Identification

Name
Benzylpenicillin
Accession Number
DB01053
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.

Type
Small Molecule
Groups
Approved, Vet approved
Structure
Thumb
Weight
Average: 334.39
Monoisotopic: 334.098727764
Chemical Formula
C16H18N2O4S
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
  • Benzylpenicillin
  • Benzylpénicilline
  • Benzylpenicillinic acid
  • Benzylpenicillinum
  • Free penicillin II
  • PCG
  • Penicillin G
  • PG

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.

Associated Conditions
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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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)
USolute carrier family 22 member 8
substrate
inhibitor
Humans
USolute carrier family 15 member 1
substrate
inhibitor
Humans
USolute carrier family 15 member 2
inhibitor
Humans
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.

Hover over products below to view reaction partners

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

Adverse Effects
Learn about our commercial Adverse Effects data.
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Toxicity

Oral LD50 in rat is 8900 mg/kg MSDS. 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
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
AcemetacinAcemetacin may decrease the excretion rate of Benzylpenicillin which could result in a higher serum level.
AcenocoumarolBenzylpenicillin may increase the anticoagulant activities of Acenocoumarol.
AcetazolamideAcetazolamide may decrease the excretion rate of Benzylpenicillin which could result in a higher serum level.
Acetyl sulfisoxazoleAcetyl sulfisoxazole may decrease the excretion rate of Benzylpenicillin which could result in a higher serum level.
AcetylcysteineThe excretion of Benzylpenicillin can be decreased when combined with Acetylcysteine.
Acetylsalicylic acidThe excretion of Benzylpenicillin can be decreased when combined with Acetylsalicylic acid.
AcyclovirThe excretion of Benzylpenicillin can be decreased when combined with Acyclovir.
Adefovir dipivoxilThe excretion of Adefovir dipivoxil can be decreased when combined with Benzylpenicillin.
AllopurinolThe excretion of Allopurinol can be decreased when combined with Benzylpenicillin.
AlprostadilThe excretion of Alprostadil can be decreased when combined with Benzylpenicillin.
Additional Data Available
  • Extended Description
    Extended Description
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    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity
    Available for Purchase

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

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

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  • Action
    Action
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Food Interactions
No interactions found.

Products

Purchasing individual compounds or compound libraries for your research?
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Product Ingredients
IngredientUNIICASInChI Key
Benethamine penicillinO3S7RWT8R5751-84-8JAQPGQYDZJZOIN-LQDWTQKMSA-N
Benzathine benzylpenicillinSSZ1S4I0US1538-09-6BVGLIYRKPOITBQ-ANPZCEIESA-N
Benzylpenicillin benzathine hydrateRIT82F58GK41372-02-5WIDKTXGNSOORHA-CJHXQPGBSA-N
Benzylpenicillin calciumZ1GL5S1Z1Z973-53-5PEWXRXAGXPYMIB-ANPZCEIESA-L
Benzylpenicillin potassiumVL775ZTH4C113-98-4IYNDLOXRXUOGIU-LQDWTQKMSA-M
Benzylpenicillin sodiumYS5LY7JF4N69-57-8FCPVYOBCFFNJFS-LQDWTQKMSA-M
International/Other Brands
Pentids
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Bicillin L-AInjection, suspension1200000 [iU]/2mLIntramuscularPfizer Laboratories Div Pfizer Inc1952-06-27Not applicableUS flag
Bicillin L-AInjection, suspension1200000 [iU]/2mLIntramuscularA S Medication Solutions1952-06-27Not applicableUS flag
Bicillin L-AInjection, suspension1200000 [iU]/2mLIntramuscularA-S Medication Solutions1952-06-27Not applicableUS flag
Bicillin L-AInjection, suspension1200000 [iU]/2mLIntramuscularPhysicians Total Care, Inc.1994-08-042013-06-30US flag
Bicillin L-AInjection, suspension600000 [iU]/1mLIntramuscularPfizer Laboratories Div Pfizer Inc1952-06-27Not applicableUS flag
Bicillin L-AInjection, suspension2400000 [iU]/4mLIntramuscularPhysicians Total Care, Inc.1994-06-142011-06-30US flag
Bicillin L-AInjection, suspension1200000 [iU]/2mLIntramuscularNucare Pharmaceuticals,inc.1952-06-27Not applicableUS flag
Bicillin L-AInjection, suspension2400000 [iU]/4mLIntramuscularPfizer Laboratories Div Pfizer Inc1952-06-27Not applicableUS flag
Bicillin L-AInjection, suspension600000 [iU]/1mLIntramuscularPhysicians Total Care, Inc.2008-08-272012-06-30US flag
Bicillin L-ASuspension1200000 unitIntramuscularPfizer Canada Ulc2008-06-11Not applicableCanada flag
Additional Data Available
  • Application Number
    Application Number
    Available for Purchase

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

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  • Product Code
    Product Code
    Available for Purchase

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

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Buffered Penicillin G PotassiumInjection, powder, for solution5000000 [iU]/1Intramuscular; IntravenousHF Acquisition Co LLC, DBA HealthFirst2020-01-29Not applicableUS flag
Novo-pen G 500TabletOralNovopharm Limited1966-12-312005-08-10Canada flag
Penicillin G PotassiumInjection, powder, for solution20000000 [iU]/1IntravenousAthenex Pharmaceutical Division, Llc.2019-05-21Not applicableUS flag
Penicillin G PotassiumPowder, for solution20000000 [iU]/1IntravenousFresenius Kabi USA, LLC2009-09-012016-04-19US flag
Penicillin G PotassiumInjection, powder, for solution5000000 [iU]/1Intramuscular; IntravenousWG Critical Care, LLC2012-05-10Not applicableUS flag
Penicillin G PotassiumInjection, powder, for solution5000000 [iU]/1Intramuscular; IntravenousAthenex Pharmaceutical Division, Llc.2019-05-21Not applicableUS flag
Penicillin G PotassiumPowder, for solution5000000 [iU]/1Intramuscular; Intrapleural; Intrathecal; IntravenousFresenius Kabi USA, LLC2009-09-012011-12-12US flag
Penicillin G PotassiumInjection, powder, for solution20000000 [iU]/1Intramuscular; IntravenousSandoz Inc2001-08-30Not applicableUS flag
Penicillin G PotassiumInjection, powder, for solution1000000 [iU]/1Intramuscular; IntravenousWG Critical Care, LLC2012-05-10Not applicableUS flag
Penicillin G PotassiumInjection, powder, for solution20000000 [iU]/1IntravenousWG Critical Care, LLC2012-05-10Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number
    Available for Purchase

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

    Learn more
  • Product Code
    Product Code
    Available for Purchase

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

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Bicillin A-P Injection PwsBenzylpenicillin benzathine hydrate (600000 unit) + Benzylpenicillin potassium (300000 unit) + Procaine benzylpenicillin (300000 unit)Powder, for solutionIntramuscularWyeth Ayerst Canada Inc.1995-12-311996-09-10Canada flag
Bicillin A-P Injection PwsBenzylpenicillin benzathine hydrate (600000 unit) + Benzylpenicillin potassium (300000 unit) + Procaine benzylpenicillin (300000 unit)Powder, for solutionIntramuscularWyeth Ayerst Canada Inc.1995-12-311996-09-10Canada flag
Bicillin C-R 900/300Benzylpenicillin benzathine hydrate (900000 [iU]/2mL) + Procaine benzylpenicillin (300000 [iU]/2mL)Injection, suspensionIntramuscularPfizer Laboratories Div Pfizer Inc1953-05-18Not applicableUS flag
Bicillin CRBenzylpenicillin benzathine hydrate (600000 [iU]/2mL) + Procaine benzylpenicillin (600000 [iU]/2mL)Injection, suspensionIntramuscularDispensing Solutions, Inc.1953-05-18Not applicableUS flag
Bicillin CRBenzylpenicillin benzathine hydrate (600000 [iU]/2mL) + Procaine benzylpenicillin (600000 [iU]/2mL)Injection, suspensionIntramuscularPfizer Laboratories Div Pfizer Inc1953-05-18Not applicableUS flag
Bicillin CRBenzylpenicillin benzathine hydrate (600000 [iU]/2mL) + Procaine benzylpenicillin (600000 [iU]/2mL)Injection, suspensionIntramuscularPhysicians Total Care, Inc.2008-08-28Not applicableUS flag
Bicillin CRBenzylpenicillin benzathine hydrate (600000 [iU]/2mL) + Procaine benzylpenicillin (600000 [iU]/2mL)Injection, suspensionIntramuscularA-S Medication Solutions1953-05-18Not applicableUS flag
Bicillin CRBenzylpenicillin benzathine hydrate (600000 [iU]/2mL) + Procaine benzylpenicillin (600000 [iU]/2mL)Injection, suspensionIntramuscularPfizer Laboratories Div Pfizer Inc1953-05-18Not applicableUS flag

Categories

ATC Codes
J01CR50 — Combinations of penicillinsJ01CE01 — BenzylpenicillinS01AA14 — BenzylpenicillinJ01CE08 — Benzathine benzylpenicillin
Drug Categories
Chemical TaxonomyProvided by Classyfire
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-amino acid or derivatives / Alpha-dipeptide / Aromatic heteropolycyclic compound / Azacycle / Azetidine / Benzenoid / Beta-lactam / Carbonyl group / Carboxamide group / Carboxylic acid
show 21 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
penicillin (CHEBI:18208) / penams (C05551)

Chemical Identifiers

UNII
Q42T66VG0C
CAS number
61-33-6
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

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]
  2. article [Link]
  3. Webmd [Link]
  4. monograph [Link]
  5. FDA Approved Drug Products: Penicillin G Potassium Intravenous Injection [Link]
  6. FDA Approved Drug Products: Penicillin G Sodium Intravenous Injection [Link]
Human Metabolome Database
HMDB0015186
KEGG Drug
D02336
KEGG Compound
C05551
PubChem Compound
5904
PubChem Substance
46506778
ChemSpider
5693
BindingDB
50022787
RxNav
7980
ChEBI
18208
ChEMBL
CHEMBL29
ZINC
ZINC000003871701
Therapeutic Targets Database
DNC001109
PharmGKB
PA450842
PDBe Ligand
PNN
RxList
RxList Drug Page
Wikipedia
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
4CompletedTreatmentBorreliosis / Early Lyme Disease / Erythema Chronicum Migrans / Lyme Disease1
4CompletedTreatmentInfant Bacterial Meningitis1
4CompletedTreatmentSyphilis1
4RecruitingTreatmentSyphilis4
4TerminatedDiagnosticPenicillin Allergy1
4TerminatedTreatmentImpaired kidney function / S. Aureus Bacteremia / Skin and Subcutaneous Tissue Bacterial Infections1
4TerminatedTreatmentStreptococcal Infections1
4Unknown StatusTreatmentBacteremia1
4Unknown StatusTreatmentStaphylococcus Aureus1
3Active Not RecruitingTreatmentAntibiotic Resistance, Bacterial / Antibiotic Toxicity / Severe Malnutrition1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • APP Pharmaceuticals
  • Baxter International Inc.
  • C.O. Truxton Inc.
  • King Pharmaceuticals Inc.
  • Pfizer Inc.
  • Physicians Total Care Inc.
  • Sandoz
Dosage Forms
FormRouteStrength
Injection, powder, for solution1.2 MU
Injection, powder, for solutionIntramuscular2.4 MIU
Injection; powderIntramuscular600 IU
Injection1200.000 iu
Injection2400.000 iu
Injection, powder, for solution
Injection, powder, for suspensionIntramuscular240000 IU
Injection, powder, for suspensionIntramuscular1200000 IU
Injection, powder, for solutionIntramuscular; Intravenous0.6 g
Injection, powder, for solutionIntramuscular; Intravenous3 g
Powder, for solutionIntramuscular
Injection, suspensionIntramuscular
Injection, suspensionIntramuscular1200000 [iU]/2mL
Injection, suspensionIntramuscular2400000 [iU]/4mL
Injection, suspensionIntramuscular600000 [iU]/1mL
SuspensionIntramuscular1200000 unit
SuspensionIntramuscular
PowderIntramuscular1200000 IU
PowderIntramuscular2400000 IU
PowderIntramuscular600000 IU
Injection, solutionIntramuscular300000 IU
Injection, solutionIntramuscular600000 IU
TabletOral125 MG
Injection, powder, for solutionIntramuscular100000 iu
Injection, powder, for solutionIntramuscular200000 iu
Injection, solutionIntramuscular; Intravenous1000.000 i.u.
Injection, solutionIntramuscular; Intravenous1000.000 iu
Injection, solutionIntramuscular; Intravenous500000 iu
SuspensionOral
TabletOral
InjectionIntramuscular300 mg
InjectionIntramuscular600 mg
Injection, powder, for solution1000000 IU
Injection, powder, for solution5000000 IU
Injection, powder, for suspensionIntramuscular120000 IU
Injection, powder, for suspensionIntramuscular2.4 million IU
Injection, powder, for suspensionIntramuscular2400000 IU
Injection, powder, for suspensionIntramuscular2015 mg
Injection, powder, for solutionIntramuscular; Intravenous1000000 IU
Injection, powder, for solutionIntramuscular; Intravenous5000000 IU
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 solutionIntravenous
Powder, for solutionIntramuscular; Intravenous; Topical
Injection, powder, for solution0.5 MU
Injection, powder, for solution1 MU
Injection, powder, for solution5 MU
Injection, powder, for solutionIntramuscular; Intravenous5000000 [USP'U]/1
Powder, for solutionIntramuscular; Intravenous
Injection, powder, for suspension1 MU
Injection, powder, for suspension5 MU
Injection, powder, for solutionIntramuscular; Intravenous10000000 IU
Injection, powder, for solutionParenteral500000 IE
InjectionIntravenous500000 IU
InjectionIntravenous1000000 IU
InjectionIntramuscular; Intravenous1000.000 iu
Powder, for solutionIntramuscular; Intrapleural; Intrathecal; Intravenous5000000 [iU]/1
Powder, for solutionIntravenous20000000 [iU]/1
Injection, powder, for solutionIntramuscular; Intravenous1 million IU
InjectionIntramuscular100000 IU
InjectionIntramuscular200000 IU
Injection, powder, for suspension1.2 MU
Injection, powder, for suspensionParenteral1.2 Mio. I.E.
Injection, powder, for suspensionParenteral2.4 Mio. I.E.
Injection, powder, for suspensionParenteral600000 I.E.
InjectionIntramuscular300000 IU
InjectionIntramuscular; Intravenous1000000 IU
InjectionIntramuscular; Intravenous500000 IU
InjectionIntramuscular600000 IU
Injection, powder, for suspensionIntramuscular1200.000 UI/4ML
Injection, powder, for suspensionIntramuscular600000 UI/2.5ML
Injection, suspensionIntramuscular; Parenteral1200.000 UI/2.5ML
PowderIntramuscular1200.000 UI
PowderIntramuscular600000 UI
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

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]
Kind
Protein
Organism
Humans
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. 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
Humans
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]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Peptide:proton symporter activity
Specific Function
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides.
Gene Name
SLC15A2
Uniprot ID
Q16348
Uniprot Name
Solute carrier family 15 member 2
Molecular Weight
81782.77 Da
References
  1. 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]

Enzymes

Kind
Protein
Organism
Escherichia coli
Pharmacological action
Unknown
Actions
Substrate
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]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Joos RW, Hall WH: Determination of binding constants of serum albumin for penicillin. J Pharmacol Exp Ther. 1969 Mar;166(1):113-8. [PubMed:5776014]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Symporter activity
Specific Function
Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cat...
Gene Name
SLC22A5
Uniprot ID
O76082
Uniprot Name
Solute carrier family 22 member 5
Molecular Weight
62751.08 Da
References
  1. Ganapathy ME, Huang W, Rajan DP, Carter AL, Sugawara M, Iseki K, Leibach FH, Ganapathy V: beta-lactam antibiotics as substrates for OCTN2, an organic cation/carnitine transporter. J Biol Chem. 2000 Jan 21;275(3):1699-707. [PubMed:10636865]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
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
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Peptide:proton symporter activity
Specific Function
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides.
Gene Name
SLC15A2
Uniprot ID
Q16348
Uniprot Name
Solute carrier family 15 member 2
Molecular Weight
81782.77 Da
References
  1. Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [PubMed:15567297]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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
Humans
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
Humans
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
Humans
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
Humans
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
Humans
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
Humans
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
Humans
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 27, 2020 08:19

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