Isoxazolyl penicillins

Highlighted isoxazolyl ring in flucloxacillin

Isoxazolylpenicillins are a group of antibiotics that belong to the β-lactam antibiotics . They are the only representatives of this group of antibiotics that are resistant to bacterial β-lactamases . Treatment of MRSA is thus possible. It is characterized by an isoxazole ring in which nitrogen and oxygen are directly adjacent. It creates a steric shield against penicillinases , which would break down the molecule. Isoxazolylpenicillins are acid-resistant and can therefore also be administered orally, but their antimicrobial activity is weaker than that of benzylpenicillin .

The use of isoxazolylpenicillins is restricted to infections with staphylococci (“narrow-spectrum penicillins”).

Typical representatives are oxacillin , cloxacillin , dicloxacillin and flucloxacillin .

Individual evidence

^ Andre Leduc, Jean Fontaine: Etudes in vitro et in vivo d'une nouvelle pénicilline de synthèse: La 5-methyl-3-phenyl-4-isoxazolyl-pénicilline . In: Canadian Medical Association Journal . tape 86 , no. 3 , January 20, 1962, ISSN 0008-4409 , pp. 101-105 , PMID 14463458 , PMC 1848792 (free full text).
↑ ^a ^b G. Geisslinger et al .: Mutschler drug effects . 11th edition. WVG, Stuttgart 2019, p. 994.
^ ^A ^b S. Suerbaum, Gerd-Dieter Burchard, SHE Kaufmann, TF Schulz (eds.): Medical microbiology and infectious diseases . 8th edition. Springer, 2016, p. 729 . limited preview in Google Book search

↑ R. Sutherland, EAP Croydon, GN Rolinson: Flucloxacillin, a New Isoxazolyl Penicillin, Compared with Oxacillin, Cloxacillin, and Dicloxacillin . In: British Medical Journal . tape 4 , no. 5733 , November 21, 1970, ISSN 0007-1447 , pp. 455-460 , PMID 5481218 , PMC 1820086 (free full text).

↑ HHW Thijssen, H. Mattie: Active Metabolites of Isoxazolylpenicillins in Humans . In: Antimicrobial Agents and Chemotherapy . tape 10 , no. 3 , September 1976, ISSN 0066-4804 , pp. 441-446 , PMID 825029 , PMC 429767 (free full text).

[1] Andre Leduc, Jean Fontaine: Etudes in vitro et in vivo d'une nouvelle pénicilline de synthèse: La 5-methyl-3-phenyl-4-isoxazolyl-pénicilline . In: Canadian Medical Association Journal . tape 86 , no. 3 , January 20, 1962, ISSN 0008-4409 , pp. 101-105 , PMID 14463458 , PMC 1848792 (free full text).

[mutsch2019-2] G. Geisslinger et al .: Mutschler drug effects . 11th edition. WVG, Stuttgart 2019, p. 994.

[Suerbaum2016-3] A ^b S. Suerbaum, Gerd-Dieter Burchard, SHE Kaufmann, TF Schulz (eds.): Medical microbiology and infectious diseases . 8th edition. Springer, 2016, p. 729 . limited preview in Google Book search

[4] R. Sutherland, EAP Croydon, GN Rolinson: Flucloxacillin, a New Isoxazolyl Penicillin, Compared with Oxacillin, Cloxacillin, and Dicloxacillin . In: British Medical Journal . tape 4 , no. 5733 , November 21, 1970, ISSN 0007-1447 , pp. 455-460 , PMID 5481218 , PMC 1820086 (free full text).

[5] HHW Thijssen, H. Mattie: Active Metabolites of Isoxazolylpenicillins in Humans . In: Antimicrobial Agents and Chemotherapy . tape 10 , no. 3 , September 1976, ISSN 0066-4804 , pp. 441-446 , PMID 825029 , PMC 429767 (free full text).