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Namespace Prefixes

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Statements

Subject Item
n2:DB00417
rdf:type
n3:Drug
n3:description
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 <i>Streptococcus pneumoniae</i>, 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 (<i>S. agalactiae</i>), <i>S. viridans</i>, and <i>Enterococcus faecalis</i>. The natural penicillins may also be used as first or second line agents against susceptible gram positive aerobic bacilli such as <i>Bacillus anthracis</i>, <i>Corynebacterium diphtheriae</i>, and <i>Erysipelothrix rhusiopathiae</i>. Natural penicillins have limited activity against gram negative organisms; however, they may be used in some cases to treat infections caused by <i>Neisseria meningitidis</i> and <i>Pasteurella</i>. They are not generally used to treat anaerobic infections. Resistance patterns, susceptibility and treatment guidelines vary across regions.
n3:dosage
n13:271B4838-363D-11E5-9242-09173F13E4C5
n3:generalReferences
# : 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":http://www.ncbi.nlm.nih.gov/pubmed/15758893 # Gruchalla RS, Pirmohamed M: Clinical practice. Antibiotic allergy. N Engl J Med. 2006 Feb 9;354(6):601-9. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/16467547
n3:group
approved
n3:halfLife
30 to 40 minutes
n3: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
n3:manufacturer
n11:271B481C-363D-11E5-9242-09173F13E4C5 n11:271B481D-363D-11E5-9242-09173F13E4C5 n11:271B481A-363D-11E5-9242-09173F13E4C5 n11:271B481B-363D-11E5-9242-09173F13E4C5 n11:271B4819-363D-11E5-9242-09173F13E4C5 n11:271B4824-363D-11E5-9242-09173F13E4C5 n11:271B4825-363D-11E5-9242-09173F13E4C5 n11:271B4822-363D-11E5-9242-09173F13E4C5 n11:271B4823-363D-11E5-9242-09173F13E4C5 n11:271B4820-363D-11E5-9242-09173F13E4C5 n11:271B4821-363D-11E5-9242-09173F13E4C5 n11:271B481E-363D-11E5-9242-09173F13E4C5 n11:271B481F-363D-11E5-9242-09173F13E4C5 n11:271B482A-363D-11E5-9242-09173F13E4C5 n11:271B4828-363D-11E5-9242-09173F13E4C5 n11:271B4829-363D-11E5-9242-09173F13E4C5 n11:271B4826-363D-11E5-9242-09173F13E4C5 n11:271B4827-363D-11E5-9242-09173F13E4C5
owl:sameAs
n17:DB00417 n32:DB00417
dcterms:title
Penicillin V
adms:identifier
n10:Penicillin_V n18:C08126 n19:D05411 n20:DB00417 n21:27446 n22:6607 n27:6869 n28:46507164 n29:0781-1205-01 n30:PNV n33:PA164745442
n3:mechanismOfAction
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.
n3:packager
n11:271B4808-363D-11E5-9242-09173F13E4C5 n11:271B4809-363D-11E5-9242-09173F13E4C5 n11:271B4806-363D-11E5-9242-09173F13E4C5 n11:271B4807-363D-11E5-9242-09173F13E4C5 n11:271B480C-363D-11E5-9242-09173F13E4C5 n11:271B480D-363D-11E5-9242-09173F13E4C5 n11:271B480A-363D-11E5-9242-09173F13E4C5 n11:271B480B-363D-11E5-9242-09173F13E4C5 n11:271B4800-363D-11E5-9242-09173F13E4C5 n11:271B4801-363D-11E5-9242-09173F13E4C5 n11:271B47FE-363D-11E5-9242-09173F13E4C5 n11:271B47FF-363D-11E5-9242-09173F13E4C5 n11:271B4804-363D-11E5-9242-09173F13E4C5 n11:271B4805-363D-11E5-9242-09173F13E4C5 n11:271B4802-363D-11E5-9242-09173F13E4C5 n11:271B4803-363D-11E5-9242-09173F13E4C5 n11:271B4818-363D-11E5-9242-09173F13E4C5 n11:271B4816-363D-11E5-9242-09173F13E4C5 n11:271B4817-363D-11E5-9242-09173F13E4C5 n11:271B4810-363D-11E5-9242-09173F13E4C5 n11:271B4811-363D-11E5-9242-09173F13E4C5 n11:271B480E-363D-11E5-9242-09173F13E4C5 n11:271B480F-363D-11E5-9242-09173F13E4C5 n11:271B4814-363D-11E5-9242-09173F13E4C5 n11:271B4815-363D-11E5-9242-09173F13E4C5 n11:271B4812-363D-11E5-9242-09173F13E4C5 n11:271B4813-363D-11E5-9242-09173F13E4C5 n11:271B47E9-363D-11E5-9242-09173F13E4C5 n11:271B47EC-363D-11E5-9242-09173F13E4C5 n11:271B47ED-363D-11E5-9242-09173F13E4C5 n11:271B47EA-363D-11E5-9242-09173F13E4C5 n11:271B47EB-363D-11E5-9242-09173F13E4C5 n11:271B47F8-363D-11E5-9242-09173F13E4C5 n11:271B47F9-363D-11E5-9242-09173F13E4C5 n11:271B47F6-363D-11E5-9242-09173F13E4C5 n11:271B47F7-363D-11E5-9242-09173F13E4C5 n11:271B47FC-363D-11E5-9242-09173F13E4C5 n11:271B47FD-363D-11E5-9242-09173F13E4C5 n11:271B47FA-363D-11E5-9242-09173F13E4C5 n11:271B47FB-363D-11E5-9242-09173F13E4C5 n11:271B47F0-363D-11E5-9242-09173F13E4C5 n11:271B47F1-363D-11E5-9242-09173F13E4C5 n11:271B47EE-363D-11E5-9242-09173F13E4C5 n11:271B47EF-363D-11E5-9242-09173F13E4C5 n11:271B47F4-363D-11E5-9242-09173F13E4C5 n11:271B47F5-363D-11E5-9242-09173F13E4C5 n11:271B47F2-363D-11E5-9242-09173F13E4C5 n11:271B47F3-363D-11E5-9242-09173F13E4C5
n3:routeOfElimination
Mostly renal. A small percentage is eliminated by feces and the biliary route.
n3:synonym
PV Penicillin Phenoxymethyl Phenoxomethylpenicillin Phenoxymethyl Penicillin Phenoxymethylpenicillinum Phenoxymethylenepenicillinic acid (2S,5R,6R)-3,3-DIMETHYL-7-oxo-6-(2-phenoxyacetamido)-4-thia-1- azabicyclo(3.2.0)heptane-2-carboxylic acid Fenoximetilpenicilina Fenospen 6-phenoxyacetamidopenicillanic acid Phenoxymethylpenicillin (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-[(phenoxyacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Penicillin v V-cillin Oracillin Phenoxymethylpenicilline
n3:toxicity
LD<sub>50</sub> >1040 mg/kg (Orally in rats with Sodium salt); Nausea, vomiting, stomach pain, diarrhea, and, in rare cases, major motor seizures
n14:hasAHFSCode
n15:08-12-16-04
n3:foodInteraction
Absorption is increased when taken on an empty stomach (one hour before or two hours after meals).
n3:mixture
n4:271B47E8-363D-11E5-9242-09173F13E4C5 n4:271B47E6-363D-11E5-9242-09173F13E4C5 n4:271B47E7-363D-11E5-9242-09173F13E4C5 n4:271B47E4-363D-11E5-9242-09173F13E4C5 n4:271B47E5-363D-11E5-9242-09173F13E4C5
n3:proteinBinding
80%
n3:salt
n3:synthesisReference
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.
n23:hasConcept
n24:M0016142
foaf:page
n7:pen1324.shtml n8:penvk.htm n26:penicillin.html
n3:IUPAC-Name
n5:271B483D-363D-11E5-9242-09173F13E4C5
n3:InChI
n5:271B4843-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n5:271B4842-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n5:271B483F-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n5:271B4840-363D-11E5-9242-09173F13E4C5
n3:SMILES
n5:271B4841-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n5:271B4853-363D-11E5-9242-09173F13E4C5 n5:271B483B-363D-11E5-9242-09173F13E4C5
n3:logP
n5:271B4855-363D-11E5-9242-09173F13E4C5 n5:271B4839-363D-11E5-9242-09173F13E4C5 n5:271B483C-363D-11E5-9242-09173F13E4C5
n3:logS
n5:271B483A-363D-11E5-9242-09173F13E4C5
n3:pKa
n5:271B4856-363D-11E5-9242-09173F13E4C5
n14:hasATCCode
n25:J01CE02
n3:H-Bond-Acceptor-Count
n5:271B4849-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n5:271B484A-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n5:271B4844-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n5:271B4845-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n5:271B4847-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n5:271B4846-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n5:271B4848-363D-11E5-9242-09173F13E4C5
n3:absorption
25% of the dose given is absorbed, 50-60% bioavailable
n3:affectedOrganism
Borrelia burgdorferi Gram-negative Bacteria Streptococcus pyogenes Bacteria Bacillus anthracis
n3:casRegistryNumber
87-08-1
n3:category
n3:containedIn
n12:271B4835-363D-11E5-9242-09173F13E4C5 n12:271B4836-363D-11E5-9242-09173F13E4C5 n12:271B4833-363D-11E5-9242-09173F13E4C5 n12:271B4834-363D-11E5-9242-09173F13E4C5 n12:271B4837-363D-11E5-9242-09173F13E4C5 n12:271B482D-363D-11E5-9242-09173F13E4C5 n12:271B482E-363D-11E5-9242-09173F13E4C5 n12:271B482B-363D-11E5-9242-09173F13E4C5 n12:271B482C-363D-11E5-9242-09173F13E4C5 n12:271B4831-363D-11E5-9242-09173F13E4C5 n12:271B4832-363D-11E5-9242-09173F13E4C5 n12:271B482F-363D-11E5-9242-09173F13E4C5 n12:271B4830-363D-11E5-9242-09173F13E4C5
n3:Bioavailability
n5:271B484F-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n5:271B4851-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n5:271B4852-363D-11E5-9242-09173F13E4C5
n3:Melting-Point
n5:271B4854-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n5:271B484E-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n5:271B484D-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n5:271B4850-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n5:271B483E-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-acidic-
n5:271B484B-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n5:271B484C-363D-11E5-9242-09173F13E4C5