Ceftriaxone

Structural formula
General
Non-proprietary name	Ceftriaxone
other names	(6 R , 7 R ) -7 - {[(2 Z ) -2- (2-Amino-1,3-thiazol-4-yl) -2- (methoxyimino) acetyl] amino} -3 - {[( 2-methyl-5,6-dioxo-1,2,5,6-tetrahydro-1,2,4-triazin-3-yl) sulfanyl] methyl} -8-oxo-5-thia-1-azabicyclo [4.2 .0] oct-2-en-2-carboxylic acid ( IUPAC )
Molecular formula	C 18 H 18 N 8 O 7 S 3
Brief description	white to light yellow powder (disodium ceftriaxone hemiheptahydrate)
External identifiers / databases
EC number	277-405-6
ECHA InfoCard	100.070.347
PubChem	5479530
ChemSpider	4586394
DrugBank	DB01212
Wikidata	Q421713
Drug information
ATC code	J01 DD04
Drug class	β-lactam antibiotics
Mechanism of action	Inhibition of cell wall synthesis
properties
Molar mass	554.58 g · mol -1
Melting point	> 155 ° C (decomposition) (disodium ceftriaxone hemiheptahydrate)
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
H and P phrases	H: 315-317-319-334-335
	P: 261-280-305 + 351 + 338-342 + 311
Toxicological data	2200 mg kg −1 ( LD 50 , mouse , oral , disodium salt)
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Ceftriaxone is an antibiotic from the group of cephalosporins of the 3rd generation. The bactericidal effect is, as with other β-lactam antibiotics by inhibiting bacterial cell wall synthesis. Ceftriaxone was introduced by Hoffmann-La Roche in 1982 .

Spectrum of activity

Compared to the 1st and 2nd generation cephalosporins, the spectrum of activity is slightly expanded in the gram- negative range and slightly weakened in the gram-positive range . The enterococcal gap typical of cephalosporins is present in ceftriaxone, and Listeria , Legionella and Pseudomonas aeruginosa are not recorded.

Pharmacokinetics

Since ceftriaxone is not absorbed after oral administration, it is administered parenterally . Due to the high plasma protein binding , the half-life of ceftriaxone is 7–8 hours. 60% of the excretion is via the kidneys and 40% via the bile . Ceftriaxone has very good tissue penetration and also reaches therapeutically effective concentrations in the cerebrospinal fluid .

Indications

Ceftriaxone is suitable for the calculated initial therapy of the most severe, life-threatening infections , including purulent meningitis . However, spectrum gaps must be closed by combining them with other antibiotics. Ceftriaxone is also suitable for the therapy of neuroborreliosis and the single treatment of gonorrhea .

Contraindications

Ceftriaxone is contraindicated in case of allergy to cephalosporins. Caution should also be exercised in the case of penicillin allergies because of a possible cross allergy . Because of the risk of bilirubin encephalopathy, premature babies and newborns should not be given ceftriaxone - an alternative third-generation cephalosporin would then be cefotaxime .

Interactions

Ceftriaxone infusions must not be administered at the same time as calcium -containing solutions and drugs, not even via separate cannulas. In addition, calcium-containing agents may only be administered 48 hours after the last dose of ceftriaxone, otherwise dangerous calcium-ceftriaxone precipitates may form. A combination with the antibiotic chloramphenicol should be avoided, as the two drugs mutually reduce their effectiveness.

Trade names

Monopreparations

Cefotrix (D, A), Rocephin (D, A, CH), Tercefon (A), numerous generics (D, A, CH)

Individual evidence

↑ ^a ^b ^c data sheet Ceftriaxone disodium salt hemi (heptahydrate) from Sigma-Aldrich , accessed on March 16, 2011 ( PDF ).
^ The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition, 2006, pp. 322-323, ISBN 978-0-911910-00-1 .
^ Entry on ceftriaxone. In: Römpp Online . Georg Thieme Verlag, accessed on September 30, 2014.
↑ Ernst Mutschler, Monika Schäfer-Korting a. a .: Textbook of pharmacology and toxicology . 8th, completely revised and expanded edition. Wissenschaftliche Verlagsgesellschaft Stuttgart 2001. ISBN 3-8047-1763-2 . P. 797.

[Sigma-1] ta sheet Ceftriaxone disodium salt hemi (heptahydrate) from Sigma-Aldrich , accessed on March 16, 2011 ( PDF ).

[MerckIndex-2] The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition, 2006, pp. 322-323, ISBN 978-0-911910-00-1 .

[3] Entry on ceftriaxone. In: Römpp Online . Georg Thieme Verlag, accessed on September 30, 2014.

[4] Ernst Mutschler, Monika Schäfer-Korting a. a .: Textbook of pharmacology and toxicology . 8th, completely revised and expanded edition. Wissenschaftliche Verlagsgesellschaft Stuttgart 2001. ISBN 3-8047-1763-2 . P. 797.