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Penicillin V potassium

Alias: Penicillin V potassium HSDB 6315 Penicillin VK
Cat No.:V7685 Purity: ≥98%
Penicillin V Potassium (Phenoxymethylpenicillin potassium salt) is an orally bioactive antibiotic.
Penicillin V potassium
Penicillin V potassium Chemical Structure CAS No.: 132-98-9
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
250mg
Other Sizes

Other Forms of Penicillin V potassium:

  • Penicillin V-d5
  • Penicillin V
  • Penicillin V Potassium-d5 (Phenoxymethylpenicillin-d5 potassium salt)
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
Penicillin V Potassium (Phenoxymethylpenicillin potassium salt) is an orally bioactive antibiotic. Penicillin V Potassium suppresses the growth of Streptococcus, Clostridium difficile and Staphylococcus aureus and may be utilized in the treatment of otitis media, sinusitis, pharyngitis and tonsillitis.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
Streptococcus growth can be inhibited by Penicillin V (0.002-8.0 mg/L) at a minimum inhibitory concentration (MIC) of 0.004-0.008 mg/L[2]. With a MIC90 of 8 mg/L, penicillin V (0.002-8.0 mg/L) can stop Clostridium difficile from growing[3]. With a MIC of 0.016 mg/L, Penicillin V (0.004-0.063 mg/L; 18 h) suppresses the development of Staphylococcus aureus [4].
ln Vivo
In mouse thigh muscles, Penicillin V (0.063-0.25 mg/kg; single subcutaneous injection) inhibits Staphylococcus aureus growth [4]. Rats with acute suppurative otitis media (AOM) can avoid fulminant infection by administering Penicillin V (100 mg/kg) orally once a day for five days [5]. The mean area under the curve (AUC) for penicillin V (2 mg/kg; single subcutaneous injection) is 0.47 mg/L·h, and its plasma half-life is 61 minutes[4][4].
Animal Protocol
Animal/Disease Models: Specific pathogen-free (SPF) male Swiss mice (20-25 g) inoculated with Staphylococcus aureus [4]
Doses: 0.063, 0.13, 0.25 mg/kg
Route of Administration: Single subcutaneous injection
Experimental Results: Reduction in CFU number ( 1.34 × 107 counts/mL) compared with the control at a dose of 0.25 mg/kg (3.5 × 107 counts/mL).
ADME/Pharmacokinetics
Absorption, Distribution and Excretion
A dose of 1,000,000 units of the acid gives peak plasma levels of about 2 to 3 ug/ml, but the potassium salt will provide levels of 4.5 to 9 ug/ml.
Penicillin VK provides faster and higher blood levels of antibiotic than Penicillin V.
Biological Half-Life
The half-life is 0.5 to 0.6 hr.
Toxicity/Toxicokinetics
Effects During Pregnancy and Lactation
◉ Summary of Use during Lactation
Limited information indicates that penicillin V produces low levels in milk that are not expected to cause adverse effects in breastfed infants. Occasionally disruption of the infant's gastrointestinal flora, resulting in diarrhea or thrush have been reported with penicillins, but these effects have not been adequately evaluated. Penicillin V is acceptable in nursing mothers.
◉ Effects in Breastfed Infants
In one study, 12 infants were breastfed during maternal penicillin V therapy. Seven appeared normal, 3 had looser stools than normal, and 1 had a rash on the buttocks on the last day of therapy. These effects were possibly related to penicillin V in milk, but no control group was present. One infant had stains of blood in the stool, but it had happened once prior to maternal penicillin V treatment.
◉ Effects on Lactation and Breastmilk
Relevant published information was not found as of the revision date.
References

[1]. Phenoxymethylpenicillin (penicillin V) and phenethicillin. Med Clin North Am. 1970 Sep;54(5):1101-11.

[2]. In vitro effect on group A streptococci of loracarbef versus cefadroxil, cefaclor and penicillin V. Scand J Infect Dis. 1993;25(1):37-42.

[3]. In vitro susceptibility to 17 antimicrobials of clinical Clostridium difficile isolates collected in 1993-2007 in Sweden. Clin Microbiol Infect. 2010 Aug;16(8):1104-10.

[4]. Comparative pharmacodynamics and clinical pharmacokinetics of phenoxymethylpenicillin and pheneticillin. Br J Clin Pharmacol. 1985 May;19(5):657-68.

[5]. Prevention of experimental acute otitis media with penicillin V. Acta Otolaryngol. Jan-Feb 1990;109(1-2):119-23.

Additional Infomation
Penicillin vk+ is an odorless white crystalline powder. Slightly bitter taste. pH (0.5% aqueous solution) 5 to 7.5. (NTP, 1992)
Phenoxymethylpenicillin potassium is an organic potassium salt. It contains a phenoxymethylpenicillin(1-).
Penicillin V Potassium is the potassium salt of penicillin V, a member of the penicillin antibiotic family with broad-spectrum bactericidal activity. Penicillin V binds to and inactivates penicillin-binding proteins (PBPs), enzymes located on the inner membrane of the bacterial cell wall, resulting in the weakening of the bacterial cell wall and cell lysis. PBPs participate in the terminal stages of assembling the bacterial cell wall, and in reshaping the cell wall during cell division. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity.
A broad-spectrum penicillin antibiotic used orally in the treatment of mild to moderate infections by susceptible gram-positive organisms.
See also: Penicillin V (has active moiety).
Mechanism of Action
The penicillins and their metabolites are potent immunogens because of their ability to combine with proteins and act as haptens for acute antibody-mediated reactions. The most frequent (about 95 percent) or "major" determinant of penicillin allergy is the penicilloyl determinant produced by opening the beta-lactam ring of the penicillin. This allows linkage of the penicillin to protein at the amide group. "Minor" determinants (less frequent) are the other metabolites formed, including native penicillin and penicilloic acids. /Penicillins/
Bactericidal; inhibit bacterial cell wall synthesis. Action is dependent on the ability of penicillins to reach and bind penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. Penicillin-binding proteins (which include transpeptidases, carboxypeptidases, and endopeptidases) are enzymes that are involved in the terminal stages of assembling the bacterial cell wall and in reshaping the cell wall during growth and division. Penicillins bind to, and inactivate, penicillin-binding proteins, resulting in the weakening of the bacterial cell wall and lysis. /Penicillins/
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C16H17KN2O5S
Molecular Weight
388.4793
Exact Mass
388.049
CAS #
132-98-9
Related CAS #
Penicillin V-d5;1356837-87-0;Penicillin V;87-08-1;Penicillin V-13C6 potassium;Penicillin V Potassium-d5;2699607-22-0
PubChem CID
23676814
Appearance
White to off-white solid powder
Density
1.40
Boiling Point
681.4ºC at 760 mmHg
Melting Point
197-202°C
Flash Point
365.9ºC
Vapour Pressure
1.69E-19mmHg at 25°C
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
6
Rotatable Bond Count
5
Heavy Atom Count
25
Complexity
553
Defined Atom Stereocenter Count
3
SMILES
CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)COC3=CC=CC=C3)C(=O)[O-])C.[K+]
InChi Key
HCTVWSOKIJULET-LQDWTQKMSA-M
InChi Code
InChI=1S/C16H18N2O5S.K/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);/q;+1/p-1/t11-,12+,14-;/m1./s1
Chemical Name
potassium;(2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2-phenoxyacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
Synonyms
Penicillin V potassium HSDB 6315 Penicillin VK
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: Please store this product in a sealed and protected environment, avoid exposure to moisture.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~12 mg/mL (~30.89 mM)
H2O : ~6 mg/mL (~15.44 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 1.2 mg/mL (3.09 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 12.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 1.2 mg/mL (3.09 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 12.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 1.2 mg/mL (3.09 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 12.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


Solubility in Formulation 4: 100 mg/mL (257.41 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.5741 mL 12.8707 mL 25.7414 mL
5 mM 0.5148 mL 2.5741 mL 5.1483 mL
10 mM 0.2574 mL 1.2871 mL 2.5741 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT05082909 UNKNOWN STATUS Drug: Probenecid Infection, Bacterial Imperial College London 2021-12-21 Phase 1
Phase 2
NCT03208361 TERMINATED Drug: Penicillin V
Drug: Amoxicillin
Community-acquired Pneumonia (CAP) Fundacio d'Investigacio en Atencio Primaria Jordi Gol i Gurina 2013-11-05 Phase 3
NCT00823433 TERMINATED Drug: oral penicillin V Group B Streptococcus William Beaumont Hospitals 2009-01 Early Phase 1
NCT02188472 COMPLETED Drug: Penicillin V
Drug: Trimethoprim
Drug: Placebo
Oxidative Stress Henrik Enghusen Poulsen 2010-11 Phase 1
NCT04083417 UNKNOWN STATUS Drug: Phenoxymethylpenicillin
Other: No antibiotic treatment
Sore Throat
Tonsillitis
Katarina Hedin 2019-09-09 Phase 4
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