Substance

ID:300

Names and Identifiers
IUPAC name
(2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenoxyacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Brand Name
Beepen-VkCrystapen VDistaquaine VVeetidsPen-VeePenapar-VkStabicillinV-CylinaV-CylineV-TablopenApopenBeromycinCalcipenCompocillin VEskacillian VMeropeninPenicillin-VkPhenocillinPhenomycillineV-CilV-CillinVeetids '500'Acipen VFenacilinPen-OralPen-Vee KPenicillin VkPhenopenicillinUticillin VkVeetids '250'Betapen-VkLedercillin VkOracillinPfizerpen VkRobicillinRocilinV-Cillin KVebecillinVeetids '125'Eskacillin VFenospenFenoxypenOratrenOspenPen-V
Synonyms
Phenoxymethylpenicillin PotassiumPhenoxymethyl PenicillinPenicillin PhenoxymethylPenicillin V PotassiumPhenoximethylpenicillinumFenoximetilpenicilina [INN-Spanish]Phenoxymethylpenicillinic Acid Potassium SaltPhenoxymethylenepenicillinic AcidPenicillin VFenossimetilpenicillina [Dcit]Phenoxymethylpenicillinic Acid
IUPAC Traditional name
penicillin V
Registration numbers
PubChem SID
PubChem CID
CAS Number
Properties
Physical Property
Hydrophobicity(logP)
1.4
Solubility
<0.1 g/100mL
Molecule Details
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]
Molecular Spectra
No Data Available
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References
• Gruchalla RS, Pirmohamed M: Clinical practice. Antibiotic allergy. N Engl J Med. 2006 Feb 9;354(6):601-9. Pubmed
• : 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