General
Preferred name
phenoxymethylpenicillin
Synonyms
PENICILLIN V POTASSIUM ()
PENICILLIN V ()
Phenoxymethylpenicillin potassium salt ()
Penicillin V potassium salt ()
Penicillin V (Potassium) ()
PENICILLIN V BENZATHINE ()
BICILLIN V2 ()
Phenoxymethylpenicillin (potassium salt) ()
Ledercillin Vk ()
Phenoxymethylpenicillinum kalicum ()
Uticillin Vk ()
Antibiocin ()
V-Cillin-K ()
Beepen-Vk ()
Pfizerpen Vk ()
Veetids '500' ()
V-Cillin K ()
Penicillin Potassium Phenoxymethyl ()
Penapar-Vk ()
Vamosyn ()
Penicillin-Vk ()
Phenoxymethylpenicillin K ()
Pen-Vee K ()
Betapen-Vk ()
Penicillin Vk ()
Veetids ()
Potassium penicillin v ()
Primcillin ()
Veetids '125' ()
NSC-757258 ()
Phenoxymethylpenicillin Potassium ()
Beepen VK ()
Veetids '250' ()
V-Cillin ()
Phenoxymethylpenicillin ()
Vebecillin ()
Penicillin Phenoxymethyl ()
Phenomycilline ()
Phenoxymethylpenicillinum ()
Distaquaine v ()
Benzathine penicillin v ()
Penicillin Benzathine Phenoxymethyl ()
Benzathine phenoxymethylpenicillin ()
Penicillin V (potassium salt) ()
Penicillin V-d5 (potassium salt) ()
P&D ID
PD010039
CAS
132-98-9
87-08-1
5928-84-7
2699607-22-0
Tags
covalent binder
drug candidate
natural product
drug
available
Approved by
FDA
First approval
1958
Drug Status
approved
vet_approved
Drug indication
Bacterial infection
Antibacterial
Max Phase
Phase 4
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
HALF-LIFE Upon oral administration, the half-life is about 30 minutes. It can last up to 4 hours in patients with renal impairment.[L6412]
ROE 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]
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]
MOA 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.[L6412] This disrupts the third and last stage of bacterial cell wall synthesis. This subsequently leads to cell lysis.[L6412]
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.[L6418] 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.[L6415]
ABSORPTION Upon oral administration, phenoxymethylpenicillin is rapidly but incompletely absorbed.[A178612] The bioavailability of phenoxymethylpenicillin ranges from 25 to 60%.[A178618] 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.[L6412]
DESCRIPTION Phenoxymethylpenicillin is a β-lactam, natural penicillin antibacterial. It has broad-spectrum activity against Gram-positive aerobes, limited activity against Gram-negative organisms, and is not generally used against anaerobes. (GtoPdb)
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]
Compound Sets
19
Cayman Chemical Bioactives
23635
26786
ChEMBL Approved Drugs
CHEMBL1200852
CHEMBL615
ChEMBL Drugs
CHEMBL1200852
CHEMBL615
CHEMBL1396177
CHEMBL2103963
CovBinderInPDB
CBR003820
CBR006132
Drug Repurposing Hub
DrugBank
DB00417
DrugBank Approved Drugs
DB00417
DrugCentral
2083
DrugCentral Approved Drugs
2083
DrugMAP
DM8LX76
DMKVOYF
DrugMAP Approved Drugs
DM8LX76
DMKVOYF
Guide to Pharmacology
10920
MedChem Express Bioactive Compound Library
HY-B0975
NCATS Inxight Approved Drugs
Z61I075U2W
NPC Screening Collection
ReFrame library
Selleckchem Bioactive Compound Library
penicillin-v-potassium-salt
TargetMol Bioactive Compound Library
T1126
The Spectrum Collection
External IDs
83
Properties
(calculated by RDKit )
Molecular Weight
350.09
Hydrogen Bond Acceptors
5
Hydrogen Bond Donors
2
Rotatable Bonds
5
Ring Count
3
Aromatic Ring Count
1
cLogP
0.7
TPSA
95.94
Fraction CSP3
0.44
Chiral centers
3.0
Largest ring
6.0
QED
0.76
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Pathway
Microbiology&virology
Anti-infection
Target
antibiotic
Bacterial
Antibiotics,Bacterial
MOA
Antibiotic
bacterial cell wall synthesis inhibitor
Indication
pneumonia, ear infections, skin infections, throat infections, cholera, scarlet fever
Therapeutic Class
Antiinfective Agents
Antibiotics
Source data