Cefixime

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Structural formula
Structure of cefixime
General
Non-proprietary name Cefixime
other names
  • (6 R , 7 R ) -7 - [( Z ) -2- (2-Amino-4-thiazolyl) -2- (carboxymethoxyimino) glyoxylamido] -8-oxo-3-vinyl-5-thia-1-azabicyclo [4.2.0] oct-2-en-2-carboxylic acid ( IUPAC )
  • Cefiximum ( Latin )
  • Cefiximum anhydricum ( Latin )
Molecular formula
  • C 16 H 15 N 5 O 7 S 2 (cefixime)
  • C 16 H 15 N 5 O 7 S 2 3H 2 O (cefixime trihydrate)
Brief description

white, odorless powder (cefixime trihydrate)

External identifiers / databases
CAS number
  • 79350-37-1 (cefixime)
  • 125110-14-7 (cefixime trihydrate )
EC number 616-684-4
ECHA InfoCard 100.119.331
PubChem 5362065
ChemSpider 4514923
DrugBank DB00671
Wikidata Q163901
Drug information
ATC code

J01 DD08

Drug class
Mechanism of action

Inhibition of bacterial cell wall synthesis

properties
Molar mass
  • 453.45 g · mol -1 (cefixime)
  • 507,50 g · mol -1 (cefixime trihydrate)
Physical state

firmly

Melting point

218–225 ° C (cefixime trihydrate)

solubility

sparingly soluble in water (55.11 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

Cefixime trihydrate

08 - Dangerous to health

danger

H and P phrases H: 317-334
P: 261-280-342 + 311
Toxicological data
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Cefixime is a semisynthetic broad spectrum antibiotic from the group of β-lactam antibiotics and the third generation of cephalosporins . It is orally administered.

Spectrum of activity

Cefixime has a bactericidal effect against gram- positive and gram- negative bacteria .

In general, Cefixime is effective against the following pathogens:

Staphylococci (e.g. Staphylococcus aureus ) are resistant to cefixime .

pharmacology

Pharmacodynamics

Many pathogens are resistant to penicillins and some cephalosporins . These may be susceptible to cefixime as cefixime in the presence of very stable β-lactamase - enzymes is.

Mechanism of action

Cefixime inhibits bacterial cell wall synthesis . It prevents growing, dividing cells crosslinking of certain building blocks, so the out murein existing cell wall bursts and the bacteria die.

Dose-response relationship

Cefixime has a wide therapeutic range .

Ingesting large amounts of cefixime can lead to an overdose . Signs of this include symptoms such as blood in the urine , diarrhea , nausea , upper abdominal pain, and vomiting .

Pharmacokinetics

The absorption of cefixime is not food intake affected.

The half-life ( half-life ) of cefixime is 3–4 hours, but under certain circumstances it can increase to 9 hours. In patients with severe renal impairment (5–20 milliliters / minute creatinine clearance ), the half-life can increase to 11.5 hours.

The metabolism of cefixime takes place via the liver . Approximately 50 % of the absorbed dose is excreted unchanged in the urine within 24 hours .

Indications

Cefixime is used for acute and chronic bacterial infections with cefixime-sensitive bacteria such as streptococci . Which includes:

These infections also include ear, nose and throat infections such as

Also, cefixime can be used to treat

can be used.

Contraindications and restrictions on use

Cefixime must not be used if you have had severe hypersensitivity reactions to the drug or to other β-lactam antibiotics in the past. Cefixime is also contraindicated in premature and newborn babies (less than 28 days of age).

Cefixime should be used with caution

Due to the lack of teratogenic effects, cefixime can be used during pregnancy and breastfeeding .

Drug interactions

Cefixime can reduce the nephrotoxicity of certain drugs , e.g. B. aminoglycosides , and increase the risk of bleeding with simultaneous therapy with anticoagulants or platelet aggregation inhibitors .

When nifedipine is administered at the same time , the bioavailability of cefixime is increased by approx. 70%.

After using Cefixime, urine test methods based on reduction may be false positive, but not when using enzymatic methods.

Side effects

The most common side effects affect the gastrointestinal tract and manifest themselves in soft stools or even diarrhea (in 1% to 10% of those treated).

Occasionally, headaches and rashes occur.

Rarely (less than 0.1% of those treated) have hypersensitivity reactions of all degrees of severity, including anaphylactic shock . Hypersensitivity reactions have also been observed after oral administration of cephalosporins , albeit much less frequently than after intravenous or intramuscular administration.

Very rare undesirable effects (less than 1 in 10,000 patients treated) are changes in the blood count , such as: B. Decrease in the total number of white blood cells ( leukopenia ); a serious decrease in certain types of white blood cells in the blood ( agranulocytosis ) that may develop within hours ; severe decrease in all blood cells ( pancytopenia ) or decrease in the number of platelets ( thrombocytopenia ); Decrease in the number of red blood cells . Also very rare are blood clotting disorders and serum sickness- like reactions, liver inflammation , severe skin changes ( erythema exudativum multiforme and Lyell's syndrome ) and antibiotic-associated colon inflammation characterized by severe and persistent diarrhea .

Trade names

Cefixime is processed in finished medicinal products as cefixime trihydrate (cefixime 3H 2 O) and is available in the form of tablets , film-coated tablets , drinking tablets , dry juice and granules for the preparation of a suspension in the doses 200 mg and 400 mg for tablets and 100 mg / 5 ml for juices and suspensions in trade.

Monopreparations

Suprax (D), InfectoOptiCef (D), Cephoral (D, CH), Uro-Cephoral (D), Aerocef (A), Tricef (A), some generics (D)

literature

Web links

Commons : Cephalosporin Antibiotics  - Collection of Pictures, Videos and Audio Files
Wikibooks: Positive list of pediatrics  - learning and teaching materials
Wikibooks: Pharmacology and Toxicology: Antibiotics  - Learning and Teaching Materials

Individual evidence

  1. a b Data sheet Cefixime trihydrate from Sequoia Research Products, accessed on July 6, 2011.
  2. Entry on cefixime in Pharmawiki , accessed on July 6, 2011.
  3. a b Data sheet Cefixime trihydrate from Sigma-Aldrich , accessed on May 18, 2017 ( PDF ).
  4. a b c d e f g h Entry on Cefixime in the ChemIDplus database of the United States National Library of Medicine (NLM), accessed on July 6, 2011.
  5. ^ 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. 340.
  6. External identifiers or database links for cefixime trihydrate : CAS number: 125110-14-7, EC number: 635-033-5, ECHA InfoCard: 100.162.959 , PubChem : 5491577 , ChemSpider : 4590586 , DrugBank : DBSALT001818 , Wikidata : Q60025382 .