ertapenem
Trade name: invanz
Small moleculeapproved
Approved
Nov 21, 2001
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. — NCATS
Clinical trial activity
72 trials · 71 clinical orgs · 9 marketing orgs
Phase 1
5
Phase 2
37
Phase 3
30
Phase 4
19
Earliest trial started Apr 1, 2001 (NCT00229112)
Timeline
2000s
2010s
- Apr 16, 2018
ACS Dobfar — Marketing Organization
- Jun 25, 2018
Aurobindo Pharma — Marketing Organization
- Jun 25, 2018
Eugia Pharma — Marketing Organization
- Mar 19, 2019
Savior Lifetec Corp — Marketing Organization
2020s
- Mar 26, 2021
Gland Pharma Ltd — Marketing Organization
- Mar 26, 2021
Fosun — Marketing Organization
- May 2, 2023
Sun Pharmaceuticals — Marketing Organization
- Oct 31, 2024
Qilu Pharmaceutical Co., Ltd. — Marketing Organization
Indications
Approved for
Studied for
- Acute Disease · Phase 4
- Acute Kidney Injury · Phase 4
- Anti-Infective Agents, Urinary · Phase 2/Phase 3
- Appendicitis · Phase 2
- Bacteremia · Phase 3
- Bacterial Infections · Phase 4
- Burns · Phase 4
- Carbapenems · Phase 4
- Clinical Trial · Phase 4
- Colonic Neoplasms · Phase 4
- Colorectal Surgery · Phase 3
- Community-Acquired Infections · Phase 3
- Diabetes Mellitus · Phase 3
- Diabetic Foot · Phase 3
- Diverticulitis, Colonic · Phase 4
- Diverticulosis, Colonic · Phase 4
- Drug Resistance, Bacterial · Phase 4
- Endometritis · Phase 1
- Enterobacteriaceae Infections · Phase 4
- Escherichia coli Infections · Phase 4
- Esophageal and Gastric Varices · Phase 4
- Fever · Phase 4
- Gonorrhea · Phase 3
- Healthy Volunteers · Phase 4
- Hypersensitivity · Phase 4
- Hypersensitivity, Immediate · Phase 4
- Intraabdominal Infections · Phase 4
- Kidney Failure, Chronic · Phase 4
- Kidney Transplantation · Phase 2/Phase 3
- Klebsiella Infections · Phase 2/Phase 3
- Klebsiella pneumoniae · Phase 4
- Liver Cirrhosis · Phase 4
- Osteomyelitis · Phase 3
- Pelvic Infection · Phase 2
- Peritoneal Dialysis, Continuous Ambulatory · Phase 4
- Peritonitis · Phase 4
- Pharmacological and Toxicological Phenomena · Phase 4
- Plasma · Phase 4
- Pneumonia · Phase 3
- Pneumonia, Bacterial · Phase 2
- Pneumonia, Ventilator-Associated · Phase 3
- Prostatic Neoplasms · Phase 4
- Pyelonephritis · Phase 3
- Rectal Neoplasms · Phase 4
- Sepsis · Phase 4
- Soft Tissue Infections · Phase 2
- Staphylococcal Infections · Phase 2
- Surgical Wound Infection · Phase 4
- Tuberculosis · Phase 2
- Tuberculosis, Pulmonary · Phase 2
- Urinary Bladder Neoplasms · Phase 4
- Urinary Tract Infections · Phase 4
Mechanism of action
Peptidoglycan D,D-transpeptidase FtsI inhibitor
Cell shape peptidoglycan synthetase penicillin-binding protein 2 inhibitor
- Bacterial penicillin-binding proteinINHIBITOR
Bacterial penicillin-binding protein inhibitor
- D-alanyl-D-alanine carboxypeptidase DacB (dacB) ↗
- Peptidoglycan D,D-transpeptidase FtsI (ftsI) ↗
- Penicillin-binding protein 1A (mrcA) ↗
- Penicillin-binding protein 1B (mrcB) ↗
- D-alanyl-D-alanine carboxypeptidase DacA (dacA) ↗
- Peptidoglycan D,D-transpeptidase MrdA (mrdA) ↗
- D-alanyl-D-alanine carboxypeptidase DacC (dacC) ↗
Approval history
- approvedNov 21, 2001
Chemistry & pharmacology
Loading structure…
SMILES
C[C@@H](O)[C@H]1C(=O)N2C(C(=O)O)=C(S[C@@H]3CN[C@H](C(=O)Nc4cccc(C(=O)O)c4)C3)[C@H](C)[C@H]12- Mol. weight
- 475.52 g/mol
- Lipinski Ro5
- Pass
- Rule of 3
- No
- Chirality
- Single Stereoisomer
- Inorganic
- No
- Polymer
- No
- Delivery
- Parenteral
- Availability
- Prescription Only
Oral
No
Parenteral
Yes
Topical
No
Sources
- ChEMBLCHEMBL1359 ↗
- WikipediaErtapenem ↗
- NCATSG32F6EID2H ↗
- ChEMBLCHEMBL5314359 ↗
- ChEMBLCHEMBL1232 ↗
Also known as
- (1r,5s,6s,8r,2's,4's)-2-(2-(3-carboxyphenylcarbamoyl)pyrrolidin-4-ylthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid
- (1r,5s,6s,8r,2's,4's)-2-(2-(3-carboxyphenylcarbamoyl)pyrrolidin-4-ylthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid
- (4r,5r,6s)-3-((3s,5s)-5-((3-carboxyphenyl)carbamoyl)pyrrolidin-3-yl)sulfanyl-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid
- (4r,5s,6s)-3-((3s,5s)-5-((3-carboxyphenyl)carbamoyl)pyrrolidin-3-ylthio)-6-((r)-1-hydroxyethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid
- (4r,5s,6s)-3-((3s,5s)-5-((3-carboxyphenyl)carbamoyl)pyrrolidin-3-ylthio)-6-((r)-1-hydroxyethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid
- ertapenem
- ertapenem
- ertapenem
- ertapenem
- ertapenem
- ertapenem
- ertapenem
- ertapenem
- ertapenem
- ertapenem
- ertapenem disodium
- ertapenem sodium
- ertapenem sodium
- ertapenem sodium
- ertapenem sodium
- ertapenem sodium
- ertapenem sodium
- invanoz
- invanz
- invanz
- invanz
- invanz
- invanz
- l 749345
- l-749,345
- mk-0826
- mk-0826
- mk-0826
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT06920147 | Phase 4 | May 1, 2025 | University of Texas at Houston |
| NCT05224401 | Phase 3 | Jan 10, 2023 | Lund University |
| NCT05645757 | Phase 1 | Dec 12, 2022 | National Institute of Allergy and Infectious Diseases (NIAID) |
| NCT04886284 | Phase 2 | Jul 31, 2021 | McGill University |
| NCT06739382 | Phase 3 | Jan 1, 2021 | Beni Suef University, Cairo University |
| NCT04502095 | Phase 4 | Aug 4, 2020 | State University of New York, Buffalo |
| NCT03788967 | Phase 3 | Jun 3, 2019 | Spero Therapeutics |
| NCT03891433 | Phase 4 | Apr 1, 2019 | Universidad del Norte, Barranquilla |
| NCT04505683 | Phase 2/Phase 3 (Phase 3) | Dec 13, 2018 | Sihuan Pharmaceutical Holdings Group Ltd. |
| NCT03582007 | Phase 3 | Sep 30, 2018 | Polyphor Ltd. |
| NCT03358576 | Phase 3 | Sep 18, 2018 | Iterum Therapeutics |
| NCT03357614 | Phase 3 | Sep 18, 2018 | Iterum Therapeutics |
| NCT03409679 | Phase 3 | Mar 23, 2018 | Polyphor Ltd. |
| NCT05896930 | Phase 2 | Nov 9, 2017 | TASK Applied Science |
| NCT03294395 | Phase 3 | Sep 18, 2017 | Government of Netherlands, University of Amsterdam |
| NCT03234296 | N/A | Aug 9, 2017 | Kuopio University Hospital, University of Helsinki, University of Oulu, University of Tampere, University of Turku |
| NCT03218800 | Phase 3 | Jun 1, 2017 | Government of Brazil |
| NCT03257423 | N/A | Apr 4, 2017 | Jyväskylä Central Hospital, Kuopio University Hospital, University of Helsinki, University of Oulu, University of Tampere, University of Turku |
| NCT03236961 | N/A | Apr 3, 2017 | Government of Finland, Jyväskylä Central Hospital, Kuopio University Hospital, Mikkeli Central Hospital, Seinajoki Central Hospital, University of Oulu, University of Tampere, University of Turku |
| NCT03859362 | Phase 4 | Jan 31, 2017 | Prince of Songkla University |
Showing 20 of 72 trials
Page 1 / 4
Organizations
Research & Development (71)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| Merck | For profit | 19 | 14 | 3 | 2001 |
| University of Tampere | Academic/Hospital | 4 | 0 | 1 | 2009 |
| University of Turku | Academic/Hospital | 4 | 4 | 1 | 2009 |
| Kuopio University Hospital | Academic/Hospital | 3 | 0 | 1 | 2017 |
| Tetraphase Pharmaceuticals | For profit | 3 | 3 | 2 | 2011 |
| University of Oulu | Academic/Hospital | 3 | 0 | 1 | 2017 |
| Bayer | For profit | 2 | 2 | 1 | 2006 |
| Iterum Therapeutics | For profit | 2 | 2 | 1 | 2018 |
| Jiangsu Chia-tai Tianqing Pharmaceutical Co.,Ltd | For profit | 2 | 2 | 2 | 2011 |
| Jyväskylä Central Hospital | Academic/Hospital | 2 | 0 | 1 | 2017 |
| Mahidol University | Academic/Hospital | 2 | 2 | 2 | 2011 |
| Mikkeli Central Hospital | Academic/Hospital | 2 | 0 | 1 | 2009 |
| Polyphor Ltd. | For profit | 2 | 2 | 1 | 2018 |
| Seinajoki Central Hospital | Academic/Hospital | 2 | 0 | 1 | 2009 |
| University of California, Los Angeles | Academic/Hospital | 2 | 1 | 2 | 2014 |
| University of Helsinki | Academic/Hospital | 2 | 0 | 1 | 2017 |
| 3201 Hospital of Hanzhong | Academic/Hospital | 1 | 0 | 1 | 2016 |
| Aix-University of Marseille | Academic/Hospital | 1 | 1 | 1 | 2007 |
| Albany College of Pharmacy and Health Sciences | Academic/Hospital | 1 | 1 | 1 | 2009 |
| Beni Suef University | Academic/Hospital | 1 | 1 | 1 | 2021 |
71 organizations
Page 1 / 4
Marketing (10)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| ACS Dobfar | For profit | MKTG | Apr 16, 2018 |
| Aurobindo Pharma | For profit | MKTG | Jun 25, 2018 |
| Eugia Pharma | For profit | MKTG | Jun 25, 2018 |
| Fosun | For profit | MKTG | Mar 26, 2021 |
| Gland Pharma Ltd | For profit | MKTG | Mar 26, 2021 |
| Merck | For profit | NDA | Nov 21, 2001 |
| Merck | For profit | MKTG | Nov 21, 2001 |
| Qilu Pharmaceutical Co., Ltd. | For profit | MKTG | Oct 31, 2024 |
| Savior Lifetec Corp | For profit | MKTG | Mar 19, 2019 |
| Sun Pharmaceuticals | For profit | MKTG | May 2, 2023 |