, Withdrawn
ProbenecidThe serum concentration of Ampicillin can be increased when it is combined with Probenecid.Approved
PuromycinThe serum concentration of Puromycin can be decreased when it is combined with Ampicillin.Experimental
RibostamycinThe serum concentration of Ribostamycin can be decreased when it is combined with Ampicillin.Approved
SabarubicinThe serum concentration of Sabarubicin can be decreased when it is combined with Ampicillin.Investigational
SisomicinThe serum concentration of Sisomicin can be decreased when it is combined with Ampicillin.Investigational
SP1049CThe serum concentration of SP1049C can be decreased when it is combined with Ampicillin.Investigational
SpectinomycinThe serum concentration of Spectinomycin can be decreased when it is combined with Ampicillin.Approved, Vet Approved
StreptomycinThe serum concentration of Streptomycin can be decreased when it is combined with Ampicillin.Approved, Vet Approved
StreptozocinThe serum concentration of Streptozocin can be decreased when it is combined with Ampicillin.Approved
TioclomarolAmpicillin may increase the anticoagulant activities of Tioclomarol.Experimental
TobramycinThe serum concentration of Tobramycin can be decreased when it is combined with Ampicillin.Approved, Investigational
ValrubicinThe serum concentration of Valrubicin can be decreased when it is combined with Ampicillin.Approved
WarfarinAmpicillin may increase the anticoagulant activities of Warfarin.Approved
Zoptarelin doxorubicinThe serum concentration of Zoptarelin doxorubicin can be decreased when it is combined with Ampicillin.Investigational
ZorubicinThe serum concentration of Zorubicin can be decreased when it is combined with Ampicillin.Experimental
Food Interactions
  • Take on an empty stomach.

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
External Links
Human Metabolome Database
HMDB14559
KEGG Drug
D00204
KEGG Compound
C06574
PubChem Compound
6249
PubChem Substance
46505346
ChemSpider
6013
BindingDB
50350465
ChEBI
28971
ChEMBL
CHEMBL174
Therapeutic Targets Database
DAP000432
PharmGKB
PA448419
HET
AIC
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Ampicillin
ATC Codes
J01CR50 — Combinations of penicillinsS01AA19 — AmpicillinJ01CR01 — Ampicillin and enzyme inhibitorJ01CA51 — Ampicillin, combinationsJ01CA01 — 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
0RecruitingTreatmentOsteomyelitis1
1CompletedNot AvailableInfection NOS1
1CompletedTreatmentCastrate Resistant Prostate Cancer (CRPC)1
1CompletedTreatmentDystonias / DYT-11
2CompletedTreatmentAdult T-cell lymphomas/leukaemias1
2CompletedTreatmentCleft Palates1
2CompletedTreatmentMultiple Organ Dysfunction Syndrome / Sepsis1
2CompletedTreatmentUlcerative Colitis (UC)1
2RecruitingTreatmentLate-onset Sepsis1
2TerminatedTreatmentBacterial Infections and Mycoses / Sepsis1
2, 3Active Not RecruitingTreatmentChorioamnionitis1
2, 3CompletedPreventionChorioamnionitis / Neonatal Early Onset Sepsis / Neonatal Meningitis / Neonatal Pneumonia / Puerperal Endometritis1
2, 3CompletedTreatmentComplicated Intra Abdominal Infections1
2, 3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
3CompletedPreventionHerpes Zoster / Shingles1
3CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections1
3CompletedPreventionMumps / Rubella / Rubeola / Varicella1
3CompletedTreatmentInfection During Hemodialysis1
3CompletedTreatmentLung Abscess / Pneumonia, Aspiration1
3CompletedTreatmentSepsis1
3RecruitingTreatmentEnterobacteriaceae Infections1
3RecruitingTreatmentPreterm Premature Rupture of Membranes (PPROM)1
3WithdrawnPreventionPreterm Premature Ruptured Membranes1
4CompletedNot AvailablePerforated Appendicitis1
4CompletedPreventionCancer, Breast1
4CompletedTreatmentIntra-Abdominal Infections1
4CompletedTreatmentPneumonia1
4Enrolling by InvitationPreventionRenal Stones1
4RecruitingPreventionCalcium Nephrolithiasis / Urinary Tract Infections (UTIs)1
4TerminatedTreatmentCommunity Acquired Pneumonia (CAP)1
4WithdrawnPreventionVentilator-associated Bacterial Pneumonia1
Not AvailableCompletedNot AvailableDrug Metabolism During Pregnancy1
Not AvailableCompletedBasic ScienceHealthy Volunteers1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Salmonella Infections1
Not AvailableNot Yet RecruitingNot AvailableColic / Gastrointestinal Diseases1
Not AvailableNot Yet RecruitingNot AvailableNewborn; Infection1
Not AvailableRecruitingPreventionCalcium Nephrolithiasis / Sepsis / Urinary Tract Infections (UTIs)1
Not AvailableRecruitingPreventionNecrotizing Enterocolitis / Premature Birth of Newborn1
Not AvailableSuspendedNot AvailableTransient ischemia attacks1
Not AvailableUnknown StatusNot AvailableAsymptomatic Infections / Bacteriuria / Transplantation Infection / Urinary Tract Infections (UTIs)1
Not AvailableUnknown StatusTreatmentEndometritis1

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/1
CapsuleOral500 mg/1
Injection, powder, for solutionIntramuscular; Intravenous1 g/mL
Injection, powder, for solutionIntramuscular; Intravenous1 g/1
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/mL
Injection, powder, for solutionIntramuscular; Intravenous250 mg/1
Injection, powder, for solutionIntramuscular; Intravenous500 mg/500mg
Injection, powder, for solutionIntramuscular; Intravenous500 mg/1
Injection, powder, for solutionIntramuscular; Intravenous500 mg/mL
Injection, powder, for solutionIntravenous1 g/g
Injection, powder, for solutionIntravenous1 g/1
Injection, powder, for solutionIntravenous10 g/1
Injection, powder, for solutionIntravenous10 g/100mL
Injection, powder, for solutionIntravenous2 g/mL
Injection, powder, for solutionIntravenous2 g/1
SuspensionOral25 mg/mL
SuspensionOral50 mg/mL
Injection, powder, for solutionIntramuscular; Intravenous
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
LiquidOral125 mg
LiquidOral250 mg
TabletOral125 mg
Powder, for solutionOral500 mg
Powder, for solutionOral125 mg
Powder, for solutionOral250 mg
CapsuleOral250 mg
CapsuleOral500 mg
SuspensionOral125 mg
SuspensionOral250 mg
Powder, for solutionIntramuscular; Intravenous1 g
LiquidIntramuscular; Intravenous2 g
Powder, for solutionIntravenous1 g
Powder, for solutionIntramuscular; Intravenous125 mg
Capsule; tabletOral
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

Taxonomy

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
Penicillin / N-acyl-alpha amino acid or derivatives / Alpha-amino acid amide / Alpha-amino acid or derivatives / Phenylacetamide / Aralkylamine / Monocyclic benzene moiety / Benzenoid / Thiazolidine / Tertiary carboxylic acid amide
show 24 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
penicillin, beta-lactam antibiotic (CHEBI:28971) / penams (C06574)

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
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
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
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
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
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...
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
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 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
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 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
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
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
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
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
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 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 23, 2017 14:13