Identification

Name
Benzylpenicillin
Accession Number
DB01053  (APRD00646, DB11612)
Type
Small Molecule
Groups
Approved, Vet Approved
Description

Benzylpenicillin (Penicillin G) is narrow spectrum antibiotic used to treat infections caused by susceptible bacteria. It is a natural penicillin antibiotic that is administered intravenously or intramuscularly due to poor oral absorption. Penicillin G may also be used in some cases as prophylaxis against susceptible organisms.

Natural penicillins are considered the drugs of choice for several infections caused by susceptible gram positive aerobic organisms, such as Streptococcus pneumoniae, groups A, B, C and G streptococci, nonenterococcal group D streptococci, viridans group streptococci, and non-penicillinase producing staphylococcus. Aminoglycosides may be added for synergy against group B streptococcus (S. agalactiae), S. viridans, and Enterococcus faecalis. The natural penicillins may also be used as first or second line agents against susceptible gram positive aerobic bacilli such as Bacillus anthracis, Corynebacterium diphtheriae, and Erysipelothrix rhusiopathiae. Natural penicillins have limited activity against gram negative organisms; however, they may be used in some cases to treat infections caused by Neisseria meningitidis and Pasteurella. They are not generally used to treat anaerobic infections. Resistance patterns, susceptibility and treatment guidelines vary across regions.

Structure
Thumb
Synonyms
  • (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
  • 6-(2-phenylacetamido)penicillanic acid
  • Bencilpenicilina
  • bensylpenicillin
  • benzyl benicillin
  • Benzylpénicilline
  • Benzylpenicillinic acid
  • Benzylpenicillinum
  • Free penicillin II
  • PCG
  • Penicillin G
  • PG
External IDs
J01CE01
Product Ingredients
IngredientUNIICASInChI Key
Benethamine penicillinO3S7RWT8R5751-84-8JAQPGQYDZJZOIN-LQDWTQKMSA-N
Benzylpenicillin potassiumVL775ZTH4C113-98-4IYNDLOXRXUOGIU-LQDWTQKMSA-M
Benzylpenicillin sodiumYS5LY7JF4N69-57-8FCPVYOBCFFNJFS-LQDWTQKMSA-M
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
CrystapenPowder, for solution5000000 unitIntramuscular; IntravenousMylan Pharmaceuticals1994-12-31Not applicableCanada
Crystapen 1 000 000 Iu PwsPowder, for solution1000000 unitIntramuscular; IntravenousBioniche Pharma (Canada) Ltd1994-12-312014-11-24Canada
Crystapen 10000000 Iu PwsPowder, for solution10000000 unitIntramuscular; IntravenousBioniche Pharma (Canada) Ltd1994-12-312014-11-24Canada
Crystapen 10m I.U.Powder, for solution10000000 unitIntramuscular; IntravenousAlveda Pharmaceuticals IncNot applicableNot applicableCanada
Crystapen 1m I.U.Powder, for solution1000000 unitIntramuscular; IntravenousAlveda Pharmaceuticals IncNot applicableNot applicableCanada
Crystapen 5m I.U.Powder, for solution5000000 unitIntramuscular; IntravenousAlveda Pharmaceuticals Inc2008-04-30Not applicableCanada
Megacillin 500 TabletsTablet500000 unitOralMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1960-12-311998-04-21Canada
Novo-pen G 500Tablet500000 unitOralNovopharm Limited1966-12-312005-08-10Canada
Penicillin G K for Inj USP 1000000u/vialPowder, for solution1000000 unitIntramuscular; IntravenousMarsam Pharmaceuticals Inc.1993-12-311997-08-25Canada
Penicillin G K for Inj,usp 10000000u/vialPowder, for solution10000000 unitIntramuscular; IntravenousMarsam Pharmaceuticals Inc.1993-12-311997-08-25Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Penicillin G PotassiumInjection, powder, for solution20000000 [iU]/1Intramuscular; IntravenousSandoz2001-08-30Not applicableUs
Penicillin G PotassiumPowder, for solution5000000 [iU]/1Intramuscular; Intrapleural; Intrathecal; IntravenousAPP Pharmaceuticals, Inc.2009-09-01Not applicableUs
Penicillin G PotassiumInjection, powder, for solution5000000 [iU]/1Intramuscular; IntravenousWG Critical Care, LLC2012-05-10Not applicableUs
Penicillin G PotassiumPowder, for solution20000000 [iU]/1IntravenousAPP Pharmaceuticals, Inc.2009-09-01Not applicableUs
Penicillin G PotassiumInjection, powder, for solution20000000 [iU]/1IntravenousWG Critical Care, LLC2012-05-10Not applicableUs
Penicillin G PotassiumInjection, powder, for solution5000000 [iU]/1Intramuscular; IntravenousSandoz2001-08-30Not applicableUs
Penicillin G PotassiumInjection, powder, for solution1000000 [iU]/1Intramuscular; IntravenousWG Critical Care, LLC2012-05-10Not applicableUs
Penicillin G SodiumInjection, powder, for solution5000000 [USP'U]/1Intramuscular; IntravenousSandoz2001-02-26Not applicableUs
PfizerpenPowder, for solution20000000 [iU]/1IntravenousRoerig2010-06-01Not applicableUs
PfizerpenPowder, for solution5000000 [iU]/1Intramuscular; Intrapleural; Intrathecal; IntravenousRoerig2010-06-01Not applicableUs
International/Other Brands
Pentids
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Bicillin A-P Injection PwsBenzylpenicillin potassium (300000 unit) + Benzathine benzylpenicillin (600000 unit) + Procaine benzylpenicillin (300000 unit)Powder, for solutionIntramuscularWyeth Ayerst Canada Inc.1995-12-311996-09-10Canada
Categories
UNII
Q42T66VG0C
CAS number
61-33-6
Weight
Average: 334.39
Monoisotopic: 334.098727764
Chemical Formula
C16H18N2O4S
InChI Key
JGSARLDLIJGVTE-MBNYWOFBSA-N
InChI
InChI=1S/C16H18N2O4S/c1-16(2)12(15(21)22)18-13(20)11(14(18)23-16)17-10(19)8-9-6-4-3-5-7-9/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22)/t11-,12+,14-/m1/s1
IUPAC Name
(2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-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)CC1=CC=CC=C1)C(O)=O

Pharmacology

Indication

For use in the treatment of severe infections caused by penicillin G-susceptible microorganisms when rapid and high penicillin levels are required such as in the treatment of septicemia, meningitis, pericarditis, endocarditis and severe pneumonia.

Structured Indications
Pharmacodynamics

Penicillin G 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. Penicillin G has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of penicillin G results from the inhibition of cell wall synthesis and is mediated through penicillin G binding to penicillin binding proteins (PBPs). Penicillin G 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, penicillin G 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 penicillin G interferes with an autolysin inhibitor.

TargetActionsOrganism
UPenicillin-binding protein 3
inhibitor
Staphylococcus aureus (strain USA300)
UBeta-lactamase TEMNot AvailableEscherichia coli
USolute carrier family 22 member 8Not AvailableHuman
USolute carrier family 15 member 1Not AvailableHuman
USolute carrier family 15 member 2Not AvailableHuman
Absorption

Rapidly absorbed following both intramuscular and subcutaneous injection. Initial blood levels following parenteral administration are high but transient. Oral absorption in fasting, healthy humans is only about 15-30% as it is very susceptible to acid-catalyzed hydrolysis.

Volume of distribution

0.53–0.67 L/kg in adults with normal renal function

Protein binding

Bind to serum proteins (45-68%), mainly albumin.

Metabolism

About 16-30% of an intramuscular dose is metabolized to penicilloic acid, an inactive metabolite. Small amounts of 6-aminopenicillanic acid have been recovered in the urine of patients on penicillin G. A small percentage of the drug appears to be hydroxylated into one or more active metabolites, which are also excreted via urine.

Route of elimination

Penicillin G is eliminated by the kidneys. Nonrenal clearance includes hepatic metabolism and, to a lesser extent, biliary excretion.

Half life

In adults with normal renal function is reportedly 0.4–0.9 hours

Clearance

560ml/min in healthy humans

Toxicity

Oral LD50 in rat is 8900 mk/kg. Neurological adverse reactions, including convulsions, may occur with the attainment of high CSF levels of beta-lactams. Neutropenia can occur if high doses are administered consistently for over 2 weeks.

Affected organisms
  • Enteric bacteria and other eubacteria
  • Streptococcus pyogenes
  • Staphylococcus aureus
  • Staphylococcus epidermidis
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AcenocoumarolBenzylpenicillin may increase the anticoagulant activities of Acenocoumarol.Approved
AclarubicinThe serum concentration of Aclarubicin can be decreased when it is combined with Benzylpenicillin.Investigational
AmikacinThe serum concentration of Amikacin can be decreased when it is combined with Benzylpenicillin.Approved, Vet Approved
AmrubicinThe serum concentration of Amrubicin can be decreased when it is combined with Benzylpenicillin.Approved, Investigational
annamycinThe serum concentration of annamycin can be decreased when it is combined with Benzylpenicillin.Investigational
ApramycinThe serum concentration of Apramycin can be decreased when it is combined with Benzylpenicillin.Experimental, Vet Approved
ArbekacinThe serum concentration of Arbekacin can be decreased when it is combined with Benzylpenicillin.Approved
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Benzylpenicillin.Investigational
BekanamycinThe serum concentration of Bekanamycin can be decreased when it is combined with Benzylpenicillin.Experimental
ChlortetracyclineThe therapeutic efficacy of Benzylpenicillin can be decreased when used in combination with Chlortetracycline.Approved, Vet Approved
ClorindioneBenzylpenicillin may increase the anticoagulant activities of Clorindione.Experimental
DaunorubicinThe serum concentration of Daunorubicin can be decreased when it is combined with Benzylpenicillin.Approved
DemeclocyclineThe therapeutic efficacy of Benzylpenicillin can be decreased when used in combination with Demeclocycline.Approved
DibekacinThe serum concentration of Dibekacin can be decreased when it is combined with Benzylpenicillin.Experimental
DicoumarolBenzylpenicillin may increase the anticoagulant activities of Dicoumarol.Approved
DihydrostreptomycinThe serum concentration of Dihydrostreptomycin can be decreased when it is combined with Benzylpenicillin.Vet Approved
DiphenadioneBenzylpenicillin may increase the anticoagulant activities of Diphenadione.Experimental
DoxorubicinThe serum concentration of Doxorubicin can be decreased when it is combined with Benzylpenicillin.Approved, Investigational
DoxycyclineThe therapeutic efficacy of Benzylpenicillin can be decreased when used in combination with Doxycycline.Approved, Investigational, Vet Approved
EltrombopagThe serum concentration of Benzylpenicillin can be increased when it is combined with Eltrombopag.Approved
EpirubicinThe serum concentration of Epirubicin can be decreased when it is combined with Benzylpenicillin.Approved
Ethyl biscoumacetateBenzylpenicillin may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
FluindioneBenzylpenicillin may increase the anticoagulant activities of Fluindione.Investigational
FramycetinThe serum concentration of Framycetin can be decreased when it is combined with Benzylpenicillin.Approved
GeneticinThe serum concentration of Geneticin can be decreased when it is combined with Benzylpenicillin.Experimental
GentamicinThe serum concentration of Gentamicin can be decreased when it is combined with Benzylpenicillin.Approved, Vet Approved
GENTAMICIN C1AThe serum concentration of GENTAMICIN C1A can be decreased when it is combined with Benzylpenicillin.Experimental
GPX-150The serum concentration of GPX-150 can be decreased when it is combined with Benzylpenicillin.Investigational
Hygromycin BThe serum concentration of Hygromycin B can be decreased when it is combined with Benzylpenicillin.Vet Approved
IdarubicinThe serum concentration of Idarubicin can be decreased when it is combined with Benzylpenicillin.Approved
INNO-206The serum concentration of INNO-206 can be decreased when it is combined with Benzylpenicillin.Investigational
IsepamicinThe serum concentration of Isepamicin can be decreased when it is combined with Benzylpenicillin.Experimental
KanamycinThe serum concentration of Kanamycin can be decreased when it is combined with Benzylpenicillin.Approved, Vet Approved
MethotrexateThe serum concentration of Methotrexate can be increased when it is combined with Benzylpenicillin.Approved
MetrizamideThe serum concentration of Metrizamide can be decreased when it is combined with Benzylpenicillin.Approved
MicronomicinThe serum concentration of Micronomicin can be decreased when it is combined with Benzylpenicillin.Experimental
MinocyclineThe therapeutic efficacy of Benzylpenicillin 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 Benzylpenicillin resulting in a loss in efficacy.Approved
NeamineThe serum concentration of Neamine can be decreased when it is combined with Benzylpenicillin.Experimental
NeomycinThe serum concentration of Neomycin can be decreased when it is combined with Benzylpenicillin.Approved, Vet Approved
NetilmicinThe serum concentration of Netilmicin can be decreased when it is combined with Benzylpenicillin.Approved
ParomomycinThe serum concentration of Paromomycin can be decreased when it is combined with Benzylpenicillin.Approved, Investigational
PhenindioneBenzylpenicillin may increase the anticoagulant activities of Phenindione.Approved
PhenprocoumonBenzylpenicillin may increase the anticoagulant activities of Phenprocoumon.Approved
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Benzylpenicillin.Approved
PirarubicinThe serum concentration of Pirarubicin can be decreased when it is combined with Benzylpenicillin.Investigational
PlazomicinThe serum concentration of Plazomicin can be decreased when it is combined with Benzylpenicillin.Investigational
PlicamycinThe serum concentration of Plicamycin can be decreased when it is combined with Benzylpenicillin.Approved, Withdrawn
ProbenecidThe serum concentration of Benzylpenicillin can be increased when it is combined with Probenecid.Approved
PuromycinThe serum concentration of Puromycin can be decreased when it is combined with Benzylpenicillin.Experimental
RibostamycinThe serum concentration of Ribostamycin can be decreased when it is combined with Benzylpenicillin.Approved
SabarubicinThe serum concentration of Sabarubicin can be decreased when it is combined with Benzylpenicillin.Investigational
SisomicinThe serum concentration of Sisomicin can be decreased when it is combined with Benzylpenicillin.Investigational
SP1049CThe serum concentration of SP1049C can be decreased when it is combined with Benzylpenicillin.Investigational
SpectinomycinThe serum concentration of Spectinomycin can be decreased when it is combined with Benzylpenicillin.Approved, Vet Approved
StreptomycinThe serum concentration of Streptomycin can be decreased when it is combined with Benzylpenicillin.Approved, Vet Approved
StreptozocinThe serum concentration of Streptozocin can be decreased when it is combined with Benzylpenicillin.Approved
TeriflunomideThe serum concentration of Benzylpenicillin can be increased when it is combined with Teriflunomide.Approved
TioclomarolBenzylpenicillin may increase the anticoagulant activities of Tioclomarol.Experimental
TobramycinThe serum concentration of Tobramycin can be decreased when it is combined with Benzylpenicillin.Approved, Investigational
ValrubicinThe serum concentration of Valrubicin can be decreased when it is combined with Benzylpenicillin.Approved
WarfarinBenzylpenicillin may increase the anticoagulant activities of Warfarin.Approved
Zoptarelin doxorubicinThe serum concentration of Zoptarelin doxorubicin can be decreased when it is combined with Benzylpenicillin.Investigational
ZorubicinThe serum concentration of Zorubicin can be decreased when it is combined with Benzylpenicillin.Experimental
Food Interactions
Not Available

References

Synthesis Reference

Gunter Schumacher, Peter Buckel, "Plasmids for the increased production of penicillin G amidase." U.S. Patent US5053335, issued May, 1984.

US5053335
General References
  1. Eagle H, Newman E, Musselman AD, Robinson M, Birmingham M: THE RENAL CLEARANCE OF PENICILLINS F, G, K, AND X IN RABBITS AND MAN. J Clin Invest. 1947 Sep;26(5):903-18. [PubMed:16695494]
External Links
Human Metabolome Database
HMDB15186
KEGG Drug
D02336
KEGG Compound
C05551
PubChem Compound
5904
PubChem Substance
46506778
ChemSpider
5693
BindingDB
50022787
ChEBI
18208
ChEMBL
CHEMBL29
Therapeutic Targets Database
DNC001109
PharmGKB
PA450842
HET
PNN
RxList
RxList Drug Page
ATC Codes
J01CE01 — BenzylpenicillinJ01CR50 — Combinations of penicillinsS01AA14 — Benzylpenicillin
AHFS Codes
  • 08:12.16.04 — Natural Penicillins
PDB Entries
1fxv / 1gm7 / 1uob / 1uof / 3huo / 3kp2 / 5kmw
MSDS
Download (47.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingTreatmentOsteomyelitis1
3CompletedDiagnosticHistory of IgE Dependent Reaction to a Penicillin Product1
4Active Not RecruitingPreventionAcetaminophen Toxicity1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Neurosyphilis1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Dosage forms
FormRouteStrength
Powder, for solutionIntramuscular
TabletOral500000 unit
Injection, powder, for solutionIntramuscular; Intravenous1000000 [iU]/1
Injection, powder, for solutionIntramuscular; Intravenous20000000 [iU]/1
Injection, powder, for solutionIntramuscular; Intravenous5000000 [iU]/1
Injection, powder, for solutionIntravenous20000000 [iU]/1
Injection, solutionIntravenous1000000 [iU]/50mL
Injection, solutionIntravenous2000000 [iU]/50mL
Injection, solutionIntravenous3000000 [iU]/50mL
Powder, for solutionIntramuscular; Intrapleural; Intrathecal; Intravenous5000000 [iU]/1
Powder, for solutionIntravenous20000000 [iU]/1
Powder, for solutionIntravenous10000000 unit
Powder, for solutionIntramuscular; Intravenous; Topical5000000 unit
Injection, powder, for solutionIntramuscular; Intravenous5000000 [USP'U]/1
Powder, for solutionIntramuscular; Intravenous1000000 unit
Powder, for solutionIntramuscular; Intravenous10000000 unit
Powder, for solutionIntramuscular; Intravenous5000000 unit
Powder, for solutionIntramuscular; Intravenous; Topical10000000 unit
Powder, for solutionIntramuscular; Intravenous; Topical1000000 unit
Prices
Unit descriptionCostUnit
Penicillin gk 20 million unit160.26USD each
Penicillin g na 5 million unit47.91USD each
Bicillin C-R (1200000) 2ml Syringe43.0USD syringe
Penicillin g k 5 million unit42.18USD each
Pfizerpen 20 million unit vial23.41USD vial
Penicillin G Sodium 10000000 iu/vial9.35USD vial
Pfizerpen 5 million unit vial7.99USD vial
Penicillin G Sodium 5000000 iu/vial5.36USD vial
Penicillin G Sodium 1000000 iu/vial2.52USD vial
Pen g k 3 million unit/50 ml0.27USD ml
Pen g k 2 million unit/50 ml0.26USD ml
Pen g k 1 million unit/50 ml0.25USD ml
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)214-217 °CNot Available
water solubilitySlightly soluble (210 mg/L)Not Available
logP1.83HANSCH,C ET AL. (1995)
pKa2.74 (at 25 °C)MERCK INDEX (1996)
Predicted Properties
PropertyValueSource
Water Solubility0.285 mg/mLALOGPS
logP1.92ALOGPS
logP1.08ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)3.53ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area86.71 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity84.53 m3·mol-1ChemAxon
Polarizability33.54 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9059
Blood Brain Barrier-0.9954
Caco-2 permeable-0.8956
P-glycoprotein substrateSubstrate0.6253
P-glycoprotein inhibitor INon-inhibitor0.9374
P-glycoprotein inhibitor IINon-inhibitor0.9905
Renal organic cation transporterNon-inhibitor0.9485
CYP450 2C9 substrateNon-substrate0.7694
CYP450 2D6 substrateNon-substrate0.845
CYP450 3A4 substrateNon-substrate0.5133
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9187
CYP450 2D6 inhibitorNon-inhibitor0.9295
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.8802
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.96
Ames testNon AMES toxic0.9193
CarcinogenicityNon-carcinogens0.6267
BiodegradationNot ready biodegradable0.989
Rat acute toxicity1.6523 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9993
hERG inhibition (predictor II)Non-inhibitor0.9223
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

Taxonomy

Description
This compound belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Dipeptides
Alternative Parents
Penicillins / N-acyl-alpha amino acids and derivatives / Phenylacetamides / Thiazolidines / Tertiary carboxylic acid amides / Azetidines / Secondary carboxylic acid amides / Azacyclic compounds / Thiohemiaminal derivatives / Carboxylic acids
show 7 more
Substituents
Alpha-dipeptide / Penicillin / N-acyl-alpha amino acid or derivatives / Alpha-amino acid or derivatives / Phenylacetamide / Penam / Monocyclic benzene moiety / Benzenoid / Beta-lactam / Thiazolidine
show 21 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
penicillin (CHEBI:18208) / penams (C05551)

Targets

Kind
Protein
Organism
Staphylococcus aureus (strain USA300)
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Not Available
Specific Function
Penicillin binding
Gene Name
pbp3
Uniprot ID
A0A0H2XJ39
Uniprot Name
Penicillin-binding protein 3
Molecular Weight
77250.74 Da
References
  1. Beise F, Labischinski H, Bradaczek H: On the relationships between molecular conformation, affinity towards penicillin-binding proteins, and biological activity of penicillin G-sulfoxide. Z Naturforsch C. 1988 Sep-Oct;43(9-10):656-64. [PubMed:3245263]
Details
2. Beta-lactamase TEM
Kind
Protein
Organism
Escherichia coli
Pharmacological action
Unknown
General Function
TEM-type are the most prevalent beta-lactamases in enterobacteria; they hydrolyze the beta-lactam bond in susceptible beta-lactam antibiotics, thus conferring resistance to penicillins and cephalosporins. TEM-3 and TEM-4 are capable of hydrolyzing cefotaxime and ceftazidime. TEM-5 is capable of hydrolyzing ceftazidime. TEM-6 is capable of hydrolyzing ceftazidime and aztreonam. TEM-8/CAZ-2, TEM-16/CAZ-7 and TEM-24/CAZ-6 are markedly active against ceftazidime. IRT-4 shows resistance to beta-lactamase inhibitors.
Specific Function
Beta-lactamase activity
Gene Name
bla
Uniprot ID
P62593
Uniprot Name
Beta-lactamase TEM
Molecular Weight
31514.865 Da
References
  1. Joyeau R, Molines H, Labia R, Wakselman M: N-aryl 3-halogenated azetidin-2-ones and benzocarbacephems, inhibitors of beta-lactamases. J Med Chem. 1988 Feb;31(2):370-4. [PubMed:3257523]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
Gene Name
SLC22A8
Uniprot ID
Q8TCC7
Uniprot Name
Solute carrier family 22 member 8
Molecular Weight
59855.585 Da
References
  1. Takeda M, Khamdang S, Narikawa S, Kimura H, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of methotrexate transport and its drug interactions with human organic anion transporters. J Pharmacol Exp Ther. 2002 Aug;302(2):666-71. [PubMed:12130730]
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]

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
Substrate
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. 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]
  2. Tsuji A: Transporter-mediated Drug Interactions. Drug Metab Pharmacokinet. 2002;17(4):253-74. [PubMed:15618677]
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. 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
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
Gene Name
SLC22A6
Uniprot ID
Q4U2R8
Uniprot Name
Solute carrier family 22 member 6
Molecular Weight
61815.78 Da
References
  1. Jung KY, Takeda M, Kim DK, Tojo A, Narikawa S, Yoo BS, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of ochratoxin A transport by human organic anion transporters. Life Sci. 2001 Sep 21;69(18):2123-35. [PubMed:11669456]
  2. Takeda M, Khamdang S, Narikawa S, Kimura H, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of methotrexate transport and its drug interactions with human organic anion transporters. J Pharmacol Exp Ther. 2002 Aug;302(2):666-71. [PubMed:12130730]
  3. Hosoyamada M, Sekine T, Kanai Y, Endou H: Molecular cloning and functional expression of a multispecific organic anion transporter from human kidney. Am J Physiol. 1999 Jan;276(1 Pt 2):F122-8. [PubMed:9887087]
  4. Lu R, Chan BS, Schuster VL: Cloning of the human kidney PAH transporter: narrow substrate specificity and regulation by protein kinase C. Am J Physiol. 1999 Feb;276(2 Pt 2):F295-303. [PubMed:9950961]
  5. Jariyawat S, Sekine T, Takeda M, Apiwattanakul N, Kanai Y, Sophasan S, Endou H: The interaction and transport of beta-lactam antibiotics with the cloned rat renal organic anion transporter 1. J Pharmacol Exp Ther. 1999 Aug;290(2):672-7. [PubMed:10411577]
  6. Hasegawa M, Kusuhara H, Sugiyama D, Ito K, Ueda S, Endou H, Sugiyama Y: Functional involvement of rat organic anion transporter 3 (rOat3; Slc22a8) in the renal uptake of organic anions. J Pharmacol Exp Ther. 2002 Mar;300(3):746-53. [PubMed:11861777]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
Gene Name
SLC22A8
Uniprot ID
Q8TCC7
Uniprot Name
Solute carrier family 22 member 8
Molecular Weight
59855.585 Da
References
  1. Cha SH, Sekine T, Fukushima JI, Kanai Y, Kobayashi Y, Goya T, Endou H: Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney. Mol Pharmacol. 2001 May;59(5):1277-86. [PubMed:11306713]
  2. Jung KY, Takeda M, Kim DK, Tojo A, Narikawa S, Yoo BS, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of ochratoxin A transport by human organic anion transporters. Life Sci. 2001 Sep 21;69(18):2123-35. [PubMed:11669456]
  3. Takeda M, Khamdang S, Narikawa S, Kimura H, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of methotrexate transport and its drug interactions with human organic anion transporters. J Pharmacol Exp Ther. 2002 Aug;302(2):666-71. [PubMed:12130730]
  4. Mori S, Takanaga H, Ohtsuki S, Deguchi T, Kang YS, Hosoya K, Terasaki T: Rat organic anion transporter 3 (rOAT3) is responsible for brain-to-blood efflux of homovanillic acid at the abluminal membrane of brain capillary endothelial cells. J Cereb Blood Flow Metab. 2003 Apr;23(4):432-40. [PubMed:12679720]
  5. Kusuhara H, Sekine T, Utsunomiya-Tate N, Tsuda M, Kojima R, Cha SH, Sugiyama Y, Kanai Y, Endou H: Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain. J Biol Chem. 1999 May 7;274(19):13675-80. [PubMed:10224140]
  6. Hasegawa M, Kusuhara H, Sugiyama D, Ito K, Ueda S, Endou H, Sugiyama Y: Functional involvement of rat organic anion transporter 3 (rOat3; Slc22a8) in the renal uptake of organic anions. J Pharmacol Exp Ther. 2002 Mar;300(3):746-53. [PubMed:11861777]
  7. Ohtsuki S, Kikkawa T, Mori S, Hori S, Takanaga H, Otagiri M, Terasaki T: Mouse reduced in osteosclerosis transporter functions as an organic anion transporter 3 and is localized at abluminal membrane of blood-brain barrier. J Pharmacol Exp Ther. 2004 Jun;309(3):1273-81. Epub 2004 Feb 4. [PubMed:14762099]
  8. Nagata Y, Kusuhara H, Endou H, Sugiyama Y: Expression and functional characterization of rat organic anion transporter 3 (rOat3) in the choroid plexus. Mol Pharmacol. 2002 May;61(5):982-8. [PubMed:11961115]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Symporter activity
Specific Function
Sodium-ion dependent, low affinity carnitine transporter. Probably transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without...
Gene Name
SLC22A4
Uniprot ID
Q9H015
Uniprot Name
Solute carrier family 22 member 4
Molecular Weight
62154.48 Da
References
  1. Yabuuchi H, Tamai I, Nezu J, Sakamoto K, Oku A, Shimane M, Sai Y, Tsuji A: Novel membrane transporter OCTN1 mediates multispecific, bidirectional, and pH-dependent transport of organic cations. J Pharmacol Exp Ther. 1999 May;289(2):768-73. [PubMed:10215651]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds.
Gene Name
SLC22A11
Uniprot ID
Q9NSA0
Uniprot Name
Solute carrier family 22 member 11
Molecular Weight
59970.945 Da
References
  1. Babu E, Takeda M, Narikawa S, Kobayashi Y, Enomoto A, Tojo A, Cha SH, Sekine T, Sakthisekaran D, Endou H: Role of human organic anion transporter 4 in the transport of ochratoxin A. Biochim Biophys Acta. 2002 Jun 12;1590(1-3):64-75. [PubMed:12063169]
  2. Takeda M, Khamdang S, Narikawa S, Kimura H, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of methotrexate transport and its drug interactions with human organic anion transporters. J Pharmacol Exp Ther. 2002 Aug;302(2):666-71. [PubMed:12130730]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent transport of organic anions such as taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost.
Gene Name
SLCO2B1
Uniprot ID
O94956
Uniprot Name
Solute carrier organic anion transporter family member 2B1
Molecular Weight
76709.98 Da
References
  1. Tamai I, Nezu J, Uchino H, Sai Y, Oku A, Shimane M, Tsuji A: Molecular identification and characterization of novel members of the human organic anion transporter (OATP) family. Biochem Biophys Res Commun. 2000 Jun 24;273(1):251-60. [PubMed:10873595]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Thyroid hormone transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent transport of organic anions such as the thyroid hormones T3 (triiodo-L-thyronine), T4 (thyroxine) and rT3, and of estrone-3-sulfate and taurocholate.
Gene Name
SLCO4A1
Uniprot ID
Q96BD0
Uniprot Name
Solute carrier organic anion transporter family member 4A1
Molecular Weight
77192.505 Da
References
  1. Tamai I, Nezu J, Uchino H, Sai Y, Oku A, Shimane M, Tsuji A: Molecular identification and characterization of novel members of the human organic anion transporter (OATP) family. Biochem Biophys Res Commun. 2000 Jun 24;273(1):251-60. [PubMed:10873595]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent transport of organic anions such as estrone-3-sulfate (PubMed:10873595). Mediates transport of prostaglandins (PG) E1 and E2, thyroxine (T4), deltorphin II, BQ-123 an...
Gene Name
SLCO3A1
Uniprot ID
Q9UIG8
Uniprot Name
Solute carrier organic anion transporter family member 3A1
Molecular Weight
76552.135 Da
References
  1. Tamai I, Nezu J, Uchino H, Sai Y, Oku A, Shimane M, Tsuji A: Molecular identification and characterization of novel members of the human organic anion transporter (OATP) family. Biochem Biophys Res Commun. 2000 Jun 24;273(1):251-60. [PubMed:10873595]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
Gene Name
SLCO1B1
Uniprot ID
Q9Y6L6
Uniprot Name
Solute carrier organic anion transporter family member 1B1
Molecular Weight
76447.99 Da
References
  1. Tamai I, Nezu J, Uchino H, Sai Y, Oku A, Shimane M, Tsuji A: Molecular identification and characterization of novel members of the human organic anion transporter (OATP) family. Biochem Biophys Res Commun. 2000 Jun 24;273(1):251-60. [PubMed:10873595]

Drug created on June 13, 2005 07:24 / Updated on November 13, 2017 21:49