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Identification
NameBenzylpenicillin
Accession NumberDB01053  (APRD00646)
TypeSmall Molecule
GroupsApproved
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
Benzylpenicillin
Benzylpenicilline
Benzylpenicillinic acid
Benzylpenicillinum
Free penicillin II
PCG
Penicillin G
PG
External Identifiers Not Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Crystapenpowder for solution5000000 unitintramuscular; intravenousMylan Pharmaceuticals Ulc1994-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Crystapen 1 000 000 Iu Pwspowder for solution1000000 unitintramuscular; intravenousBioniche Pharma (Canada) Ltd1994-12-312014-11-24Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Crystapen 10000000 Iu Pwspowder for solution10000000 unitintramuscular; intravenousBioniche Pharma (Canada) Ltd1994-12-312014-11-24Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Crystapen 10m I.U.powder for solution10000000 unitintramuscular; intravenousAlveda Pharmaceuticals IncNot applicableNot applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Crystapen 1m I.U.powder for solution1000000 unitintramuscular; intravenousAlveda Pharmaceuticals IncNot applicableNot applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Crystapen 5m I.U.powder for solution5000000 unitintramuscular; intravenousAlveda Pharmaceuticals Inc2008-04-30Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Megacillin 500 Tabletstablet500000 unitoralMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1960-12-311998-04-21Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Novo-pen G 500tablet500000 unitoralNovopharm Limited1966-12-312005-08-10Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Penicillin G K for Inj USP 1000000u/vialpowder for solution1000000 unitintramuscular; intravenousMarsam Pharmaceuticals Inc.1993-12-311997-08-25Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Penicillin G K for Inj,usp 10000000u/vialpowder for solution10000000 unitintramuscular; intravenousMarsam Pharmaceuticals Inc.1993-12-311997-08-25Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Penicillin G K for Inj,usp 5000000u/vialpowder for solution5000000 unitintramuscular; intravenousMarsam Pharmaceuticals Inc.1993-12-311997-08-25Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Penicillin G Na for Inj USP 10000000u/vialpowder for solution10000000 unitintramuscular; intravenousMarsam Pharmaceuticals Inc.1993-12-311997-08-25Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Penicillin G Na for Inj USP 1000000u/vialpowder for solution1000000 unitintramuscular; intravenousMarsam Pharmaceuticals Inc.1993-12-311997-08-25Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Penicillin G Na for Inj USP 5000000u/vialpowder for solution5000000 unitintramuscular; intravenousMarsam Pharmaceuticals Inc.1993-12-311997-08-25Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Penicillin G Pot. for Inj. (10millioniu) USPpowder for solution10000000 unitintravenousWyeth Ayerst Canada Inc.1995-12-311996-09-10Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Penicillin G Potassiuminjection, solution1000000 [iU]/50mLintravenousBaxter Healthcare Corporation1990-06-25Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Penicillin G Potassiuminjection, solution3000000 [iU]/50mLintravenousBaxter Healthcare Corporation1990-06-25Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Penicillin G Potassiuminjection, solution2000000 [iU]/50mLintravenousBaxter Healthcare Corporation1990-06-25Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Penicillin G Potassium for Injection, USPpowder for solution10000000 unitintramuscular; intravenousPharmaceutical Partners Of Canada Inc1998-04-272008-01-10Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Penicillin G Potassium for Injection, USPpowder for solution5000000 unitintramuscular; intravenousPharmaceutical Partners Of Canada Inc1998-05-042008-01-10Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Penicillin G Potassium for Injection, USPpowder for solution1000000 unitintramuscular; intravenousPharmaceutical Partners Of Canada Inc1998-04-212008-01-10Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Penicillin G Potassium Inj 10000000iupowder for solution10000000 unitintramuscular; intravenous; topicalAyerst Laboratories1960-12-311996-09-10Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Penicillin G Potassium Inj 10000000unit/vialpowder for solution10000000 unitintravenousNovopharm Limited1992-12-312005-08-10Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Penicillin G Potassium Inj 1000000iupowder for solution1000000 unitintramuscular; intravenous; topicalAyerst Laboratories1951-12-311996-09-10Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Penicillin G Potassium Inj 1000000unit/vialpowder for solution1000000 unitintramuscular; intravenousNovopharm Limited1992-12-312005-08-10Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Penicillin G Potassium Inj 5000000iupowder for solution5000000 unitintramuscular; intravenous; topicalAyerst Laboratories1951-12-311997-08-15Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Penicillin G Potassium Inj 5000000unit/vialpowder for solution5000000 unitintramuscular; intravenousNovopharm Limited1992-12-312005-08-10Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Penicillin G Sod. for Inj. (10millioniu) USPpowder for solution10000000 unitintravenousWyeth Ayerst Canada Inc.1994-12-311996-09-10Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Penicillin G Sod. for Inj. (1millioniu) USPpowder for solution1000000 unitintramuscular; intravenousWyeth Ayerst Canada Inc.1994-12-311996-09-10Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Penicillin G Sodium for Injectionpowder for solution1000000 unitintramuscular; intravenousNorbrook Laboratories Ltd.Not applicableNot applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Penicillin G Sodium for Injection, USPpowder for solution1000000 unitintramuscular; intravenousFresenius Kabi Canada Ltd1997-01-23Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Penicillin G Sodium for Injection, USPpowder for solution10000000 unitintramuscular; intravenousTeva Canada Limited1992-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Penicillin G Sodium for Injection, USPpowder for solution1000000 unitintramuscular; intravenousTeva Canada Limited1992-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Penicillin G Sodium for Injection, USPpowder for solution5000000 unitintramuscular; intravenousTeva Canada Limited1992-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Penicillin G Sodium for Injection, USPpowder for solution5000000 unitintramuscular; intravenousFresenius Kabi Canada Ltd1997-01-23Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Penicillin G Sodium Inj 10000000iupowder for solution10000000 unitintramuscular; intravenous; topicalAyerst Laboratories1962-12-311996-09-10Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Penicillin G Sodium Inj 1000000iupowder for solution1000000 unitintramuscular; intravenous; topicalAyerst Laboratories1962-12-311996-09-10Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Penicillin G Sodium Inj 5000000iupowder for solution5000000 unitintramuscular; intravenous; topicalAyerst Laboratories1962-12-311996-09-10Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Penicillin G Potassiuminjection, powder, for solution20000000 [iU]/1intravenousWG Critical Care, LLC2012-05-10Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Penicillin G Potassiuminjection, powder, for solution5000000 [iU]/1intramuscular; intravenousWG Critical Care, LLC2012-05-10Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Penicillin G Potassiuminjection, powder, for solution1000000 [iU]/1intramuscular; intravenousWG Critical Care, LLC2012-05-10Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Penicillin G Potassiuminjection, powder, for solution20000000 [iU]/1intramuscular; intravenousSandoz Inc2001-08-30Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Penicillin G Potassiuminjection, powder, for solution5000000 [iU]/1intramuscular; intravenousSandoz Inc2001-08-30Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Penicillin G Potassiumpowder, for solution20000000 [iU]/1intravenousAPP Pharmaceuticals, LLC2009-09-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Penicillin G Potassiumpowder, for solution5000000 [iU]/1intramuscular; intrapleural; intrathecal; intravenousAPP Pharmaceuticals, LLC2009-09-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Penicillin G Sodiuminjection, powder, for solution5000000 [USP'U]/1intramuscular; intravenousSandoz Inc2001-02-26Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Pfizerpenpowder, for solution5000000 [iU]/1intramuscular; intrapleural; intrathecal; intravenousRoerig2010-06-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Pfizerpenpowder, for solution20000000 [iU]/1intravenousRoerig2010-06-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Over the Counter ProductsNot Available
International Brands
NameCompany
PentidsNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Benzylpenicillin potassium
ThumbNot applicableDBSALT000981
Benzylpenicillin sodium
Thumb
  • InChI Key: FCPVYOBCFFNJFS-LQDWTQKMSA-M
  • Monoisotopic Mass: 356.080672407
  • Average Mass: 356.372
DBSALT000726
Categories
CAS number61-33-6
WeightAverage: 334.39
Monoisotopic: 334.098727764
Chemical FormulaC16H18N2O4S
InChI KeyInChIKey=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][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)CC1=CC=CC=C1)C(O)=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as penicillins. These are organic compounds containing the penicillin core structure, which is structurally characterized by a penam ring bearing two methyl groups at position 2, and an amide group at position 6 [starting from the sulfur atom at position 1].
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactams
Sub ClassBeta lactams
Direct ParentPenicillins
Alternative Parents
Substituents
  • Penicillin
  • N-acyl-alpha amino acid or derivatives
  • Phenylacetamide
  • Alpha-amino acid or derivatives
  • Benzenoid
  • Monocyclic benzene moiety
  • Thiazolidine
  • Tertiary carboxylic acid amide
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azetidine
  • Azacycle
  • Dialkylthioether
  • Hemithioaminal
  • Thioether
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationFor 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.
PharmacodynamicsPenicillin 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 actionBy 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.
AbsorptionRapidly 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 bindingBind 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.

SubstrateEnzymesProduct
Benzylpenicillin
Not Available
6-aminopenicillanic acidDetails
Benzylpenicillin
Not Available
Penicilloic acidDetails
Route of eliminationPenicillin G is eliminated by the kidneys. Nonrenal clearance includes hepatic metabolism and, to a lesser extent, biliary excretion.
Half lifeIn adults with normal renal function is reportedly 0.4–0.9 hours
Clearance

560ml/min in healthy humans

ToxicityOral 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
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 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
Powder, for solutionintramuscular; intrapleural; intrathecal; intravenous5000000 [iU]/1
Powder, for solutionintravenous20000000 [iU]/1
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.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point214-217 °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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot 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
External Links
ATC CodesJ01CE01S01AA14
AHFS Codes
  • 08:12.16.04
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (47.7 KB)
Interactions
Drug Interactions
Drug
AcenocoumarolBenzylpenicillin may increase the anticoagulant activities of Acenocoumarol.
AmikacinThe serum concentration of Amikacin can be decreased when it is combined with Benzylpenicillin.
BiotinThe therapeutic efficacy of Benzylpenicillin can be decreased when used in combination with Biotin.
DemeclocyclineThe therapeutic efficacy of Benzylpenicillin can be decreased when used in combination with Demeclocycline.
DoxycyclineThe therapeutic efficacy of Benzylpenicillin can be decreased when used in combination with Doxycycline.
GentamicinThe serum concentration of Gentamicin can be decreased when it is combined with Benzylpenicillin.
KanamycinThe serum concentration of Kanamycin can be decreased when it is combined with Benzylpenicillin.
MethotrexateThe serum concentration of Methotrexate can be increased when it is combined with Benzylpenicillin.
MinocyclineThe therapeutic efficacy of Benzylpenicillin can be decreased when used in combination with Minocycline.
Mycophenolate mofetilThe serum concentration of the active metabolites of Mycophenolate mofetil can be reduced when Mycophenolate mofetil is used in combination with Benzylpenicillin resulting in a loss in efficacy.
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.
NeomycinThe serum concentration of Neomycin can be decreased when it is combined with Benzylpenicillin.
ProbenecidThe serum concentration of Benzylpenicillin can be increased when it is combined with Probenecid.
StreptomycinThe serum concentration of Streptomycin can be decreased when it is combined with Benzylpenicillin.
TetracyclineThe therapeutic efficacy of Benzylpenicillin can be decreased when used in combination with Tetracycline.
TobramycinThe serum concentration of Tobramycin can be decreased when it is combined with Benzylpenicillin.
WarfarinBenzylpenicillin may increase the anticoagulant activities of Warfarin.
Food InteractionsNot Available

Targets

1. Penicillin-binding protein 3

Kind: Protein

Organism: Staphylococcus aureus (strain USA300)

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Penicillin-binding protein 3 Q2FGH1 Details

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

2. Beta-lactamase TEM

Kind: Protein

Organism: Escherichia coli

Pharmacological action: unknown

Components

Name UniProt ID Details
Beta-lactamase TEM P62593 Details

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

3. Solute carrier family 22 member 8

Kind: Protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Solute carrier family 22 member 8 Q8TCC7 Details

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

4. Solute carrier family 15 member 1

Kind: Protein

Organism: Human

Pharmacological action: unknown

Components

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

References:

  1. Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. Pubmed

5. Solute carrier family 15 member 2

Kind: Protein

Organism: Human

Pharmacological action: unknown

Components

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

References:

  1. Pedretti A, De Luca L, Marconi C, Regazzoni L, Aldini G, Vistoli G: Fragmental modeling of hPepT2 and analysis of its binding features by docking studies and pharmacophore mapping. Bioorg Med Chem. 2011 Aug 1;19(15):4544-51. doi: 10.1016/j.bmc.2011.06.027. Epub 2011 Jun 16. Pubmed

Transporters

1. Solute carrier family 22 member 5

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

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

References:

  1. Ganapathy ME, Huang W, Rajan DP, Carter AL, Sugawara M, Iseki K, Leibach FH, Ganapathy V: beta-lactam antibiotics as substrates for OCTN2, an organic cation/carnitine transporter. J Biol Chem. 2000 Jan 21;275(3):1699-707. Pubmed

2. Solute carrier family 15 member 1

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

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

References:

  1. Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. Pubmed
  2. Tsuji A: Transporter-mediated Drug Interactions. Drug Metab Pharmacokinet. 2002;17(4):253-74. Pubmed

3. Solute carrier family 15 member 2

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

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

References:

  1. Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. Pubmed

4. Solute carrier family 22 member 6

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 6 Q4U2R8 Details

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
  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
  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
  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
  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
  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

5. Solute carrier family 22 member 8

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 8 Q8TCC7 Details

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
  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
  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
  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
  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
  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
  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
  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

6. Solute carrier family 22 member 4

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 4 Q9H015 Details

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

7. Solute carrier family 22 member 11

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 11 Q9NSA0 Details

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
  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

8. Solute carrier organic anion transporter family member 2B1

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Solute carrier organic anion transporter family member 2B1 O94956 Details

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

9. Solute carrier organic anion transporter family member 4A1

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Solute carrier organic anion transporter family member 4A1 Q96BD0 Details

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

10. Solute carrier organic anion transporter family member 3A1

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Solute carrier organic anion transporter family member 3A1 Q9UIG8 Details

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

11. Solute carrier organic anion transporter family member 1B1

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Solute carrier organic anion transporter family member 1B1 Q9Y6L6 Details

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

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2015 15:35