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

[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=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 233 Target ID: CHEMBL2354204 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2001/21337lbl.pdf	Inhibitor 8297
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 8297
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 8297

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 8429	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 8429	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 8429	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 8429	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 8429	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
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 1737 inhibitor 1587	substrate 1037 inhibitor 1767	substrate 1217 inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1524 CYP2E1 882 P-gp 1461 BSEP 402 MRP2 383 MRP3 157 MRP4 204	CYP1A2 1054 CYP2E1 667 P-gp 1537

Drug as perpetrator

Target	Modality	Activity
BSEP 403	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP3 207	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP4 238	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
CYP1A2 1692	inhibitor 3277 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 1819	inhibitor 3277 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 1925	inhibitor 3277 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 1891	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21337_Invanz_biopharmr.pdf#PAGE=3 Page: (ClinP) 3	no
CYP2E1 970	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21337_Invanz_biopharmr.pdf#PAGE=3 Page: (ClinP) 3	no
P-gp 1650	inhibitor 3277 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 475	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	yes [IC50 56.2 uM]

Drug as victim

Target	Modality	Activity
CYP1A2 1054	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21337_Invanz_biopharmr.pdf#PAGE=3 Page: (ClinP) 3	no
CYP2C9 1037	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21337_Invanz_biopharmr.pdf#PAGE=3 Page: (ClinP) 3	no
CYP2D6 1217	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21337_Invanz_biopharmr.pdf#PAGE=3 Page: (ClinP) 3	no
CYP2E1 667	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21337_Invanz_biopharmr.pdf#PAGE=3 Page: (ClinP) 3	no
CYP3A4 1737	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21337_Invanz_biopharmr.pdf#PAGE=3 Page: (ClinP) 3	no
P-gp 1537	substrate 3367 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
In vitro evaluation of ertapenem (MK-0826), a long-acting carbapenem, tested against selected resistant strains.	2001 Aug	11589478
Gateways to Clinical Trials.	2002 Apr	12087878
In vitro activity of ertapenem (MK-0826) against multi-drug resistant Streptococcus pneumoniae compared with 13 other antimicrobials.	2002 Aug	12297363
Gateways to clinical trials.	2002 Jan-Feb	11980386
In vitro activity of ertapenem against bacterial isolates from cancer patients.	2002 Jul	12106955
Broad resistance due to plasmid-mediated AmpC beta-lactamases in clinical isolates of Escherichia coli.	2002 Jul 15	12087519
Comparative in-vitro activities of ertapenem against aerobic bacterial pathogens isolated from patients with complicated intra-abdominal infections.	2002 Jun	12120874
Comparative in vitro activities of ertapenem against aerobic and facultative bacterial pathogens from patients with complicated skin and skin structure infections.	2002 Jun	12088620
Ertapenem once daily versus piperacillin-tazobactam 4 times per day for treatment of complicated skin and skin-structure infections in adults: results of a prospective, randomized, double-blind multicenter study.	2002 Jun 1	12015692
Safety and local tolerability of intramuscularly administered ertapenem diluted in lidocaine: a prospective, randomized, double-blind study versus intramuscular ceftriaxone.	2002 Mar	11952026
Ertapenem (Invanz)--a new parenteral carbapenem.	2002 Mar 18	11941264
Use of surrogate antimicrobial agents to predict susceptibility to ertapenem.	2002 May	12052630
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
Comparative in vitro activities of ertapenem against bacterial pathogens from patients with acute pelvic infection.	2002 Nov	12407133
Modified high-performance liquid chromatographic method for the determination of ertapenem in human urine: enhanced selectivity and automation.	2002 Nov 5	12361748
Ertapenem monotherapy versus combination therapy with ceftriaxone plus metronidazole for treatment of complicated intra-abdominal infections in adults.	2002 Sep	12385694
General microbiology and in vitro susceptibility of anaerobes isolated from complicated skin and skin-structure infections in patients enrolled in a comparative trial of ertapenem versus piperacillin-tazobactam.	2002 Sep 1	12173120
Intra-abdominal anaerobic infections: bacteriology and therapeutic potential of newer antimicrobial carbapenem, fluoroquinolone, and desfluoroquinolone therapeutic agents.	2002 Sep 1	12173118
Ertapenem versus piperacillin-tazobactam for treatment of mixed anaerobic complicated intra-abdominal, complicated skin and skin structure, and acute pelvic infections.	2002 Winter	12697078
Resistance in Enterobacteriaceae: results of a multicenter surveillance study, 1995-2000.	2003 Aug	12940583
New drugs 2003, part I.	2003 Feb	12582288
Ertapenem versus piperacillin/tazobactam in the treatment of complicated intraabdominal infections: results of a double-blind, randomized comparative phase III trial.	2003 Feb	12560782
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
[Comparative in vitro activity of ertapenem against aerobic and anaerobic bacteria].	2003 Jun	12973459
Ertapenem therapy for community-acquired pneumonia in the elderly.	2003 Nov	14687380
New therapies for pneumococcal meningitis.	2004 Apr	15102588
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 Feb	15078001
Stability and compatibility of reconstituted ertapenem with commonly used i.v. infusion and coinfusion solutions.	2004 Jan 1	14725119
Intra-abdominal infections: review of the bacteriology, antimicrobial susceptibility and the role of ertapenem in their therapy.	2004 Jun	15150181
In vitro susceptibility of recent antibiotic-resistant urinary pathogens to ertapenem and 12 other antibiotics.	2004 Jun	15117925
Gateways to clinical trials.	2004 Mar	15071612
Exploring the effectiveness of tazobactam against ceftazidime resistant Escherichia coli: insights from the comparison between susceptibility testing and beta-lactamase inhibition.	2004 May 1	15109726
Selectivity of ertapenem for Pseudomonas aeruginosa mutants cross-resistant to other carbapenems.	2005 Mar	15705643
In vitro activity of ertapenem against bacteraemic pneumococci: report of a French multicentre study including 339 strains.	2005 Mar	15705639

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 `Fri Dec 15 15:59:28 GMT 2023` Edited by `admin` on `Fri Dec 15 15:59:28 GMT 2023`
Record UNII	G32F6EID2H
Record Status	`Validated (UNII)`
Record Version

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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 [WHO-DD]

Common Name

English

ertapenem [INN]

Common Name

English

ERTAPENEM [VANDF]

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000011294