Cefalexin

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Structural formula
Structure of cefalexin
General
Non-proprietary name Cefalexin
other names
  • (6 R , 7 R ) -7 - [( R ) -2-amino-2-phenylacetamido] -3-methyl-8-oxo-5-thia-1-azabicyclo [4.2.0] oct-2-en- 2-carboxylic acid ( IUPAC )
  • Cefalexinum ( Latin )
  • Cephalexin
Molecular formula C 16 H 17 N 3 O 4 S
Brief description

white solid

External identifiers / databases
CAS number 15686-71-2
EC number 239-773-6
ECHA InfoCard 100.036.142
PubChem 27447
ChemSpider 25541
DrugBank DB00567
Wikidata Q411417
Drug information
ATC code

J01 DB01

Drug class
Mechanism of action

Inhibition of cell wall synthesis

properties
Molar mass 347.39 g · mol -1
Physical state

firmly

Melting point

326.8 ° C

pK s value

4.5

solubility

bad in water (1.79 mg l −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
08 - Dangerous to health

danger

H and P phrases H: 317-334
P: 261-280-342 + 311
Toxicological data

1495 mg kg −1 ( LD 50 ,  mouse ,  oral )

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

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

indication

Cefalexin is mainly used for bacterial infections in the urinary and genital organs , the respiratory tract , the skin and soft tissue, the ear, nose and throat area , the bones and joints as well as the teeth .

Working principle

Cefalexin acts on bacterial cells primarily during their division by inhibiting the septum-specific synthesis of peptidoglycan . So it inhibits enzymes that cause the formation of the new cell wall during cell division. Pathogens that are multiplying are thereby damaged and ultimately killed. The effectiveness essentially depends on the period of time during which the active substance level is above the minimum inhibitory concentration (MIC) of the pathogen.

The elimination half-life with normal kidney function is about one hour. It can be prolonged in patients with kidney failure .

application

Cefalexin is taken orally (whole with liquid).

Side effects

Hypersensitivity reactions and gastrointestinal complaints (diarrhea, vomiting, nausea) are reported as possible side effects. As with all cephalosporins, there is cross-resistance with penicillins .

In addition, if there is an existing penicillin allergy, the possible cross allergy must be taken into account.

Interactions

Cefalexin can under certain circumstances falsely simulate positive results in the determination of sugar in the urine . For this reason, methods for determining urine sugar are recommended that are based , for example, on enzymatic glucose oxidase reactions. The direct Coombs test (test to determine antibodies on red blood cells) can also be false positive. Cefalexin can also interfere with the determination of ketone bodies in the urine.

Trade names

Monopreparations

Keflex (A), Ospexin (A), Sanaxin (A) and generics (D, A)

Veterinary medicine

Cefazid, Cephacare, CefaDog (CH), Chassot-Cefaseptin, Rilexine, Therios, Ubrolexin Suspension (combined with Kanamycin )

literature

  • Michael Fresenius, Michael Heck: Repetition Intensive Care Medicine: Preparation for the examination "Special Intensive Care Medicine" . 2., completely revised and updated edition. Springer, Heidelberg 2006, ISBN 3-540-21479-8 .

Web links

Individual evidence

  1. ↑ a b c d data sheet cefalexin from Sigma-Aldrich , accessed on May 14, 2017 ( PDF ).
  2. ↑ a b c Entry on Cefalexin in the DrugBank of the University of Alberta .
  3. ↑ a b ratiopharm GmbH: Product Information Cephalexin-ratiopharm 500 mg / 100 mg film-coated tablets . As of April 2018.
  4. ^ 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.