Penicillin G potassium salt Chemical Properties

Melting point:

214-217 C

alpha 

D22 +285° (c = 0.748 in water)

refractive index 

294 ° (C=1, H2O)

storage temp. 

Sealed in dry,Store in freezer, under -20°C

solubility 

H₂O: 100 mg/mL

form 

powder

color 

Needles from butanol (aq)

PH

pH (10g/L, 25℃) : 5.0～7.5

Water Solubility 

Soluble in water (100 mg/ml), methanol, ethanol (sparingly), and alcohol. Insoluble in chloroform.

Merck 

14,7094

BRN 

3832841

Stability:

Hygroscopic

InChIKey

IYNDLOXRXUOGIU-LQDWTQKMSA-M

SMILES

N12C([C@@H](NC(=O)CC3=CC=CC=C3)[C@@]1([H])SC(C)(C)[C@@H]2C([O-])=O)=O.[K+] |&1:2,13,19,r|

EPA Substance Registry System

Penicillin G Potassium (113-98-4)

Safety Information

Hazard Codes 

Xn,C,F

Risk Statements 

42/43-34-11

Safety Statements 

36/37-45-36/37/39-26-16-60-37-24-22

WGK Germany 

2

RTECS 

XH9700000

F 

10-23

TSCA 

Yes

HS Code 

29411000

Toxicity

LD50 oral in rabbit: 5848mg/kg

MSDS

• Language:English Provider:potassium [2S-(2alpha,5alpha,6beta)]-3,3-dimethyl-7-oxo-6-(phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• Language:English Provider:SigmaAldrich

Penicillin G potassium salt Usage And Synthesis

Description

Benzylpenicillin potassiumwas the first crystalline penicillin produced on an industrial scale , . It is produced in the pure state by the addition of phenylacetate to a culture of Penicillium chrysogenum. The crystalline benzylpenicillin potassium contains 1598 U/mg.

Chemical Properties

Penicillin G potassium salt is also known as Potassium benzylpenicillin, it is white crystalline powder, odorless or slightly specific odor, hygroscopic. Soluble in water, physiological saline, glucose solution. The aqueous solution of it is easy to fail when placed at room temperature, and it will fail rapidly in the presence of acid, alkali, oxidant, etc. Penicillin G potassium salt has good antibacterial effect on Streptococcus such as Streptococcus hemolyticus, Streptococcus pneumoniae and Staphylococcus without penicillinase.

Uses

Penicillin G is a narrow spectrum antibiotic derived from Streptococcus pneumoniae. Penicillin G potassium salt is used as a cell culture additive as an antibiotics. Use to inhibit the synthesis of bacterial cell walls by inhibition of the cell wall peptidoglycan chain cross-lining. It is the drug of choice for groups A, B, C and G streptococci, nonenterococcal group D streptococci, viridians group streptococci, and non-penicillinase producing staphylococcus. The potassium salt has been used to study murosomes of staphylococci and the penicillin-induced lysis of Streptococcus mutans.

Preparation

Penicillin G potassium salt is a highly effective and low toxicity antibiotic, which is obtained by salt formation of Chlorpheniramine maleate and maleic acid.

Definition

ChEBI: Penicillin G potassium salt is organic potassium salt of benzylpenicillin. It is an antibiotic substance produced by Penicillium sp. Antibacterial. It contains a benzylpenicillin(1-).

brand name

Pentids (Apothecon); Pfizerpen (Pfizer).

General Description

Penicillin G Potassium is the potassium salt form of penicillin G, a broad-spectrum penicillin antibiotic. Penicillin G potassium binds to penicillin binding proteins (PBP), the enzymes that catalyze the synthesis of peptidoglycan, which is a critical component of the bacterial cell wall. This leads to the interruption of cell wall synthesis, consequently leading to bacterial cell growth inhibition and cell lysis.

Biochem/physiol Actions

Mode of Action: Penicillin G acts by inhibiting cell wall synthesis through binding to penicillin binding proteins (PBPs), inhibiting peptidoglycan chain cross-linking.
Antimicrobial spectrum: This product is active against gram-positive and gram-negative bacteria.

Safety Profile

Poison by intracerebral andintravenous routes. Moderately toxic by intraperitonealroute. Mutation data reported. See other penicillin entries.When heated to decomposition it emits toxic fumes ofNOx and SOx.

Synthesis

Synthesis of (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid as (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2- Potassium carboxylate was performed in the following general steps: first, 1000 mL of the activated charcoal-treated extract (containing about 100,000 Oxford units of penicillin G/mL) was dissolved in n-butyl acetate. Subsequently, a 50% (w/w) aqueous solution of K2CO3 was added to this solution, ensuring that the molar amount of potassium in the mixture was about 1.0 equivalent of penicillin G. Next, a volume of liquid was evaporated by heating the mixture under vacuum using a rotary film evaporator (bath temperature 45-48°C) (see Table 1 for specific evaporation volumes). After evaporation was completed, methanol was added to the residue and stirred at 25°C for 1 hour. Afterwards, the suspension was filtered and the wet filter cake was washed with 70 mL of n-butyl acetate and finally the wet filter cake was dried. Table 1 details the total volume of evaporation and the volume of the aqueous layer in the distillate after the addition of penicillin G potassium salt to n-butyl acetate (values in parentheses), as well as the moisture content of the evaporated residue. All experiments yielded white penicillin G potassium crystals in high yields (defined as 100% relative to the penicillin content in the activated charcoal-treated extract) with limited loss of penicillin from the mother liquor. The penicillin G potassium content of the crystals obtained in Experiment 1 was 99.3%, indicating excellent quality of the crystals.

References

[1] Patent: WO2007/63107, 2007, A1. Location in patent: Page/Page column 7-8
[2] Patent: WO2007/63107, 2007, A1. Location in patent: Page/Page column 7

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