ERTAPENEM

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H25N3O7S
Molecular Weight	475.515
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@@H](O)[C@@H]1[C@H]2[C@@H](C)C(S[C@@H]3CN[C@@H](C3)C(=O)NC4=CC(=CC=C4)C(O)=O)=C(N2C1=O)C(O)=O

InChI

InChIKey=JUZNIMUFDBIJCM-ANEDZVCMSA-N

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

HIDE SMILES / InChI

Molecular Formula	C22H25N3O7S
Molecular Weight	475.515
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	6 / 6
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2001/21337lbl.pdf
Curator's Comment: description was created based on several sources, including: https://www.drugs.com/ppa/ertapenem.html | https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=33f3b99b-fa82-42e0-26bf-f49891ae3d22 | http://www.rxlist.com/invanz-drug.htm

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 Target	Pharmacology	Condition	Potency
Bacterial penicillin-binding protein 234 Target ID: CHEMBL2354204 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2001/21337lbl.pdf	Inhibitor 8504
Penicillin-binding protein 2 24 Target ID: P0AD65 Gene ID: 945240.0 Gene Symbol: mrdA Target Organism: Escherichia coli (strain K12) Sources: https://www.ncbi.nlm.nih.gov/pubmed/10223931	Inhibitor 8504
Peptidoglycan synthase FtsI 5 Target ID: P0AD68 Gene ID: 944799.0 Gene Symbol: ftsI Target Organism: Escherichia coli (strain K12) Sources: https://www.ncbi.nlm.nih.gov/pubmed/10223931	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Complicated intra-abdominal infections 20 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2001/21337lbl.pdf	Curative	Approved 8583	INVANZ Approved Use To reduce the development of drug-resistant bacteria and maintain the effectiveness of INVANZ® and other antibacterial drugs, INVANZ should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Treatment INVANZ is indicated for the treatment of adult patients and pediatric patients (3 months of age and older) with the following moderate to severe infections caused by susceptible isolates of the designated microorganisms [see Dosage and Administration (2) Launch Date 2001
Complicated skin and skin structure infections 11 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2001/21337lbl.pdf	Curative	Approved 8583	INVANZ Approved Use To reduce the development of drug-resistant bacteria and maintain the effectiveness of INVANZ® and other antibacterial drugs, INVANZ should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Treatment INVANZ is indicated for the treatment of adult patients and pediatric patients (3 months of age and older) with the following moderate to severe infections caused by susceptible isolates of the designated microorganisms [see Dosage and Administration (2) Launch Date 2001
Community acquired pneumonia 6 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2001/21337lbl.pdf	Curative	Approved 8583	INVANZ Approved Use To reduce the development of drug-resistant bacteria and maintain the effectiveness of INVANZ® and other antibacterial drugs, INVANZ should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Treatment INVANZ is indicated for the treatment of adult patients and pediatric patients (3 months of age and older) with the following moderate to severe infections caused by susceptible isolates of the designated microorganisms [see Dosage and Administration (2) Launch Date 2001
Complicated urinary tract infections including pyelonephritis 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2001/21337lbl.pdf	Curative	Approved 8583	INVANZ Approved Use To reduce the development of drug-resistant bacteria and maintain the effectiveness of INVANZ® and other antibacterial drugs, INVANZ should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Treatment INVANZ is indicated for the treatment of adult patients and pediatric patients (3 months of age and older) with the following moderate to severe infections caused by susceptible isolates of the designated microorganisms [see Dosage and Administration (2) Launch Date 2001
Acute pelvic infections including postpartum endomyometritis, septic abortion and post surgical gynecologic infections 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2001/21337lbl.pdf	Curative	Approved 8583	INVANZ Approved Use To reduce the development of drug-resistant bacteria and maintain the effectiveness of INVANZ® and other antibacterial drugs, INVANZ should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Treatment INVANZ is indicated for the treatment of adult patients and pediatric patients (3 months of age and older) with the following moderate to severe infections caused by susceptible isolates of the designated microorganisms [see Dosage and Administration (2) Launch Date 2001

C_max

Value	Dose	Analyte	Population
663.1 ug/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT02159859	1 g 3 times / week multiple, intravenous dose: 1 g route of administration: intravenous experiment type: multiple co-administered:	ERTAPENEM plasma	Homo sapiens population: unhealthy age: sex: food status:
70.6 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12709348	1 g single, intramuscular dose: 1 g route of administration: Intramuscular experiment type: SINGLE co-administered:	ERTAPENEM plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
75.7 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12709348	1 g 1 times / day multiple, intramuscular dose: 1 g route of administration: Intramuscular experiment type: MULTIPLE co-administered:	ERTAPENEM plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
155 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021337Orig1s021.pdf	1 g single, intravenous dose: 1 g route of administration: Intravenous experiment type: SINGLE co-administered:	ERTAPENEM plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
6225 ug*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT02159859	1 g 3 times / week multiple, intravenous dose: 1 g route of administration: intravenous experiment type: multiple co-administered:	ERTAPENEM plasma	Homo sapiens population: unhealthy age: sex: food status:
541.8 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12709348	1 g single, intramuscular dose: 1 g route of administration: Intramuscular experiment type: SINGLE co-administered:	ERTAPENEM plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
506.4 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12709348	1 g 1 times / day multiple, intramuscular dose: 1 g route of administration: Intramuscular experiment type: MULTIPLE co-administered:	ERTAPENEM plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
19.3 h Clinical Trial https://clinicaltrials.gov/ct2/show/NCT02159859	1 g 3 times / week multiple, intravenous dose: 1 g route of administration: intravenous experiment type: multiple co-administered:	ERTAPENEM plasma	Homo sapiens population: unhealthy age: sex: food status:
3.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12709348	1 g single, intramuscular dose: 1 g route of administration: Intramuscular experiment type: SINGLE co-administered:	ERTAPENEM plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
3.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12709348	1 g 1 times / day multiple, intramuscular dose: 1 g route of administration: Intramuscular experiment type: MULTIPLE co-administered:	ERTAPENEM plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
4 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021337Orig1s021.pdf	1 g single, intravenous dose: 1 g route of administration: Intravenous experiment type: SINGLE co-administered:	ERTAPENEM plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
10% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021337Orig1s021.pdf	1 g single, intravenous dose: 1 g route of administration: Intravenous experiment type: SINGLE co-administered:		ERTAPENEM plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
3 g 1 times / day steady, intravenous Highest studied dose Dose: 3 g, 1 times / day Route: intravenous Route: steady Dose: 3 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12384357	healthy, 18-49 years Health Status: healthy Age Group: 18-49 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/12384357	Sources: https://pubmed.ncbi.nlm.nih.gov/12384357
500 mg 1 times / day steady, intravenous Dose: 500 mg, 1 times / day Route: intravenous Route: steady Dose: 500 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/32487528	unhealthy, 59 years Health Status: unhealthy Age Group: 59 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/32487528	Disc. AE: Encephalopathy... AEs leading to discontinuation/dose reduction: Encephalopathy (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/32487528
1 g 1 times / day steady, intravenous Recommended Dose: 1 g, 1 times / day Route: intravenous Route: steady Dose: 1 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/27056357	unhealthy, 71 years Health Status: unhealthy Age Group: 71 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/27056357	Disc. AE: Hallucinations, Delirium... AEs leading to discontinuation/dose reduction: Hallucinations (1 patient) Delirium (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/27056357
1 g 1 times / day steady, intravenous\|intramuscular Recommended Dose: 1 g, 1 times / day Route: intravenous\|intramuscular Route: steady Dose: 1 g, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21337_Invanz_Medr_P4.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21337_Invanz_Medr_P4.pdf	Disc. AE: Rash, Confusion... AEs leading to discontinuation/dose reduction: Rash (1 patient) Confusion (1 patient) Seizure (1 patient) Thrombocytopenia (1 patient) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21337_Invanz_Medr_P4.pdf
1 g 3 times / day single, intravenous Overdose Dose: 1 g, 3 times / day Route: intravenous Route: single Dose: 1 g, 3 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/21337lbl.pdf	healthy Health Status: healthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/21337lbl.pdf	Other AEs: Diarrhea, Dizziness... Other AEs: Diarrhea (1 patient) Dizziness (1 patient) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/21337lbl.pdf

AEs

AE	Significance	Dose	Population
Encephalopathy	1 patient Disc. AE	500 mg 1 times / day steady, intravenous Dose: 500 mg, 1 times / day Route: intravenous Route: steady Dose: 500 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/32487528	unhealthy, 59 years Health Status: unhealthy Age Group: 59 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/32487528
Delirium	1 patient Disc. AE	1 g 1 times / day steady, intravenous Recommended Dose: 1 g, 1 times / day Route: intravenous Route: steady Dose: 1 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/27056357	unhealthy, 71 years Health Status: unhealthy Age Group: 71 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/27056357
Hallucinations	1 patient Disc. AE	1 g 1 times / day steady, intravenous Recommended Dose: 1 g, 1 times / day Route: intravenous Route: steady Dose: 1 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/27056357	unhealthy, 71 years Health Status: unhealthy Age Group: 71 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/27056357
Confusion	1 patient Disc. AE	1 g 1 times / day steady, intravenous\|intramuscular Recommended Dose: 1 g, 1 times / day Route: intravenous\|intramuscular Route: steady Dose: 1 g, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21337_Invanz_Medr_P4.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21337_Invanz_Medr_P4.pdf
Rash	1 patient Disc. AE	1 g 1 times / day steady, intravenous\|intramuscular Recommended Dose: 1 g, 1 times / day Route: intravenous\|intramuscular Route: steady Dose: 1 g, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21337_Invanz_Medr_P4.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21337_Invanz_Medr_P4.pdf
Seizure	1 patient Disc. AE	1 g 1 times / day steady, intravenous\|intramuscular Recommended Dose: 1 g, 1 times / day Route: intravenous\|intramuscular Route: steady Dose: 1 g, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21337_Invanz_Medr_P4.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21337_Invanz_Medr_P4.pdf
Thrombocytopenia	1 patient Disc. AE	1 g 1 times / day steady, intravenous\|intramuscular Recommended Dose: 1 g, 1 times / day Route: intravenous\|intramuscular Route: steady Dose: 1 g, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21337_Invanz_Medr_P4.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21337_Invanz_Medr_P4.pdf
Diarrhea	1 patient	1 g 3 times / day single, intravenous Overdose Dose: 1 g, 3 times / day Route: intravenous Route: single Dose: 1 g, 3 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/21337lbl.pdf	healthy Health Status: healthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/21337lbl.pdf
Dizziness	1 patient	1 g 3 times / day single, intravenous Overdose Dose: 1 g, 3 times / day Route: intravenous Route: single Dose: 1 g, 3 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/21337lbl.pdf	healthy Health Status: healthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/21337lbl.pdf

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946 inhibitor 2252	substrate 1193 inhibitor 2438	substrate 1388 inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2E1 1060 P-gp 1741 BSEP 550 MRP2 499 MRP3 246 MRP4 290	CYP1A2 1197 CYP2E1 729 P-gp 2052

Drug as perpetrator

Target	Modality	Activity
BSEP 554	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP3 326	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP4 345	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21337_Invanz_pharmr.pdf#page=9 \| https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21337_Invanz_biopharmr.pdf#PAGE=3 \| https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21337_Invanz_biopharmr.pdf#page=23 Page: (Pharm) 9, (ClinP) 3, 23	no [IC50 >500 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21337_Invanz_pharmr.pdf#page=9 \| https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21337_Invanz_biopharmr.pdf#PAGE=3 \| https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21337_Invanz_biopharmr.pdf#page=23 Page: (Pharm) 9, (ClinP) 3, 23	no [IC50 >500 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21337_Invanz_pharmr.pdf#page=9 \| https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21337_Invanz_biopharmr.pdf#PAGE=3 \| https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21337_Invanz_biopharmr.pdf#page=23 Page: (Pharm) 9, (ClinP) 3, 23	no [IC50 >500 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21337_Invanz_biopharmr.pdf#PAGE=3 Page: (ClinP) 3	no
CYP2E1 1146	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21337_Invanz_biopharmr.pdf#PAGE=3 Page: (ClinP) 3	no
P-gp 1932	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21337_Invanz_biopharmr.pdf#PAGE=3 \| https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21337_Invanz_biopharmr.pdf#PAGE=23 Page: (ClinP) 3, 23	no
MRP2 625	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	yes [IC50 56.2 uM]

Drug as victim

Target	Modality	Activity
CYP1A2 1197	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21337_Invanz_biopharmr.pdf#PAGE=3 Page: (ClinP) 3	no
CYP2C9 1193	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21337_Invanz_biopharmr.pdf#PAGE=3 Page: (ClinP) 3	no
CYP2D6 1388	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21337_Invanz_biopharmr.pdf#PAGE=3 Page: (ClinP) 3	no
CYP2E1 729	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21337_Invanz_biopharmr.pdf#PAGE=3 Page: (ClinP) 3	no
CYP3A4 1946	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21337_Invanz_biopharmr.pdf#PAGE=3 Page: (ClinP) 3	no
P-gp 2052	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21337_Invanz_biopharmr.pdf#PAGE=3 \| https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21337_Invanz_biopharmr.pdf#PAGE=23 Page: (ClinP) 3, 23	no

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:404903	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:404903
ChemicalBook	CB0722982	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB0722982
MolPort	MolPort-005-935-353	https://www.molport.com/shop/molecule-link/MolPort-005-935-353
ZINC	ZINC000003918453	http://zinc15.docking.org/substances/ZINC000003918453

PubMed

Title	Date	PubMed
Penetration of ertapenem into different pulmonary compartments of patients undergoing lung surgery.	2005-06	15901747
Activity of three {beta}-lactams (ertapenem, meropenem and ampicillin) against intraphagocytic Listeria monocytogenes and Staphylococcus aureus.	2005-06	15860552
Antibacterial susceptibility of extended-spectrum beta-lactamase-producing Klebsiella pneumoniae and Escherichia coli.	2005-05	15909461
Comparative activity of doripenem and three other carbapenems tested against Gram-negative bacilli with various beta-lactamase resistance mechanisms.	2005-05	15878447
Characterization of a new integron containing bla(VIM-1) and aac(6')-IIc in an Enterobacter cloacae clinical isolate from Greece.	2005-05	15761066
Gateways to clinical trials.	2005-04	15834452
In vitro activity of antimicrobial agents against extended-spectrum beta-lactamase-producing Escherichia coli and Klebsiella pneumoniae at a tertiary care center in Lebanon.	2005-04	15798666
Gateways to clinical trials.	2005-03	15834466
Selectivity of ertapenem for Pseudomonas aeruginosa mutants cross-resistant to other carbapenems.	2005-03	15705643
In vitro activity of ertapenem against bacteraemic pneumococci: report of a French multicentre study including 339 strains.	2005-03	15705639
Ertapenem: review of a new carbapenem.	2005-02	15757455
[Activity of ertapenem and 19 other antimicrobial agents against beta-lactam-resistant Streptococcus pneumoniae and Haemophilus influenzae respiratory tract isolates].	2005-02	15743576
Ertapenem-associated seizures in a peritoneal dialysis patient.	2005-02	15644469
Distribution and characteristics of Escherichia coli clonal group A.	2005-01	15705341
Pharmacodynamic modeling of carbapenems and fluoroquinolones against bacteria that produce extended-spectrum beta-lactamases.	2004-11	15639692
In vitro activity of ertapenem against selected respiratory pathogens.	2004-11	15472001
[Investigation of the in-vitro effectiveness of ertapenem against Pseudomonas aeruginosa strains isolated from intensive care unit patients].	2004-10	15700661
Gateways to clinical trials.	2004-10	15605126
Appropriate use of the carbapenems.	2004-10	15566108
Ertapanem therapy for community-acquired pneumonia in the elderly.	2004-10	15450074
Beta-lactam antibiotics: newer formulations and newer agents.	2004-09	15308278
Optimizing antimicrobial pharmacodynamics: dosage strategies for meropenem.	2004-08	15476901
Doripenem (S-4661), a novel carbapenem: comparative activity against contemporary pathogens including bactericidal action and preliminary in vitro methods evaluations.	2004-07	15190031
Activity of ertapenem against Neisseria gonorrhoeae.	2004-07	15175267
Gateways to clinical trials.	2004-06	15319815
Treatment of complicated community-acquired infections with ertapenem, the first Group 1 carbapenem. Introduction.	2004-06	15228047
Emerging issues in infective endocarditis.	2004-06	15207065
Ertapenem: a new opportunity for outpatient parenteral antimicrobial therapy.	2004-06	15150187
Safety and tolerability of ertapenem.	2004-06	15150186
Treatment of complicated urinary tract infection in adults: combined analysis of two randomized, double-blind, multicentre trials comparing ertapenem and ceftriaxone followed by appropriate oral therapy.	2004-06	15150185
Ertapenem versus ceftriaxone for the treatment of community-acquired pneumonia in adults: combined analysis of two multicentre randomized, double-blind studies.	2004-06	15150184
Treatment of polymicrobial infections: post hoc analysis of three trials comparing ertapenem and piperacillin-tazobactam.	2004-06	15150183
Complicated infections of skin and skin structures: when the infection is more than skin deep.	2004-06	15150182
Intra-abdominal infections: review of the bacteriology, antimicrobial susceptibility and the role of ertapenem in their therapy.	2004-06	15150181
Pharmacokinetics and pharmacodynamics of ertapenem: an overview for clinicians.	2004-06	15150180
In vitro activity of ertapenem: review of recent studies.	2004-06	15150179
Ertapenem: a Group 1 carbapenem with distinct antibacterial and pharmacological properties.	2004-06	15150178
Antimicrobial susceptibility of the pathogens of bacteraemia in the UK and Ireland 2001-2002: the BSAC Bacteraemia Resistance Surveillance Programme.	2004-06	15128723
In vitro susceptibility of recent antibiotic-resistant urinary pathogens to ertapenem and 12 other antibiotics.	2004-06	15117925
Exploring the effectiveness of tazobactam against ceftazidime resistant Escherichia coli: insights from the comparison between susceptibility testing and beta-lactamase inhibition.	2004-05-01	15109726
Comparative disposition of [14C]ertapenem, a novel carbapenem antibiotic, in rat, monkey and man.	2004-04	15268982
Gateways to clinical trials.	2004-04	15148527
New therapies for pneumococcal meningitis.	2004-04	15102588
Efficacy of ertapenem against methicillin-susceptible Staphylococcus aureus in complicated skin/skin structure infections: results of a double-blind clinical trial versus piperacillin-tazobactam.	2004-03	15164963
Gateways to clinical trials.	2004-03	15071612
Management of complicated appendicitis and comparison of outcome with other primary sites of intra-abdominal infection: results of a trial comparing ertapenem and piperacillin-tazobactam.	2004-02	15078001
Stability and compatibility of reconstituted ertapenem with commonly used i.v. infusion and coinfusion solutions.	2004-01-01	14725119
Newer treatment options for skin and soft tissue infections.	2004	15257625
Ertapenem as initial antimicrobial monotherapy for patients with chronic obstructive pulmonary disease hospitalized with typical community-acquired pneumonia.	2004	15219264
[Efficacy of invanz proven in the treatment of intra-abdominal infections in one of the largest studies yet conducted on surgical patients].	2003	15637790

Patents

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:15:35 GMT 2025` Edited by `admin` on `Mon Mar 31 18:15:35 GMT 2025`
Record UNII	G32F6EID2H
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ERTAPENEM

Official Name

English

ERTAPENEM [MI]

Preferred Name

English

(4R,5S,6S)-3-(((3S,5S)-5-((M-CARBOXYPHENYL)CARBAMOYL)-3-PYRROLIDINYL)THIO)-6-((1R)-1-HYDROXYETHYL)-4-METHYL-7-OXO-1-AZABICYCLO(3.2.0)HEPT-2-ENE-2-CARBOXYLIC ACID

Systematic Name

English

1-AZABICYCLO(3.2.0)HEPT-2-ENE-2-CARBOXYLIC ACID, 3-((5-(((3-CARBOXYPHENYL)AMINO)CARBONYL)-3-PYRROLIDINYL)THIO)-6-(1-HYDROXYETHYL)-4-METHYL-7-OXO-, (4R-(3(3S*,5S*), 4.ALPHA.,5.BETA.,6.BETA.(R*)))-

Systematic Name

English

Ertapenem [WHO-DD]

Common Name

English

ertapenem [INN]

Common Name

English

ERTAPENEM [VANDF]

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000011294