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
Recent developments in carbapenems.	2002 Apr	11922861
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
A prospective, multicenter, randomized, double-blind study comparing ertapenem and ceftriaxone followed by appropriate oral therapy for complicated urinary tract infections in adults.	2002 Jul	12100914
Efficient one-pot synthesis of the 2-aminocarbonylpyrrolidin-4-ylthio-containing side chain of the new broad-spectrum carbapenem antibiotic ertapenem.	2002 Jul 12	12098287
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
Ertapenem. A review of its microbiologic, pharmacokinetic and clinical aspects.	2002 Mar	12532175
Safety and local tolerability of intramuscularly administered ertapenem diluted in lidocaine: a prospective, randomized, double-blind study versus intramuscular ceftriaxone.	2002 Mar	11952026
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 (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
[New approaches to antibacterial therapy of infections in the surgical practice].	2003	12968465
Ertapenem: a review of its use in the management of bacterial infections.	2003	12921489
Ertapenem once a day versus piperacillin-tazobactam every 6 hours for treatment of acute pelvic infections: a prospective, multicenter, randomized, double-blind study.	2003	12839630
[Carbapenem antibiotic ertapenem in the treatment of extrahospital intraabdominal infections].	2003	12744138
[Problems of pharmacotherapy of infections in the aged].	2003 Aug	14671813
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
Efficacy of ertapenem in the treatment of serious infections caused by Enterobacteriaceae: analysis of pooled clinical trial data.	2003 May	12697633
Ertapenem, the first of a new group of carbapenems.	2003 Oct	12951340
Properties and potential of ertapenem.	2003 Sep	12917243
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
Gateways to clinical trials.	2004 Apr	15148527
New therapies for pneumococcal meningitis.	2004 Apr	15102588
Optimizing antimicrobial pharmacodynamics: dosage strategies for meropenem.	2004 Aug	15476901
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
Evaluation of outpatient treatment with ertapenem in a double blind controlled clinical trial of complicated skin/skin structure infections.	2004 Jan	14667790
Activity of ertapenem against Neisseria gonorrhoeae.	2004 Jul	15175267
Ertapenem: a Group 1 carbapenem with distinct antibacterial and pharmacological properties.	2004 Jun	15150178
Antimicrobial susceptibility of the pathogens of bacteraemia in the UK and Ireland 2001-2002: the BSAC Bacteraemia Resistance Surveillance Programme.	2004 Jun	15128723
In vitro susceptibility of recent antibiotic-resistant urinary pathogens to ertapenem and 12 other antibiotics.	2004 Jun	15117925
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
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
Distribution and characteristics of Escherichia coli clonal group A.	2005 Jan	15705341

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