Chemical Properties
Crystalline Solid
Originator
Oracilline ,Theraplix ,France ,1954
Uses
Penicillin V Potassium bactericidal against penicillin-susceptible microorganisms during the stage of active multiplication. It inhibits biosynthesis of cell-wall mucopeptide. It is used to treat or prevent infections that are proven or strongly suspected to be caused by bacteria.
Uses
Penicillin antibacterial.
Definition
ChEBI: Phenoxymethylpenicillin potassium is an organic potassium salt. It contains a phenoxymethylpenicillin(1-).
Application
Phenoxymethylpenicillin potassium was first obtained at Lilly Research Laboratories in 1948, following the addition of phenoxyacetic acid to a culture of Penicillium chrysogenum. Its industrial-scale production was established in 1953. Its usefulness as an orally active penicillin was suggested by Spitzy et al. in 1955. It is less hygroscopic and much more stable against gastric acid than benzylpenicillin, and it has been used orally for therapy of infections caused by Streptococcus, Staphylococcus, and other gram-positive bacteria as well as Neisseria and Leptospira.
Manufacturing Process
The following description is taken from US Patent 2,941,995. A solution of phenoxyacetyl chloride (360 mg) in dry acetone (5 ml) was added dropwise during 10 minutes to a stirred solution of 6-aminopenicillanic acid (450 mg, approximately 75% pure) in 3% aqueous bicarbonate (18 ml), and acetone (12 ml). When addition was complete the mixture was stirred at room temperature for 30 minutes and then extracted with ether (30 ml in 3 portions), only the aqueous phase being retained. This aqueous solution was covered with butanol (5 ml) and adjusted to pH 2 by the addition of N hydrochloric acid. After separating the layers, the aqueous phase was extracted with two 2.5 ml portions of butanol, adjusting to pH 2 each time. The combined butanol solutions (which at this stage contained the free penicillanic acid) were washed with water (3 x 2 ml) and then shaken with water (10 ml) to which sufficient 3% sodium bicarbonate solution was added to bring the aqueous phase to pH 7. The butanol solution was further extracted with two 5 ml portions of water to each of which was added enough bicarbonate solution to produce an aqueous phase of pH 7. The combined aqueous solutions were washed with ether (20 ml) and then evaporated at low temperature and pressure to leave the crude sodium salt of phenoxymethyl penicillin which, after drying in a vacuum desiccator, was obtained as a slightly hygroscopic powder (591 mg).
brand name
V-Cillin(Lilly).
Therapeutic Function
Antibacterial
General Description
Odorless white crystalline powder. Slightly bitter taste. pH (0.5% aqueous solution) 5 to 7.5.
Air & Water Reactions
Water soluble.
Reactivity Profile
Penicillin V potassium salt is the potassium salt of penicillin v. Penicillin V potassium salt is incompatible with acids, oxidizing agents (especially in the presence of trace metals), heavy metal ions such as copper, lead, zinc and mercury; glycerol, sympathomimetic amines, thiomersal, wood alcohols, cetostearyl alcohol, hard paraffins, macrogols, cocoa butter and many ionic an nonionic surface-active agents. Penicillin V potassium salt is also incompatible with alkalis, compounds leached from vulcanized rubber, hydrochlorides of tetracyclines and organic peroxides. Other incompatibilities include reducing agents, alcohols, other hydroxy compounds, self-emulsifying stearyl alcohol, emulsifying wax, lanolin, crude cholinesterated bases, glycol, sugars, amines, aminacrine hydrochloride, ephedrine, procaine, rubber tubing, thiamine hydrochloride, zinc oxide, oxidized cellulose, iodine, iodides, thiols, chlorocresol and resorcinol. Penicillin V potassium salt may also be incompatible with naphthalene oils and vitamin B.
Fire Hazard
Flash point data for Penicillin V potassium salt are not available; however, Penicillin V potassium salt is probably combustible.
Safety Profile
Moderately toxic by ingestion, intramuscular, intraperitoneal, and intravenous routes. Human mutation data reported. Questionable carcinogen with no experimental evidence. When heated to decomposition it emits very toxic fumes of NOx, K2O, and SOx. Used
References
[1] Chinese Chemical Letters, 2015, vol. 26, # 1, p. 113 - 117
