Substance
ID:1383
Names and Identifiers
Synonyms
IMPImipenemN-formimidoylthienamycinImipenem, n-formimidoyl thienamycinImipemide
IUPAC Traditional name
IPM
IUPAC name
(5R,6S)-3-({2-[(E)-(aminomethylidene)amino]ethyl}sulfanyl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
Brand Name
Tienamycin
Properties
Physical Property
Solubility
10 mg/mL [MERCK INDEX (1996)]
Molecule Details
Drug Groups
approved
Description
Semisynthetic thienamycin that has a wide spectrum of antibacterial activity against gram-negative and gram-positive aerobic and anaerobic bacteria, including many multiresistant strains. It is stable to beta-lactamases. Clinical studies have demonstrated high efficacy in the treatment of infections of various body systems. Its effectiveness is enhanced when it is administered in combination with cilastatin, a renal dipeptidase inhibitor. [PubChem]
Indication
For the treatment of bacterial infections caused by susceptible bacteria.
Pharmacology
Imipenem is a beta-lactam antibiotic belongings to the subgroup of carbapenems. 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. Imipenem is rapidly degraded by the renal enzyme dehydropeptidase when administered alone, and is always co-administered with cilastatin to prevent this inactivation.
Affected Organisms
Enteric bacteria and other eubacteria
Biotransformation
Renal.
Absorption
Imipenem is not effectively absorbed from the gastrointestinal tract and therefore must be administered parenterally.
Half Life
1 hour
Protein Binding
20% binds to plasma proteins
References
•
Kattan JN, Villegas MV, Quinn JP: New developments in carbapenems. Clin Microbiol Infect. 2008 Dec;14(12):1102-11.
[Pubmed]
•
Pastel DA: Imipenem-cilastatin sodium, a broad-spectrum carbapenem antibiotic combination. Clin Pharm. 1986 Sep;5(9):719-36.
[Pubmed]
•
Clissold SP, Todd PA, Campoli-Richards DM: Imipenem/cilastatin. A review of its antibacterial activity, pharmacokinetic properties and therapeutic efficacy. Drugs. 1987 Mar;33(3):183-241.
[Pubmed]
•
Buckley MM, Brogden RN, Barradell LB, Goa KL: Imipenem/cilastatin. A reappraisal of its antibacterial activity, pharmacokinetic properties and therapeutic efficacy. Drugs. 1992 Sep;44(3):408-44.
[Pubmed]
•
Richerson MA, Ambrose PG, Quintiliani R, Nightingale CH: Formulary review of the carbapenems: comparison of imipenem/cilastatin and meropenem. Conn Med. 1998 Mar;62(3):165-9.
[Pubmed]
•
Birnbaum J, Kahan FM, Kropp H, MacDonald JS: Carbapenems, a new class of beta-lactam antibiotics. Discovery and development of imipenem/cilastatin. Am J Med. 1985 Jun 7;78(6A):3-21.
[Pubmed]
•
Hellinger WC, Brewer NS: Imipenem. Mayo Clin Proc. 1991 Oct;66(10):1074-81.
[Pubmed]
•
Kahan FM, Kropp H, Sundelof JG, Birnbaum J: Thienamycin: development of imipenen-cilastatin. J Antimicrob Chemother. 1983 Dec;12 Suppl D:1-35.
[Pubmed]
External Links
Molecular Spectra
No Data Available
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References
• Clissold SP, Todd PA, Campoli-Richards DM: Imipenem/cilastatin. A review of its antibacterial activity, pharmacokinetic properties and therapeutic efficacy. Drugs. 1987 Mar;33(3):183-241. Pubmed
• Kattan JN, Villegas MV, Quinn JP: New developments in carbapenems. Clin Microbiol Infect. 2008 Dec;14(12):1102-11. Pubmed
• Pastel DA: Imipenem-cilastatin sodium, a broad-spectrum carbapenem antibiotic combination. Clin Pharm. 1986 Sep;5(9):719-36. Pubmed
• Buckley MM, Brogden RN, Barradell LB, Goa KL: Imipenem/cilastatin. A reappraisal of its antibacterial activity, pharmacokinetic properties and therapeutic efficacy. Drugs. 1992 Sep;44(3):408-44. Pubmed
• Birnbaum J, Kahan FM, Kropp H, MacDonald JS: Carbapenems, a new class of beta-lactam antibiotics. Discovery and development of imipenem/cilastatin. Am J Med. 1985 Jun 7;78(6A):3-21. Pubmed
• Hellinger WC, Brewer NS: Imipenem. Mayo Clin Proc. 1991 Oct;66(10):1074-81. Pubmed
• Kahan FM, Kropp H, Sundelof JG, Birnbaum J: Thienamycin: development of imipenen-cilastatin. J Antimicrob Chemother. 1983 Dec;12 Suppl D:1-35. Pubmed
• Richerson MA, Ambrose PG, Quintiliani R, Nightingale CH: Formulary review of the carbapenems: comparison of imipenem/cilastatin and meropenem. Conn Med. 1998 Mar;62(3):165-9. Pubmed