Benzylpenicillin Health Dictionary

The name given by Sir Alexander Fleming, in 1929, to an antibacterial substance produced by the mould Penicillium notatum. The story of penicillin is one of the most dramatic in the history of medicine, and its introduction into medicine initiated a new era in therapeutics comparable only to the introduction of ANAESTHESIA by Morton and Simpson and of ANTISEPTICS by Pasteur and Lister. The two great advantages of penicillin are that it is active against a large range of bacteria and that, even in large doses, it is non-toxic. Penicillin di?uses well into body tissues and ?uids and is excreted in the urine, but it penetrates poorly into the cerebrospinal ?uid.

Penicillin is a beta-lactam antibiotic, one of a group of drugs that also includes CEPHALOSPORINS. Drugs of this group have a four-part beta-lactam ring in their molecular structure and they act by interfering with the cell-wall growth of mutliplying bacteria.

Among the organisms to which it has been, and often still is, active are: streptococcus, pneumococcus, meningococcus, gonococcus, and the organisms responsible for syphilis and for gas gangrene (for more information on these organisms and the diseases they cause, refer to the separate dictionary entries). Most bacteria of the genus staphylococcus are now resistant because they produce an enzyme called PENICILLINASE that destroys the antibiotic. A particular problem has been the evolution of strains resistant to methicillin – a derivative originally designed to conquer the resistance problem. These bacteria, known as METHICILLINRESISTANT STAPHYLOCOCCUS AUREUS (MRSA), are an increasing problem, especially after major surgery. Some are also resistant to other antibiotics such as vancomycin.

An important side-e?ect of penicillins is hypersensitivity which causes rashes and sometimes ANAPHYLAXIS, which can be fatal.

Forms of penicillin These include the following broad groups: benzylpenicillin and phenoxymethyl-penicillin; penicillinase-resistant penicillins; broad-spectrum penicillins; antipseudomonal penicillins; and mecillinams. BENZYLPENICILLIN is given intramuscularly, and is the form that is used when a rapid action is required. PHENOXYMETHYLPENICILLIN (also called penicillin V) is given by mouth and used in treating such disorders as TONSILLITIS. AMPICILLIN, a broad-spectrum antibiotic, is another of the penicillins derived by semi-synthesis from the penicillin nucleus. It, too, is active when taken by mouth, but its special feature is that it is active against gram-negative (see GRAM’S STAIN) micro-organisms such as E. coli and the salmonellae. It has been superceded by amoxicillin to the extent that prescriptions for ampicillin written by GPs in the UK to be dispensed to children have fallen by 95 per cent in the last ten years. CARBENICILLIN, a semi-synthetic penicillin, this must be given by injection, which may be painful. Its main use is in dealing with infections due to Pseudomonas pyocanea. It is the only penicillin active against this micro-organism which can be better dealt with by certain non-penicillin antibiotics. PIPERACILLIN AND TICARCILLIN are carboxypenicillins used to treat infections caused by Pseudomonas aeruginosa and Proteus spp. FLUCLOXACILLIN, also a semi-synthetic penicillin, is active against penicillin-resistant staphylococci and has the practical advantage of being active when taken by mouth. TEMOCILLIN is another penicillinase-resistant penicillin, e?ective against most gram-negative bacteria. AMOXICILLIN is an oral semi-synthetic penicillin with the same range of action as ampicillin but less likely to cause side-effects. MECILLINAM is of value in the treatment of infections with salmonellae (see FOOD POISONING), including typhoid fever, and with E. coli (see ESCHERICHIA). It is given by injection. There is a derivative, pivmecillinam, which can be taken by mouth. TICARCILLIN is a carboxypenicillin used mainly for serious infections caused by Pseudomonas aeruginosa, though it is also active against some gram-negative bacilli. Ticarcillin is available only in combination with clarulanic acid.... penicillin

Antibiotic is the term used to describe any antibacterial agent derived from micro-organisms, although most of them are now prepared synthetically. Such agents destroy or inhibit the growth of other micro-organisms: examples are penicillin, cephalosporin, amino-glycosides, streptomycin, and tetracycline.

Penicillin was the ?rst antibiotic to be discovered and used in the 1940s. The discovery and isolation in 1958 of the penicillin nucleus, 6-amino penicillanic acid (6-PNA), allowed many new penicillins to be synthesised. These are now the largest single group of antibiotics used in clinical medicine. Most staphylococci (see STAPHYLOCOCCUS) have now developed resistance to benzylpenicillin, the early form of the drug, because they produce penicillinases – enzymes which break down the drug. Other types of penicillin such as cloxacillin and ?ucoxacillin are not affected and are used against penicillin-resistant staphylococci.

The cephalosporins are derived from the compound cephalosporin C, which is obtained by fermentation of the mould cephalosporium.

The cephalosporin nucleus 7 amino cephalosporanic (7-ICA) acid has been the basis for the production of the semi-synthetic compounds of the cephalosporin nucleus. The ?rst semi-synthetic cephalosporin, cephalothin, appeared in 1962; it was followed by cephaloridine in 1964. The original cephalosporins had to be given by injection, but more recent preparations can be given by mouth. The newer preparations are less readily destroyed by betalactamases and so they have a much broader spectrum of antibacterial activity. The newer cephalosporins include cephalexin, cefazolin, cephacetrile, cephapirin, cefamandole, cefuroxine, cephrodine, cefodroxil and cefotaxine. Inactivation of beta-lactamase is the basis of bacterial resistance both to the penicillins and to the cephalosporins, so that attempts to prepare these antibiotics with resistance to betalactamase is of great importance. A synthetic inhibitor of beta-lactamase called clavulanic acid has been synthesised; this is used in combination with the penicillins and cephalosporins to prevent resistance. The cephamycins are a new addition to the beta-lactam antibiotics. They are similar in structure to the cephalosporins but are produced, not by fungi, but by actinomycetes.

Overuse and misuse of antibiotics have resulted in many bacteria becoming resistant to them. Hospitals, in particular, have problems with METHICILLIN-RESISTANT STAPHYLOCOCCUS AUREUS (MRSA). Combinations of antibiotics are needed to combat resistant strains of bacteria, another example being Mycobacterium tuberculosis.... antibiotics

Most staphylococci (see STAPHYLOCOCCUS) have now evolved resistance to benzylpenicillin (see PENICILLIN) because of their ability to produce PENICILLINASE. Cloxacillin and ?ucloxacillin are antibiotics still e?ective against most staphylococci; at one time methicillin was used to combat resistant strains, but in hospital environments bacteria acquired immunity to this powerful drug (now withdrawn from use) and to cloxacillin. RIFAMPICIN, VANCOMYCIN, TEICOPLANIN and temocillin are still active against most penicillinase-producing gram-negative bacteria (see GRAM’S STAIN). There is, however, a growing threat to health because of the rise in the number of antibiotic-resistant bacteria, particularly in hospitals. The bacteria themselves are not more virulent than others, but the di?culty in treating them with a safe and e?ective antibiotic mean that they are more dangerous. It is likely that lapses in normal hygienic practice – such as frequent hand-washing – has resulted in an increase in MRSA disease.... methicillin-resistant staphylococcus aureus (mrsa)

A bacterial ENZYME capable of neutralising the antibacterial properties of PENICILLIN and other beta-lactam antibiotics such as the CEPHALOSPORINS. Most staphylococci are now resistant to benzylpenicillin because they produce this enzyme; cloxacillin, ?ucloxacillin and temocillin are not inactivated.... penicillinase