Phenoxymethylpenicillin

History

In 1946, the Austrian company Biochemie was founded in Kundl at a derelict brewery, suggested by French chemist Michel Rambaud, who obtained a small Penicillium culture from France. Persistent contamination led biologist Ernst Brandl in 1951 to add phenoxyethanol as a disinfectant, which unexpectedly increased penicillin production.

The resulting penicillin was phenoxymethylpenicillin, formed when phenoxyethanol fermented to phenoxyacetic acid and was incorporated via biosynthesis. Brandl recognized that this form resisted stomach acid and could be taken orally. Eli Lilly had originally discovered it in 1948 while studying penicillin precursors but did not exploit it further.

Medical uses

Phenoxymethylpenicillin is indicated for infections caused by Streptococcus pyogenes, including tonsillitis, pharyngitis, and streptococcal skin infections. It is used for mild uncomplicated anthrax, early-stage Lyme disease in pregnant women or young children, and primary or secondary prophylaxis of rheumatic fever. It also prevents pneumococcal infection in those with spleen disorders and in children with sickle cell disease. Dental abscesses and moderate-to-severe gingivitis (with metronidazole) are additional uses.

It is less active than benzylpenicillin against Gram-negative bacteria but has similar Gram-positive activity. Because absorption can be unpredictable, it is reserved for mild to moderate infections; therapy should be guided by bacteriological studies except for Streptococcus pyogenes. It is not effective against beta-lactamase-producing bacteria.

Did You Know?

• Penicillin V was named 'V' for Vertraulich (German for confidential), not for the Roman numeral 5.
• Penicillin VK is the potassium salt of penicillin V.
• A previous hypersensitivity reaction to any penicillin is a contraindication.