Benzylpenicillin penicilline

The first penicillin was benzylpenicillin (penicillin G, R = C6H5 CH2 C0 NH-), which is made by growing suitable strains of Penicillium chrysogenum on a carbohydrate medium. 

PhCHa benzylpenicillin = penicillin G (usual fermentation product)... 

The only penicillins used in their natural form are benzylpenicillin (penicillin G) and phenoxymethylpenicillin (penicillin V). The remainder of penicillins in clinical use are derived from 6-APA and most penicillins having useful biological properties have resulted from acylation of 6-APA using standard procedures. 

Currently, penicillin (benzylpenicillin, penicillin G) is made in huge amounts (tens of thousands of tons) by the microbiological industry. 

Penicillin was the first antibiotic to find practical use in medicine. Commercial production began in the early 1940s and benzylpenicillin (penicillin G), one of several natural penicillins that differ in the R group boxed in the structure above, became one of the most important of all drugs. Most effective against gram-positive bacteria, at higher con-... 

Benzylpenicillin (penicillin G, originally just penicillin ) is the first antibiotic to have been manufactured in bulk. It is still universally prescribed and is also used as input material for some semisynthetic antibiotics (Chapter 10). Developments associated with the penicillin fermentation process have been a significant factor in the development of modern biotechnology and therefore it is an appropriate example to illustrate key aspects of manufacture. 

Like benzylpenicillin, penicillin V is still used in its own right, but can also be used as a starting material for the manufacture of semisynthetic penicillins which cannot be made by direct fermentation. 

Benzylpenicillin Penicillin notatum, P. chrysogenum Antibacterial drug... 

Many of the medical products reviewed here find multiple applications. Thus procaine compounded with benzylpenicillin, penicillin G is an antimicrobial veterinary drug, approved in the US as a postexposure prophylaxis following inhalation of anthrax, providing that the strains do not have penicillin resistance. 

Penicillium chrysogenum on complex solid media, with the result that they were mixtures differing from one another in the identity of the side-chain moiety. When a sufficient supply of phenylacetic acid is present in liquid media, this is preferentially incorporated into the molecule to produce mainly benzylpenicillin (penicillin G in the old nomenclature). Use of phenoxyacetic acid instead leads to phenoxymethyl penicillin (penicillin V). More than two dozen different penicillins have been made in this way, but these two are the only ones that remain in clinical use. The bicyclic penicillin nucleus itself is prepared biosynthetically via a complex process from an acylated cysteinyl valyl peptide. The complete exclusion of side chain precursor acids from the medium produces the fundamental penicillin nucleus, 6-APA, but in poor yield. By itself, 6-APA has only very weak antibiotic activity, but when substituted on its primary amino group with a suitable... 

---