Cefaloridin

Structural formula
General
Non-proprietary name	Cefaloridin
other names	3- (1-Pyridiniumylmethyl) -7- [2- (2-thienyl) -acetamido] -3-cephem-4-carboxylate ( IUPAC ); Cefaloridinum ( Latin );
Molecular formula	C 19 H 17 N 3 O 4 S 2
External identifiers / databases
EC number	200-052-6
ECHA InfoCard	100,000,048
PubChem	5773
ChemSpider	5569
DrugBank	DB09008
Wikidata	Q5063323
Drug information
ATC code	J01 DB02
Drug class	β-lactam antibiotic; 1st generation cephalosporins;
Mechanism of action	Disturbance of cell wall synthesis
properties
Molar mass	415.48 g mol −1
Physical state	firmly
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Caution
H and P phrases	H: 317
	P: 261-280
Toxicological data	2.5–4 g kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Cefaloridine is an antibiotic in the class of cephalosporins counts of first-generation semi-synthetic is made. Because of its nephrotoxicity (toxic effect on the kidneys), it was hardly used any more in the 1980s.

Cefaloridin was patented by Glaxo in 1965 after the synthesis of 7-aminocephalospranic acid ( Cepaloridin-Glaxo ).

indication

Cefaloridin is effective against streptococcal , pneumococcal and staphylococcal infections . Indole-positive Proteus species and Pseudomonas aeruginosa are resistant to this antibiotic. Cefaloridin has been used to treat infections of the blood, bone, joints, respiratory tract, skin and urinary tract, and as a prophylactic during surgery. In veterinary medicine , it was used in dogs and cats to treat infections of the respiratory, intestinal and urinary tracts.

Working principle

The cefaloridin molecules bind to specific penicillin- binding proteins , which are located in the bacterial cell wall. This prevents further synthesis of the bacterial cell wall.

The antibiotic is eliminated from the body through the kidneys.

Application

Cefaloridin is to be administered parenterally ( intravenously , intramuscularly ).

Side effects

Cefaloridin is highly nephrotoxic , which is why it is hardly used anymore.

synthesis

The synthesis of cefaloridin or cefalotin takes place via a semisynthesis , which in this case means the acylation of an amino group . The 7-aminocephalospranic acid (7-ACA for short) to be acylated is converted from penicillin G with the help of N , N ′ -bis (trimethylsilyl) urea through a chemical reaction .

First, the reaction of 7-ACA ( 2 ) with thiophenylacetyl chloride ( 1 ) in acetone forms cefalotin ( 3 ).

Synthesis of cefalotin from 7-ACA and thiophenylacetyl chloride

Cefaloridine is formed by heating cefalotin, thiocyanate , pyridine and phosphoric acid and then adjusting the pH value with mineral acid.

At a physiological pH , the cefaloridin molecule is present as a zwitterion .

Individual evidence

↑ ^a ^b bldpharm: SDS Cephaloridine , accessed December 27, 2019.
↑ ^a ^b ^c Entry on Cefaloridine in the DrugBank of the University of Alberta , accessed May 22, 2019.
↑ ^a ^b Mutschler / Lemmer (ed.): Dictionary of Pharmacy. Volume 2 - Pharmacology, basic medical concepts , WVG Stuttgart 1985. p. 105.
↑ Ed .: Jürgen Falbe ... arr. By Eckard Amelingmeier ... by Hermann Römpp]: Römpp-Lexikon Chemie / 1, A-Cl . 10., completely revised. Edition. Thieme, Stuttgart 1996, ISBN 3-13-734610-X , p. 631 .
↑ Mason IS, Kietzmann M: Cephalosporins - pharmacological basis of clinical use in veterinary dermatology . In: Veterinary Dermatology . Vol. 10, No. 3 , 1999, p. 187-92 , doi : 10.1046 / j.1365-3164.1999.00183.x .
↑ ^a ^b ^c Gunter Schmidt: Cephalosporins . In: Chemistry in Our Time . tape 10 , no. 6 , 1976, p. 189-195 , doi : 10.1002 / ciuz.19760100605 .
↑ Chaudhary RK, Srivastava AK: Disposition and dosage regimen of cephaloridine in calves . In: Veterinary Research Communications . Vol. 13, No. 4 , 1989, pp. 325-9 , doi : 10.1007 / BF00420839 , PMID 2781723 .
^ Martindale: The Complete Drug Reference . 38th edition. Pharmaceutical Press, London 2014, ISBN 978-0-85711-139-5 , pp. 235 .
↑ Alle Bruggink (Ed.): Synthesis of β-Lactam Antibiotics: Chemistry, Biocatalysis & Process Integration. Springer Science + Business Media, ISBN 978-0-7923-7060-4 , p. 15 .
↑ Entry on CEPHALORIDINE in the Hazardous Substances Data Bank , accessed on May 27, 2019.

[bldpharm-1] rm: SDS Cephaloridine , accessed December 27, 2019.

[DrugBank-2] Entry on Cefaloridine in the DrugBank of the University of Alberta , accessed May 22, 2019.

[WdP-3] Mutschler / Lemmer (ed.): Dictionary of Pharmacy. Volume 2 - Pharmacology, basic medical concepts , WVG Stuttgart 1985. p. 105.

[4] Ed .: Jürgen Falbe ... arr. By Eckard Amelingmeier ... by Hermann Römpp]: Römpp-Lexikon Chemie / 1, A-Cl . 10., completely revised. Edition. Thieme, Stuttgart 1996, ISBN 3-13-734610-X , p. 631 .

[Mason-5] Mason IS, Kietzmann M: Cephalosporins - pharmacological basis of clinical use in veterinary dermatology . In: Veterinary Dermatology . Vol. 10, No. 3 , 1999, p. 187-92 , doi : 10.1046 / j.1365-3164.1999.00183.x .

[:1-6] Gunter Schmidt: Cephalosporins . In: Chemistry in Our Time . tape 10 , no. 6 , 1976, p. 189-195 , doi : 10.1002 / ciuz.19760100605 .

[7] Chaudhary RK, Srivastava AK: Disposition and dosage regimen of cephaloridine in calves . In: Veterinary Research Communications . Vol. 13, No. 4 , 1989, pp. 325-9 , doi : 10.1007 / BF00420839 , PMID 2781723 .

[8] Martindale: The Complete Drug Reference . 38th edition. Pharmaceutical Press, London 2014, ISBN 978-0-85711-139-5 , pp. 235 .

[9] Alle Bruggink (Ed.): Synthesis of β-Lactam Antibiotics: Chemistry, Biocatalysis & Process Integration. Springer Science + Business Media, ISBN 978-0-7923-7060-4 , p. 15 .

[HSDB-10] Entry on CEPHALORIDINE in the Hazardous Substances Data Bank , accessed on May 27, 2019.