Cefazolin

Structural formula
General
Non-proprietary name	Cefazolin
other names	(6 R , 7 R ) -3 - [(5-Methyl-1,3,4-thiadiazol-2-yl) -thiomethyl] -8-oxo-7- [2- (1 H -tetrazol-1-yl ) -acetamido] -5-thia-1-azabicyclo [4.2.0] oct-2-en-2-carboxylic acid ( IUPAC ); Cefazolinum ( Latin );
Molecular formula	C 14 H 14 N 8 O 4 S 3
External identifiers / databases
EC number	247-362-8
ECHA InfoCard	100,043,042
PubChem	33255
ChemSpider	30723
DrugBank	DB01327
Wikidata	Q415739
Drug information
ATC code	J01 DB04
Drug class	β-lactam antibiotic; 1st generation cephalosporins;
Mechanism of action	The cell wall synthesis of the bacteria is disturbed
properties
Molar mass	454.51 g · mol -1
Physical state	firmly
Melting point	198–200 ° C (decomposition)
pK s value	2.50 (60 ° C)
solubility	poor in water (214 mg l −1 , 25 ° C)
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances danger
H and P phrases	H: 317-334
	P: 261-280-342 + 311
Toxicological data	3000 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 .

Cefazolin is a semi-synthetic antibiotic from the class of the first generation cephalosporins .

indication

Cefazolin is mainly used for bacterial infections of the skin . It can also be used for moderate bacterial infections of the lungs ( pneumonia and bronchitis ), bones , joints , stomach , blood , heart valves and the urinary tract ( kidney pelvis , urinary bladder , ureter , prostate gland ). Another area of application is the prophylactic administration to prevent infections during operations, for example in open heart surgery or surgical interventions on bones and joints.

Working principle

Cefazolin inhibits the build-up of the cell wall of bacteria . This kills the pathogen. However, cefazolin is only effective against certain pathogens. For example against staphylococci , Escherichia coli and Streptococcus pneumoniae . A number of other pathogens, such as Proteus vulgaris , Enterobacter cloacae , and other streptococcal strains, are largely resistant to cefazolin .

The dominant elimination half-life with normal kidney function is two hours.

Application

Cefazolin sodium is administered intravenously or intramuscularly injected .

Side effects

Hypersensitivity reactions and gastrointestinal complaints (diarrhea, vomiting, nausea) are reported as possible side effects. Other undesirable effects are allergic reactions, changes in the blood count, kidney inflammation and, with high doses, headaches.

Trade names

Monopreparations

Basocef (D), Celidocin (D, veterinary medicine), Kefzol (A, CH), Servazolin (A), various generics (D, A, CH)

Individual evidence

↑ Entry on cefazolin. In: Römpp Online . Georg Thieme Verlag, accessed on November 10, 2014.
^ ES Rattie, JJ Zimmerman, LJ Ravin: Degradation kinetics of a new cephalosporin derivative in aqueous solution , in: Journal of Pharmaceutical Sciences , 1979 , 68 , 1369-1374; doi: 10.1002 / jps.2600681108 .
↑ ^a ^b Entry on cefazolin in the ChemIDplus database of the United States National Library of Medicine (NLM) .
↑ ^a ^b Data sheet Cefazolin sodium salt from Sigma-Aldrich , accessed on November 5, 2016 ( PDF ).
↑ Classification according to the consensus conference of the Paul Ehrlich Society ( Memento from September 18, 2012 in the Internet Archive ).
↑ Cefazolin ( Memento from September 28, 2004 in the Internet Archive )
↑ Cefazolin ( Memento of September 10, 2012 in the Internet Archive ), accessed on November 22, 2007.
^ Marianne Abele-Horn: Antimicrobial Therapy. Decision support for the treatment and prophylaxis of infectious diseases. With the collaboration of Werner Heinz, Hartwig Klinker, Johann Schurz and August Stich, 2nd, revised and expanded edition. Peter Wiehl, Marburg 2009, ISBN 978-3-927219-14-4 , p. 339.

[1] Entry on cefazolin. In: Römpp Online . Georg Thieme Verlag, accessed on November 10, 2014.

[2] ES Rattie, JJ Zimmerman, LJ Ravin: Degradation kinetics of a new cephalosporin derivative in aqueous solution , in: Journal of Pharmaceutical Sciences , 1979 , 68 , 1369-1374; doi: 10.1002 / jps.2600681108 .

[ChemIDplus-3] Entry on cefazolin in the ChemIDplus database of the United States National Library of Medicine (NLM) .

[Sigma-4] Data sheet Cefazolin sodium salt from Sigma-Aldrich , accessed on November 5, 2016 ( PDF ).

[5] Classification according to the consensus conference of the Paul Ehrlich Society ( Memento from September 18, 2012 in the Internet Archive ).

[6] Cefazolin ( Memento from September 28, 2004 in the Internet Archive )

[7] Cefazolin ( Memento of September 10, 2012 in the Internet Archive ), accessed on November 22, 2007.

[8] Marianne Abele-Horn: Antimicrobial Therapy. Decision support for the treatment and prophylaxis of infectious diseases. With the collaboration of Werner Heinz, Hartwig Klinker, Johann Schurz and August Stich, 2nd, revised and expanded edition. Peter Wiehl, Marburg 2009, ISBN 978-3-927219-14-4 , p. 339.