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{{drugbox
__NOTOC__
| IUPAC_name = 3-[5-[(3-carboxyphenyl) carbamoyl]pyrrolidin-3-yl] sulfanyl-7-(1-hydroxyethyl)- 2-methyl- 6-oxo-5-azabicyclo[3.2.0] hept-3-ene-4-carboxylic acid
{{Ertapenem}}
| image = Ertapenem.svg
{{CMG}}; {{AE}} {{SS}}
| CAS_number = 153832-46-3
| ATC_prefix = J01
| ATC_suffix = DH03
| ATC_supplemental =
| PubChem = 150610
| DrugBank = APRD00952
| C = 22 | H = 25 | N = 3 | O = 7 | S = 1
| molecular_weight = 475.516 g/mol
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| pregnancy_category =
| legal_status =
| routes_of_administration =
}}
{{SI}}
{{EH}}


==Overview==
==Overview==
'''Ertapenem''' is a [[carbapenem]] [[antibiotic]] marketed by [[Merck & Co.|Merck]] as '''Invanz®'''.  It is structurally very similar to [[meropenem]] in that it possess a 1-β-methyl group.


==Indications==
Ertapenem is a [[carbapenem]] [[antibiotic]] marketed by [[Merck & Co.|Merck]] as INVANZ®.  It is structurally very similar to [[meropenem]] in that it possess a 1-β-methyl group.
Ertapenem has been designed to be effective against [[Gram negative]] [[bacterium|bacteria]].  It is not active against [[MRSA]], [[ampicillin]]-resistant [[Enterococcus|enterococci]], ''[[Pseudomonas aeruginosa]]'' or ''[[Acinetobacter]]'' species.  Ertapenem also has clinically useful activity against [[anaerobic bacteria]].


Ertapenem is marketed by Merck as a first-line treatment for community-acquired infections.  It should not be used as empirical treatment for hospital-acquired infections because of its lack of activity against ''Pseudomonas aeruginosa''.  In practice, it is reserved primarily for use against [[Extended spectrum beta-lactamase|ESBL]]-producing and high level AmpC-producing Gram-negative bacteria.
==Category==


==Dosage==
Carbapenem
Ertapenem is dosed as 1g given by [[intravenous]] injection over 30 minutes, or 1g diluted with 3.2ml of 1% [[lidocaine]] given [[intramuscular|intramuscularly]].  There is no [[Wiktionary:oral|oral]] preparation of ertapenem available.  Ertapenem cannot be mixed with glucose.


The marketing slogan for ertapenem is "The Power of One", because the dose is one [[gram]], once a day.
==US Brand Names==


==Pharmacology==
INVANZ<sup>®</sup>
Unlike [[imipenem]] and [[meropenem]], ertapenem is highly protein bound, which explains its long half life (4 hours).


Ertapenem is [[excretion|excreted]] primarily (80%) by the kidneys.  Metabolism by the liver is not clinically important and does not affect dosing.
==FDA Package Insert==


Patients on [[haemodialysis]] should be given ertapenem at least 6 hours before dialysis.  If it is given less than six hours before dialysis, then the patient should be given an additional dose of 150mg IV after dialysis.  Ideally, patients on haemodialysis should be given ertapenem immediately following dialysis.
'''  [[Ertapenem description|Description]]'''
'''| [[Ertapenem clinical pharmacology|Clinical Pharmacology]]'''
'''| [[Ertapenem microbiology|Microbiology]]'''
'''| [[Ertapenem indications and usage|Indications and Usage]]'''
'''| [[Ertapenem contraindications|Contraindications]]'''
'''| [[Ertapenem warnings and precautions|Warnings and Precautions]]'''
'''| [[Ertapenem adverse reactions|Adverse Reactions]]'''
'''| [[Ertapenem overdosage|Overdosage]]'''
'''| [[Ertapenem clinical studies|Clinical Studies]]'''
'''| [[Ertapenem dosage and administration|Dosage and Administration]]'''
'''| [[Ertapenem how supplied|How Supplied]]'''
'''| [[Ertapenem labels and packages|Labels and Packages]]'''


===Resistance===
==Mechanism of action==
Acquired resistance to ertapenem is usually mediated by up-regulation of efflux mechanisms and by the selection of porin-deficient mutants.  Organisms that produce a metallo-[[beta-lactamase|&beta;-lactamase]] are innately immune to ertapenem (as well as all [[carbapenem]]s) (Reference needed).


==Side effects==
Ertapenem has in vitro activity against Gram-positive and Gram-negative aerobic and anaerobic bacteria. The bactericidal activity of ertapenem results from the inhibition of cell wall synthesis and is mediated through ertapenem binding to [[penicillin binding proteins]] (PBPs). In [[Escherichia coli]], it has strong affinity toward [[Penicillin binding proteins|PBPs]] 1a, 1b, 2, 3, 4 and 5 with preference for [[Penicillin binding proteins|PBPs]] 2 and 3.
There are few [[Adverse drug reaction|adverse effect]]s of ertapenem. The only absolute contra-indication is a previous [[anaphylaxis|anaphylactic reaction]] to ertapenem or other β-lactam antibiotic.  There are no studies done in pregnant women, so the manufacturers cannot comment on its safety in pregnancy. In 2006, Ertapenem is now approved for pediatric use in certain infections. Ertapenem is not recommended for children under 3 months of age and children with meningitis.
 
Use of all antibiotics is associated with increased rates of [[antibiotic resistance|resistance]] (although carbapenem resistance is currently rare). There is particular worry that although ertapenem has no clinically useful activity against ''[[Pseudomonas aeruginosa]]'', widespread use of ertapenem could still lead to increased carbapenem resistance in ''Pseudomonas'' (Livermore et al. 2005).
 
Like many antibiotics, ''[[Clostridium difficile]]'' [[pseudomembranous colitis|colitis]] has been associated with its use.


==References==
==References==
*{{ cite journal
{{Reflist|2}}
| author=Livermore DM, Mushtaq S, Warner M
| title=Selectivity of ertapenem for ''Pseudomonas aeruginosa'' mutants cross-resistant to other carbapenems
| journal=J Antimicrob Chemother
| year=2005
| volume=55
| issue=3
| pages=306&ndash;311
| url=http://jac.oxfordjournals.org/cgi/content/abstract/55/3/306
}}


{{CephalosporinAntiBiotics}}
[[Category:Antibiotics]]
[[Category:Carbapenem antibiotics]]
[[Category:Wikinfect]]
{{SIB}}
{{WH}}
{{WS}}

Latest revision as of 22:17, 5 January 2014

Ertapenem
INVANZ® FDA Package Insert
Description
Clinical Pharmacology
Microbiology
Indications and Usage
Contraindications
Warnings and Precautions
Adverse Reactions
Overdosage
Clinical Studies
Dosage and Administration
How Supplied
Labels and Packages

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]; Associate Editor(s)-in-Chief: Sheng Shi, M.D. [2]

Overview

Ertapenem is a carbapenem antibiotic marketed by Merck as INVANZ®. It is structurally very similar to meropenem in that it possess a 1-β-methyl group.

Category

Carbapenem

US Brand Names

INVANZ®

FDA Package Insert

Description | Clinical Pharmacology | Microbiology | Indications and Usage | Contraindications | Warnings and Precautions | Adverse Reactions | Overdosage | Clinical Studies | Dosage and Administration | How Supplied | Labels and Packages

Mechanism of action

Ertapenem has in vitro activity against Gram-positive and Gram-negative aerobic and anaerobic bacteria. The bactericidal activity of ertapenem results from the inhibition of cell wall synthesis and is mediated through ertapenem binding to penicillin binding proteins (PBPs). In Escherichia coli, it has strong affinity toward PBPs 1a, 1b, 2, 3, 4 and 5 with preference for PBPs 2 and 3.

References

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