Cefradine

from Wikipedia, the free encyclopedia
Structural formula
Structure of cefradine
General
Non-proprietary name Cefradine
other names
  • 7 - [( R ) -2-Amino-2- (1,4-cyclohexadien-1-yl) -acetamido] -3-methyl-3-cephem-4-carboxylic acid ( IUPAC )
  • (6 R , 7 R ) -7 - [[(2 R ) -amino (cyclohexa-1,4-dienyl) acetyl] amino] -3-methyl-8-oxo-5-thia-1-azabicyclo [4.2. 0] oct-2-en-2-carboxylic acid
  • Cefradinum ( Latin )
Molecular formula C 16 H 19 N 3 O 4 S
Brief description

White to pale yellow, hygroscopic powder, slightly soluble in water, practically insoluble in ethanol 96% and hexane

External identifiers / databases
CAS number
  • 38821-53-3
  • 75975-70-1 (monohydrate)
  • 58456-86-3 (dihydrate)
  • 31828-50-9 (ununit hydrate)
  • 57584-26-6 (monosodium salt)
EC number 254-137-8
ECHA InfoCard 100.049.199
PubChem 38103
ChemSpider 34933
DrugBank DB01333
Wikidata Q2734674
Drug information
ATC code

J01 DB09

Drug class
Mechanism of action

The cell wall synthesis of the bacteria is disturbed

properties
Molar mass 349.405 g · mol -1
Physical state

firmly

Melting point

140-142 ° C (monohydrate)

pK s value

2.63

safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
07 - Warning 08 - Dangerous to health

danger

H and P phrases H: 315-317-319-334-335
P: 261-280-284-304 + 340-305 + 351 + 338-342 + 311
Toxicological data

3539 mg kg −1 ( LD 50 ,  mouse ,  iv )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Cefradin is an antibiotic that is used to treat various bacterial diseases caused by sensitive microorganisms . It is produced semisynthetically and comes from the class of the cephalosporins of the 1st generation.

This antibiotic was patented by Squibb in 1969 .

indication

Cefradine is used in various bacterial infections by appropriately sensitive organisms. These include, for example, urinary tract infection , septicemia , pneumonia , otitis media , endocarditis or bronchitis .

Working principle

Like all cephalosporins, the cefradin molecules bind to specific penicillin-binding proteins which are located in the bacterial cell wall and which are required for the reconstruction of the bacterial cell wall. This prevents further synthesis of the bacterial cell wall.

Cefradin is effective against both gram-positive and gram-negative bacteria and is effective against most strains of penicillinase- producing staphylococci .

Application and metabolism

Cephradine is usually orally administered. It is acid-stable and is quickly absorbed by the body. Food intake slows down the absorption, but does not reduce it. Cefradin can also be administered intramuscularly due to its good absorption . The plasma concentrations measured after ingestion are almost identical for oral and intramuscular administration.

Cefradine is stable to many beta-lactamases . It is poorly bound to plasma proteins and has a large volume of distribution , resulting in high tissue levels.

More than 90% of the antibiotic is excreted unchanged in the urine within six hours.

Finished medicinal products

Dexef ( F ), Nicef ( UK )

Individual evidence

  1. ↑ European Pharmacopoeia, 9th edition, basic work 2017, official German edition (Ph. Eur. 9.0). Monograph Cefradin .
  2. ↑ a b c d Entry on cefradine. In: Römpp Online . Georg Thieme Verlag, accessed on May 22, 2019.
  3. ↑ a b Data sheet Cephradine from Sigma-Aldrich , accessed on May 22, 2019 ( PDF ).
  4. ↑ a b c Entry on Cefradine in the DrugBank of the University of Alberta , accessed May 22, 2019.
  5. ↑ a b Entry on CEPHRADIN in the Hazardous Substances Data Bank , accessed on May 22, 2019.
  6. ↑ a b Summary of Product Characteristics. Nicef Capsules 250 mg / Cefradine Capsules 250 mg , Strides Pharma UK Ltd. As of May 2017.