Imipenem

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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
Clinical data
Trade namesPrimaxin
AHFS/Drugs.comInternational Drug Names
MedlinePlusa686013
Pregnancy cat.B3 (AU) C (US)
Legal statusPrescription Only (S4) (AU) -only (CA) POM (UK) -only (US)
RoutesIM, IV
Pharmacokinetic data
Protein binding20%
MetabolismRenal
Half-life38 minutes (children), 60 minutes (adults)
ExcretionUrine (70%)
Identifiers
CAS number74431-23-5 YesY
ATC codeJ01DH51
PubChemCID 5282372
DrugBankDB01598
ChemSpider4445535 YesY
UNII71OTZ9ZE0A YesY
KEGGD00206 YesY
ChEBICHEBI:51799 YesY
ChEMBLCHEMBL43708 YesY
Chemical data
FormulaC12H17N3O4S 
Mol. mass299.347 g/mol
 YesY (what is this?)  (verify)
 
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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
Clinical data
Trade namesPrimaxin
AHFS/Drugs.comInternational Drug Names
MedlinePlusa686013
Pregnancy cat.B3 (AU) C (US)
Legal statusPrescription Only (S4) (AU) -only (CA) POM (UK) -only (US)
RoutesIM, IV
Pharmacokinetic data
Protein binding20%
MetabolismRenal
Half-life38 minutes (children), 60 minutes (adults)
ExcretionUrine (70%)
Identifiers
CAS number74431-23-5 YesY
ATC codeJ01DH51
PubChemCID 5282372
DrugBankDB01598
ChemSpider4445535 YesY
UNII71OTZ9ZE0A YesY
KEGGD00206 YesY
ChEBICHEBI:51799 YesY
ChEMBLCHEMBL43708 YesY
Chemical data
FormulaC12H17N3O4S 
Mol. mass299.347 g/mol
 YesY (what is this?)  (verify)

Imipenem (Primaxin) is an intravenous β-lactam antibiotic developed in 1980.[1] It has an extremely broad spectrum of activity.[citation needed]

Imipenem belongs to the subgroup of carbapenems. It is derived from a compound called thienamycin, which is produced by the bacterium Streptomyces cattleya. Imipenem has a broad spectrum of activity against aerobic and anaerobic, Gram-positive and Gram-negative bacteria. It is particularly important for its activity against Pseudomonas aeruginosa and the Enterococcus species. It is not active against MRSA, however. Imipenem and other drugs in the carbapenem class are typically restricted in use, to avoid widespread bacterial resistance.[citation needed].

Mechanism of action[edit]

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.[citation needed]

Spectrum of Bacterial Susceptibility and Resistance[edit]

Acinetobacter anitratus, Acinetobacter calcoaceticus, Actinomyces odontolyticus, Aeromonas hydrophila, Bacteroides distasonis, Bacteroides uniformis, and Clostridium perfringens species are generally susceptible to Imipenem, while some Acinetobacter baumannii, Acinetobacter spp., Bacteroides fragilis and Enterococcus faecalis have developed resistance to Imipenem to varying degrees. Not many species are resistant to imipenem except Pseudomonas aeruginosa (Oman) and Stenotrophomonas maltophilia. [2]

Coadministration with cilastatin[edit]

Imipenem is rapidly degraded by the renal enzyme dehydropeptidase 1 when administered alone, and is always coadministered with cilastatin to prevent this inactivation (imipenem/cilastatin).[citation needed]

Adverse effects[edit]

Common adverse drug reactions are nausea and vomiting. People who are allergic to penicillin and other beta-lactam antibiotics should take caution if taking imipenem, as cross-reactivity rates are low. At high doses, imipenem is actually seizuregenic.[citation needed]

References[edit]

  1. ^ Kesado, Tadataka; Hashizume, Terutaka; Asahi, Yoshinari (1980). "Antibacterial activities of a new stabilized thienamycin, N-formimidoyl thienamycin, in comparison with other antibiotics". Antimicrobial agents and chemotherapy 17 (6): 912–7. PMC 283902. PMID 6931548. 
  2. ^ "Imipenem spectrum of bacterial susceptibility and Resistance". Retrieved 4 May 2012. 

External links[edit]

Further reading[edit]