Cefotaxime

Structural formula
General
Non-proprietary name	Cefotaxime
other names	7- (2- (2-Amino-4-thiazolyl) -2-methoxyiminoacetamido) -cephalosporanic acid; (6 R , 7 R ) -3- (Acetyloxymethyl) -7 - ((2- (2-amino-1,3-thiazol-4-yl) -2 ( Z ) -methoxyiminoacetyl) amino) -8-oxo- 5-thia-1-azabicyclo [4.2.0] oct-2-ene-2-carboxylic acid;
Molecular formula	C 16 H 17 N 5 O 7 S 2
External identifiers / databases
EC number	264-299-1
ECHA InfoCard	100.058.436
PubChem	5742673
ChemSpider	4674877
DrugBank	DB00493
Wikidata	Q417968
Drug information
ATC code	J01 DD01
Drug class	β-lactam antibiotics; (3rd generation cephalosporins)
properties
Molar mass	455.47 g · mol -1
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	20,000 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 .

Cefotaxime is an antibiotic from the group of third generation cephalosporins . According to the Paul Ehrlich Institute group classification , it belongs to group 3a of the parenteral cephalosporins.

The bactericidal effect is, as with other β-lactam antibiotics by inhibiting bacterial cell wall synthesis.

Spectrum of activity

In contrast to group 1 cephalosporins (e.g. cefazolin ), cefotaxime is more effective against gram-negative bacteria such as gonococci , meningococci and Enterobacteriaceae . However, compared to the other representatives of its group 3a ( ceftriaxone , ceftizoxime , cefmenoxime ) , cefotaxime is relatively poorly effective against Pseudomonas .

Cefotaxime not only blocks the division of bacteria, including cyanobacteria , but also the division of cyanelles, the photosynthetically active organelles of the Glaucocystaceae , and the chloroplasts of bladder moss . However , they have no effect on the division of the plastids in more highly developed vascular plants such as tomatoes . This is an indication that in higher plants due to evolutionary changes in plastid division, β-lactam antibiotics generally no longer have any effect on chloroplasts.

Indications

Cefotaxime with its wide spectrum is suitable for the calculated initial therapy of the most severe, life-threatening infections such as pneumonia , sepsis or meningitis . The gaps in effectiveness are mainly closed in combination with an aminoglycoside or acylaminopenicillin . Furthermore, cefotaxime is suitable for the therapy of neuroborreliosis .

Trade names

Monopreparations

Claforan (D, A), various generics (D, A)

Web links

Entry on cefotaxime at Vetpharm, accessed on August 11, 2012.

literature

Thomas Karow, Ruth Lang: Pharmacology and Toxicology. 2003.
Eckard Oberdisse, Eberhard Hackenthal, Klaus Kuschinsky: Pharmacology and Toxicology. Springer, Berlin et al. 1997, ISBN 3-540-61953-4 .

Individual evidence

↑ ^a ^b Data sheet Cefotaxime sodium salt from Sigma-Aldrich , accessed on May 13, 2017 ( PDF ).
^ Entry on cefotaxime in the DrugBank of the University of Alberta .
↑ Classification according to the consensus conference of the Paul Ehrlich Society .
↑ ^a ^b Britta Kasten, Ralf Reski : β-lactam antibiotics inhibit chloroplast division in a moss (Physcomitrella patens) but not in tomato (Lycopersicon esculentum) . In: J. Plant Physiol. 150: 137-140 (1997); doi : 10.1016 / S0176-1617 (97) 80193-9 .

[Sigma-1] Data sheet Cefotaxime sodium salt from Sigma-Aldrich , accessed on May 13, 2017 ( PDF ).

[DrugBank-2] Entry on cefotaxime in the DrugBank of the University of Alberta .

[3] Classification according to the consensus conference of the Paul Ehrlich Society .

[Reski-4] Britta Kasten, Ralf Reski : β-lactam antibiotics inhibit chloroplast division in a moss (Physcomitrella patens) but not in tomato (Lycopersicon esculentum) . In: J. Plant Physiol. 150: 137-140 (1997); doi : 10.1016 / S0176-1617 (97) 80193-9 .