Ampicillin

Overview

Description
An antibiotic related to penicillin that is used to treat a wide variety of infections in the body caused by bacteria.
Description
An antibiotic related to penicillin that is used to treat a wide variety of infections in the body caused by bacteria.
DrugBank ID
DB00415
Type
Small Molecule
US Approved
YES
Other Approved
YES

Identification

Summary

Ampicillin is a penicillin derivative used for the treatment of a variety of infections caused by gram-positive and gram-negative bacteria as well as some anaerobes.

Brand Names
Unasyn
Generic Name
Ampicillin
DrugBank Accession Number
DB00415
Background

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
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

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to treatBacterial infectionCombination Product in combination with: Sulbactam (DB09324)••••••••••••
Treatment ofBacterial meningitis•••••••••••••••••••••• ••••••• ••• ••••••••
Treatment ofEndocarditis•••••••••••••••••••••• ••••••• ••• ••••••••
Treatment ofGastrointestinal infections••••••••••••
Treatment ofGenitourinary tract infection••••••••••••
Contraindications & Blackbox Warnings
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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
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Toxicity

Not Available

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.
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.
Food Interactions
  • Take on an empty stomach.

Products

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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 solution125 mg / vialIntramuscular; IntravenousFresenius Kabi Italia S.R.L.Not applicableNot applicableCanada flag
Ampicillin for Injection, USPPowder, for solution1 g / vialIntramuscular; IntravenousFresenius Kabi Italia S.R.L.1998-08-14Not applicableCanada flag
Ampicillin for Injection, USPPowder, for solution2 g / vialIntramuscular; IntravenousSterimax IncNot applicableNot applicableCanada flag
Ampicillin for Injection, USPPowder, for solution250 mg / vialIntramuscular; IntravenousSterimax IncNot applicableNot applicableCanada flag
Ampicillin for Injection, USPPowder, for solution2 g / vialIntravenousFresenius Kabi Italia S.R.L.1998-07-27Not applicableCanada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AmpicillinCapsule500 mg/1OralPD-Rx Pharmaceuticals, Inc.1988-02-252018-06-18US flag
AmpicillinInjection, powder, for solution2 g/1Intramuscular; IntravenousSandoz S.P.A.1971-03-03Not applicableUS flag
AmpicillinInjection, powder, for solution10 g/1IntravenousSandoz S.P.A.1971-03-03Not applicableUS flag
AmpicillinInjection, powder, for solution1 g/1Intramuscular; IntravenousFresenius Kabi Italia S.R.L.2001-01-032019-03-31US flag
AmpicillinInjection, powder, for solution500 mg/1Intramuscular; IntravenousSandoz S.P.A.1971-03-03Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
ALFASID 1 G IM/IV ENJEKSIYON ICIN TOZ ICEREN FLAKON, 1 ADETAmpicillin (1000 mg) + Sulbactam (500 mg)Injection, powder, for solutionIntramuscular; IntravenousYAVUZ İLAÇ ECZA DEPOSU MEDİKAL ÜRÜNLER SAN.VE TİC. A.Ş.2011-06-08Not applicableTurkey flag
ALFASID 1 GR IM ENJ. ICIN TOZ ICEREN FLAKON, 1 ADETAmpicillin (1000 mg) + Sulbactam (500 mg)Injection, powder, for solutionIntramuscular; IntravenousYAVUZ İLAÇ ECZA DEPOSU MEDİKAL ÜRÜNLER SAN.VE TİC. A.Ş.2011-01-20Not applicableTurkey flag
ALFASID 250 MG IM ENJ.ICIN TOZ ICEREN FLAKON, 1 ADETAmpicillin sodium (250 mg) + Sulbactam (125 mg)Injection, powder, for solutionIntramuscular; IntravenousYAVUZ İLAÇ ECZA DEPOSU MEDİKAL ÜRÜNLER SAN.VE TİC. A.Ş.2009-07-03Not applicableTurkey flag
ALFASID 250 MG IM/IV ENJ.ICIN TOZ ICEREN FLAKON, 1 ADETAmpicillin sodium (250 mg) + Sulbactam (125 mg)Injection, powder, for solutionIntramuscular; IntravenousYAVUZ İLAÇ ECZA DEPOSU MEDİKAL ÜRÜNLER SAN.VE TİC. A.Ş.2009-07-03Not applicableTurkey flag
ALFASID 500 MG IM ENJ.ICIN TOZ ICEREN FLAKONAmpicillin (1000 mg) + Sulbactam (500 mg)Injection, powder, for solutionIntramuscularYAVUZ İLAÇ ECZA DEPOSU MEDİKAL ÜRÜNLER SAN.VE TİC. A.Ş.2008-05-14Not applicableTurkey 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)
Affected organisms
  • Enteric bacteria and other eubacteria
  • Gram-negative Bacteria
  • Gram-positive Bacteria
  • Streptococcus pyogenes
  • Streptococcus pneumoniae
  • Neisseria meningitidis
  • Listeria monocytogenes
  • Haemophilus influenzae

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][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](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
PDB Entries
1h8s / 1nx9 / 2rdd / 3ita / 3kp3 / 3ndv / 4gcp / 4kr4
MSDS
Download (71.8 KB)

Clinical Trials

Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package
PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns
Not AvailableCompletedNot AvailableAntibiotic Resistant Infection / Bacterial Infections / Surgical Site Infections1somestatusstop reasonjust information to hide
Not AvailableCompletedNot AvailableDrug Metabolism During Pregnancy1somestatusstop reasonjust information to hide
Not AvailableCompletedNot AvailableInfection1somestatusstop reasonjust information to hide
Not AvailableCompletedNot AvailableListeria Monocytogenes1somestatusstop reasonjust information to hide
Not AvailableCompletedNot AvailableLung Abscess / Peritonitis / Pneumonia1somestatusstop reasonjust information to hide

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, solutionIntravenous1 g/3mL
Tablet, film coatedOral500 mg
SolutionIntramuscular500.000 mg
Tablet, film coatedOral
Injection, powder, for solutionIntramuscular; Intravenous1.5 g
Injection, powder, for solutionIntramuscular; Intravenous1 g
SuspensionOral2.5 g
Injection, powder, for solutionParenteral1000 mg
Powder, for suspensionOral250000 g
Capsule, coatedOral500 mg
Capsule, coatedOral50000000 mg
Injection, powder, for suspensionParenteral500 mg
Capsule, coatedOral250 mg
TabletOral250 mg
TabletOral1 g
Powder, for suspensionOral5 g
Powder, for suspensionOral2.5 g
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
Injection, powder, for solutionIntravenous250 mg/1
Injection, powder, for solutionIntravenous500 mg/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
SuspensionOral125 mg/5mL
SuspensionOral25 mg/1mL
SuspensionOral250 mg/5mL
SuspensionOral50 mg/1mL
Syrup
TabletOral
Injection, powder, for solutionIntramuscular; Intravenous
Injection, powder, for solutionIntravenous
Injection, powder, for suspensionIntramuscular; Intravenous
Powder, for solutionIntramuscular; Intravenous10 g / vial
Powder, for solutionIntramuscular; Intravenous2 g / vial
Powder, for solutionIntramuscular; Intravenous1000 mg / vial
Powder, for solutionIntramuscular; Intravenous2000 mg / vial
Powder, for solutionIntramuscular; Intravenous500 mg / vial
Injection, powder, for solutionParenteral
CapsuleOral
Injection, powder, for solution1 G
Injection, powder, for solutionIntramuscular; Intravenous500 MG/2.5ML
PowderIntramuscular; Intravenous1000 MG
PowderIntramuscular; Intravenous250 MG
Injection, powder, for solutionIntramuscular
SuspensionOral
Powder, for solutionIntravenous2 g / vial
OintmentOphthalmic
Solution / dropsOral
InjectionIntramuscular; Intravenous1 gr
InjectionIntramuscular; Intravenous250 mg
InjectionIntramuscular; Intravenous500 mg
TabletOral1000 mg
Injection, powder, for solutionIntramuscular; Intravenous2 g
Injection, powder, for solutionParenteral1 G/4mL
Injection, powder, for solutionParenteral500 MG/2.5mL
Powder, for suspensionOral250 MG/5ML
Powder, for suspensionOral250 MG
SolutionIntramuscular1 G
SolutionIntramuscular250 MG
SolutionIntramuscular500 MG
Solution / dropsOral2 g/20ml
SuspensionOral3 g
Granule
Tablet, solubleOral250 mg
SolutionParenteral250.000 mg
LiquidOral125 mg / 5 mL
TabletOral
InjectionIntramuscular
TabletOral1.00 g
TabletOral500.000 mg
Powder, for suspensionOral5000 mg
Injection, solutionIntramuscular
Syrup125 MG/5ML
TabletOral1 gr
TabletOral500 mg
CapsuleOral500.00 mg
SuspensionOral4.500 g
SuspensionOral1.500 g
Powder, for solutionOral500 mg / 5 mL
Powder, for solutionOral125 mg / 5 mL
Powder, for solutionOral250 mg / 5 mL
SuspensionOral125 mg / 5 mL
SuspensionOral250 mg / 5 mL
InjectionIntramuscular; Intravenous1 g
CapsuleOral
Injection, powder, for solution
Injection, powder, for solutionIntramuscular; Intravenous250 mg
SuspensionOral10.0000 g
Powder, for solutionIntramuscular; Intravenous1 g / vial
LiquidIntramuscular; Intravenous2 g / vial
Powder, for solutionIntravenous1 g / vial
Powder, for solutionIntramuscular; Intravenous125 mg / vial
Powder, for solutionIntramuscular; Intravenous250 mg / vial
SuspensionOral80 ml
Solution / dropsOral30 ml
SuspensionOral8 ml
CapsuleOral500.000 mg
TabletOral500.00 mg
Powder, for suspensionOral
Capsule; tabletOral
Injection, powder, for solution
Syrup250 MG/5ML
Injection, powder, for solutionParenteral1 g
Injection, powder, for solutionParenteral2 g
Injection, powder, for solutionParenteral500 mg
Injection, powder, for solutionIntramuscular; Intravenous500 mg
Injection, solutionIntramuscular; Intravenous
InjectionIntramuscular; Intravenous
CapsuleOral250 mg / cap
CapsuleOral500 mg / cap
Powder
Injection, powder, for solutionIntramuscular; Intravenous1 g
Injection, powder, for solutionIntramuscular; Intravenous2 g
Injection, powder, for solutionIntramuscular; Intravenous500 mg
Injection, powder, lyophilized, for solutionIntramuscular; Intravenous
Injection, powder, for solution1 g/vial
Injection, powder, for solution250 mg
Injection, powder, for solution500 mg
CapsuleOral250 mg
CapsuleOral500 mg
Powder, for suspensionOral125 mg/5ml
TabletOral125 mg
Tablet, film coatedOral125 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)7.23Chemaxon
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-MSsplash10-0a4i-1900000000-328e5756b2a2047f3401
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-08fr-0900000000-6d870bf80a4241037435
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-05fr-0090000000-bc4ad3aec4b104f07040
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-05fr-1195000000-f2340abfc6e6ef0dc6ff
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-1900000000-bfdfe0aeec55edc64ac9
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-1900000000-4c86b6c7dbd999d30714
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9610000000-f6a8ba010bee500887f0
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-187.2334665
predicted
DarkChem Lite v0.1.0
[M-H]-186.2928665
predicted
DarkChem Lite v0.1.0
[M-H]-186.1541665
predicted
DarkChem Lite v0.1.0
[M-H]-187.8294665
predicted
DarkChem Lite v0.1.0
[M-H]-181.85304
predicted
DeepCCS 1.0 (2019)
[M+H]+186.2035665
predicted
DarkChem Lite v0.1.0
[M+H]+184.6127665
predicted
DarkChem Lite v0.1.0
[M+H]+184.6295665
predicted
DarkChem Lite v0.1.0
[M+H]+187.0363665
predicted
DarkChem Lite v0.1.0
[M+H]+184.24861
predicted
DeepCCS 1.0 (2019)
[M+Na]+185.7261665
predicted
DarkChem Lite v0.1.0
[M+Na]+185.2847665
predicted
DarkChem Lite v0.1.0
[M+Na]+190.3734641
predicted
DarkChem Lite v0.1.0
[M+Na]+186.2603665
predicted
DarkChem Lite v0.1.0
[M+Na]+190.16115
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
Pharmacological action
Yes
Actions
Inhibitor
General Function
Cell wall formation. Synthesis of cross-linked peptidoglycan (PG) from the lipid intermediates (By similarity). Binds dansylated lipid II and catalyzes the polymerization of glycan chains (PubMed:12867450, PubMed:22487093). Hydrolyzes S2d (N-benzoyl-D-alanylmercaptoacetic acid) molecule, a synthetic thiolester analog of cell wall stem peptide (PubMed:10217767, PubMed:22487093). Active against bocillin, a fluorescent penicillin. No transpeptidase activity with non-fluorescent lysine-containing lipid II as substrate (PubMed:22487093).
Specific Function
acyltransferase activity
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. [Article]
Kind
Protein
Organism
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
Pharmacological action
Yes
Actions
Inhibitor
General Function
Not Available
Specific Function
acyltransferase activity
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. [Article]
  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. [Article]
Kind
Protein
Organism
Streptococcus pneumoniae
Pharmacological action
Yes
Actions
Inhibitor
General Function
Removes C-terminal D-alanyl residues from sugar-peptide cell wall precursors.
Specific Function
serine-type D-Ala-D-Ala carboxypeptidase activity
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. [Article]
  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. [Article]
Kind
Protein
Organism
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
Pharmacological action
Yes
Actions
Inhibitor
General Function
Cell wall formation.
Specific Function
penicillin binding
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. [Article]
Kind
Protein
Organism
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
Pharmacological action
Yes
Actions
Inhibitor
General Function
A transpeptidase that forms peptide cross-links between adjacent glycan strands in cell wall peptidoglycan (PG). Part of the elongasome machinery that synthesizes peripheral PG.
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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Electrogenic proton-coupled amino-acid transporter that transports oligopeptides of 2 to 4 amino acids with a preference for dipeptides. Transports neutral and monovalently charged peptides with a proton to peptide stoichiometry of 1:1 or 2:1 (By similarity) (PubMed:15521010, PubMed:18367661, PubMed:19685173, PubMed:26320580, PubMed:7896779, PubMed:8914574, PubMed:9835627). Primarily responsible for the absorption of dietary di- and tripeptides from the small intestinal lumen (By similarity). Mediates transepithelial transport of muramyl and N-formylated bacterial dipeptides contributing to recognition of pathogenic bacteria by the mucosal immune system (PubMed:15521010, PubMed:9835627)
Specific Function
dipeptide transmembrane transporter activity
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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Proton-coupled amino-acid transporter that transports oligopeptides of 2 to 4 amino acids with a preference for dipeptides (PubMed:16434549, PubMed:18367661, PubMed:7756356). Transports neutral and anionic dipeptides with a proton to peptide stoichiometry of 2:1 or 3:1 (By similarity). In kidney, involved in the absorption of circulating di- and tripeptides from the glomerular filtrate (PubMed:7756356). Can also transport beta-lactam antibiotics, such as the aminocephalosporin cefadroxil, and other antiviral and anticancer drugs (PubMed:16434549). Transports the dipeptide-like aminopeptidase inhibitor bestatin (By similarity). Also able to transport carnosine (PubMed:31073693). Involved in innate immunity by promoting the detection of microbial pathogens by NOD-like receptors (NLRs) (By similarity). Mediates transport of bacterial peptidoglycans across the plasma membrane or, in macrophages, the phagosome membrane: catalyzes the transport of certain bacterial peptidoglycans, such as muramyl dipeptide (MDP), the NOD2 ligand (PubMed:20406817)
Specific Function
dipeptide transmembrane transporter activity
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. [Article]
Details
8. Angiopoietin-1 receptor
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Tyrosine-protein kinase that acts as a cell-surface receptor for ANGPT1, ANGPT2 and ANGPT4 and regulates angiogenesis, endothelial cell survival, proliferation, migration, adhesion and cell spreading, reorganization of the actin cytoskeleton, but also maintenance of vascular quiescence. Has anti-inflammatory effects by preventing the leakage of pro-inflammatory plasma proteins and leukocytes from blood vessels. Required for normal angiogenesis and heart development during embryogenesis. Required for post-natal hematopoiesis. After birth, activates or inhibits angiogenesis, depending on the context. Inhibits angiogenesis and promotes vascular stability in quiescent vessels, where endothelial cells have tight contacts. In quiescent vessels, ANGPT1 oligomers recruit TEK to cell-cell contacts, forming complexes with TEK molecules from adjoining cells, and this leads to preferential activation of phosphatidylinositol 3-kinase and the AKT1 signaling cascades. In migrating endothelial cells that lack cell-cell adhesions, ANGT1 recruits TEK to contacts with the extracellular matrix, leading to the formation of focal adhesion complexes, activation of PTK2/FAK and of the downstream kinases MAPK1/ERK2 and MAPK3/ERK1, and ultimately to the stimulation of sprouting angiogenesis. ANGPT1 signaling triggers receptor dimerization and autophosphorylation at specific tyrosine residues that then serve as binding sites for scaffold proteins and effectors. Signaling is modulated by ANGPT2 that has lower affinity for TEK, can promote TEK autophosphorylation in the absence of ANGPT1, but inhibits ANGPT1-mediated signaling by competing for the same binding site. Signaling is also modulated by formation of heterodimers with TIE1, and by proteolytic processing that gives rise to a soluble TEK extracellular domain. The soluble extracellular domain modulates signaling by functioning as decoy receptor for angiopoietins. TEK phosphorylates DOK2, GRB7, GRB14, PIK3R1; SHC1 and TIE1
Specific Function
ATP binding
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. [Article]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Other/unknown
General Function
Binds water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs (Probable). Its main function is the regulation of the colloidal osmotic pressure of blood (Probable). Major zinc transporter in plasma, typically binds about 80% of all plasma zinc (PubMed:19021548). Major calcium and magnesium transporter in plasma, binds approximately 45% of circulating calcium and magnesium in plasma (By similarity). Potentially has more than two calcium-binding sites and might additionally bind calcium in a non-specific manner (By similarity). The shared binding site between zinc and calcium at residue Asp-273 suggests a crosstalk between zinc and calcium transport in the blood (By similarity). The rank order of affinity is zinc > calcium > magnesium (By similarity). Binds to the bacterial siderophore enterobactin and inhibits enterobactin-mediated iron uptake of E.coli from ferric transferrin, and may thereby limit the utilization of iron and growth of enteric bacteria such as E.coli (PubMed:6234017). Does not prevent iron uptake by the bacterial siderophore aerobactin (PubMed:6234017)
Specific Function
antioxidant activity
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
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. doi: 10.1159/000136629. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General 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 (PubMed:10454528, PubMed:10525100, PubMed:10966938, PubMed:17509700, PubMed:20722056, PubMed:33124720). Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Relative uptake activity ratio of carnitine to TEA is 11.3 (PubMed:10454528, PubMed:10525100, PubMed:10966938). In intestinal epithelia, transports the quorum-sensing pentapeptide CSF (competence and sporulation factor) from Bacillus Subtilis wich induces cytoprotective heat shock proteins contributing to intestinal homeostasis (PubMed:18005709). May also contribute to regulate the transport of organic compounds in testis across the blood-testis-barrier (Probable)
Specific Function
(R)-carnitine transmembrane transporter activity
Gene Name
SLC22A5
Uniprot ID
O76082
Uniprot Name
Organic cation/carnitine transporter 2
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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Electrogenic proton-coupled amino-acid transporter that transports oligopeptides of 2 to 4 amino acids with a preference for dipeptides. Transports neutral and monovalently charged peptides with a proton to peptide stoichiometry of 1:1 or 2:1 (By similarity) (PubMed:15521010, PubMed:18367661, PubMed:19685173, PubMed:26320580, PubMed:7896779, PubMed:8914574, PubMed:9835627). Primarily responsible for the absorption of dietary di- and tripeptides from the small intestinal lumen (By similarity). Mediates transepithelial transport of muramyl and N-formylated bacterial dipeptides contributing to recognition of pathogenic bacteria by the mucosal immune system (PubMed:15521010, PubMed:9835627)
Specific Function
dipeptide transmembrane transporter activity
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Proton-coupled amino-acid transporter that transports oligopeptides of 2 to 4 amino acids with a preference for dipeptides (PubMed:16434549, PubMed:18367661, PubMed:7756356). Transports neutral and anionic dipeptides with a proton to peptide stoichiometry of 2:1 or 3:1 (By similarity). In kidney, involved in the absorption of circulating di- and tripeptides from the glomerular filtrate (PubMed:7756356). Can also transport beta-lactam antibiotics, such as the aminocephalosporin cefadroxil, and other antiviral and anticancer drugs (PubMed:16434549). Transports the dipeptide-like aminopeptidase inhibitor bestatin (By similarity). Also able to transport carnosine (PubMed:31073693). Involved in innate immunity by promoting the detection of microbial pathogens by NOD-like receptors (NLRs) (By similarity). Mediates transport of bacterial peptidoglycans across the plasma membrane or, in macrophages, the phagosome membrane: catalyzes the transport of certain bacterial peptidoglycans, such as muramyl dipeptide (MDP), the NOD2 ligand (PubMed:20406817)
Specific Function
dipeptide transmembrane transporter activity
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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Bidirectional proton-coupled monocarboxylate transporter (PubMed:12946269, PubMed:32946811, PubMed:33333023). Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, acetate and the ketone bodies acetoacetate and beta-hydroxybutyrate, and thus contributes to the maintenance of intracellular pH (PubMed:12946269, PubMed:33333023). The transport direction is determined by the proton motive force and the concentration gradient of the substrate monocarboxylate. MCT1 is a major lactate exporter (By similarity). Plays a role in cellular responses to a high-fat diet by modulating the cellular levels of lactate and pyruvate that contribute to the regulation of central metabolic pathways and insulin secretion, with concomitant effects on plasma insulin levels and blood glucose homeostasis (By similarity). Facilitates the protonated monocarboxylate form of succinate export, that its transient protonation upon muscle cell acidification in exercising muscle and ischemic heart (PubMed:32946811). Functions via alternate outward- and inward-open conformation states. Protonation and deprotonation of 309-Asp is essential for the conformational transition (PubMed:33333023)
Specific Function
carboxylic acid transmembrane transporter activity
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. [Article]

Drug created at June 13, 2005 13:24 / Updated at November 06, 2024 19:54