| InChI | InChI=1S/C22H25N3O7S/c1-9-16-15(10(2)26)20(28)25(16)17(22(31)32)18(9)33-13-7-14(23-8-13)19(27)24-12-5-3-4-11(6-12)21(29)30/h3-6,9-10,13-16,23,26H,7-8H2,1-2H3,(H,24,27)(H,29,30)(H,31,32)/t9-,10-,13+,14+,15-,16-/m1/s1 |
| Reference | 1. J Antimicrob Chemother. 2004 Jun;53 Suppl 2:ii75-81.
<br/>
Safety and tolerability of ertapenem.
<br/>
Teppler H(1), Gesser RM, Friedland IR, Woods GL, Meibohm A, Herman G, Mistry G,
Isaacs R.
<br/>
Author information: <br/>
(1)Merck Research Laboratories, West Point, PA 19486, USA.
<br/>
Ertapenem is a Group 1 carbapenem that was licensed in the USA in November 2001
and in Europe in April 2002. Its safety profile has been assessed in 240 healthy
volunteers participating in 12 clinical pharmacology studies and in 2046 patients
enrolled in five Phase IIa and eight Phase IIb/III clinical trials. The most
common drug-related adverse events (AEs) reported in trials comparing ertapenem
and piperacillin-tazobactam and in trials comparing ertapenem and ceftriaxone
were: diarrhoea (ertapenem versus piperacillin-tazobactam 5.0% versus 7.0%;
ertapenem versus ceftriaxone 5.6% versus 5.9%); infused vein complications
(ertapenem versus piperacillin-tazobactam 4.5% versus 7.9%; ertapenem versus
ceftriaxone 3.2% versus 4.6%); nausea (ertapenem versus piperacillin-tazobactam
2.5% versus 3.4%; ertapenem versus ceftriaxone 3.4% versus 3.3%); and elevations
in alanine aminotransferase levels (ertapenem versus piperacillin-tazobactam 8.8%
versus 7.3%; ertapenem versus ceftriaxone 8.3% versus 6.9%). Most
ertapenem-related AEs were reported as mild-to-moderate in intensity. Ertapenem
was not associated with prolongation of the QTc interval. Local reactions of
moderate-to-severe intensity at the infusion site were infrequent and occurred
with similar frequency in the ertapenem and comparator treatment groups. No
overall differences in safety were observed between elderly (aged > or = 65 years
and > or = 75 years) and younger patients. Ertapenem, 1 g once a day given by
intravenous infusion or intramuscular injection, was generally well tolerated and
had overall safety and tolerability profiles similar to those of
piperacillin-tazobactam and ceftriaxone.
<br/><br/>
2. J Antimicrob Chemother. 2004 Jun;53 Suppl 2:ii11-21.
<br/>
In vitro activity of ertapenem: review of recent studies.
<br/>
Wexler HM(1).
<br/>
Author information: <br/>
(1)GLA VA Healthcare System and UCLA School of Medicine, Los Angeles, CA, USA.
[email protected]
<br/>
Ertapenem is a long-acting, 1beta-methyl parenteral Group 1 carbapenem antibiotic
that has a broad antibacterial spectrum and once-a-day dosing supported by
clinical studies. Ertapenem is active against both Gram-positive and
Gram-negative bacteria, including Enterobacteriaceae, Streptococcus pneumoniae
and most species of anaerobic bacteria. Isolates from a variety of infections
(intra-abdominal infections, skin/soft-tissue infections, community-acquired
pneumonia, pelvic infections and urinary tract infections) are inhibited by
ertapenem. It has restricted activity against nosocomial pathogens such as
Pseudomonas aeruginosa, Acinetobacter species, methicillin-resistant
staphylococci and enterococci. Ertapenem has potent activity against the majority
of anaerobic isolates from intra-abdominal infections, and against most of the
aerobes isolated from these infections, with the exceptions of the nosocomial
pathogens mentioned above. MIC(90)s for most species of Enterobacteriaceae were
<1 mg/L, significantly lower than those of imipenem. MIC(90)s for most
Bacteroides fragilis group isolates ranged from 1 to 4 mg/L, and MIC(90)s were
species specific for Clostridium, ranging from 0.06 mg/L for Clostridium
perfringens to 4 mg/L for Clostridium clostridioforme. Ertapenem was equivalent
to or better than piperacillin-tazobactam in activity against most anaerobic
species isolated from these infections, and was more potent than
piperacillin-tazobactam and ceftriaxone against the most common skin pathogens
(e.g. methicillin-susceptible Staphylococcus aureus). Ertapenem was highly active
against most of the pathogens isolated from patients with community-acquired
pneumonia, except for isolates of methicillin-resistant S. aureus (which are
infrequent causes of community-acquired infection); these isolates were also
resistant to ceftriaxone. Resistance to ertapenem is most commonly attributable
to a variety of mechanisms including alterations in penicillin-binding proteins
in Gram-positive organisms, and combinations of potent metallo-beta-lactamase
enzymes, porin protein defects and efflux pumps in Gram-negative organisms.
<br/><br/>
3. Drugs Today (Barc). 2002 Mar;38(3):195-213.
<br/>
Ertapenem. A review of its microbiologic, pharmacokinetic and clinical aspects.
<br/>
Cunha BA(1).
<br/>
Author information: <br/>
(1)Infectious Disease Division, Winthrop-University Hospital, Mineola, New York
11501, USA.
<br/>
Ertapenem sodium (trade name Invanz, also designated as MK-0826, MK-826 and
L-749345), manufactured by Merck & Co., Inc. is a structurally unique parenteral
1 beta-methyl carbapenem. It has a broad spectrum of antimicrobial activity,
including common community-acquired Gram-positive and Gram-negative aerobic and
anaerobic pathogens, and restricted activity against nosocomial pathogens such as
Pseudomonas aeruginosa, Acinetobacter species, methicillin-resistant
staphylococci and enterococci. Ertapenem demonstrates excellent activity against
cephalosporin-resistant enteric organisms producing extended spectrum
beta-lactamases (ESBLs) or AmpC beta-lactamases and excellent activity against
penicillin-resistant Streptococcus pneumoniae. Its high level of protein binding
and serum half-life of 4 h allows it to be dosed once daily. Ertapenem may be
administered intravenously or intramuscularly and has an excellent adverse
reaction and tolerability profile. Invanz was approved by the United States Food
and Drug Administration in November 2001 for the treatment of adult patients with
moderate to severe infections caused by designated strains of susceptible
microorganisms. The infections include complicated intraabdominal infections,
complicated skin and skin structure infections, community-acquired pneumonia,
complicated urinary tract infections including pyelonephritis and acute pelvic
infections including postpartum endomyometritis, septic abortion and post
surgical gynecologic infections. Invanz has also been approved in Mexico, Brazil
and New Zealand.
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