Cefapirin

from Wikipedia, the free encyclopedia
Structural formula
Structure of cefapirin
General
Non-proprietary name Cefapirin
other names
  • (6 R , 7 R ) -3- (Acetyloxymethyl) -8-oxo-7 - [(2-pyridin-4-ylsulfanylacetyl) amino] -5-thia-1-azabicyclo [4.2.0] oct-2-ene -2-carboxylic acid ( IUPAC )
  • Cefapirinum ( Latin )
Molecular formula
  • C 17 H 17 N 3 O 6 S 2
  • C 17 H 16 N 3 NaO 6 S 2 ( sodium salt )
External identifiers / databases
CAS number
  • 21593-23-7
  • 24356-60-3 (sodium salt)
EC number 244-466-5
ECHA InfoCard 100.040.409
PubChem 30699
ChemSpider 28486
DrugBank DB01139
Wikidata Q549803
Drug information
ATC code

J01 DB08

Drug class
Mechanism of action

Disturbance of cell wall synthesis

properties
Molar mass 423.46 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

Cefapirin sodium

07 - Warning 08 - Dangerous to health

danger

H and P phrases H: 315-317-319-334-335
P: 261-280-305 + 351 + 338-342 + 311-362
Toxicological data

14000 mg 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 .

Cefapirin is an antibiotic that is used to treat infections caused by susceptible bacteria . It is produced semisynthetically and belongs to the class of cephalosporins of the 1st generation.

In Germany, cefapirin is only approved for use in animals; it is not used in human medicine.

indication

Cefapirine has a broad spectrum of activity against gram-positive and gram-negative organisms. Cefapirin, like most cephalosporins, is therefore effective in treating many infections such as otitis media or urinary tract infections. Compared to beta-lactamases is Cefapirin resistant than penicillins . It can therefore be used against staphylococcal infections.

In veterinary medicine, cefapirin is used to treat or prevent mastitis in cows, and also to treat subacute and chronic endometritis in cows .

Working principle

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

Application

Cefapirin is administered intramammary (ie through the teat canal into the mammary gland) or intrauterine .

Chemical-pharmaceutical information

The water-soluble cefapirine sodium and cefapirine benzathine (2: 1) are used in pharmaceuticals.

Cefapirin should be stored dry and at room temperature so it can be used for 24 months. A reconstituted solution can be kept at room temperature for 12 hours and in the refrigerator for 10 days. Color changes can occur, but these do not indicate a loss of effectiveness.

Side effects

The most common side effects are hypersensitivity reactions and changes in liver function. However, signs of white blood cell disorder and anemia could also be seen.

synthesis

The synthesis of cefapirine 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 . The 7-ACA is then acylated in a dehydrochlorinating environment.

Trade names (veterinary medicine)

Monopreparations

Masti-Safe (D), Metricure (D)

Combination preparations

with prednisolone : Mastiplan LC (D)

Individual evidence

  1. ↑ a b Data sheet cefapirin sodium from Sigma-Aldrich , accessed on May 21, 2019 ( PDF ).
  2. ↑ a b c d e Entry on cefapirine in the DrugBank of the University of Alberta , accessed on May 22, 2019.
  3. ↑ Metricure available again. In: topagrar online. July 9, 2018, accessed May 20, 2019 .
  4. ↑ Gunter Schmidt: Cephalosporins . In: Chemistry in Our Time . tape 10 , no. 6 , 1976, p. 189-195 , doi : 10.1002 / ciuz.19760100605 .
  5. ↑ RM Stockler, DE Morin, RK Lantz, WL Hurley, PD Constable: Effect of milk fraction on concentrations of cephapirin and desacetylcephapirin in bovine milk after intramammary infusion of cephapirin sodium . In: Journal of Veterinary Pharmacology and Therapeutics . tape 32 , no. 4 , 2009, p. 345-352 , doi : 10.1111 / j.1365-2885.2008.01048.x .
  6. ↑ Intervet Deutschland GmbH: Specialist information Mastisafe . As of March 2016.
  7. ↑ Intervet Deutschland GmbH: Specialist information Metricure . As of November 2012.
  8. ↑ European Pharmacopoeia Commission (ed.): European Pharmacopoeia, 9th edition, basic work 2017. Monograph: Cefapirin sodium .
  9. ↑ External identifiers of or database links for cefapirine sodium, IUPAC name: sodium [(6R, 7R) -3 - [(acetyloxy) methyl] -8-oxo-7 - [[[(pyridin-4-yl ) sulfanyl] acetyl] amino] -5-thia-1-azabicyclo [4.2.0] oct-2-en-2-carboxylate] : CAS number: 24356-60-3, EC number: 246-194-2 , ECHA InfoCard: 100.041.980 , PubChem : 23675312 , ChemSpider : 390127 , DrugBank : DB01139 , Wikidata : Q27106128 .
  10. ↑ External identifiers or database links for cefapirine benzathine : CAS number: 97468-37-6, EC number: 619-270-1 , ECHA InfoCard: 100.108.326 , PubChem : 167441 , ChemSpider : 146482 , Wikidata : Q27271322 .
  11. ↑ Entry on cefapirin at Vetpharm, accessed on May 20, 2019.
  12. ↑ Alle Bruggink (Ed.): Synthesis of β-Lactam Antibiotics: Chemistry, Biocatalysis & Process Integration. Springer Science + Business Media, ISBN 978-0-7923-7060-4 , p. 15 .
  13. ↑ Entry on CEPHAPIRIN in the Hazardous Substances Data Bank , accessed on May 27, 2019.