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Imipenem: Wikis

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Imipenem
Systematic (IUPAC) name
(5R,6S)-6-[(1R)-1-hydroxyethyl]-3-({2-[(iminomethyl)amino]ethyl}thio)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
Identifiers
CAS number 74431-23-5
ATC code J01DH51
PubChem 47317
Chemical data
Formula C 12H17N3O4S 
Mol. mass 299.347 g/mol
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability  ?
Metabolism Renal
Half life 60 minutes
Excretion  ?
Therapeutic considerations
Pregnancy cat. C(US)
Legal status
Routes IM, IV

Imipenem is an intravenous β-lactam antibiotic developed in 1985. It has an extremely broad spectrum of activity. Imipenem belongs to the subgroup of carbapenems. It is derived from a compound called thienamycin, which is produced by the bacteria Streptomyces cattleya. Imipenem has a broad spectrum of activity against aerobic and anaerobic Gram positive as well as Gram negative bacteria. It is particularly important for its activity against Pseudomonas aeruginosa and the Enterococcus species. It is not active against methicillin-resistant Staphylococcus aureus, however. Imipenem and other drugs in the carbapenem class are typically restricted in use, in order to avoid widespread bacterial resistance.

Contents

Method of action

Imipenem acts as an antimicrobial through inhibiting cell wall synthesis of various gram-positive and gram-negative bacteria. It remains very stable in the presence of beta-lactamase (both penicillinase and cephalosporinase) produced by some bacteria, and is a strong inhibitor of beta-lactamases from some gram-negative bacteria that are resistant to most beta-lactam antibiotics.

Co-administration with cilastatin

Imipenem is rapidly degraded by the renal enzyme dehydropeptidase 1 when administered alone, and is always co-administered with cilastatin to prevent this inactivation.

Adverse effects

Common adverse drug reactions are nausea and vomiting. People who are allergic to penicillin and other beta-lactam antibiotics should not take imipenem. Imipenem can also cause seizures.

References

^  Clissold SP, Todd PA, Campoli Richards DM. Imipenem/Cilastatin: A reivew of its anti-bacterial activity, pharmacokinetic properties and therapeutic efficacy. Drugs 1987; 33: 183–241.

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