Phenoxymethylpenicillin

Overview

Description
A type of penicillin antibiotic that is used to prevent and treat various skin, respiratory and other infections in the body caused by bacteria.
Description
A type of penicillin antibiotic that is used to prevent and treat various skin, respiratory and other infections in the body caused by bacteria.
DrugBank ID
DB00417
Type
Small Molecule
US Approved
YES
Other Approved
YES
Clinical Trials
Phase 0
2
Phase 1
3
Phase 2
1
Phase 3
1
Phase 4
8
Therapeutic Categories
  • Natural Penicillins
  • Penicillins

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
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

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofActinomycosis••• •••••
Treatment ofAnimal bite••• •••••
Treatment ofAnthrax••• •••••
Prophylaxis ofBacterial endocarditis•••••••••••••••••••••• ••••• ••••••••• •••••••• ••••••••••• •••••••• ••••• •••••••• •••••• ••••••••••• ••••••••• •••••••• ••••• •••••••
Treatment ofBacterial infections••••••••••••
Contraindications & Blackbox Warnings
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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

TargetActionsOrganism
AMecA PBP2' (penicillin binding protein 2')
inhibitor
Staphylococcus aureus
APenicillin-binding protein 1ANot AvailableClostridium perfringens (strain 13 / Type A)
UD-alanyl-D-alanine carboxypeptidase DacBNot AvailableEscherichia coli (strain K12)
UPenicillin acylaseNot AvailableLysinibacillus sphaericus
USolute carrier family 15 member 1Not AvailableHumans
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.

Hover over products below to view reaction partners

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
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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.
DrugInteraction
AcemetacinAcemetacin may decrease the excretion rate of Phenoxymethylpenicillin which could result in a higher serum level.
AcenocoumarolPhenoxymethylpenicillin may increase the anticoagulant activities of Acenocoumarol.
AmbroxolThe risk or severity of methemoglobinemia can be increased when Phenoxymethylpenicillin is combined with Ambroxol.
AmikacinThe serum concentration of Amikacin can be decreased when it is combined with Phenoxymethylpenicillin.
ArticaineThe risk or severity of methemoglobinemia can be increased when Phenoxymethylpenicillin is combined with Articaine.
Food Interactions
  • Take on an empty stomach. Absorption is increased 1 hour before or 2 hours after food.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Phenoxymethylpenicillin benzathine3T4EMH59ZU5928-84-7BBTOYUUSUQNIIY-ANPZCEIESA-N
Phenoxymethylpenicillin potassium146T0TU1JB132-98-9HCTVWSOKIJULET-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
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Beepen-VKTablet500 mg/1OralGlaxosmithkline Inc2007-08-042007-08-06US flag
Beepen-VKPowder, for solution125 mg/5mLOralGlaxosmithkline Inc2007-08-042007-08-06US flag
Beepen-VKTablet250 mg/1OralGlaxosmithkline Inc2007-08-042007-08-06US flag
Beepen-VKPowder, for solution250 mg/5mLOralGlaxosmithkline Inc2007-08-042007-08-06US flag
Ledercillin Vk - Tab 400000 UnitTablet400000 unit / tabOralWyeth Ayerst Canada Inc.1997-06-132000-08-02Canada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo Pen VkPowder, for solution125 mg / 5 mLOralApotex Corporation1985-12-31Not applicableCanada flag
Apo Pen VkPowder, for solution300 mg / 5 mLOralApotex Corporation1985-12-31Not applicableCanada flag
Novo-pen Vk Syr 500000/5mlPowder, for solution300 mg / 5 mLOralNovopharm Limited1977-12-312018-01-24Canada flag
Novo-pen-VK 500 TabTablet500000 unitOralNovopharm Limited1966-12-312015-10-26Canada flag
Nu-pen-VK Tablets 300mgTablet300 mgOralNu Pharm Inc1990-12-312012-09-04Canada flag

Categories

ATC Codes
J01CR50 — Combinations of penicillinsJ01CE10 — Benzathine phenoxymethylpenicillinJ01CE02 — Phenoxymethylpenicillin
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 / 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
  1. 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]
  2. Gruchalla RS, Pirmohamed M: Clinical practice. Antibiotic allergy. N Engl J Med. 2006 Feb 9;354(6):601-9. [Article]
  3. 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]
  4. Josefsson K, Bergan T: Pharmacokinetics of phenoxymethylpenicillin in volunteers. Chemotherapy. 1982;28(4):241-6. doi: 10.1159/000238084. [Article]
  5. 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]
  6. 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]
  7. Phenoxymethylpenicillin (Penicillin V) Monograph - Government of Western Australia Child and Adolescents Health Service [Link]
  8. Phenoxymethyl Penicillin 250mg/5ml Oral Solution Sugar Free (syringe) - eMC [Link]
  9. phenoxymethylpenicillin (penicillin v) - King Edward Memorial Hospital [Link]
  10. Penicillin V potassium - GLOWM [Link]
Human Metabolome Database
HMDB0014561
KEGG Drug
D05411
KEGG Compound
C08126
PubChem Compound
6869
PubChem Substance
46507164
ChemSpider
6607
BindingDB
50370584
RxNav
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
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package
PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns
Not AvailableCompletedPreventionInfection / Sickle Cell Disease (SCD) / Zinc Deficiency1somestatusstop reasonjust information to hide
Not AvailableCompletedTreatmentPost Streptococcal Movement Disorder / Sydenham Chorea1somestatusstop reasonjust information to hide
Not AvailableUnknown StatusTreatmentPeritonsillar Abscess1somestatusstop reasonjust information to hide
4CompletedPreventionCellulitis/Erysipelas of the Leg1somestatusstop reasonjust information to hide
4CompletedPreventionInfectious Diseases1somestatusstop reasonjust information to hide

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
FormRouteStrength
Powder, for solutionOral125 mg / 5 mL
Powder, for solutionOral300 mg / 5 mL
GranuleOral125 MG/5ML
Powder, for solutionOral125 mg/5mL
Powder, for solutionOral250 mg/5mL
TabletOral250 mg/1
TabletOral500 mg/1
Tablet, film coatedOral708 mg
SyrupOral300000 iu/5ml
Tablet, film coatedOral1200.000 i.u.
SyrupOral300000 i.u./5ml
Tablet
SyrupOral
PowderParenteral250000 IU
PowderParenteral300000 IU
GranuleOral400000 IU
PowderParenteral500000 IU
Tablet, film coatedOral1200000 IU
PowderParenteral30 G
Tablet, film coatedOral1500000 IU
TabletOral400000 unit / tab
TabletOral800000 unit / tab
TabletOral250 mg / tab
TabletOral500 mg / tab
Powder, for solutionOral40000 unit / mL
Powder, for solutionOral80000 unit / mL
TabletOral500000 unit
Tablet, film coatedOral1000000 IU
Tablet, film coatedOral
SuspensionOral400000 IU/5ml
Tablet, film coatedOral500 mg
SolutionOral750000 IU/5ml
GranuleOral40 g/100 ml
Tablet, film coatedOral1.5 M UI
Tablet, film coatedOral1 M UI
LiquidOral180 mg / 5 mL
SuspensionOral200000 unit / 5 mL
SuspensionOral500000 unit / 5 mL
Tablet1000 mg
SuspensionOral250 mg/5ml
Tablet, film coatedOral1 Mio. I.E.
Tablet, film coatedOral1.5 Mio. I.E.
TabletOral300 mg
SuspensionOral180 mg / 5 mL
SuspensionOral300 mg / 5 mL
TabletOral300 mg / tab
PowderParenteral40 g/100 ml
Capsule
GranuleOral60 g/100 ml
Tablet1.5 M UI
Tablet1 M UI
TabletOropharyngeal500 mg/1
For solutionOral25 mg/1mL
For solutionOral50 mg/1mL
Tablet, film coatedOral250 mg/1
Tablet, film coatedOral500 mg/1
Tablet, film coatedOral1.2 M UI
SyrupOral125 mg/5ml
SyrupOral250 mg/5ml
Tablet1 Mio. I.E.
TabletOral1500000 IU
Powder, for solutionOral5.544 g
Tablet500 MG
Tablet50000 IU
Tablet, film coatedOral330 mg
SuspensionOral250000 unit / 5 mL
TabletOral500000 unit / tab
Granule, for solutionOral250 mg/5ml
Powder, for suspensionOral125 mg/5ml
Capsule250 mg
Tablet125 mg
Powder, for suspensionOral62.5 mg/5ml
Tablet, film coatedOral125 mg
Tablet, film coatedOral250 mg
Tablet250 mg
Tablet312.5 mg
Prices
Unit descriptionCostUnit
Penicillin V Potassium 250 mg/5ml Solution 100ml Bottle12.99USD bottle
Penicillin V Potassium 500 mg tablet0.77USD tablet
Penicillin V Potassium 250 mg tablet0.47USD tablet
Veetids 500 mg tablet0.43USD tablet
Penicillin vk 500 mg tablet0.4USD tablet
Veetids 250 mg tablet0.24USD tablet
Penicillin vk 250 mg tablet0.23USD tablet
Apo-Pen-Vk 300 mg Tablet0.07USD tablet
Novo-Pen-Vk 300 mg Tablet0.07USD tablet
Nu-Pen-Vk 300 mg Tablet0.07USD tablet
Apo-Pen-Vk 25 mg/ml Liquid0.06USD ml
Apo-Pen-Vk 60 mg/ml Liquid0.06USD ml
Novo-Pen-Vk 60 mg/ml Liquid0.06USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubility<0.1 g/100mLNot Available
logP2.09HANSCH,C ET AL. (1995)
pKa2.79SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.454 mg/mLALOGPS
logP1.78ALOGPS
logP0.76Chemaxon
logS-2.9ALOGPS
pKa (Strongest Acidic)3.39Chemaxon
pKa (Strongest Basic)-4.9Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area95.94 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity85.77 m3·mol-1Chemaxon
Polarizability34.37 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.9071
Blood Brain Barrier-1.0
Caco-2 permeable-0.8957
P-glycoprotein substrateSubstrate0.6858
P-glycoprotein inhibitor INon-inhibitor0.9131
P-glycoprotein inhibitor IINon-inhibitor0.9726
Renal organic cation transporterNon-inhibitor0.9219
CYP450 2C9 substrateNon-substrate0.8176
CYP450 2D6 substrateNon-substrate0.847
CYP450 3A4 substrateSubstrate0.5576
CYP450 1A2 substrateNon-inhibitor0.8802
CYP450 2C9 inhibitorNon-inhibitor0.8501
CYP450 2D6 inhibitorNon-inhibitor0.8725
CYP450 2C19 inhibitorNon-inhibitor0.8361
CYP450 3A4 inhibitorNon-inhibitor0.8257
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8785
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.7079
BiodegradationNot ready biodegradable0.9747
Rat acute toxicity1.8953 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9995
hERG inhibition (predictor II)Non-inhibitor0.8344
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-MSsplash10-0006-9322000000-4de191c98a42f568cb80
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-01ow-4902000000-a5bf8c0c040ba29970cc
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0090000000-bde093ec71c4c01140f9
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-06r2-5901000000-de551c16b9bbb8439bb6
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4l-6295000000-4554c331523731214859
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9320000000-b9de12bb2afff9dc834b
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-3900000000-056c0751022392a04c36
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-187.5012274
predicted
DarkChem Lite v0.1.0
[M-H]-184.4134274
predicted
DarkChem Lite v0.1.0
[M-H]-180.0337
predicted
DeepCCS 1.0 (2019)
[M+H]+185.2708274
predicted
DarkChem Lite v0.1.0
[M+H]+182.1132274
predicted
DarkChem Lite v0.1.0
[M+H]+182.39171
predicted
DeepCCS 1.0 (2019)
[M+Na]+186.3128274
predicted
DarkChem Lite v0.1.0
[M+Na]+182.7846274
predicted
DarkChem Lite v0.1.0
[M+Na]+189.24754
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Staphylococcus aureus
Pharmacological action
Yes
Actions
Inhibitor
General Function
Not Available
Specific Function
penicillin binding
Gene Name
mecA
Uniprot ID
Q53707
Uniprot Name
MecA PBP2' (penicillin binding protein 2')
Molecular Weight
76265.485 Da
References
  1. 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
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 strands) and a penicillin-sensitive transpeptidase C-terminal domain (cross-linking of the peptide subunits).
Specific Function
penicillin binding
Gene Name
pbpA
Uniprot ID
Q8XJ01
Uniprot Name
Penicillin-binding protein 1A
Molecular Weight
75176.35 Da
References
  1. 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]
  2. 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
Not involved in transpeptidation but exclusively catalyzes a DD-carboxypeptidase and DD-endopeptidase reaction.
Specific Function
carboxypeptidase activity
Gene Name
dacB
Uniprot ID
P24228
Uniprot Name
D-alanyl-D-alanine carboxypeptidase DacB
Molecular Weight
51797.85 Da
References
  1. 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
Catalyzes the hydrolysis of penicillin V to 6-aminopenicillanate (6-APA) (PubMed:30243389, PubMed:3026906, PubMed:9009066). Exhibits high specificity for penicillin V (PubMed:9009066). Penicillin G and other related compounds are hydrolyzed at less than 10% of the rate of penicillin V (PubMed:9009066). Among the cephalosporins, cephalosporin C is resistant to cleavage, whereas cephalosporin G is cleaved at about 1% of the rate of cleavage of penicillin V (PubMed:9009066).
Specific Function
penicillin amidase activity
Gene Name
Not Available
Uniprot ID
P12256
Uniprot Name
Penicillin acylase
Molecular Weight
37457.375 Da
References
  1. 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
Electrogenic proton-coupled amino-acid transporter that transports oligopeptides of 2 to 4 amino acids with a preference for dipeptides. Transports neutral and monovalently charged peptides with a proton to peptide stoichiometry of 1:1 or 2:1 (By similarity) (PubMed:15521010, PubMed:18367661, PubMed:19685173, PubMed:26320580, PubMed:7896779, PubMed:8914574, PubMed:9835627). Primarily responsible for the absorption of dietary di- and tripeptides from the small intestinal lumen (By similarity). Mediates transepithelial transport of muramyl and N-formylated bacterial dipeptides contributing to recognition of pathogenic bacteria by the mucosal immune system (PubMed:15521010, PubMed:9835627)
Specific Function
dipeptide transmembrane transporter activity
Gene Name
SLC15A1
Uniprot ID
P46059
Uniprot Name
Solute carrier family 15 member 1
Molecular Weight
78805.265 Da
References
  1. 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 November 09, 2024 06:16