Cefuroxime

Structural formula
General
Non-proprietary name	Cefuroxime
other names	(6 R , 7 R ) -4- (carbamoyloxymethyl) -8 - [(2 Z ) - (2-furyl) -2-methoxyimino-acetyl] amino-7-oxo-2-thia-6-azabicyclo [4.2. 0] oct-4-en-5-carboxylic acid
Molecular formula	C 16 H 16 N 4 O 8 S; C 20 H 22 N 4 O 10 S (cefuroxime axetil) ;
Brief description	white, crystalline substance (cefuroxime) ; colorless solid (cefuroxime sodium salt) ;
External identifiers / databases
EC number	259-560-1
ECHA InfoCard	100.054.127
PubChem	5479529
ChemSpider	4586393
DrugBank	DB01112
Wikidata	Q413728
Drug information
ATC code	J01 DC02
Drug class	β-lactam antibiotics
properties
Molar mass	424.39 g · mol -1 (cefuroxime) ; 446.37 g · mol -1 (cefuroxime sodium salt) ; 510.47 g · mol -1 (cefuroxime axetil) ;
pK s value	2.5
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: 317-334
	P: 280
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Cefuroxime is a drug and a chemical compound belonging to the group of β-lactam antibiotics . The substance is used in medicine as an antibiotic and is one of the second-generation cephalosporins . The bactericidal effect is based on the inhibition of an enzyme that is required for the construction of the peptidoglycan cell wall.

Spectrum of activity

Compared to first-generation cephalosporins, cefuroxime shows a stronger effect against gram-negative rods, especially against Haemophilus influenzae and Enterobacteriaceae. Cefuroxime has a high stability towards β-lactamases .

Indications

Cefuroxime is used for acute and chronic bacterial infections, e.g. B. the respiratory tract, the kidneys, the skin. It is also used to treat sepsis . Cefuroxime is the only 2nd generation cephalosporin that can penetrate the liquor and is therefore the first choice for meningitis caused by pathogens sensitive to cefuroxime. In addition, cefuroxime is often used as an antibiotic prophylaxis to prevent postoperative wound infections during surgical interventions.

application

Cefuroxime sodium is given intravenously. Cefuroximaxetil is available for oral administration as a tablet or suspension.

Side effects

Symptoms in the gastrointestinal system (nausea, diarrhea, vomiting) as well as dizziness and headaches are known. There is also a risk of an allergic reaction; if there is an allergy to β- lactam antibiotics - such as penicillin - a cross-reaction is possible.

Stereochemistry

Structural formula of cefuroxime axetil, a mixture of two diastereomers. The stereochemistry only differs in the side chain (the configuration information there is marked in blue ).

Trade names

Monopreparations

Cefurax (D, A), Cefurox (D), Curocef (A), Elobact (D), Zinacef (CH), Zinnat (A, CH), numerous generic drugs (D, A, CH)

literature

Karow / Lang: Pharmacology and Toxicology , 2003
Mutschler: drug effects , 8th edition 2001

Individual evidence

↑ ^a ^b ^c M. Albinus, F. von Bruchhausen (Ed.), S. Ebel (Ed.), AW Frahm (Ed.), E. Hackenthal (Ed.): Hagers Handbook of Pharmaceutical Practice: Volume 7 Substances A –D. 5th edition 1993, Springer Berlin, ISBN 3-540-52688-9 , pp. 797-799.
^ The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals , 14th Edition (Merck & Co., Inc.), Whitehouse Station, NJ, USA, 2006; P. 323, ISBN 978-0-911910-00-1 .
↑ ^a ^b Data sheet Cefuroxime sodium salt from Sigma-Aldrich , accessed on October 22, 2016 ( PDF ).
↑ D. Adam, HW Doerr, H. Link, H. Lode: Die Infektiologie. 1st edition 2004, Springer Berlin / Heidelberg / New York, ISBN 3-540-00075-5 , p. 115.
↑ Kostja Steiner: Anesthesia at hand: Dosages - algorithms - laboratory values at hand . Schattauer Verlag, 2016, ISBN 978-3-7945-3123-3 ( google.de [accessed on January 13, 2020]).
^ Stefan Maier, Christian Eckmann, Axel Kramer: Perioperative antibiotic prophylaxis: an update. Retrieved January 13, 2020 .

[hager-1] M. Albinus, F. von Bruchhausen (Ed.), S. Ebel (Ed.), AW Frahm (Ed.), E. Hackenthal (Ed.): Hagers Handbook of Pharmaceutical Practice: Volume 7 Substances A –D. 5th edition 1993, Springer Berlin, ISBN 3-540-52688-9 , pp. 797-799.

[MERCK_Index-2] The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals , 14th Edition (Merck & Co., Inc.), Whitehouse Station, NJ, USA, 2006; P. 323, ISBN 978-0-911910-00-1 .

[Sigma-3] Data sheet Cefuroxime sodium salt from Sigma-Aldrich , accessed on October 22, 2016 ( PDF ).

[4] D. Adam, HW Doerr, H. Link, H. Lode: Die Infektiologie. 1st edition 2004, Springer Berlin / Heidelberg / New York, ISBN 3-540-00075-5 , p. 115.

[5] Kostja Steiner: Anesthesia at hand: Dosages - algorithms - laboratory values at hand . Schattauer Verlag, 2016, ISBN 978-3-7945-3123-3 ( google.de [accessed on January 13, 2020]).

[6] Stefan Maier, Christian Eckmann, Axel Kramer: Perioperative antibiotic prophylaxis: an update. Retrieved January 13, 2020 .