Imipenem

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Structural formula
Structural formula of imipenem
General
Non-proprietary name Imipenem
other names

Latin : Imipenemum

Molecular formula C 12 H 17 N 3 O 4 S
Brief description

white to almost white or pale yellow powder

External identifiers / databases
CAS number
  • 64221-86-9
  • 74431-23-5 (monohydrate)
EC number 264-734-5
ECHA InfoCard 100.058.831
PubChem 104838
ChemSpider 94631
DrugBank DB01598
Wikidata Q425152
Drug information
ATC code

J01 DH51

Drug class

β-lactam antibiotics , carbapenems

Mechanism of action

Inhibition of cell wall synthesis

properties
Molar mass 299.35 g · mol -1
pK s value

~ 3.2; ~ 9.9

safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
Toxicological data

1972 mg kg −1 ( LD 50 ,  rat ,  iv )

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

Imipenem is an antibiotic drug and chemically belongs to the group of carbapenems .

pharmacology

Imipenem is a β-lactam antibiotic that has a bactericidal effect by inhibiting bacterial cell wall synthesis . Since the substance is rapidly broken down in the proximal tubular cells of the kidneys by a renal dipeptidase , imipenem is only given in combination with cilastatin . Cilastatin inhibits dipeptidase and enables therapeutically effective concentrations of the imipeneme.

Spectrum of activity

The spectrum of activity is broad in the gram-positive, gram-negative, aerobic and anaerobic range. There are gaps in effectiveness for Clostridium difficile , Enterococcus faecium , Legionella , Mycoplasma , MRSA , Stenotrophomonas maltophilia and only moderate effectiveness against Pseudomonas .

Pharmacokinetics

Imipenem is hardly absorbed and must therefore be given parenterally . The plasma half-life is one hour, the volume of distribution is 0.2 l / kg, and the plasma protein binding is 25%. 70% of imipenem is excreted unchanged via the kidneys (renally), 30% is metabolized via the liver (hepatic metabolism). Imipenem is dialyzable.

application areas

Indications for imipenem are severe polymicrobial infections or sepsis.

Side effects

Possible side effects are rashes, gastrointestinal intolerance, dizziness, cramps, epileptic seizures, vein irritation, brown discoloration of the tongue and changes in the blood count, such as eosinophilia , leukopenia , thrombocytopenia , thrombocytosis and, rarely, agranulocytosis . Increases in transaminases, alkaline phosphatase and creatinine are possible.

Individual evidence

  1. ↑ Data sheet IMIPENEM CRS (PDF) at EDQM , accessed on July 25, 2009.
  2. ↑ a b Entry on Imipenem. In: Römpp Online . Georg Thieme Verlag, accessed on July 12, 2019.
  3. ↑ Data sheet Imipenem monohydrate from Sigma-Aldrich , accessed on April 5, 2011 ( PDF ).
  4. ↑ Entry on imipenem in the ChemIDplus database of the United States National Library of Medicine (NLM) .

Trade names

Combination preparations with cilastatin: Tienam (CH, EU), Zienam (EU), Primaxin (USA)