Phenoxymethylpenicillin

Identification

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Name
Phenoxymethylpenicillin
Accession Number
DB00417  (APRD00423, DB08415)
Type
Small Molecule
Groups
Approved, Vet approved
Description

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

Structure
Thumb
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
Product Ingredients
IngredientUNIICASInChI Key
Phenoxymethylpenicillin benzathine3T4EMH59ZU5928-84-7BBTOYUUSUQNIIY-ANPZCEIESA-N
Phenoxymethylpenicillin potassium146T0TU1JB132-98-9HCTVWSOKIJULET-LQDWTQKMSA-M
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Beepen-VKTablet500 mg/1OralGlaxoSmithKline2007-08-042007-08-06Us
Beepen-VKTablet250 mg/1OralGlaxoSmithKline2007-08-042007-08-06Us
Beepen-VKPowder, for solution250 mg/5mLOralGlaxoSmithKline2007-08-042007-08-06Us
Beepen-VKPowder, for solution125 mg/5mLOralGlaxoSmithKline2007-08-042007-08-06Us
Ledercillin Vk - Tab 400000 UnitTabletOralWyeth Ayerst Canada Inc.1997-06-132000-08-02Canada
Ledercillin Vk - Tab 800000unitsTabletOralWyeth Ayerst Canada Inc.1996-12-272001-04-23Canada
Ledercillin Vk Tab 400000unitTabletOralLederle Cyanamid Canada Inc.1969-12-311997-08-14Canada
Ledercillin Vk Tab 800000unitTabletOralLederle Cyanamid Canada Inc.1969-12-311997-08-14Canada
Nadopen V 200Powder, for solutionOralLioh Inc.1969-12-312006-08-25Canada
Nadopen V 400Powder, for solutionOralLioh Inc.1972-12-312006-08-25Canada
Additional Data Available
  • Application Number
    Application Number

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

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  • Product Code
    Product Code

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

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo Pen VkPowder, for solutionOralApotex Corporation1985-12-31Not applicableCanada
Apo Pen VkPowder, for solutionOralApotex Corporation1985-12-31Not applicableCanada
Novo-pen Vk Syr 500000/5mlPowder, for solutionOralNovopharm Limited1977-12-312018-01-24Canada
Novo-pen-VK 500 TabTabletOralNovopharm Limited1966-12-312015-10-26Canada
Nu-pen-VK Tablets 300mgTabletOralNu Pharm Inc1990-12-312012-09-04Canada
Penicillin V PotasiumTablet250 mg/1OralA-S Medication Solutions1995-11-302017-06-30Us
Penicillin V PotasiumTablet500 mg/1OralPhysicians Total Care, Inc.1995-02-22Not applicableUs
Penicillin V PotasiumTablet500 mg/1Oralbryant ranch prepack1995-11-302012-10-01Us
Penicillin V PotasiumTablet250 mg/1OralPhysicians Total Care, Inc.2003-09-30Not applicableUs
Penicillin V PotasiumTablet500 mg/1OralAidarex Pharmaceuticals LLC1995-11-30Not applicableUs
Additional Data Available
  • Application Number
    Application Number

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

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  • Product Code
    Product Code

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

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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
Categories
UNII
Z61I075U2W
CAS number
87-08-1
Weight
Average: 350.39
Monoisotopic: 350.093642386
Chemical Formula
C16H18N2O5S
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

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

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

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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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.

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
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

Affected organisms
  • Bacteria
  • Gram-negative Bacteria
  • Bacillus anthracis
  • Corynebacterium diphtheriae
  • Streptococcus pyogenes
  • Leptospira interrogans
  • Listeria monocytogenes
  • Borrelia burgdorferi
  • Neisseria gonorrhoeae
  • Clostridium
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
(R)-warfarinPhenoxymethylpenicillin may increase the anticoagulant activities of (R)-warfarin.
(S)-WarfarinPhenoxymethylpenicillin may increase the anticoagulant activities of (S)-Warfarin.
4-hydroxycoumarinPhenoxymethylpenicillin may increase the anticoagulant activities of 4-hydroxycoumarin.
AcemetacinAcemetacin may decrease the excretion rate of Phenoxymethylpenicillin which could result in a higher serum level.
AcenocoumarolPhenoxymethylpenicillin may increase the anticoagulant activities of Acenocoumarol.
Adenovirus type 7 vaccine liveThe therapeutic efficacy of Adenovirus type 7 vaccine live can be decreased when used in combination with Phenoxymethylpenicillin.
AlcuroniumThe therapeutic efficacy of Alcuronium can be increased when used in combination with Phenoxymethylpenicillin.
AmikacinThe serum concentration of Amikacin can be decreased when it is combined with Phenoxymethylpenicillin.
Anthrax immune globulin humanThe therapeutic efficacy of Anthrax immune globulin human can be decreased when used in combination with Phenoxymethylpenicillin.
Anthrax vaccineThe therapeutic efficacy of Anthrax vaccine can be decreased when used in combination with Phenoxymethylpenicillin.
Additional Data Available
  • Extended Description
    Extended Description

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  • Severity
    Severity

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

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Food Interactions
  • Absorption is increased when taken on an empty stomach (one hour before or two hours after meals).

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. [PubMed:15758893]
  2. Gruchalla RS, Pirmohamed M: Clinical practice. Antibiotic allergy. N Engl J Med. 2006 Feb 9;354(6):601-9. [PubMed:16467547]
  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. [PubMed:30181520]
  4. Josefsson K, Bergan T: Pharmacokinetics of phenoxymethylpenicillin in volunteers. Chemotherapy. 1982;28(4):241-6. doi: 10.1159/000238084. [PubMed:6811219]
  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. [PubMed:3924086]
  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. [PubMed:23594463]
  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]
External Links
Human Metabolome Database
HMDB0014561
KEGG Drug
D05411
KEGG Compound
C08126
PubChem Compound
6869
PubChem Substance
46507164
ChemSpider
6607
BindingDB
50370584
ChEBI
27446
ChEMBL
CHEMBL615
Therapeutic Targets Database
DAP001165
PharmGKB
PA164745442
HET
PNV
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Penicillin_V
ATC Codes
J01CR50 — Combinations of penicillinsJ01CE10 — Benzathine phenoxymethylpenicillinJ01CE02 — Phenoxymethylpenicillin
AHFS Codes
  • 08:12.16.04 — Natural Penicillins
PDB Entries
2z71
FDA label
Download (195 KB)
MSDS
Download (37.1 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingTreatmentOsteomyelitis1
0TerminatedPreventionGroup B Streptococcus1
1CompletedBasic ScienceOxidative Stress1
1CompletedDevice FeasibilityHealthy Volunteers1
1CompletedTreatmentPhenoxymethylpenicillin1
4CompletedPreventionCellulitis/Erysipelas of the Leg1
4CompletedTreatmentBorreliosis / Early Lyme Disease / Erythema Chronicum Migrans / Lyme Disease1
4CompletedTreatmentTonsillitis1
4Not Yet RecruitingTreatmentAbscesses / Cellulitis / Wound Infections1
4Not Yet RecruitingTreatmentThroat Pain / Tonsillitis1
4RecruitingPreventionInfectious Diseases1
4RecruitingTreatmentPeriimplantitis / Periodontal Diseases1
Not AvailableCompletedPreventionInfection NOS / Sickle Cell Disorders / Zinc Deficiency1
Not AvailableCompletedTreatmentPost Streptococcal Movement Disorder / Sydenham Chorea1
Not AvailableNot Yet RecruitingTreatmentPeritonsillar Abscess1

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/5mL
Powder, for solutionOral250 mg/5mL
TabletOral250 mg/1
TabletOral500 mg/1
Powder, for solutionOral
TabletOral
LiquidOral
For solutionOral25 mg/1mL
For solutionOral50 mg/1mL
Tablet, film coatedOral250 mg/1
Tablet, film coatedOral500 mg/1
SuspensionOral
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-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Alpha-dipeptide / Penicillin / N-acyl-alpha amino acid or derivatives / Alpha-amino acid or derivatives / Phenoxy compound / Phenol ether / Penam / Alkyl aryl ether / Monocyclic benzene moiety / Benzenoid
show 24 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
penicillin (CHEBI:27446)

Targets

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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
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
  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. [PubMed:19289525]
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
  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. [PubMed:10592235]
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
  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. [PubMed:10592235]
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
  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. [PubMed:15974593]

Drug created on June 13, 2005 07:24 / Updated on October 13, 2019 23:23