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 Y
ATC code	J01DH51
PubChem	CID 5282372
DrugBank	DB01598
ChemSpider	4445535 Y
UNII	71OTZ9ZE0A Y
KEGG	D00206 Y
ChEBI	CHEBI:51799 Y
ChEMBL	CHEMBL43708 Y
Chemical data
Formula	C12H17N3O4S
Mol. mass	299.347 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C12H17N3O4S.H2O/c1-6(16)9-7-4-8(20-3-2-14-5-13)10(12(18)19)15(7)11(9)17;/h5-7,9,16H,2-4H2,1H3,(H2,13,14)(H,18,19);1H2/t6-,7-,9-;/m1./s1 Y Key:GSOSVVULSKVSLQ-JJVRHELESA-N Y
Y(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]}

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

Main article: Imipenem/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

• Clissold, SP; Todd, PA; Campoli-Richards, DM (1987). "Imipenem/cilastatin. A review of its antibacterial activity, pharmacokinetic properties and therapeutic efficacy". Drugs 33 (3): 183–241. PMID 3552595. http://adisonline.com/drugs/Abstract/1987/33030/Imipenem_Cilastatin__A_Review_of_its_Antibacterial.1.aspx. 
• Buckley, MM; Brogden, RN; Barradell, LB; Goa, KL (1992). "Imipenem/cilastatin. A reappraisal of its antibacterial activity, pharmacokinetic properties and therapeutic efficacy". Drugs 44 (3): 408–44. PMID 1382937. http://adisonline.com/drugs/Abstract/1992/44030/Imipenem_Cilastatin__A_Reappraisal_of_its.8.aspx.