Ertapenem
Highest phase reached
Approved
Drug type
Small molecule
First approval year
2001
- First approval year
- 2001
- Listing at source
- Listed
- Highest phase reached
- Approved
- Drug type
- Small molecule
- Drug name
- Ertapenem
- Molecular weight
- 475.52
- 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
- ertapenem
- Ertapenem
- ertapenem [INN]
- ERTAPENEM [MI]
- ERTAPENEM [VANDF]
- Ertapenem [WHO-DD]
- ertapenem inn
- ertapenem mi
- ertapenem vandf
- ertapenem who dd
- ATC classification codes
- J01DH03
Sources for recorded values
- CAS registry numbers
- 153832-46-3
- ChEMBL ID
- CHEMBL1359
- InChIKey
- JUZNIMUFDBIJCM-ANEDZVCMSA-N
- PubChem compound IDs
- 150610
- RxNorm IDs (RxCUI)
- 325642
- FDA ingredient codes (UNII)
- G32F6EID2H
- Applicant
- MSD SUB MERCK
- Approval date
- 21 Nov 2001
- Application number
- NDA021337
- Status
- Authorised
- Status date
- 18 Apr 2002
- Authorisation date
- 18 Apr 2002
- Approved indications
- Treatment Treatment of the following infections when caused by bacteria known or very likely to be susceptible to ertapenem and when parenteral therapy is required: intra-abdominal infections; community-acquired pneumonia; acute gynaecological infections; diabetic foot infections of the skin and soft tissue. Prevention Invanz is indicated in adults for the prophylaxis of surgical site infection following elective colorectal surgery. Consideration should be given to official guidance on the appropriate use of antibacterial agents.
- Product number
- EMEA/H/C/000389
- Authorisation holder
- Merck Sharp & Dohme B.V.
- Priority medicines scheme
- No
- Generic
- No
- Biosimilar
- No
- Generic medicines
- 1
- Biosimilar medicines
- 0
- Advanced therapy
- No
- Conditional approval
- No
- Additional monitoring
- No
- Accelerated assessment
- No
- Exceptional circumstances
- No
Therapeutic areas
- Community-Acquired Infections
- Gram-Negative Bacterial Infections
- Pneumonia, Bacterial
- Staphylococcal Infections
- Streptococcal Infections
- Surgical Wound Infection
European medicines record
- First in class
- No
- Orphan designation
- No
- Availability
- Prescription only
- United States (FDA)
- Approved
- European Union (EMA)
- Authorised
- Pharmacology name
- ertapenem
- Type
- Synthetic organic
- Drug name stem
- -penem
- Approval recorded by Guide to Pharmacology
- Yes
Administration routes
- Parenteral
- Mechanism
- Bacterial penicillin-binding protein inhibitor
- Action type
- Inhibitor
- Target
- Bacterial penicillin-binding protein
- Protein identifier
- P02918
- Mechanism
- Bacterial penicillin-binding protein inhibitor
- Action type
- Inhibitor
- Target
- Bacterial penicillin-binding protein
- Protein identifier
- P02919
- Mechanism
- Bacterial penicillin-binding protein inhibitor
- Action type
- Inhibitor
- Target
- Bacterial penicillin-binding protein
- Protein identifier
- P08506
- Mechanism
- Bacterial penicillin-binding protein inhibitor
- Action type
- Inhibitor
- Target
- Bacterial penicillin-binding protein
- Protein identifier
- P0AD65
- Mechanism
- Bacterial penicillin-binding protein inhibitor
- Action type
- Inhibitor
- Target
- Bacterial penicillin-binding protein
- Protein identifier
- P0AD68
- Mechanism
- Bacterial penicillin-binding protein inhibitor
- Action type
- Inhibitor
- Target
- Bacterial penicillin-binding protein
- Protein identifier
- P0AEB2
- Mechanism
- Bacterial penicillin-binding protein inhibitor
- Action type
- Inhibitor
- Target
- Bacterial penicillin-binding protein
- Protein identifier
- P24228
- Mechanism
- Cell shape peptidoglycan synthetase penicillin-binding protein 2 inhibitor
- Action type
- Inhibitor
- Target
- Cell shape peptidoglycan synthetase penicillin-binding protein 2
- Protein identifier
- Q2TL65
- Mechanism
- Peptidoglycan D,D-transpeptidase FtsI inhibitor
- Action type
- Inhibitor
- Target
- Peptidoglycan D,D-transpeptidase FtsI
- Protein identifier
- C3TQQ7
- Mechanism
- Bacterial penicillin-binding protein inhibitor
- Action type
- Inhibitor
- Target
- Bacterial penicillin-binding protein
- Mechanism
- Cell shape peptidoglycan synthetase penicillin-binding protein 2 inhibitor
- Action type
- Inhibitor
- Target
- Cell shape peptidoglycan synthetase penicillin-binding protein 2
- Mechanism
- Peptidoglycan D,D-transpeptidase FtsI inhibitor
- Action type
- Inhibitor
- Target
- Peptidoglycan D,D-transpeptidase FtsI
- Action type
- Inhibitor
- Gene symbol
- mrcA
- Protein identifier
- P02918
- Organism
- Escherichia coli (strain K12)
- Action type
- Inhibitor
- Gene symbol
- mrcB
- Protein identifier
- P02919
- Organism
- Escherichia coli (strain K12)
- Action type
- Inhibitor
- Gene symbol
- dacB
- Protein identifier
- P24228
- Organism
- Escherichia coli (strain K12)
- Condition
- Gonorrhea
- Highest recorded phase
- 3
- Condition identifier
- DOID:7551
- Subject identifier
- D006069
- Condition
- Infections
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000544
- Subject identifier
- D007239
- Condition
- Bacterial Infections
- Highest recorded phase
- 4
- Condition identifier
- EFO:0000771
- Subject identifier
- D001424
- Condition
- Osteomyelitis
- Highest recorded phase
- 3
- Condition identifier
- EFO:0003102
- Subject identifier
- D010019
- Condition
- Urinary Tract Infections
- Highest recorded phase
- 3
- Condition identifier
- EFO:0003103
- Subject identifier
- D014552
- Condition
- Pneumonia
- Highest recorded phase
- 3
- Condition identifier
- EFO:0003106
- Subject identifier
- D011014
- Condition
- Renal Insufficiency, Chronic
- Highest recorded phase
- 2
- Condition identifier
- EFO:0003884
- Subject identifier
- D051436
- Condition
- Appendicitis
- Highest recorded phase
- 2
- Condition identifier
- EFO:0007149
- Subject identifier
- D001064
- Condition
- Tuberculosis, Pulmonary
- Highest recorded phase
- 2
- Condition identifier
- EFO:1000049
- Subject identifier
- D014397
- Condition
- Pyelonephritis
- Highest recorded phase
- 2
- Condition identifier
- EFO:1001141
- Subject identifier
- D011704
- Condition
- Endometritis
- Highest recorded phase
- 1
- Condition identifier
- EFO:1001312
- Subject identifier
- D004716
- Condition
- Diabetic Foot
- Highest recorded phase
- 3
- Condition identifier
- EFO:1001459
- Subject identifier
- D017719
- Condition
- Tuberculosis
- Highest recorded phase
- 2
- Condition identifier
- MONDO:0018076
- Subject identifier
- D014376
- Condition identifier
- EFO_0000544
- Highest recorded phase
- 2
- Condition identifier
- EFO_0000544
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000771
- Condition identifier
- EFO_0003102
- Highest recorded phase
- 3
- Condition identifier
- EFO_0003103
- Highest recorded phase
- 3
- Condition identifier
- EFO_0003106
- Highest recorded phase
- 3
- Condition identifier
- EFO_0003884
- Highest recorded phase
- 2
- Condition identifier
- EFO_0007149
- Highest recorded phase
- 2
- Condition identifier
- EFO_0009632
- Condition identifier
- EFO_1000710
- Condition identifier
- EFO_1001312
- Highest recorded phase
- 1
- Condition identifier
- EFO_1001459
- Highest recorded phase
- 3
- Condition identifier
- EFO_1001865
- Highest recorded phase
- 3
- Condition identifier
- HP_0000010
- Condition identifier
- MONDO_0003529
- Highest recorded phase
- 3
- Condition identifier
- MONDO_0004652
- Highest recorded phase
- 4
- Condition identifier
- MONDO_0005002
- Highest recorded phase
- 2
- Condition identifier
- MONDO_0005015
- Condition identifier
- MONDO_0005113
- Highest recorded phase
- 4
- Condition identifier
- MONDO_0005229
- Highest recorded phase
- 2
- Condition identifier
- MONDO_0005294
- Condition identifier
- MONDO_0005649
- Highest recorded phase
- 2
- Condition identifier
- MONDO_0006052
- Highest recorded phase
- 2
- Condition identifier
- MONDO_0006559
- Condition identifier
- MONDO_0018076
- Highest recorded phase
- 2
And 4 more, listed on the interactive page.
- Event
- acute generalised exanthematous pustulosis
- Reports
- 9
- Reporting signal score
- 15.8702
- Event
- adenovirus infection
- Reports
- 7
- Reporting signal score
- 21.4168
- Event
- agitation
- Reports
- 15
- Reporting signal score
- 10.2591
- Event
- avian influenza
- Reports
- 7
- Reporting signal score
- 47.3006
- Event
- biliary sepsis
- Reports
- 8
- Reporting signal score
- 38.856
- Event
- chronic sinusitis
- Reports
- 12
- Reporting signal score
- 41.0691
- Event
- clostridium difficile colitis
- Reports
- 14
- Reporting signal score
- 31.1671
- Event
- clostridium difficile infection
- Reports
- 42
- Reporting signal score
- 121.656
- Event
- clostridium test positive
- Reports
- 20
- Reporting signal score
- 87.786
- Event
- confusional state
- Reports
- 57
- Reporting signal score
- 72.5601
- Event
- convulsion
- Reports
- 18
- Reporting signal score
- 14.6794
- Event
- delirium
- Reports
- 20
- Reporting signal score
- 28.1368
- Event
- drug reaction with eosinophilia and systemic symptoms
- Reports
- 16
- Reporting signal score
- 21.0144
- Event
- drug resistance
- Reports
- 13
- Reporting signal score
- 16.7998
- Event
- dyspepsia
- Reports
- 15
- Reporting signal score
- 13.1236
- Event
- dyspnoea
- Reports
- 4
- Reporting signal score
- 11.7757
- Event
- encephalopathy
- Reports
- 36
- Reporting signal score
- 81.0454
- Event
- eosinophilia
- Reports
- 12
- Reporting signal score
- 17.3371
- Event
- epilepsy
- Reports
- 13
- Reporting signal score
- 15.358
- Event
- erythema multiforme
- Reports
- 8
- Reporting signal score
- 12.0748
- Event
- escherichia bacteraemia
- Reports
- 5
- Reporting signal score
- 14.3172
- Event
- escherichia infection
- Reports
- 7
- Reporting signal score
- 14.1825
- Event
- escherichia test positive
- Reports
- 8
- Reporting signal score
- 30.4311
- Event
- factor v inhibition
- Reports
- 3
- Reporting signal score
- 12.5586
- Event
- fatigue
- Reports
- 4
- Reporting signal score
- 15.8656
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- Dose
- 1 gram
- Route
- Intravenous
- How often
- Once daily
- Do not mix or co-infuse with other medications
- Do not use diluents containing dextrose
- Infused over 30 minutes
- Hydrogen bond acceptors
- 7
- Hydrogen bond donors
- 5
- Polar surface area
- 156.27
- Calculated partition coefficient (ALogP)
- 0.94
- Calculated partition coefficient (XLogP)
- -1.5
- Prodrug
- No
- Chirality
- Single enantiomer
- Inorganic
- No
- Rule-of-five violations
- 0
- Rotatable bonds
- 7
- Heavy atoms
- 33
- Molecular formula
- C22H25N3O7S
- Monoisotopic mass
- 475.14132132
- Natural product
- Yes
- Recorded assays
- 1,792
- Active assays
- 6
Active assay types
- Confirmatory
- Anti-Bacterial Agents
Oral bioavailability
- Median
- 0.59
- Mean
- 0.59
- Minimum
- 0.53
- Maximum
- 0.65
- Unit
- %
- Assays
- 2
- Standard deviation
- 0.0848528
- Summary method
- median
- Censored results excluded
- 0
- Other units excluded
- 0
- Unknown units excluded
- 0
Measurement types
- F
Plasma protein binding
- Median
- 84
- Mean
- 84
- Minimum
- 84
- Maximum
- 84
- Unit
- %
- Assays
- 1
- Standard deviation
- 0
- Summary method
- median
- Censored results excluded
- 0
- Other units excluded
- 0
- Unknown units excluded
- 0
Measurement types
- PPB
Related records
Trials (59)
- A Phase II Study of Faropenem in the Treatment of Adult Community-acquired Bacterial Pneumonia
- A Phase III Study of Faropenem in the Treatment of Adult Community-acquired Bacterial Pneumonia
- A Single Center, Prospective Clinical Trial of Intravenous Ertapenem in the Treatment of Hurley Stage II or III Hidradenitis Suppurativa
- A Study to Assess Efficacy and Safety Intravenous Benapenem in Patients With Complicated Urinary Tract Infection (cUTI) or Acute Pyelonephritis (AP)
- Acute Appendicitis and Microbiota - Etiology of Appendicitis and Antibiotic Therapy Effects
- An Observational Study of Ertapenem in Outpatient Parenteral Antibiotic Therapy (OPAT) for Complicated Urinary Tract Infections.
- Antibiotic Prophylaxis in Patients Undergoing GVO
- Antibiotics for Klebsiella Liver Abscess Study
- Antibiotics Versus Surgery in Acute Appendicitis
- Antibiotics vs. Placebo in Acute Uncomplicated Appendicitis
- Appendicectomy Versus Antibiotics in the Treatment of Acute Uncomplicated Appendicitis
- Assessment of Prostatic Tissue Concentration of Ertapenem After a Pre-operative Administration
- Clinical Trial Comparing ERAT vs Antibiotic Therapy vs Appendectomy for Treatment of Uncomplicated Acute Appendicitis
- Clinical Trial to Study the Safety and Effectiveness of MK0826 and Other Antibiotic Therapy in Patients With Complicated Urinary Tract Infection (0826-054)
- Combination Cefazolin With Ertapenem for Methicillin-susceptible Staphylococcus Aureus Bacteremia
- Comparing Oral Versus Parenteral Antimicrobial Therapy
- Comparison of Ertapenem Distribution in the Muscle of Six Healthy Volunteers and Six Critically Ill Patients by Microdialysis
- Concentration of Ertapenem in Colorectal Tissue
- Early Short-term Antibiotic Therapy in Penetrating Abdominal Trauma, 3 vs 7 Days
- Efficacy and Safety Study of Eravacycline Compared With Ertapenem in Complicated Intra-abdominal Infections
Approved for (5)
- Bacterial infectious disease
- Bacterial pneumonia
- Gram-negative bacterial infections
- Staphylococcal infection
- Streptococcal infection
In development for (13)
- Acute pyelonephritis Phase 3
- Appendicitis Phase 2
- Bacterial infectious disease with sepsis Phase 2
- Chronic kidney disease Phase 2
- Chronic obstructive pulmonary disease Phase 2
- Endometritis Phase 1
- Gonorrhea Phase 3
- Osteomyelitis Phase 3
- Pneumonia Phase 3
- Pulmonary tuberculosis Phase 2
- Pyelonephritis Phase 2
- Tuberculosis Phase 2
- Urinary tract infection Phase 3
Other linked conditions (3)
- Diabetes mellitus
- Hidradenitis suppurativa
- Peripheral vascular disease