Phenoxymethylpenicillin

Identification

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

Phenoxymethylpenicillin (Penicillin V) is narrow spectrum antibiotic used to treat mild to moderate infections caused by susceptible bacteria. It is a natural penicillin antibiotic that is administered orally. Penicillin V 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.

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
  • 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
Ledercillin Vk - Tab 400000 UnitTablet400000 unitOralWyeth Ayerst Canada Inc.1997-06-132000-08-02Canada
Ledercillin Vk - Tab 800000unitsTablet800000 unitOralWyeth Ayerst Canada Inc.1996-12-272001-04-23Canada
Ledercillin Vk Tab 400000unitTablet250 mgOralLederle Cyanamid Canada Inc.1969-12-311997-08-14Canada
Ledercillin Vk Tab 800000unitTablet500 mgOralLederle Cyanamid Canada Inc.1969-12-311997-08-14Canada
Nadopen V 200Powder, for solution40000 unitOralLioh Inc.1969-12-312006-08-25Canada
Nadopen V 400Powder, for solution80000 unitOralLioh Inc.1972-12-312006-08-25Canada
Nadopen V Tab 500000iuTablet500000 unitOralLioh Inc.1960-12-312006-08-25Canada
Novo-pen Vk Syr 500000/5mlPowder, for solution300 mgOralNovopharm Limited1977-12-31Not applicableCanada
Novo-pen-VK 500 TabTablet500000 unitOralNovopharm Limited1966-12-312015-10-26Canada
Nu-pen-VK Tablets 300mgTablet300 mgOralNu Pharm Inc1990-12-312012-09-04Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo Pen VkPowder, for solution125 mgOralApotex Corporation1985-12-31Not applicableCanada
Apo Pen VkPowder, for solution300 mgOralApotex Corporation1985-12-31Not applicableCanada
Penicillin V PotasiumTablet250 mg/1OralA S Medication Solutions1995-11-302017-06-20Us
Penicillin V PotasiumTablet250 mg/1OralRed Pharm Drug, Inc.1995-11-30Not applicableUs
Penicillin V PotasiumTablet250 mg/1OralSandoz1995-11-30Not applicableUs
Penicillin V PotasiumTablet500 mg/1OralRed Pharm Drug, Inc.2001-01-01Not applicableUs
Penicillin V PotasiumTablet500 mg/1OralAidarex Pharmaceuticals LLC1995-11-30Not applicableUs
Penicillin V PotasiumTablet250 mg/1OralPhysicians Total Care, Inc.2003-09-30Not applicableUs
Penicillin V PotasiumTablet250 mg/1OralAvera Mc Kennan Hospital2015-03-30Not applicableUs
Penicillin V PotasiumTablet500 mg/1OralSandoz1995-11-30Not applicableUs
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Penicillin V PotassiumTablet, film coated500 mg/1OralDenton Pharma, Inc.2017-06-29Not applicableUs
International/Other Brands
Apo-Pen-VK / Beepen-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][[email protected]]12SC(C)(C)[[email protected]@H](N1C(=O)[[email protected]]2NC(=O)COC1=CC=CC=C1)C(O)=O

Pharmacology

Indication

For the treatment of mild to moderately severe infections (e.g. dental infection, infections in the heart, middle ear infections, rheumatic fever, scarlet fever, skin infections, upper and lower respiratory tract infections) due to microorganisms.

Structured Indications
Pharmacodynamics

Penicillin V exerts a bactericidal action against penicillin-sensitive microorganisms during the stage of active multiplication. It acts through the inhibition of biosynthesis of cell-wall mucopeptide. It is not active against the penicillinase-producing bacteria, which include many strains of staphylococci. The drug exerts high in vitro activity against staphylococci (except penicillinase-producing strains), streptococci (groups A, C, G, H, L and M), and pneumococci. Other organisms sensitive in vitro to penicillin V are Corynebacteriumdiphtheriae, Bacillus anthracis, Clostridia, Actinomycesbovis, Streptobacillusmoniliformis, Listeria monocytogenes, Leptospira, and Neisseria gonorrhoeae. Treponemapallidum is extremely sensitive.

Mechanism of action

By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, Penicillin V 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 V interferes with an autolysin inhibitor.

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 AvailableHuman
Absorption

25% of the dose given is absorbed, 50-60% bioavailable

Volume of distribution
Not Available
Protein binding

80%

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

Mostly renal. A small percentage is eliminated by feces and the biliary route.

Half life

30 to 40 minutes

Clearance
Not Available
Toxicity

LD50 >1040 mg/kg (Orally in rats with Sodium salt); Nausea, vomiting, stomach pain, diarrhea, and, in rare cases, major motor seizures

Affected organisms
  • Bacteria
  • Gram-negative Bacteria
  • Bacillus anthracis
  • Streptococcus pyogenes
  • Borrelia burgdorferi
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AcenocoumarolPhenoxymethylpenicillin may increase the anticoagulant activities of Acenocoumarol.Approved
AclarubicinThe serum concentration of Aclarubicin can be decreased when it is combined with Phenoxymethylpenicillin.Investigational
AmikacinThe serum concentration of Amikacin can be decreased when it is combined with Phenoxymethylpenicillin.Approved, Vet Approved
AmrubicinThe serum concentration of Amrubicin can be decreased when it is combined with Phenoxymethylpenicillin.Approved, Investigational
annamycinThe serum concentration of annamycin can be decreased when it is combined with Phenoxymethylpenicillin.Investigational
ApramycinThe serum concentration of Apramycin can be decreased when it is combined with Phenoxymethylpenicillin.Experimental, Vet Approved
ArbekacinThe serum concentration of Arbekacin can be decreased when it is combined with Phenoxymethylpenicillin.Approved, Investigational
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Phenoxymethylpenicillin.Investigational
BekanamycinThe serum concentration of Bekanamycin can be decreased when it is combined with Phenoxymethylpenicillin.Experimental
ChlortetracyclineThe therapeutic efficacy of Phenoxymethylpenicillin can be decreased when used in combination with Chlortetracycline.Approved, Investigational, Vet Approved
ClorindionePhenoxymethylpenicillin may increase the anticoagulant activities of Clorindione.Experimental
DaunorubicinThe serum concentration of Daunorubicin can be decreased when it is combined with Phenoxymethylpenicillin.Approved
DemeclocyclineThe therapeutic efficacy of Phenoxymethylpenicillin can be decreased when used in combination with Demeclocycline.Approved
DibekacinThe serum concentration of Dibekacin can be decreased when it is combined with Phenoxymethylpenicillin.Experimental
DicoumarolPhenoxymethylpenicillin may increase the anticoagulant activities of Dicoumarol.Approved
DihydrostreptomycinThe serum concentration of Dihydrostreptomycin can be decreased when it is combined with Phenoxymethylpenicillin.Investigational, Vet Approved
DiphenadionePhenoxymethylpenicillin may increase the anticoagulant activities of Diphenadione.Experimental
DoxorubicinThe serum concentration of Doxorubicin can be decreased when it is combined with Phenoxymethylpenicillin.Approved, Investigational
DoxycyclineThe therapeutic efficacy of Phenoxymethylpenicillin can be decreased when used in combination with Doxycycline.Approved, Investigational, Vet Approved
EpirubicinThe serum concentration of Epirubicin can be decreased when it is combined with Phenoxymethylpenicillin.Approved
Ethyl biscoumacetatePhenoxymethylpenicillin may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
FluindionePhenoxymethylpenicillin may increase the anticoagulant activities of Fluindione.Investigational
FramycetinThe serum concentration of Framycetin can be decreased when it is combined with Phenoxymethylpenicillin.Approved
GeneticinThe serum concentration of Geneticin can be decreased when it is combined with Phenoxymethylpenicillin.Experimental
GentamicinThe serum concentration of Gentamicin can be decreased when it is combined with Phenoxymethylpenicillin.Approved, Vet Approved
GENTAMICIN C1AThe serum concentration of GENTAMICIN C1A can be decreased when it is combined with Phenoxymethylpenicillin.Experimental
GPX-150The serum concentration of GPX-150 can be decreased when it is combined with Phenoxymethylpenicillin.Investigational
Hygromycin BThe serum concentration of Hygromycin B can be decreased when it is combined with Phenoxymethylpenicillin.Vet Approved
IdarubicinThe serum concentration of Idarubicin can be decreased when it is combined with Phenoxymethylpenicillin.Approved
INNO-206The serum concentration of INNO-206 can be decreased when it is combined with Phenoxymethylpenicillin.Investigational
IsepamicinThe serum concentration of Isepamicin can be decreased when it is combined with Phenoxymethylpenicillin.Experimental
KanamycinThe serum concentration of Kanamycin can be decreased when it is combined with Phenoxymethylpenicillin.Approved, Investigational, Vet Approved
MethotrexateThe serum concentration of Methotrexate can be increased when it is combined with Phenoxymethylpenicillin.Approved
MetrizamideThe serum concentration of Metrizamide can be decreased when it is combined with Phenoxymethylpenicillin.Approved
MicronomicinThe serum concentration of Micronomicin can be decreased when it is combined with Phenoxymethylpenicillin.Experimental
MinocyclineThe therapeutic efficacy of Phenoxymethylpenicillin can be decreased when used in combination with Minocycline.Approved, Investigational
Mycophenolic acidThe serum concentration of the active metabolites of Mycophenolic acid can be reduced when Mycophenolic acid is used in combination with Phenoxymethylpenicillin resulting in a loss in efficacy.Approved
NeamineThe serum concentration of Neamine can be decreased when it is combined with Phenoxymethylpenicillin.Experimental
NeomycinThe serum concentration of Neomycin can be decreased when it is combined with Phenoxymethylpenicillin.Approved, Vet Approved
NetilmicinThe serum concentration of Netilmicin can be decreased when it is combined with Phenoxymethylpenicillin.Approved, Investigational
ParomomycinThe serum concentration of Paromomycin can be decreased when it is combined with Phenoxymethylpenicillin.Approved, Investigational
PhenindionePhenoxymethylpenicillin may increase the anticoagulant activities of Phenindione.Approved, Investigational
PhenprocoumonPhenoxymethylpenicillin may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Phenoxymethylpenicillin.Approved
PirarubicinThe serum concentration of Pirarubicin can be decreased when it is combined with Phenoxymethylpenicillin.Investigational
PlazomicinThe serum concentration of Plazomicin can be decreased when it is combined with Phenoxymethylpenicillin.Investigational
PlicamycinThe serum concentration of Plicamycin can be decreased when it is combined with Phenoxymethylpenicillin.Approved, Investigational, Withdrawn
ProbenecidThe serum concentration of Phenoxymethylpenicillin can be increased when it is combined with Probenecid.Approved
PuromycinThe serum concentration of Puromycin can be decreased when it is combined with Phenoxymethylpenicillin.Experimental
RibostamycinThe serum concentration of Ribostamycin can be decreased when it is combined with Phenoxymethylpenicillin.Approved, Investigational
SabarubicinThe serum concentration of Sabarubicin can be decreased when it is combined with Phenoxymethylpenicillin.Investigational
SisomicinThe serum concentration of Sisomicin can be decreased when it is combined with Phenoxymethylpenicillin.Investigational
SP1049CThe serum concentration of SP1049C can be decreased when it is combined with Phenoxymethylpenicillin.Investigational
SpectinomycinThe serum concentration of Spectinomycin can be decreased when it is combined with Phenoxymethylpenicillin.Approved, Investigational, Vet Approved
StreptomycinThe serum concentration of Streptomycin can be decreased when it is combined with Phenoxymethylpenicillin.Approved, Vet Approved
StreptozocinThe serum concentration of Streptozocin can be decreased when it is combined with Phenoxymethylpenicillin.Approved
TioclomarolPhenoxymethylpenicillin may increase the anticoagulant activities of Tioclomarol.Experimental
TobramycinThe serum concentration of Tobramycin can be decreased when it is combined with Phenoxymethylpenicillin.Approved, Investigational
ValrubicinThe serum concentration of Valrubicin can be decreased when it is combined with Phenoxymethylpenicillin.Approved
WarfarinPhenoxymethylpenicillin may increase the anticoagulant activities of Warfarin.Approved
Zoptarelin doxorubicinThe serum concentration of Zoptarelin doxorubicin can be decreased when it is combined with Phenoxymethylpenicillin.Investigational
ZorubicinThe serum concentration of Zorubicin can be decreased when it is combined with Phenoxymethylpenicillin.Experimental
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]
External Links
Human Metabolome Database
HMDB14561
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 penicillinsJ01CE02 — PhenoxymethylpenicillinJ01CE10 — Benzathine phenoxymethylpenicillin
AHFS Codes
  • 08:12.16.04 — Natural Penicillins
PDB Entries
2z71
MSDS
Download (37.1 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingTreatmentOsteomyelitis1
0TerminatedPreventionGroup B Streptococcus1
1CompletedBasic ScienceOxidative Stress1
1CompletedTreatmentPhenoxymethylpenicillin1
4CompletedPreventionCellulitis/Erysipelas of the Leg1
4CompletedTreatmentBorreliosis / Early Lyme Disease / Erythema Chronicum Migrans / Lyme Disease1
4Not Yet RecruitingTreatmentAbscesses / Cellulitis / Wound Infections1
4RecruitingTreatmentTonsillitis1

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
Dosage forms
FormRouteStrength
Powder, for solutionOral125 mg
TabletOral400000 unit
TabletOral800000 unit
TabletOral500 mg
Powder, for solutionOral40000 unit
Powder, for solutionOral80000 unit
Powder, for solutionOral300 mg
TabletOral300 mg
LiquidOral180 mg
SuspensionOral200000 unit
SuspensionOral180 mg
SuspensionOral300 mg
For solutionOral25 mg/mL
For solutionOral50 mg/mL
Powder, for solutionOral125 mg/5mL
Powder, for solutionOral250 mg/5mL
TabletOral250 mg/1
TabletOral500 mg/1
Tablet, film coatedOral250 mg/1
Tablet, film coatedOral500 mg/1
SuspensionOral250000 unit
SuspensionOral500000 unit
TabletOral500000 unit
TabletOral250 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
melting point (°C)120-128 °CNot Available
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
Human
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 November 19, 2017 20:33