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Namespace Prefixes

PrefixIRI
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Statements

Subject Item
n2:DB01598
rdf:type
n3:Drug
n3: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]
n3:generalReferences
# Kattan JN, Villegas MV, Quinn JP: New developments in carbapenems. Clin Microbiol Infect. 2008 Dec;14(12):1102-11. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/19076841 # Pastel DA: Imipenem-cilastatin sodium, a broad-spectrum carbapenem antibiotic combination. Clin Pharm. 1986 Sep;5(9):719-36. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/3530614 # 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":http://www.ncbi.nlm.nih.gov/pubmed/3552595 # 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":http://www.ncbi.nlm.nih.gov/pubmed/1382937 # 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":http://www.ncbi.nlm.nih.gov/pubmed/9573653 # 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":http://www.ncbi.nlm.nih.gov/pubmed/3859213 # Hellinger WC, Brewer NS: Imipenem. Mayo Clin Proc. 1991 Oct;66(10):1074-81. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/1921491 # Kahan FM, Kropp H, Sundelof JG, Birnbaum J: Thienamycin: development of imipenen-cilastatin. J Antimicrob Chemother. 1983 Dec;12 Suppl D:1-35. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/6365872
n3:group
approved
n3:halfLife
1 hour
n3:indication
For the treatment of bacterial infections caused by susceptible bacteria.
owl:sameAs
n8:DB01598 n9:DB01598
dcterms:title
Imipenem
adms:identifier
n13:Imipenem n15:104838 n16:46505744 n17:471744 n18:PA449968 n19:94631 n20:DB01598
n3:mechanismOfAction
Imipenem acts as an antimicrobial through the inhibition of cell wall synthesis of various gram-positive and gram-negative bacteria. This inhibition of cell wall synthesis in gram-negative bateria is attained by binding to pencillin binding proteins (PBPs). In E. coli and selected strains of P. aeruginosa, imipenem has shown to have the highest affinity to PBP-2, PBP-1a, and PBP-1b. This preferential binding to PBP-2 and PBP-1b results in the direct conversion of the individual cell to a spheroblast, which leads to rapid cell lysis and death without filament formation.
n3:packager
n10:271B5A4F-363D-11E5-9242-09173F13E4C5 n10:271B5A50-363D-11E5-9242-09173F13E4C5
n3:synonym
IMP Imipenem Imipemide (5R,6S)-3-(2-Formimidoylamino-ethylsulfanyl)-6-((R)-1-hydroxy-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid N-formimidoylthienamycin (5R,6S)-3-((2-(Formimidoylamino)ethyl)thio)-6-((R)-1-hydroxyethyl)-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid N-Formimidoyl thienamycin Imipenem, n-formimidoyl thienamycin Imipenemum (5R,6S)-6-((R)-1-Hydroxyethyl)-3-(2-(iminomethylamino)ethylthio)-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carbonsaeure Imipenem anhydrous
n3:mixture
n11:271B5A4E-363D-11E5-9242-09173F13E4C5
n3:proteinBinding
20% binds to plasma proteins
n3:synthesisReference
Maurizio Zenoni, "Imipenem production process." U.S. Patent US20020095034, issued July 18, 2002.
n5:hasConcept
n6:M0023689
n3:IUPAC-Name
n4:271B5A55-363D-11E5-9242-09173F13E4C5
n3:InChI
n4:271B5A5B-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n4:271B5A5A-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n4:271B5A57-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n4:271B5A58-363D-11E5-9242-09173F13E4C5
n3:SMILES
n4:271B5A59-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n4:271B5A6B-363D-11E5-9242-09173F13E4C5 n4:271B5A53-363D-11E5-9242-09173F13E4C5
n3:logP
n4:271B5A54-363D-11E5-9242-09173F13E4C5 n4:271B5A51-363D-11E5-9242-09173F13E4C5
n3:logS
n4:271B5A52-363D-11E5-9242-09173F13E4C5
n3:pKa
n4:271B5A6C-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Acceptor-Count
n4:271B5A61-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n4:271B5A62-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n4:271B5A5C-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n4:271B5A5D-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n4:271B5A5F-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n4:271B5A5E-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n4:271B5A60-363D-11E5-9242-09173F13E4C5
n3:absorption
Imipenem is not effectively absorbed from the gastrointestinal tract and therefore must be administered parenterally.
n3:affectedOrganism
Enteric bacteria and other eubacteria
n3:casRegistryNumber
74431-23-5
n3:category
n3:Bioavailability
n4:271B5A67-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n4:271B5A69-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n4:271B5A6A-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n4:271B5A66-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n4:271B5A65-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n4:271B5A68-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n4:271B5A56-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-acidic-
n4:271B5A63-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n4:271B5A64-363D-11E5-9242-09173F13E4C5