Ertapenem
drugOn this page
Also known as ErtrapenemERTAPENEMEErtapenem sodium
Summary
Ertapenem (CHEMBL1359) is an approved small-molecule antibacterial drug (ATC J01DH03); indicated across 13 conditions including bacterial infectious disease and gonorrhea.
At a glance
- Status: Approved (max clinical phase 4)
- Modality: Small molecule
- ATC class: J01DH03
- Indications: 13 conditions
- Clinical trials: 61
- Chemistry: 475.5 Da · C22H25N3O7S
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL1359 |
| Name | Ertapenem |
| Type | Small molecule |
| Max phase | 4 |
| FDA approved | yes |
| PubChem CID | 150610 |
| ChEBI | CHEBI:404903 |
| ATC | J01DH03 |
| Molecular formula | C22H25N3O7S |
| Molecular weight | 475.5 |
| InChIKey | JUZNIMUFDBIJCM-ANEDZVCMSA-N |
SMILES: C[C@@H]1[C@@H]2[C@H](C(=O)N2C(=C1S[C@H]3C[C@H](NC3)C(=O)NC4=CC=CC(=C4)C(=O)O)C(=O)O)[C@@H](C)O
IUPAC name: (4R,5S,6S)-3-[(3S,5S)-5-[(3-carboxyphenyl)carbamoyl]pyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
ChEBI definition: Meropenem in which the one of the two methyl groups attached to the amide nitrogen is replaced by hydrogen while the other is replaced by a 3-carboxyphenyl group. The sodium salt is used for the treatment of moderate to severe susceptible infections including intra-abdominal and acute gynaecological infections, pneumonia, and infections of the skin and of the urinary tract.
Pharmacological roles (ChEBI): antibacterial drug.
Also known as: Ertapenem, ertapenem, Ertrapenem, ERTAPENEME, ERTAPENEM, Ertapenem sodium
Parent form; salt/anhydrous children: CHEMBL1232, CHEMBL5314359
Patent coverage: 4,362 distinct patent families (17,126 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.
Targets
Targets
Broader ChEMBL bioactivity targets: 3 (assay-derived). Sample: Estrogen receptor, Prostaglandin G/H synthase 1, 3’,5’-cyclic-AMP phosphodiesterase 4A.
Bioactivity
ChEMBL activities: 1 potent at pChembl ≥ 5 of 4 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| PDE4A | 5.79 | AC50 | 1620 | nM | CHEMBL_ACT_25207190 |
Target pathways
No target-pathway data for this drug (no mapped target genes).
Indications & clinical
Indications
13 indications (1 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).
| Indication | Trial phase | MONDO | EFO |
|---|---|---|---|
| bacterial infectious disease | 4 | MONDO:0005113 | EFO:0000771 |
| gonorrhea | 3 | MONDO:0004277 | DOID:7551 |
| urinary tract infection | 3 | MONDO:0100338 | EFO:0003103 |
| pneumonia | 3 | MONDO:0005249 | EFO:0003106 |
| osteomyelitis | 3 | MONDO:0005246 | EFO:0003102 |
| chronic kidney disease | 2 | MONDO:0005300 | EFO:0003884 |
| appendicitis | 2 | MONDO:0005649 | EFO:0007149 |
| pyelonephritis | 2 | MONDO:0006939 | EFO:1001141 |
| tuberculosis | 2 | MONDO:0018076 | MONDO:0018076 |
| pulmonary tuberculosis | 2 | MONDO:0006052 | EFO:1000049 |
| endometritis | 1 | MONDO:0000918 | EFO:1001312 |
2 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.
Clinical trials
Total trials: 61.
Phase distribution
| Phase | Trials |
|---|---|
| PHASE4 | 20 |
| PHASE3 | 17 |
| Not specified | 9 |
| PHASE2 | 8 |
| PHASE1 | 4 |
| PHASE2/PHASE3 | 3 |
Top trials by phase / activity
| NCT | Phase | Status | Title |
|---|---|---|---|
| NCT04140578 | PHASE4 | RECRUITING | Antibiotic Prophylaxis in Patients Undergoing GVO |
| NCT06920147 | PHASE4 | NOT_YET_RECRUITING | PRevention Of Trauma-related Infections Through an Embedded Clinical Trials Network |
| NCT00097734 | PHASE4 | UNKNOWN | Study to Evaluate the Duration of Treatment With Ertapenem in Acute Attacks of Sigmoid Diverticulitis |
| NCT00489138 | PHASE4 | TERMINATED | Prospective, Open-label Study of Pharmacokinetics of Ertapenem in the Muscle Using Microdialysis in Mechanically Ventilated Intensive Care Unit Patients, Treated or Not by Norepinephrine |
| NCT00535652 | PHASE4 | COMPLETED | Concentration of Ertapenem in Colorectal Tissue |
| NCT00630513 | PHASE4 | COMPLETED | T.E.A. Study Three Days Ertapenem Versus Three Days Ampicillin- Sulbactam |
| NCT00877370 | PHASE4 | COMPLETED | Pharmacokinetics of Ertapenem in Continuous Venovenous Hemodialysis |
| NCT00939952 | PHASE4 | COMPLETED | Ertapenem Pharmacokinetics in Patients in Continuous Ambulatory Peritoneal Dialysis |
| NCT01148771 | PHASE4 | COMPLETED | Pharmacokinetics (PK) of Ertapenem Intravenous (IV) Bolus Versus Standard Infusion |
| NCT01159379 | PHASE4 | UNKNOWN | Safety of Ertapenem in Beta-lactam Allergic Patients. |
| NCT01297842 | PHASE4 | UNKNOWN | Ertapenem Versus Meropenem/Imipenem for ESBL+ Gram-negative Infections |
| NCT01421901 | PHASE4 | UNKNOWN | Antibiotics Versus Surgery in Acute Appendicitis |
| NCT01497990 | PHASE4 | COMPLETED | Pharmacokinetics Ertapenem Burns |
| NCT01723150 | PHASE4 | COMPLETED | Antibiotics for Klebsiella Liver Abscess Study |
| NCT02041767 | PHASE4 | COMPLETED | Assessment of Prostatic Tissue Concentration of Ertapenem After a Pre-operative Administration |
| NCT02505386 | PHASE4 | COMPLETED | Pharmacokinetics of Ertapenem in Patients Aged Over 75 |
| NCT03859362 | PHASE4 | UNKNOWN | Ertapenem in Patients With Urosepsis |
| NCT03891433 | PHASE4 | SUSPENDED | Piperacillin/Tazobactam Versus Carbapenems in Non-bacteremic UTI Due to -ESBL-producing Enterobacteriaceae |
| NCT04502095 | PHASE4 | COMPLETED | Prophylactic Antibiotics for Urinary Tract Infections After Robot-Assisted Radical Cystectomy |
| NCT05977868 | PHASE4 | TERMINATED | Comparing Oral Versus Parenteral Antimicrobial Therapy |
| NCT00090272 | PHASE3 | COMPLETED | A Single Dose of a Marketed Drug Being Studied for a New Indication to Treat Surgical Site Infection Following Colorectal Surgery as Compared to a Marketed Drug Approved for This Indication (0826-039) |
| NCT00366249 | PHASE3 | COMPLETED | Study Evaluating the Safety and Efficacy of a Once-daily Dose of Tigecycline vs Ertapenem in Diabetic Foot Infections (DFI) With a Substudy in Patients With Diabetic Foot Infections Complicated by Osteomyelitis. |
| NCT00379951 | PHASE3 | COMPLETED | A Study to Assess the Safety, Tolerability and Efficacy of Ertapenem Sodium in the Treatment of Complicated Urinary Tract Infections (0826-048) |
| NCT00492726 | PHASE3 | COMPLETED | Therapy of Complicated Intra-Abdominal Infections With Moxifloxacin or Ertapenem |
| NCT01014013 | PHASE3 | COMPLETED | Safety and Tolerability of Ertapenem Sodium in the Treatment of Complicated Urinary Tract Infections (0826-055) |
| NCT01069900 | PHASE3 | COMPLETED | Moxifloxacin in Pediatric Subjects With Complicated Intra-abdominal Infection |
| NCT01203046 | PHASE2/PHASE3 | COMPLETED | Early Short-term Antibiotic Therapy in Penetrating Abdominal Trauma, 3 vs 7 Days |
| NCT01254344 | PHASE3 | COMPLETED | Efficacy and Safety of Ertapenem Sodium (MK-0826) Following Colorectal Surgery in Chinese Adults (MK-0826-056) |
| NCT01370616 | PHASE3 | COMPLETED | Ertapenem Sodium (MK-0826) Versus Piperacillin/Tazobactam Sodium for the Treatment of Diabetic Foot Infections in Chinese Adults (MK-0826-061) |
| NCT01844856 | PHASE3 | COMPLETED | Efficacy and Safety Study of Eravacycline Compared With Ertapenem in Complicated Intra-abdominal Infections |
| NCT01937832 | PHASE3 | UNKNOWN | A Phase III Study of Faropenem in the Treatment of Adult Community-acquired Bacterial Pneumonia |
| NCT02729116 | PHASE2/PHASE3 | UNKNOWN | Sitafloxacin and Ertapenem Treatment for Acute Urinary Tract Infection Caused by E. Coli or K. Pneumoniae in Post-kidney Transplantation Patients |
| NCT03032510 | PHASE3 | COMPLETED | Efficacy and Safety Study of Eravacycline Compared With Ertapenem in Participants With Complicated Urinary Tract Infections |
| NCT03218800 | PHASE3 | TERMINATED | Ertapenem Administered Subcutaneously Versus Intravenously |
| NCT03294395 | PHASE3 | COMPLETED | New AntiBiotic Treatment Options for Uncomplicated Anogenital GOnorrhoea |
| NCT03357614 | PHASE3 | COMPLETED | Sulopenem Followed by Sulopenem-etzadroxil/Probenecid vs Ertapenem Followed by Cipro for Complicated UTI in Adults |
| NCT03358576 | PHASE3 | COMPLETED | Sulopenem Versus Ertapenem for Complicated Intra-abdominal Infection (cIAI) |
| NCT03788967 | PHASE3 | COMPLETED | Study to Assess the Efficacy, Safety and Pharmacokinetics of Orally Administered Tebipenem Pivoxil Hydrobromide (SPR994) Compared to Intravenous Ertapenem in Participants With Complicated Urinary Tract Infection (cUTI) or Acute Pyelonephritis (AP) |
| NCT04505683 | PHASE2/PHASE3 | COMPLETED | A Study to Assess Efficacy and Safety Intravenous Benapenem in Patients With Complicated Urinary Tract Infection (cUTI) or Acute Pyelonephritis (AP) |
| NCT06739382 | PHASE3 | COMPLETED | Management of Ventilation Acquired Pneumonia Caused by Pseudomonas and Acinetobacter Organisms in a Pediatric Center |
Clinical evidence (CIViC)
No CIViC predictive evidence (expected for non-precision-medicine drugs).
Pharmacology
Pharmacogenomics
No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.
Related molecules
Related molecules
No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).