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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H23N3O7S.2Na
Molecular Weight 519.478
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ERTAPENEM DISODIUM

SMILES

[Na+].[Na+].[H][C@]12[C@@H](C)C(S[C@@H]3CN[C@@H](C3)C(=O)NC4=CC=CC(=C4)C([O-])=O)=C(N1C(=O)[C@]2([H])[C@@H](C)O)C([O-])=O

InChI

InChIKey=KMVRATCHVMUJHM-SHZCTIMHSA-L
InChI=1S/C22H25N3O7S.2Na/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);;/q;2*+1/p-2/t9-,10-,13+,14+,15-,16-;;/m1../s1

HIDE SMILES / InChI

Description

Ertapenem is a carbapenem antibiotic marketed by Merck as Invanz. 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. Ertapenem has been designed to be effective against Gram-negative and Gram-positive bacteria. The most common drug-related adverse experiences in patients treated with INVANZ, including those who were switched to therapy with an oral antimicrobial, were diarrhea (5.5%), infused vein complication (3.7%), nausea (3.1%), headache (2.2%), vaginitis in females (2.1%), phlebitis/thrombophlebitis (1.3%), and vomiting (1.1%). The coadministration with probenecid to extend the half-life of ertapenem is not recommended.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
INVANZ
Curative
INVANZ
Curative
INVANZ
Curative
INVANZ
Curative
INVANZ

Cmax

ValueDoseCo-administeredAnalytePopulation
75.7 μg/mL
1 g 1 times / day multiple, intramuscular
ERTAPENEM plasma
Homo sapiens
70.6 μg/mL
1 g single, intramuscular
ERTAPENEM plasma
Homo sapiens
155 μg/mL
1 g single, intravenous
ERTAPENEM plasma
Homo sapiens
663.1 ug/mL
1 g 3 times / week multiple, intravenous
ERTAPENEM plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
506.4 μg × h/mL
1 g 1 times / day multiple, intramuscular
ERTAPENEM plasma
Homo sapiens
541.8 μg × h/mL
1 g single, intramuscular
ERTAPENEM plasma
Homo sapiens
6225 ug*h/mL
1 g 3 times / week multiple, intravenous
ERTAPENEM plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
3.5 h
1 g 1 times / day multiple, intramuscular
ERTAPENEM plasma
Homo sapiens
3.8 h
1 g single, intramuscular
ERTAPENEM plasma
Homo sapiens
4 h
1 g single, intravenous
ERTAPENEM plasma
Homo sapiens
19.3 h
1 g 3 times / week multiple, intravenous
ERTAPENEM plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
10%
1 g single, intravenous
ERTAPENEM plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
1 g given once a day. Intravenous infusion for up to 14 days or intramuscular injection for up to 7 days.
Route of Administration: Other
In Vitro Use Guide
The MICs of ertapenem are MIC(50) = 0.032 μg/ml; MIC(90) = 0.064 μg/ml in vitro activity of ertapenem against N.gonorrhoeae isolates.