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Penicillin V

Catalog No. DB00417 Name DrugBank
CAS Number 87-08-1 Website http://www.ualberta.ca/
M. F. C16H18N2O5S Telephone (780) 492-3111
M. W. 350.38952 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 300

SYNONYMS

IUPAC name
(2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenoxyacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
IUPAC Traditional name
penicillin V
Brand Name
Ledercillin Vk
Phenocillin
V-Cillin K
Eskacillian V
V-Cylina
Beromycin
Betapen-Vk
Crystapen V
Distaquaine V
Fenacilin
Oratren
Pen-Oral
Robicillin
Stabicillin
Vebecillin
Calcipen
Compocillin V
Eskacillin V
Fenospen
Fenoxypen
Oracillin
Ospen
Penapar-Vk
Phenomycilline
Phenopenicillin
Rocilin
V-Cyline
Veetids
Veetids '250'
Veetids '500'
Acipen V
Apopen
Beepen-Vk
Meropenin
Pen-V
Pen-Vee
Pen-Vee K
Penicillin Vk
Penicillin-Vk
Pfizerpen Vk
Uticillin Vk
V-Cil
V-Cillin
V-Tablopen
Veetids '125'
Synonyms
Phenoxymethylpenicillin Potassium
Fenossimetilpenicillina [Dcit]
Phenoxymethyl Penicillin
Fenoximetilpenicilina [INN-Spanish]
Penicillin Phenoxymethyl
Penicillin V Potassium
Phenoxymethylpenicillinic Acid
Phenoxymethylpenicillinic Acid Potassium Salt
Phenoxymethylenepenicillinic Acid
Phenoximethylpenicillinum

DATABASE IDS

PubChem SID 46507164
PubChem CID 6869
CAS Number 87-08-1

PROPERTIES

Hydrophobicity(logP) 1.4
Solubility <0.1 g/100mL

DETAILS

Description (English)
Item Information
Drug Groups approved
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 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.
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
Pharmacology Penicillin V is a penicillin beta-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms. The name "penicillin" can either refer to several variants of penicillin available, or to the group of antibiotics derived from the penicillins. Penicillin V has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of Penicillin V results from the inhibition of cell wall synthesis and is mediated through Penicillin V binding to penicillin binding proteins (PBPs). Penicillin V is stable against hydrolysis by a variety of beta-lactamases, including penicillinases, and cephalosporinases and extended spectrum beta-lactamases.
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
Biotransformation 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.
Absorption 25% of the dose given is absorbed, 50-60% bioavailable
Half Life 30 to 40 minutes
Protein Binding 80%
Elimination Mostly renal. A small percentage is eliminated by feces and the biliary route.
References
: 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]
Gruchalla RS, Pirmohamed M: Clinical practice. Antibiotic allergy. N Engl J Med. 2006 Feb 9;354(6):601-9. [Pubmed]
External Links
Wikipedia
RxList
PDRhealth
Drugs.com

REFERENCES

  • : 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
  • Gruchalla RS, Pirmohamed M: Clinical practice. Antibiotic allergy. N Engl J Med. 2006 Feb 9;354(6):601-9. Pubmed