ERTAPENEM

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H25N3O7S
Molecular Weight	475.5167
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@]1([H])[C@]2([H])[C@@]([H])([C@@]([H])(C)O)C(=O)N2C(=C1S[C@@]3([H])C[C@@]([H])(C(=Nc4cccc(c4)C(=O)O)O)NC3)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

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 226 Target ID: CHEMBL2354204 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2001/21337lbl.pdf	Inhibitor 7701
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 7701
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 7701

Conditions

Condition	Modality	Highest Phase	Product
Complicated intra-abdominal infections 17 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2001/21337lbl.pdf	Curative	Approved 7997	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 1.00630082E12
Complicated skin and skin structure infections 9 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2001/21337lbl.pdf	Curative	Approved 7997	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 1.00630082E12
Community acquired pneumonia 6 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2001/21337lbl.pdf	Curative	Approved 7997	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 1.00630082E12
Complicated urinary tract infections including pyelonephritis 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2001/21337lbl.pdf	Curative	Approved 7997	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 1.00630082E12
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 7997	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 1.00630082E12

C_max

Value	Dose	Analyte	Population
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
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
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
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:

AUC

Value	Dose	Analyte	Population
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
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
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:

T_1/2

Value	Dose	Analyte	Population
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
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
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
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:

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 (starting) Dose: 500 mg, 1 times / day Route: intravenous Route: steady Dose: 500 mg, 1 times / day Co-administed with:: vancomycin(1250 mg intravenous loading dose followed by 500 mg intravenously once the following day) Sources: https://pubmed.ncbi.nlm.nih.gov/32487528	unhealthy, 59 years n = 1 Health Status: unhealthy Age Group: 59 years Sex: M Population Size: 1 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 Co-administed with:: daptomycin(1 g daily) Sources: https://pubmed.ncbi.nlm.nih.gov/27056357	unhealthy, 71 years n = 1 Health Status: unhealthy Condition: osteomyelitis Age Group: 71 years Sex: M Population Size: 1 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 Page: p. 184	unhealthy, adult n = 319 Health Status: unhealthy Age Group: adult Population Size: 319 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21337_Invanz_Medr_P4.pdf Page: p. 184	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 Page: p. 184
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 n = 1 Health Status: healthy Population Size: 1 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 (starting) Dose: 500 mg, 1 times / day Route: intravenous Route: steady Dose: 500 mg, 1 times / day Co-administed with:: vancomycin(1250 mg intravenous loading dose followed by 500 mg intravenously once the following day) Sources: https://pubmed.ncbi.nlm.nih.gov/32487528	unhealthy, 59 years n = 1 Health Status: unhealthy Age Group: 59 years Sex: M Population Size: 1 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 Co-administed with:: daptomycin(1 g daily) Sources: https://pubmed.ncbi.nlm.nih.gov/27056357	unhealthy, 71 years n = 1 Health Status: unhealthy Condition: osteomyelitis Age Group: 71 years Sex: M Population Size: 1 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 Co-administed with:: daptomycin(1 g daily) Sources: https://pubmed.ncbi.nlm.nih.gov/27056357	unhealthy, 71 years n = 1 Health Status: unhealthy Condition: osteomyelitis Age Group: 71 years Sex: M Population Size: 1 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 Page: p. 184	unhealthy, adult n = 319 Health Status: unhealthy Age Group: adult Population Size: 319 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21337_Invanz_Medr_P4.pdf Page: p. 184
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 Page: p. 184	unhealthy, adult n = 319 Health Status: unhealthy Age Group: adult Population Size: 319 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21337_Invanz_Medr_P4.pdf Page: p. 184
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 Page: p. 184	unhealthy, adult n = 319 Health Status: unhealthy Age Group: adult Population Size: 319 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21337_Invanz_Medr_P4.pdf Page: p. 184
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 Page: p. 184	unhealthy, adult n = 319 Health Status: unhealthy Age Group: adult Population Size: 319 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21337_Invanz_Medr_P4.pdf Page: p. 184
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 n = 1 Health Status: healthy Population Size: 1 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 n = 1 Health Status: healthy Population Size: 1 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/21337lbl.pdf

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1470 inhibitor 1172	substrate 865 inhibitor 1318	substrate 1038 inhibitor 1421

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1268 CYP2E1 761 P-gp 1089 BSEP 363 MRP2 341 MRP3 148 MRP4 194	CYP1A2 892 CYP2E1 567 P-gp 1223

Drug as perpetrator

Target	Modality	Activity
BSEP 364	inhibitor 2614 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP3 200	inhibitor 2614 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP4 226	inhibitor 2614 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
CYP1A2 1406	inhibitor 2614 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 1362	inhibitor 2614 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 1462	inhibitor 2614 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 1455	inhibitor 2614 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21337_Invanz_biopharmr.pdf#PAGE=3 Page: (ClinP) 3	no
CYP2E1 841	inhibitor 2614 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21337_Invanz_biopharmr.pdf#PAGE=3 Page: (ClinP) 3	no
P-gp 1255	inhibitor 2614 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 421	inhibitor 2614 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	yes [IC50 56.2 uM]

Drug as victim

Target	Modality	Activity
CYP1A2 892	substrate 2752 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21337_Invanz_biopharmr.pdf#PAGE=3 Page: (ClinP) 3	no
CYP2C9 865	substrate 2752 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21337_Invanz_biopharmr.pdf#PAGE=3 Page: (ClinP) 3	no
CYP2D6 1038	substrate 2752 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21337_Invanz_biopharmr.pdf#PAGE=3 Page: (ClinP) 3	no
CYP2E1 567	substrate 2752 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21337_Invanz_biopharmr.pdf#PAGE=3 Page: (ClinP) 3	no
CYP3A4 1470	substrate 2752 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21337_Invanz_biopharmr.pdf#PAGE=3 Page: (ClinP) 3	no
P-gp 1223	substrate 2752 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
Ertapenem. A review of its microbiologic, pharmacokinetic and clinical aspects.	2002 Mar	12532175
A prospective, randomized, double-blind multicenter comparison of parenteral ertapenem and ceftriaxone for the treatment of hospitalized adults with community-acquired pneumonia.	2002 Nov	12501873
Comparative in vitro activity of ertapenem against bacterial pathogens isolated from patients with lower respiratory tract infections.	2002 Nov	12445016
Modified high-performance liquid chromatographic method for the determination of ertapenem in human urine: enhanced selectivity and automation.	2002 Nov 5	12361748
In vitro activity of ertapenem against common clinical isolates in relation to human pharmacokinetics.	2002 Oct	12462428
Ertapenem (MK-0826), a new carbapenem: comparative in vitro activity against clinically significant anaerobes.	2002 Oct	12458126
Ertapenem monotherapy versus combination therapy with ceftriaxone plus metronidazole for treatment of complicated intra-abdominal infections in adults.	2002 Sep	12385694
[Efficacy of invanz proven in the treatment of intra-abdominal infections in one of the largest studies yet conducted on surgical patients].	2003	15637790
Ertapenem: a review of its use in the management of bacterial infections.	2003	12921489
[Carbapenem antibiotic ertapenem in the treatment of extrahospital intraabdominal infections].	2003	12744138
Mutation prevention concentration of ceftriaxone, meropenem, imipenem, and ertapenem against three strains of Streptococcus pneumoniae.	2003 Apr	12729997
NmcA carbapenem-hydrolyzing enzyme in Enterobacter cloacae in North America.	2003 Aug	12967501
Resistance in Enterobacteriaceae: results of a multicenter surveillance study, 1995-2000.	2003 Aug	12940583
Assay methodology for the quantitation of unbound ertapenem, a new carbapenem antibiotic, in human plasma.	2003 Jan 5	12450519
[New Beta-lactam agent in the treatment of intra-abdominal sepsis: double blind and randomized stage III study of ertapenem versus piperacillin/tazobactam].	2003 Jul-Sep	14532920
Efficacy of ertapenem in the treatment of serious infections caused by Enterobacteriaceae: analysis of pooled clinical trial data.	2003 May	12697633
In vitro activity of ertapenem against anaerobes isolated from the respiratory tract.	2003 Oct	14568599
Properties and potential of ertapenem.	2003 Sep	12917243
Gateways to clinical trials.	2004 Apr	15148527
Optimizing antimicrobial pharmacodynamics: dosage strategies for meropenem.	2004 Aug	15476901
Stability and compatibility of reconstituted ertapenem with commonly used i.v. infusion and coinfusion solutions.	2004 Jan 1	14725119
Column-switching technique for the sensitive determination of ertapenem in human cerebrospinal fluid using liquid chromatography and ultraviolet absorbance detection.	2004 Jan 5	14659431
Doripenem (S-4661), a novel carbapenem: comparative activity against contemporary pathogens including bactericidal action and preliminary in vitro methods evaluations.	2004 Jul	15190031
Activity of ertapenem against Neisseria gonorrhoeae.	2004 Jul	15175267
Gateways to clinical trials.	2004 Jun	15319815
Emerging issues in infective endocarditis.	2004 Jun	15207065
Ertapenem: a new opportunity for outpatient parenteral antimicrobial therapy.	2004 Jun	15150187
Safety and tolerability of ertapenem.	2004 Jun	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 Jun	15150185
Ertapenem versus ceftriaxone for the treatment of community-acquired pneumonia in adults: combined analysis of two multicentre randomized, double-blind studies.	2004 Jun	15150184
Complicated infections of skin and skin structures: when the infection is more than skin deep.	2004 Jun	15150182
Intra-abdominal infections: review of the bacteriology, antimicrobial susceptibility and the role of ertapenem in their therapy.	2004 Jun	15150181
Pharmacokinetics and pharmacodynamics of ertapenem: an overview for clinicians.	2004 Jun	15150180
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 Mar	15164963
Pharmacodynamic modeling of carbapenems and fluoroquinolones against bacteria that produce extended-spectrum beta-lactamases.	2004 Nov	15639692
In vitro activity of ertapenem against selected respiratory pathogens.	2004 Nov	15472001
Gateways to clinical trials.	2004 Oct	15605126
Appropriate use of the carbapenems.	2004 Oct	15566108
Ertapanem therapy for community-acquired pneumonia in the elderly.	2004 Oct	15450074
Beta-lactam antibiotics: newer formulations and newer agents.	2004 Sep	15308278
Gateways to clinical trials.	2005 Apr	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 Apr	15798666
Ertapenem-associated seizures in a peritoneal dialysis patient.	2005 Feb	15644469
Penetration of ertapenem into different pulmonary compartments of patients undergoing lung surgery.	2005 Jun	15901747
Activity of three {beta}-lactams (ertapenem, meropenem and ampicillin) against intraphagocytic Listeria monocytogenes and Staphylococcus aureus.	2005 Jun	15860552
Gateways to clinical trials.	2005 Mar	15834466
Selectivity of ertapenem for Pseudomonas aeruginosa mutants cross-resistant to other carbapenems.	2005 Mar	15705643
Antibacterial susceptibility of extended-spectrum beta-lactamase-producing Klebsiella pneumoniae and Escherichia coli.	2005 May	15909461
Comparative activity of doripenem and three other carbapenems tested against Gram-negative bacilli with various beta-lactamase resistance mechanisms.	2005 May	15878447
Characterization of a new integron containing bla(VIM-1) and aac(6')-IIc in an Enterobacter cloacae clinical isolate from Greece.	2005 May	15761066

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.

Name

Type

Language

ERTAPENEM

Official 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 [MI]

Common Name

English

ERTAPENEM [INN]

Common Name

English

ERTAPENEM [VANDF]

Common Name

English

ERTAPENEM [WHO-DD]

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000011294