Identification
- Summary
Benzylpenicillin is a penicillin used for the treatment of infections caused by gram-positive cocci, in particular streptococcal infections. This form of penicillin is typically used in intravenous or long-acting injectable formulations due to poor oral absorption.
- Brand Names
- Bicillin, Bicillin L-A, Pfizerpen
- Generic Name
- Benzylpenicillin
- DrugBank Accession Number
- DB01053
- Background
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
Structure for Benzylpenicillin (DB01053)
- 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.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
- Actinomycosis
- Acute Rheumatic Fever
- Anthrax
- Bloodstream Infections (BSI)
- Clostridium Botulinum Toxin Adverse Reaction
- Diphtheria
- Empyema
- Endocarditis
- Endocarditis caused by Erysipelothrix infections
- Fusospirochetosis
- Gas Gangrene
- Gonococcal infections
- Gram-Negative Bacterial Infections
- Haverhill fever
- Listeria infection
- Meningitis
- Meningococcal Meningitis
- Pasteurella infections
- Pericarditis
- Pneumonia
- Syphilis
- Tetanus
- Rat bite fever
- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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.
Target Actions Organism UPenicillin-binding protein 3 inhibitorStaphylococcus aureus (strain USA300) USolute carrier family 22 member 8 substrateinhibitorHumans USolute carrier family 15 member 1 substrateinhibitorHumans USolute carrier family 15 member 2 inhibitorHumans - 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.
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- 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- 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.
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAcamprosate The excretion of Acamprosate can be decreased when combined with Benzylpenicillin. Acemetacin Acemetacin may decrease the excretion rate of Benzylpenicillin which could result in a higher serum level. Acenocoumarol Benzylpenicillin may increase the anticoagulant activities of Acenocoumarol. Acetazolamide Acetazolamide may decrease the excretion rate of Benzylpenicillin which could result in a higher serum level. Acetyl sulfisoxazole Acetyl sulfisoxazole may decrease the excretion rate of Benzylpenicillin which could result in a higher serum level. Acetylcysteine The excretion of Benzylpenicillin can be decreased when combined with Acetylcysteine. Acetylsalicylic acid The excretion of Benzylpenicillin can be decreased when combined with Acetylsalicylic acid. Acyclovir The excretion of Benzylpenicillin can be decreased when combined with Acyclovir. Adefovir dipivoxil The excretion of Adefovir dipivoxil can be decreased when combined with Benzylpenicillin. Allopurinol The excretion of Allopurinol can be decreased when combined with Benzylpenicillin. 
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- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Benethamine penicillin O3S7RWT8R5 751-84-8 JAQPGQYDZJZOIN-LQDWTQKMSA-N Benzathine benzylpenicillin SSZ1S4I0US 1538-09-6 BVGLIYRKPOITBQ-ANPZCEIESA-N Benzylpenicillin benzathine hydrate RIT82F58GK 41372-02-5 WIDKTXGNSOORHA-CJHXQPGBSA-N Benzylpenicillin calcium Z1GL5S1Z1Z 973-53-5 PEWXRXAGXPYMIB-ANPZCEIESA-L Benzylpenicillin potassium VL775ZTH4C 113-98-4 IYNDLOXRXUOGIU-LQDWTQKMSA-M Benzylpenicillin sodium YS5LY7JF4N 69-57-8 FCPVYOBCFFNJFS-LQDWTQKMSA-M - International/Other Brands
- Pentids
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Bicillin L-A Injection, suspension 1200000 [iU]/2mL Intramuscular Nucare Pharmaceuticals,inc. 1952-06-27 Not applicable US 
Bicillin L-A Injection, suspension 2400000 [iU]/4mL Intramuscular Physicians Total Care, Inc. 1994-06-14 2011-06-30 US Bicillin L-A Injection, suspension 2400000 [iU]/4mL Intramuscular Pfizer Laboratories Div Pfizer Inc 1952-06-27 Not applicable US Bicillin L-A Injection, suspension 600000 [iU]/1mL Intramuscular Physicians Total Care, Inc. 2008-08-27 2012-06-30 US Bicillin L-A Injection, suspension 1200000 [iU]/2mL Intramuscular Remedy Repack 2015-04-06 2015-11-11 US Bicillin L-A Injection, suspension 600000 [iU]/1mL Intramuscular A-S Medication Solutions 1952-06-27 2022-12-31 US Bicillin L-A Suspension 1200000 unit / 2 mL Intramuscular Pfizer Canada Ulc 2008-06-11 Not applicable Canada 
Bicillin L-A Injection, suspension 1200000 [iU]/2mL Intramuscular Pfizer Laboratories Div Pfizer Inc 1952-06-27 Not applicable US Bicillin L-A Injection, suspension 1200000 [iU]/2mL Intramuscular A-S Medication Solutions 1952-06-27 Not applicable US Bicillin L-A Injection, suspension 1200000 [iU]/2mL Intramuscular A S Medication Solutions 1952-06-27 Not applicable US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Buffered Penicillin G Potassium Injection, powder, for solution 5000000 [iU]/1 Intramuscular; Intravenous HF Acquisition Co LLC, DBA HealthFirst 2020-01-29 Not applicable US Novo-pen G 500 Tablet 500000 unit Oral Novopharm Limited 1966-12-31 2005-08-10 Canada Penicillin G Potassium Powder, for solution 5000000 [iU]/1 Intramuscular; Intrapleural; Intrathecal; Intravenous Fresenius Kabi USA, LLC 2009-09-01 2011-12-12 US Penicillin G Potassium Injection, powder, for solution 20000000 [iU]/1 Intramuscular; Intravenous Sandoz Inc 2001-08-30 Not applicable US Penicillin G Potassium Injection, powder, for solution 5000000 [iU]/1 Intramuscular; Intravenous Athenex Pharmaceutical Division, Llc. 2019-05-21 Not applicable US Penicillin G Potassium Injection, powder, for solution 1000000 [iU]/1 Intramuscular; Intravenous WG Critical Care, LLC 2012-05-10 Not applicable US Penicillin G Potassium Injection, powder, for solution 20000000 [iU]/1 Intravenous WG Critical Care, LLC 2012-05-10 Not applicable US Penicillin G Potassium Injection, powder, for solution 5000000 [iU]/1 Intramuscular; Intravenous Sandoz Inc 2001-08-30 Not applicable US Penicillin G Potassium Powder, for solution 20000000 [iU]/1 Intravenous Fresenius Kabi USA, LLC 2009-09-01 2016-04-19 US Penicillin G Potassium Injection, powder, for solution 20000000 [iU]/1 Intravenous Athenex Pharmaceutical Division, Llc. 2019-05-21 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image BENZAPEN 6.3.3 IM ENJ TOZ ICEREN FLAKON, 1 ADET Benzathine benzylpenicillin (600 IU) + Benzylpenicillin sodium (300 IU) + Procaine benzylpenicillin (300 IU) Injection; Powder Intramuscular TÜM-EKİP İLAÇ A.Ş. 2020-08-14 Not applicable Turkey 
BENZAPEN 6.3.3 IM ENJ TOZ ICEREN FLAKON, 1 ADET Benzathine benzylpenicillin (600 IU) + Benzylpenicillin sodium (300 IU) + Procaine benzylpenicillin (300 IU) Injection; Powder Intramuscular TÜM-EKİP İLAÇ A.Ş. 2020-08-14 Not applicable Turkey Bicillin A-P Injection Pws Benzylpenicillin benzathine hydrate (600000 unit / 2 mL) + Benzylpenicillin potassium (300000 unit / 2 mL) + Procaine benzylpenicillin (300000 unit / 2 mL) Powder, for solution Intramuscular Wyeth Ayerst Canada Inc. 1995-12-31 1996-09-10 Canada Bicillin A-P Injection Pws Benzylpenicillin benzathine hydrate (600000 unit / 2 mL) + Benzylpenicillin potassium (300000 unit / 2 mL) + Procaine benzylpenicillin (300000 unit / 2 mL) Powder, for solution Intramuscular Wyeth Ayerst Canada Inc. 1995-12-31 1996-09-10 Canada Bicillin C-R 900/300 Benzylpenicillin benzathine hydrate (900000 [iU]/2mL) + Procaine benzylpenicillin (300000 [iU]/2mL) Injection, suspension Intramuscular Pfizer Laboratories Div Pfizer Inc 1953-05-18 Not applicable US Bicillin CR Benzylpenicillin benzathine hydrate (600000 [iU]/2mL) + Procaine benzylpenicillin (600000 [iU]/2mL) Injection, suspension Intramuscular Physicians Total Care, Inc. 2008-08-28 Not applicable US Bicillin CR Benzylpenicillin benzathine hydrate (600000 [iU]/2mL) + Procaine benzylpenicillin (600000 [iU]/2mL) Injection, suspension Intramuscular A-S Medication Solutions 1953-05-18 Not applicable US Bicillin CR Benzylpenicillin benzathine hydrate (600000 [iU]/2mL) + Procaine benzylpenicillin (600000 [iU]/2mL) Injection, suspension Intramuscular Pfizer Laboratories Div Pfizer Inc 1953-05-18 Not applicable US Bicillin CR Benzylpenicillin benzathine hydrate (600000 [iU]/2mL) + Procaine benzylpenicillin (600000 [iU]/2mL) Injection, suspension Intramuscular Dispensing Solutions, Inc. 1953-05-18 Not applicable US Bicillin CR Benzylpenicillin benzathine hydrate (600000 [iU]/2mL) + Procaine benzylpenicillin (600000 [iU]/2mL) Injection, suspension Intramuscular Pfizer Laboratories Div Pfizer Inc 1953-05-18 Not applicable US
Categories
- ATC Codes
- J01CR50 — Combinations of penicillins
- J01CR — Combinations of penicillins, incl. beta-lactamase inhibitors
- J01C — BETA-LACTAM ANTIBACTERIALS, PENICILLINS
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- J01CE — Beta-lactamase sensitive penicillins
- J01C — BETA-LACTAM ANTIBACTERIALS, PENICILLINS
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- Drug Categories
- Amides
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antibacterials for Systemic Use
- Antiinfectives for Systemic Use
- Beta-Lactam Antibacterials
- Beta-Lactamase Sensitive Penicillins
- beta-Lactams
- Heterocyclic Compounds, Fused-Ring
- Lactams
- Natural Penicillins
- OAT1/SLC22A6 inhibitors
- OAT3/SLC22A8 Inhibitors
- OAT3/SLC22A8 Substrates
- OATP1B1/SLCO1B1 Substrates
- OATP2B1/SLCO2B1 substrates
- Ophthalmologicals
- Penicillin G
- Penicillins
- Sensory Organs
- Sulfur Compounds
- 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)
- Affected organisms
- Enteric bacteria and other eubacteria
- Streptococcus pyogenes
- Staphylococcus aureus
- Staphylococcus epidermidis
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][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]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
- 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. [Article]
- article [Link]
- Webmd [Link]
- monograph [Link]
- FDA Approved Drug Products: Penicillin G Potassium Intravenous Injection [Link]
- FDA Approved Drug Products: Penicillin G Sodium Intravenous Injection [Link]
- External Links
- Human Metabolome Database
- HMDB0015186
- KEGG Drug
- D02336
- KEGG Compound
- C05551
- PubChem Compound
- 5904
- PubChem Substance
- 46506778
- ChemSpider
- 5693
- BindingDB
- 50022787
- 7980
- ChEBI
- 18208
- ChEMBL
- CHEMBL29
- ZINC
- ZINC000003871701
- Therapeutic Targets Database
- DNC001109
- PharmGKB
- PA450842
- PDBe Ligand
- PNN
- RxList
- RxList Drug Page
- Wikipedia
- Benzylpenicillin
- PDB Entries
- 1fxv / 1gm7 / 1uob / 1uof / 3huo / 3kp2 / 5kmw
- MSDS
- Download (47.7 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Diagnostic Penicillin Allergy 1 4 Completed Treatment Acute Kidney Injury (AKI) / Neurologic toxicity / Sepsis 1 4 Completed Treatment Borreliosis / Early Lyme Disease / Erythema Chronicum Migrans / Lyme Disease 1 4 Completed Treatment Infant Bacterial Meningitis 1 4 Completed Treatment Syphilis 2 4 Not Yet Recruiting Treatment Bone and Joint Infections / Endovascular Infection / Gastrointestinal Tract Infections / Genitourinary tract infection / Pulmonary Infections / Skin and Soft Tissue Infections (SSTIs) 1 4 Recruiting Diagnostic Penicillin Allergy / Penicillin Reaction 1 4 Recruiting Treatment Bacteremia caused by Staphylococcus Aureus 1 4 Recruiting Treatment Complicated Urinary Tract Infection / Infection / Pediatric Infectious Diseases 1 4 Recruiting Treatment Early Syphilis 1
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
Form Route Strength Injection, powder, for solution Intramuscular Injection; powder Intramuscular Injection 1200.000 iu Injection Injection 2400.000 iu Injection, powder, for solution Injection, solution Injection, powder, for solution 1000.000 UI/4ML Injection, powder, for solution 1000.000 UI Injection, powder, for solution Intramuscular; Intravenous 0.6 g Injection, powder, for solution Intramuscular; Intravenous 3 g Powder, for solution Intramuscular Injection, suspension Intramuscular Injection, suspension Intramuscular 1200000 [iU]/2mL Injection, suspension Intramuscular 2400000 [iU]/4mL Injection, suspension Intramuscular 600000 [iU]/1mL Suspension Intramuscular 1200000 unit / 2 mL Powder Intramuscular 2400000 IU Powder Intramuscular 600000 IU Injection, solution Intramuscular Tablet Oral Injection, powder, for solution Intramuscular Injection, solution Intramuscular; Intravenous 1000.000 i.u. Injection, solution Intramuscular; Intravenous 1000.000 iu Injection, solution Intramuscular; Intravenous 500000 iu Injection, powder, for suspension Parenteral 2400000 IU Injection, powder, for suspension Parenteral 12000000 IU Suspension Oral 250000 unit / 5 mL Suspension Oral 500000 unit / 5 mL Tablet Oral 500000 unit / tab Tablet Oral 500000 unit Injection, powder, for solution 5000000 IU Injection, powder, for solution Parenteral 1200000 IU Injection, powder, for suspension Intramuscular 1200000 IU Injection, powder, for suspension Parenteral 1200000 IU Injection, powder, for suspension Intramuscular 120000 IU Injection, powder, for suspension Intramuscular 240000 IU Injection, powder, for suspension Intramuscular 2.4 million IU Injection, powder, for suspension Intramuscular 2015 mg Injection, powder, for solution Intramuscular 100000 IU Injection, powder, for suspension Intramuscular 2400000 IU Injection, powder, for solution Parenteral 5000000 IU Injection, powder, for solution Intramuscular; Intravenous 5000000 IU Injection, powder, for suspension Oral 120000 IU Injection, powder, for solution Intramuscular; Intravenous 1000000 [iU]/1 Injection, powder, for solution Intramuscular; Intravenous 20000000 [iU]/1 Injection, powder, for solution Intramuscular; Intravenous 5000000 [iU]/1 Injection, powder, for solution Intravenous 20000000 [iU]/1 Injection, solution Intravenous 1000000 [iU]/50mL Injection, solution Intravenous 2000000 [iU]/50mL Injection, solution Intravenous 3000000 [iU]/50mL Powder, for solution Intravenous 10000000 unit / vial Powder, for solution Intramuscular; Intravenous 1000000 unit / vial Powder, for solution Intramuscular; Intravenous; Topical 5000000 unit / vial Injection, powder, for solution Intramuscular; Intravenous 5000000 [USP'U]/1 Powder, for solution Intramuscular; Intravenous 10000000 unit / vial Powder, for solution Intramuscular; Intravenous 5000000 unit / vial Powder, for solution Intramuscular; Intravenous; Topical 10000000 unit / vial Powder, for solution Intramuscular; Intravenous; Topical 1000000 unit / vial Injection, powder, for solution Intramuscular; Intravenous 5,000,000 IU/vial Injection, powder, for solution Intramuscular; Intravenous 1000000 IU Injection, powder, for solution Intramuscular; Intravenous 10000000 IU Injection, powder, for solution Parenteral Injection Intravenous 500000 IU Injection Intravenous 1000000 IU Injection Intramuscular; Intravenous 1000.000 iu Injection Intramuscular; Intravenous Powder, for solution Intramuscular; Intrapleural; Intrathecal; Intravenous 5000000 [iU]/1 Powder, for solution Intravenous 20000000 [iU]/1 Injection, powder, for solution Intramuscular; Intravenous 1 million IU Injection Intramuscular Injection, powder, for suspension Parenteral Injection Intramuscular; Intravenous 1000000 IU Injection Intramuscular; Intravenous 500000 IU Injection, powder, for suspension Intramuscular 1200000 IU/4ML Injection, powder, for suspension Intramuscular 600000 UI/2.5ML Injection, suspension Intramuscular 1200000 IU/2.5ML Powder Intramuscular 1200000 IU Powder Intramuscular 600000 UI Powder Intramuscular 1.2 MU/1vial - Prices
Unit description Cost Unit Penicillin gk 20 million unit 160.26USD each Penicillin g na 5 million unit 47.91USD each Bicillin C-R (1200000) 2ml Syringe 43.0USD syringe Penicillin g k 5 million unit 42.18USD each Pfizerpen 20 million unit vial 23.41USD vial Penicillin G Sodium 10000000 iu/vial 9.35USD vial Pfizerpen 5 million unit vial 7.99USD vial Penicillin G Sodium 5000000 iu/vial 5.36USD vial Penicillin G Sodium 1000000 iu/vial 2.52USD vial Pen g k 3 million unit/50 ml 0.27USD ml Pen g k 2 million unit/50 ml 0.26USD ml Pen g k 1 million unit/50 ml 0.25USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 214-217 °C Not Available water solubility Slightly soluble (210 mg/L) Not Available logP 1.83 HANSCH,C ET AL. (1995) pKa 2.74 (at 25 °C) MERCK INDEX (1996) - Predicted Properties
Property Value Source Water Solubility 0.285 mg/mL ALOGPS logP 1.92 ALOGPS logP 1.08 Chemaxon logS -3.1 ALOGPS pKa (Strongest Acidic) 3.53 Chemaxon pKa (Strongest Basic) -2.8 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 86.71 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 84.53 m3·mol-1 Chemaxon Polarizability 33.53 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.9059 Blood Brain Barrier - 0.9954 Caco-2 permeable - 0.8956 P-glycoprotein substrate Substrate 0.6253 P-glycoprotein inhibitor I Non-inhibitor 0.9374 P-glycoprotein inhibitor II Non-inhibitor 0.9905 Renal organic cation transporter Non-inhibitor 0.9485 CYP450 2C9 substrate Non-substrate 0.7694 CYP450 2D6 substrate Non-substrate 0.845 CYP450 3A4 substrate Non-substrate 0.5133 CYP450 1A2 substrate Non-inhibitor 0.9046 CYP450 2C9 inhibitor Non-inhibitor 0.9187 CYP450 2D6 inhibitor Non-inhibitor 0.9295 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor Non-inhibitor 0.8802 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.96 Ames test Non AMES toxic 0.9193 Carcinogenicity Non-carcinogens 0.6267 Biodegradation Not ready biodegradable 0.989 Rat acute toxicity 1.6523 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9993 hERG inhibition (predictor II) Non-inhibitor 0.9223
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- 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
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- 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
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- 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
- Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- 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
- Pedretti A, De Luca L, Marconi C, Regazzoni L, Aldini G, Vistoli G: Fragmental modeling of hPepT2 and analysis of its binding features by docking studies and pharmacophore mapping. Bioorg Med Chem. 2011 Aug 1;19(15):4544-51. doi: 10.1016/j.bmc.2011.06.027. Epub 2011 Jun 16. [Article]
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
- 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. [Article]
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
- Joos RW, Hall WH: Determination of binding constants of serum albumin for penicillin. J Pharmacol Exp Ther. 1969 Mar;166(1):113-8. [Article]
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
- Ganapathy ME, Huang W, Rajan DP, Carter AL, Sugawara M, Iseki K, Leibach FH, Ganapathy V: beta-lactam antibiotics as substrates for OCTN2, an organic cation/carnitine transporter. J Biol Chem. 2000 Jan 21;275(3):1699-707. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- 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
- Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [Article]
- Tsuji A: Transporter-mediated Drug Interactions. Drug Metab Pharmacokinet. 2002;17(4):253-74. [Article]
- 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
- Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- 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
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- 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
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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
- 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. [Article]
- 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
- 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. [Article]
- 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. [Article]
- 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
- 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. [Article]
- 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
- 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. [Article]
- 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
- 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. [Article]
- 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
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at December 05, 2023 12:31