Imipenem


Imipenem
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
AHFS/Drugs.com International Drug Names
MedlinePlus a686013
Pregnancy cat. C(US)
Legal status  ?
Routes IM, IV
Pharmacokinetic data
Metabolism Renal
Half-life 60 minutes
Identifiers
CAS number 74431-23-5 YesY
ATC code J01DH51
PubChem CID 5282372
DrugBank DB01598
ChemSpider 4445535 YesY
UNII 71OTZ9ZE0A YesY
KEGG D00206 YesY
ChEBI CHEBI:51799 YesY
ChEMBL CHEMBL43708 YesY
Chemical data
Formula C12H17N3O4S 
Mol. mass 299.347 g/mol
SMILES eMolecules & PubChem
 YesY(what is this?)  (verify)

Imipenem 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]

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.[citation needed]

Coadministration with cilastatin

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

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

  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. http://aac.asm.org/cgi/pmidlookup?view=long&pmid=6931548. 

Further reading


Wikimedia Foundation. 2010.

Look at other dictionaries:

  • Imipenem — Nombre (IUPAC) sistemático (5R,6S) 3 [2 (aminomethylideneamino)ethylsulfanyl] 6 (1 hydroxyethyl) 7 oxo 1 azabicyclo[3.2.0]hept 2 ene 2 carboxy …   Wikipedia Español

  • Imipenem — Imipénem Imipénem Général No CAS …   Wikipédia en Français

  • Imipénem — Général No CAS …   Wikipédia en Français

  • Imipenem — См. Имипенем (Источник: «Словарь терминов микробиологии») …   Словарь микробиологии

  • imipenem — antibiótico beta lactámico de amplio espectro. Para prolongar su efecto antibacteriano en el organismo se asocia a la cilastatina, un inhibidor de su metabolismo Diccionario ilustrado de Términos Médicos.. Alvaro Galiano. 2010 …   Diccionario médico

  • Imipenem — Strukturformel Allgemeines Freiname Imipenem Andere Namen …   Deutsch Wikipedia

  • Imipenem — ИМИПЕНЕМ ( Imiреnеm ). N Формимидоилтиенамицин, или (5S,6R) 3 [[2 (формимидоиламиноэтил)тио] 6 [R] 1 гидроксиэтил] 7 оксо 1 азабицикло[3.2.0] гепт 2 ен 2 карбоновая кислота. Синоним: Imiреmidе. Имипен является антибиотиком широкого спектра… …   Словарь медицинских препаратов

  • imipenem — noun A broad spectrum beta lactam antibiotic …   Wiktionary

  • imipenem — A thienamycin antibiotic with broad spectrum activity used, in combination with cilastin, to treat a variety of infections. * * * im·i·pen·em .im ə pen əm n a semisynthetic beta lactam C12H17N3O4S·H2O that is derived from an antibiotic produced… …   Medical dictionary

  • imipenem — An antibiotic drug used to treat severe or very resistant infection. It belongs to the family of drugs called carbapenems …   English dictionary of cancer terms


Share the article and excerpts

Direct link
Do a right-click on the link above
and select “Copy Link”

We are using cookies for the best presentation of our site. Continuing to use this site, you agree with this.