Identification
- Summary
Phenoxymethylpenicillin is a penicillin antibiotic used to prevent and treat mild to moderately severe infections in the respiratory tract, skin, and soft tissues.
- Brand Names
- Pen VK
- Generic Name
- Phenoxymethylpenicillin
- DrugBank Accession Number
- DB00417
- Background
Phenoxymethylpenicillin is a narrow spectrum antibiotic also commonly referred to as Penicillin V or Penicillin VK.3 It is a phenoxymethyl analog of Penicillin G, or benzylpenicillin. An orally active naturally penicillin, phenoxymethylpenicillin is used to treat mild to moderate infections in the respiratory tract, skin, and soft tissues caused by penicillin G-sensitive microorganisms. Phenoxymethylpenicillin has also be used in some cases as prophylaxis against susceptible organisms. While there have been no controlled clinical efficacy studies that were conducted, phenoxymethylpenicillin has been suggested by the American Heart Association and the American Dental Association for use as an oral regimen for prophylaxis against bacterial endocarditis in patients with congenital heart disease or rheumatic or other acquired valvular heart disease when they undergo dental procedures and surgical procedures of the upper respiratory tract, except for those who are at an elevated risk for endocarditis.Label
- Type
- Small Molecule
- Groups
- Approved, Vet approved
- Structure
Structure for Phenoxymethylpenicillin (DB00417)
- Weight
- Average: 350.39
Monoisotopic: 350.093642386 - Chemical Formula
- C16H18N2O5S
- Synonyms
- (2S,5R,6R)-3,3-DIMETHYL-7-OXO-6-(2-PHENOXYACETAMIDO)-4-THIA-1- AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID
- (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(phenoxyacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
- 6-phenoxyacetamidopenicillanic acid
- Fenoximetilpenicilina
- Oracillin
- Penicillin Phenoxymethyl
- Penicillin V
- Phenoxomethylpenicillin
- Phenoxymethyl Penicillin
- Phenoxymethylenepenicillinic acid
- Phenoxymethylpenicillin
- Phénoxyméthylpénicilline
- Phenoxymethylpenicillinum
- PV
Pharmacology
- Indication
Indicated for the treatment of mild to moderately severe infections due to penicillin G-sensitive microorganisms, with the use of bacteriological studies (including sensitivity tests) and clinical response.Label
Phenoxymethylpenicillin may be used for the treatment of:
- mild to moderate infections of the upper respiratory tract, scarlet fever, and mild erysipelas caused by Streptococcus without bacteremia
- mild to moderately severe infections of the respiratory tract caused by Pneumococcus
- mild infections of the skin and soft tissues caused by penicillin G-sensitive Staphylococcus
- mild to moderately severe infections of the oropharynx caused by Fusospirochetosis, including Vincent’s gingivitis and pharyngitis, usually respond to oral penicillin therapy
Off-label
Indicated for use as prophylaxis against bacterial endocarditis in patients with congenital heart disease or rheumatic or other acquired valvular heart disease when they undergo dental procedures and surgical procedures of the upper respiratory tract.Label
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
- Animal bite
- Anthrax
- Bacterial Endocarditis
- Bacterial Infections
- Community Acquired Pneumonia (CAP)
- Erythema Chronicum Migrans
- Gingivitis, Necrotizing Ulcerative
- Lower Respiratory Tract Infection (LRTI)
- Scarlet Fever
- Skin and Subcutaneous Tissue Bacterial Infections
- Streptococcal Pharyngitis
- Tonsillitis streptococcal
- Mild Otitis media
- Mild bacterial upper respiratory tract infections
- Moderate Otitis media
- Moderate bacterial upper respiratory tract infections
- Prophylaxis of Rheumatic fever
- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Phenoxymethylpenicillin works against penicillin-sensitive microorganisms with bactericidal effects. It targets the bacteria during its active multiplication stage by interfering with bacterial cell wall peptidoglycan synthesis. In vitro, phenoxymethylpenicillin was shown to be active against staphylococci (except penicillinase-producing strains), streptococci (groups A, C, G, H, L and M), and pneumococci, as well as Corynebacterium diphtheriae, Bacillus anthracis, Clostridia, Actinomyces bovis, Streptobacillus moniliformis, Listeria monocytogenes, Leptospira, Neisseria gonorrhoeae, and Treponema pallidum.Label
- Mechanism of action
Phenoxymethylpenicillin inhibits the biosynthesis of cell wall mucopeptide Label by binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, which are critical in the cell wall synthesis and maintenance, as well as cell division.8 This disrupts the third and last stage of bacterial cell wall synthesis. This subsequently leads to cell lysis.8
Target Actions Organism AMecA PBP2' (penicillin binding protein 2') inhibitorStaphylococcus aureus APenicillin-binding protein 1A Not Available Clostridium perfringens (strain 13 / Type A) UD-alanyl-D-alanine carboxypeptidase DacB Not Available Escherichia coli (strain K12) UPenicillin acylase Not Available Lysinibacillus sphaericus USolute carrier family 15 member 1 Not Available Humans - Absorption
Upon oral administration, phenoxymethylpenicillin is rapidly but incompletely absorbed.4 The bioavailability of phenoxymethylpenicillin ranges from 25 to 60%.6 Compared to the free acid form of the drug, the calcium or potassium salts of phenoxymethylpenicillin displays better absorption profiles. It is reported that fasting state enhances the drug absorption. The peak plasma concentrations of 200 to 700 ng/mL are achieved in 2 hours following an oral dose of 125 mg. Following an oral dose of 500 mg, the peak plasma concentrations of 3 to 5 μg/mL are reached in 30 to 60 minutes post-dose.8
- Volume of distribution
Following intravenous administration, the volume of distribution at steady state was 35.4 L.5 Small amounts of the drug can be found in various tissues, with the highest amount found in the kidneys, with lesser amounts in the liver, skin, and intes tines. Phenoxymethylpenicillin was found in the cerebrospinal fluid.Label Phenoxymethylpenicillin was detectable in the placenta and human breast milk.8
- Protein binding
Upon oral administration, about 50-80% of the drug is bound to plasma proteins.8,Label
- Metabolism
About 35-70% of an oral 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
While the drug is rapidly excreted, only 25% of the total dose is detected in the urine. Renal excretion may be delayed in neonates, young infants, and patients with renal impairment.Label
- Half-life
Upon oral administration, the half-life is about 30 minutes. It can last up to 4 hours in patients with renal impairment.8
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
The oral LD50 is >1040 mg/kg in rats. Nausea, vomiting, black hairy tongue, and epigastric distress are common reactions to oral penicillins.Label In rare cases, neuromuscular sensitivity and seizures may be seen with antibiotics and supportive treatments are advised and further drug absorption should be limited through induced emesis or gastric lavage, followed by administration of activated charcoal.10 Severe hypersensitivity reactions, often leading to death, have been reported with penicillin therapies.Label Although phenoxymethylpenicillin was shown to be excreted in human breast milk, the use of this drug in pregnant or nursing women is regarded generally safe.9
- 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 softwareAcemetacin Acemetacin may decrease the excretion rate of Phenoxymethylpenicillin which could result in a higher serum level. Acenocoumarol Phenoxymethylpenicillin may increase the anticoagulant activities of Acenocoumarol. Ambroxol The risk or severity of methemoglobinemia can be increased when Phenoxymethylpenicillin is combined with Ambroxol. Amikacin The serum concentration of Amikacin can be decreased when it is combined with Phenoxymethylpenicillin. Articaine The risk or severity of methemoglobinemia can be increased when Phenoxymethylpenicillin is combined with Articaine. Atracurium The therapeutic efficacy of Atracurium can be increased when used in combination with Phenoxymethylpenicillin. Atracurium besylate The therapeutic efficacy of Atracurium besylate can be increased when used in combination with Phenoxymethylpenicillin. BCG vaccine The therapeutic efficacy of BCG vaccine can be decreased when used in combination with Phenoxymethylpenicillin. Benzocaine The risk or severity of methemoglobinemia can be increased when Phenoxymethylpenicillin is combined with Benzocaine. Benzyl alcohol The risk or severity of methemoglobinemia can be increased when Phenoxymethylpenicillin is combined with Benzyl alcohol. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- Take on an empty stomach. Absorption is increased 1 hour before or 2 hours after food.
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 Phenoxymethylpenicillin benzathine 3T4EMH59ZU 5928-84-7 BBTOYUUSUQNIIY-ANPZCEIESA-N Phenoxymethylpenicillin potassium 146T0TU1JB 132-98-9 HCTVWSOKIJULET-LQDWTQKMSA-M - Product Images
- International/Other Brands
- Apo-Pen-VK / Betapen-VK / Crystapen V / Distaquaine V / Fenospen / Fenoxypen / Ledercillin VK / Oratren / Ospen / Pen-Oral / Pen-V / Pen-Vee / Pen-Vee K / Penicillin VK / Pfizerpen VK / Phenocillin / Robicillin VK / Rocilin / Uticillin VK / V-Cillin / Veetids
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Beepen-VK Powder, for solution 250 mg/5mL Oral GlaxoSmithKline 2007-08-04 2007-08-06 US 
Beepen-VK Tablet 500 mg/1 Oral GlaxoSmithKline 2007-08-04 2007-08-06 US Beepen-VK Powder, for solution 125 mg/5mL Oral GlaxoSmithKline 2007-08-04 2007-08-06 US Beepen-VK Tablet 250 mg/1 Oral GlaxoSmithKline 2007-08-04 2007-08-06 US Ledercillin Vk - Tab 400000 Unit Tablet 400000 unit / tab Oral Wyeth Ayerst Canada Inc. 1997-06-13 2000-08-02 Canada 
Ledercillin Vk - Tab 800000units Tablet 800000 unit / tab Oral Wyeth Ayerst Canada Inc. 1996-12-27 2001-04-23 Canada Ledercillin Vk Tab 400000unit Tablet 250 mg / tab Oral Lederle Cyanamid Canada Inc. 1969-12-31 1997-08-14 Canada Ledercillin Vk Tab 800000unit Tablet 500 mg / tab Oral Lederle Cyanamid Canada Inc. 1969-12-31 1997-08-14 Canada Nadopen V 200 Powder, for solution 40000 unit / mL Oral Lioh Inc. 1969-12-31 2006-08-25 Canada Nadopen V 400 Powder, for solution 80000 unit / mL Oral Lioh Inc. 1972-12-31 2006-08-25 Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Apo Pen Vk Powder, for solution 300 mg / 5 mL Oral Apotex Corporation 1985-12-31 Not applicable Canada Apo Pen Vk Powder, for solution 125 mg / 5 mL Oral Apotex Corporation 1985-12-31 Not applicable Canada Novo-pen Vk Syr 500000/5ml Powder, for solution 300 mg / 5 mL Oral Novopharm Limited 1977-12-31 2018-01-24 Canada Novo-pen-VK 500 Tab Tablet 500000 unit Oral Novopharm Limited 1966-12-31 2015-10-26 Canada Nu-pen-VK Tablets 300mg Tablet 300 mg Oral Nu Pharm Inc 1990-12-31 2012-09-04 Canada Penicillin V Potasium Tablet 500 mg/1 Oropharyngeal REMEDYREPACK INC. 2020-01-07 Not applicable US Penicillin V Potasium Tablet 500 mg/1 Oral Avera McKennan Hospital 2015-05-26 2017-05-24 US Penicillin V Potasium Tablet 250 mg/1 Oral Sandoz Inc 1995-11-30 2023-05-31 US Penicillin V Potasium Tablet 500 mg/1 Oral Physicians Total Care, Inc. 1995-02-22 Not applicable US Penicillin V Potasium Tablet 500 mg/1 Oral RedPharm Drug, Inc. 2001-01-01 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
- Aza Compounds
- Azabicyclo Compounds
- Beta-Lactam Antibacterials
- Beta-Lactamase Sensitive Penicillins
- beta-Lactams
- Heterocyclic Compounds, Fused-Ring
- Lactams
- Natural Penicillins
- Penicillin G
- Penicillins
- 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 / Phenoxy compounds / Phenol ethers / Alkyl aryl ethers / Thiazolidines / Tertiary carboxylic acid amides / Secondary carboxylic acid amides / Azetidines / Thiohemiaminal derivatives show 9 more
- Substituents
- Alkyl aryl ether / Alpha-amino acid or derivatives / Alpha-dipeptide / Aromatic heteropolycyclic compound / Azacycle / Azetidine / Benzenoid / Beta-lactam / Carbonyl group / Carboxamide group show 24 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- penicillin (CHEBI:27446)
- Affected organisms
- Bacteria
- Gram-negative Bacteria
- Bacillus anthracis
- Corynebacterium diphtheriae
- Streptococcus pyogenes
- Leptospira interrogans
- Listeria monocytogenes
- Borrelia burgdorferi
- Neisseria gonorrhoeae
- Clostridium
Chemical Identifiers
- UNII
- Z61I075U2W
- CAS number
- 87-08-1
- InChI Key
- BPLBGHOLXOTWMN-MBNYWOFBSA-N
- InChI
- InChI=1S/C16H18N2O5S/c1-16(2)12(15(21)22)18-13(20)11(14(18)24-16)17-10(19)8-23-9-6-4-3-5-7-9/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-phenoxyacetamido)-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)COC1=CC=CC=C1)C(O)=O
References
- Synthesis Reference
Hephzibah Sivaraman, Archana Pundle, Cheravakkattu Suresh, George Dodson, James Brannigan, "Process for production of large amount of penicillin V acylase." U.S. Patent US20050142652, issued June 30, 2005.
US20050142652- General References
- Authors unspecified: Inadvertent use of Bicillin C-R to treat syphilis infection--Los Angeles, California, 1999-2004. MMWR Morb Mortal Wkly Rep. 2005 Mar 11;54(9):217-9. [Article]
- Gruchalla RS, Pirmohamed M: Clinical practice. Antibiotic allergy. N Engl J Med. 2006 Feb 9;354(6):601-9. [Article]
- Skarpeid PL, Hoye S: Phenoxymethylpenicillin Versus Amoxicillin for Infections in Ambulatory Care: A Systematic Review. Antibiotics (Basel). 2018 Sep 4;7(3). pii: antibiotics7030081. doi: 10.3390/antibiotics7030081. [Article]
- Josefsson K, Bergan T: Pharmacokinetics of phenoxymethylpenicillin in volunteers. Chemotherapy. 1982;28(4):241-6. doi: 10.1159/000238084. [Article]
- Overbosch D, Mattie H, van Furth R: Comparative pharmacodynamics and clinical pharmacokinetics of phenoxymethylpenicillin and pheneticillin. Br J Clin Pharmacol. 1985 May;19(5):657-68. doi: 10.1111/j.1365-2125.1985.tb02693.x. [Article]
- Llor C, Arranz J, Morros R, Garcia-Sangenis A, Pera H, Llobera J, Guillen-Sola M, Carandell E, Ortega J, Hernandez S, Miravitlles M: Efficacy of high doses of oral penicillin versus amoxicillin in the treatment of adults with non-severe pneumonia attended in the community: study protocol for a randomised controlled trial. BMC Fam Pract. 2013 Apr 17;14:50. doi: 10.1186/1471-2296-14-50. [Article]
- Phenoxymethylpenicillin (Penicillin V) Monograph - Government of Western Australia Child and Adolescents Health Service [Link]
- Phenoxymethyl Penicillin 250mg/5ml Oral Solution Sugar Free (syringe) - eMC [Link]
- phenoxymethylpenicillin (penicillin v) - King Edward Memorial Hospital [Link]
- Penicillin V potassium - GLOWM [Link]
- External Links
- Human Metabolome Database
- HMDB0014561
- KEGG Drug
- D05411
- KEGG Compound
- C08126
- PubChem Compound
- 6869
- PubChem Substance
- 46507164
- ChemSpider
- 6607
- BindingDB
- 50370584
- 7984
- ChEBI
- 27446
- ChEMBL
- CHEMBL615
- ZINC
- ZINC000003831282
- Therapeutic Targets Database
- DAP001165
- PharmGKB
- PA164745442
- PDBe Ligand
- PNV
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Phenoxymethylpenicillin
- PDB Entries
- 2z71
- FDA label
- Download (195 KB)
- MSDS
- Download (37.1 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Prevention Cellulitis/Erysipelas of the Leg 1 4 Completed Prevention Infectious Diseases 1 4 Completed Treatment Borreliosis / Early Lyme Disease / Erythema Chronicum Migrans / Lyme Disease 1 4 Completed Treatment Periimplantitis / Periodontal Disease 1 4 Completed Treatment Tonsillitis 1 4 Unknown Status Treatment Abscesses / Cellulitis / Wound Infections 1 4 Unknown Status Treatment Sore Throat / Tonsillitis 1 3 Terminated Treatment Community Acquired Pneumonia (CAP) 1 2 Not Yet Recruiting Treatment Rheumatic Heart Disease 1 1 Completed Basic Science Stress Oxidative 1
Pharmacoeconomics
- Manufacturers
- Eli lilly and co
- Glaxosmithkline
- Apothecon inc div bristol myers squibb
- Lederle laboratories div american cyanamid co
- Parke davis div warner lambert co
- American antibiotics llc
- Dava pharmaceuticals inc
- Mylan pharmaceuticals inc
- Purepac pharmaceutical co
- Teva pharmaceuticals usa inc
- Wyeth ayerst laboratories
- Pfizer laboratories div pfizer inc
- Apothecon sub bristol myers squibb co
- Bristol laboratories inc div bristol myers co
- Aurobindo pharma ltd
- Ivax pharmaceuticals inc sub teva pharmaceuticals usa
- Sandoz inc
- Pharmacia and upjohn co
- Packagers
- Advanced Pharmaceutical Services Inc.
- American Antibiotics LLC
- Apogee Bio Pharm Corp.
- Apotheca Inc.
- A-S Medication Solutions LLC
- Aurobindo Pharma Ltd.
- Bristol-Myers Squibb Co.
- Bryant Ranch Prepack
- C.O. Truxton Inc.
- Carlisle Laboratories Inc.
- Casa De Amigos Pharmacy
- Central Texas Community Health Centers
- Clonmel Healthcare Ltd.
- DAVA Pharmaceuticals
- Direct Dispensing Inc.
- Dispensing Solutions
- Diversified Healthcare Services Inc.
- E.R. Squibb and Sons LLC
- Golden State Medical Supply Inc.
- Greenstone LLC
- H.J. Harkins Co. Inc.
- Kaiser Foundation Hospital
- Lake Erie Medical and Surgical Supply
- Liberty Pharmaceuticals
- Major Pharmaceuticals
- Medpharm Inc.
- Novopharm Ltd.
- Nucare Pharmaceuticals Inc.
- Palmetto Pharmaceuticals Inc.
- Par Pharmaceuticals
- Patient First Corp.
- PCA LLC
- PD-Rx Pharmaceuticals Inc.
- Pharmedix
- Physicians Total Care Inc.
- Preferred Pharmaceuticals Inc.
- Prepackage Specialists
- Prescription Dispensing Service Inc.
- Rebel Distributors Corp.
- Redpharm Drug
- Sandhills Packaging Inc.
- Sandoz
- Southwood Pharmaceuticals
- St Mary's Medical Park Pharmacy
- Stat Scripts LLC
- Talbert Medical Management Corp.
- Teva Pharmaceutical Industries Ltd.
- Veratex Corp.
- Dosage Forms
Form Route Strength Powder, for solution Oral 125 mg / 5 mL Powder, for solution Oral 300 mg / 5 mL Granule Oral 125 MG/5ML Powder, for solution Oral 125 mg/5mL Powder, for solution Oral 250 mg/5mL Tablet Oral 250 mg/1 Tablet Oral 500 mg/1 Tablet, film coated Oral 708 mg Syrup Oral 300000 iu/5ml Syrup Oral Powder Parenteral 250000 IU Powder Parenteral 300000 IU Granule Oral 400000 IU Powder Parenteral 500000 IU Tablet, film coated Oral 1200000 IU Powder Parenteral 30 G Tablet, film coated Oral 1500000 IU Tablet Oral 400000 unit / tab Tablet Oral 800000 unit / tab Tablet Oral 250 mg / tab Tablet Oral 500 mg / tab Powder, for solution Oral 40000 unit / mL Powder, for solution Oral 80000 unit / mL Tablet Oral 500000 unit Tablet, film coated Oral 1000000 IU Tablet, film coated Oral Suspension Oral 400000 IU/5ml Solution Oral 750000 IU/5ml Granule Oral 40 g/100 ml Tablet, film coated Oral 1.5 M UI Tablet, film coated Oral 1 M UI Liquid Oral 180 mg / 5 mL Suspension Oral 200000 unit / 5 mL Suspension Oral 500000 unit / 5 mL Tablet 1000 mg Suspension Oral 250 mg/5ml Tablet Oral 300 mg Suspension Oral 180 mg / 5 mL Suspension Oral 300 mg / 5 mL Tablet Oral 300 mg / tab Powder Parenteral 40 g/100 ml Capsule Granule Oral 60 g/100 ml Tablet 1.5 M UI Tablet 1 M UI Tablet Oropharyngeal 500 mg/1 For solution Oral 25 mg/1mL For solution Oral 50 mg/1mL Tablet, film coated Oral 250 mg/1 Tablet, film coated Oral 500 mg/1 Tablet, film coated Oral 1.2 M UI Syrup Oral 125 mg/5ml Syrup Oral 250 mg/5ml Tablet Tablet Oral 1500000 IU Powder, for solution Oral 5.544 g Suspension Oral 250000 unit / 5 mL Tablet Oral 500000 unit / tab Granule, for solution Oral 250 mg/5ml Powder, for suspension Oral 125 mg/5ml Capsule 250 mg Tablet 125 mg Powder, for suspension Oral 62.5 mg/5ml Tablet, film coated Oral 125 mg Tablet, film coated Oral 250 mg Tablet 250 mg Tablet 312.5 mg - Prices
Unit description Cost Unit Penicillin V Potassium 250 mg/5ml Solution 100ml Bottle 12.99USD bottle Penicillin V Potassium 500 mg tablet 0.77USD tablet Penicillin V Potassium 250 mg tablet 0.47USD tablet Veetids 500 mg tablet 0.43USD tablet Penicillin vk 500 mg tablet 0.4USD tablet Veetids 250 mg tablet 0.24USD tablet Penicillin vk 250 mg tablet 0.23USD tablet Apo-Pen-Vk 300 mg Tablet 0.07USD tablet Novo-Pen-Vk 300 mg Tablet 0.07USD tablet Nu-Pen-Vk 300 mg Tablet 0.07USD tablet Apo-Pen-Vk 25 mg/ml Liquid 0.06USD ml Apo-Pen-Vk 60 mg/ml Liquid 0.06USD ml Novo-Pen-Vk 60 mg/ml Liquid 0.06USD 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 water solubility <0.1 g/100mL Not Available logP 2.09 HANSCH,C ET AL. (1995) pKa 2.79 SANGSTER (1994) - Predicted Properties
Property Value Source Water Solubility 0.454 mg/mL ALOGPS logP 1.78 ALOGPS logP 0.76 Chemaxon logS -2.9 ALOGPS pKa (Strongest Acidic) 3.39 Chemaxon pKa (Strongest Basic) -4.9 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 95.94 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 85.77 m3·mol-1 Chemaxon Polarizability 34.37 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 - 0.9071 Blood Brain Barrier - 1.0 Caco-2 permeable - 0.8957 P-glycoprotein substrate Substrate 0.6858 P-glycoprotein inhibitor I Non-inhibitor 0.9131 P-glycoprotein inhibitor II Non-inhibitor 0.9726 Renal organic cation transporter Non-inhibitor 0.9219 CYP450 2C9 substrate Non-substrate 0.8176 CYP450 2D6 substrate Non-substrate 0.847 CYP450 3A4 substrate Substrate 0.5576 CYP450 1A2 substrate Non-inhibitor 0.8802 CYP450 2C9 inhibitor Non-inhibitor 0.8501 CYP450 2D6 inhibitor Non-inhibitor 0.8725 CYP450 2C19 inhibitor Non-inhibitor 0.8361 CYP450 3A4 inhibitor Non-inhibitor 0.8257 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8785 Ames test Non AMES toxic 0.9132 Carcinogenicity Non-carcinogens 0.7079 Biodegradation Not ready biodegradable 0.9747 Rat acute toxicity 1.8953 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9995 hERG inhibition (predictor II) Non-inhibitor 0.8344
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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Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
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- Kind
- Protein
- Organism
- Staphylococcus aureus
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Penicillin binding
- Specific Function
- Not Available
- Gene Name
- mecA
- Uniprot ID
- Q53707
- Uniprot Name
- MecA PBP2' (penicillin binding protein 2')
- Molecular Weight
- 76265.485 Da
References
- Lemaire S, Glupczynski Y, Duval V, Joris B, Tulkens PM, Van Bambeke F: Activities of ceftobiprole and other cephalosporins against extracellular and intracellular (THP-1 macrophages and keratinocytes) forms of methicillin-susceptible and methicillin-resistant Staphylococcus aureus. Antimicrob Agents Chemother. 2009 Jun;53(6):2289-97. doi: 10.1128/AAC.01135-08. Epub 2009 Mar 16. [Article]
- Kind
- Protein
- Organism
- Clostridium perfringens (strain 13 / Type A)
- Pharmacological action
- Yes
- General Function
- Transferase activity, transferring glycosyl groups
- Specific Function
- Cell wall formation. Synthesis of cross-linked peptidoglycan from the lipid intermediates. The enzyme has a penicillin-insensitive transglycosylase N-terminal domain (formation of linear glycan str...
- Gene Name
- pbpA
- Uniprot ID
- Q8XJ01
- Uniprot Name
- Penicillin-binding protein 1A
- Molecular Weight
- 75176.35 Da
References
- Williamson R: Resistance of Clostridium perfringens to beta-lactam antibiotics mediated by a decreased affinity of a single essential penicillin-binding protein. J Gen Microbiol. 1983 Aug;129(8):2339-42. doi: 10.1099/00221287-129-8-2339. [Article]
- Murphy TF, Barza M, Park JT: Penicillin-binding proteins in Clostridium perfringens. Antimicrob Agents Chemother. 1981 Dec;20(6):809-13. doi: 10.1128/aac.20.6.809. [Article]
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Unknown
- General Function
- Serine-type d-ala-d-ala carboxypeptidase activity
- Specific Function
- Not involved in transpeptidation but exclusively catalyzes a DD-carboxypeptidase and DD-endopeptidase reaction.
- Gene Name
- dacB
- Uniprot ID
- P24228
- Uniprot Name
- D-alanyl-D-alanine carboxypeptidase DacB
- Molecular Weight
- 51797.85 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Kind
- Protein
- Organism
- Lysinibacillus sphaericus
- Pharmacological action
- Unknown
- General Function
- Penicillin amidase activity
- Specific Function
- The enzyme catalyzes the conversion of penicillin to 6-aminopenicillanate The precursor, furthermore, acts as a self-processing peptidase that cleaves off the propeptide. All peptidase activity is ...
- Gene Name
- Not Available
- Uniprot ID
- P12256
- Uniprot Name
- Penicillin acylase
- Molecular Weight
- 37457.375 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Proton-dependent oligopeptide secondary active transmembrane transporter activity
- Specific Function
- Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products.
- Gene Name
- SLC15A1
- Uniprot ID
- P46059
- Uniprot Name
- Solute carrier family 15 member 1
- Molecular Weight
- 78805.265 Da
References
- Biegel A, Gebauer S, Hartrodt B, Brandsch M, Neubert K, Thondorf I: Three-dimensional quantitative structure-activity relationship analyses of beta-lactam antibiotics and tripeptides as substrates of the mammalian H+/peptide cotransporter PEPT1. J Med Chem. 2005 Jun 30;48(13):4410-9. [Article]
Drug created at June 13, 2005 13:24 / Updated at September 28, 2023 01:14