Piperacillin
drugOn this page
Also known as PeracinPiperacilinaPiperacillin anhydrousPiperacillin hydratePiperacillin monohydrateanhydrousPiperacillinepiperacillin-tazobactamPIPERACILLIN SODIUM
Summary
Piperacillin (CHEMBL702) is an approved small-molecule antibacterial drug (ATC J01CA12); indicated across 21 conditions including bacterial infectious disease and pseudomonas infection.
At a glance
- Status: Approved (max clinical phase 4)
- Modality: Small molecule
- ATC class: J01CA12
- Indications: 21 conditions
- Clinical trials: 83
- Chemistry: 517.6 Da · C23H27N5O7S
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL702 |
| Name | Piperacillin |
| Type | Small molecule |
| Max phase | 4 |
| FDA approved | no |
| PubChem CID | 43672 |
| ChEBI | CHEBI:8232 |
| ATC | J01CA12 |
| Molecular formula | C23H27N5O7S |
| Molecular weight | 517.6 |
| InChIKey | IVBHGBMCVLDMKU-GXNBUGAJSA-N |
SMILES: CCN1CCN(C(=O)C1=O)C(=O)N[C@H](C2=CC=CC=C2)C(=O)N[C@H]3[C@@H]4N(C3=O)[C@H](C(S4)(C)C)C(=O)O
IUPAC name: (2S,5R,6R)-6-[[(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
ChEBI definition: A penicillin in which the substituent at position 6 of the penam ring is a 2-[(4-ethyl-2,3-dioxopiperazin-1-yl)carboxamido]-2-phenylacetamido group.
Pharmacological roles (ChEBI): antibacterial drug.
Also known as: Peracin, Piperacilina, Piperacillin, Piperacillin anhydrous, Piperacillin hydrate, Piperacillin monohydrate, anhydrous, Piperacilline, piperacillin, piperacillin-tazobactam, PIPERACILLINE, PIPERACILLIN
Parent form; salt/anhydrous children: CHEMBL1200820
Patent coverage: 9,099 distinct patent families (31,650 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
No target linkage available.
Bioactivity
No ChEMBL bioactivity rows at pChembl ≥ 5 (expected for biologics / antibodies).
Target pathways
No target-pathway data for this drug (no mapped target genes).
Indications & clinical
Indications
21 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 |
| Pseudomonas infection | 3 | MONDO:0005141 | EFO:0001076 |
| abscess | 3 | MONDO:0005227 | EFO:0003030 |
| pneumonia | 3 | MONDO:0005249 | EFO:0003106 |
| toxic shock syndrome | 3 | MONDO:0001881 | EFO:0006834 |
| bacterial pneumonia | 3 | MONDO:0004652 | EFO:1001272 |
| acute cholecystitis | 3 | MONDO:0043994 | EFO:1001289 |
| urinary tract infection | 3 | MONDO:0100338 | EFO:0003103 |
| hematopoietic and lymphoid system neoplasm | 3 | MONDO:0002334 | MONDO:0044881 |
| influenza | 3 | MONDO:0005812 | EFO:0007328 |
| severe acute respiratory syndrome | 3 | MONDO:0005091 | MONDO:0100096 |
| infectious disease | 2 | MONDO:0005550 | EFO:0005741 |
| graft versus host disease | 2 | MONDO:0013730 | MONDO:0013730 |
| appendicitis | 2 | MONDO:0005649 | EFO:0007149 |
| otitis media | 1 | MONDO:0005441 | EFO:0004992 |
| osteomyelitis | 0 | MONDO:0005246 | EFO:0003102 |
5 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.
Clinical trials
Total trials: 83.
Phase distribution
| Phase | Trials |
|---|---|
| Not specified | 25 |
| PHASE4 | 22 |
| PHASE3 | 16 |
| PHASE2 | 10 |
| PHASE1 | 7 |
| PHASE2/PHASE3 | 2 |
| PHASE1/PHASE2 | 1 |
Top trials by phase / activity
| NCT | Phase | Status | Title |
|---|---|---|---|
| NCT03671967 | PHASE4 | RECRUITING | PipEracillin Tazobactam Versus mERoPENem for Treatment of Bloodstream Infections Caused by Cephalosporin-resistant Enterobacteriaceae (PETERPEN) |
| NCT06184659 | PHASE4 | RECRUITING | Empirical Meropenem Versus Piperacillin/Tazobactam for Adult Patients With Sepsis |
| NCT06712641 | PHASE4 | RECRUITING | Aminoglycosides in Early Sepsis |
| NCT06954129 | PHASE4 | RECRUITING | A Pragmatic Clinical Trial Comparing the Risk of Acute Kidney Injury During Treatment With Vancomycin and Piperacillin-Tazobactam vs. Vancomycin and Cefepime in Hospitalized Patients |
| NCT07556107 | PHASE4 | NOT_YET_RECRUITING | The Vancomycin Piperacillin/Tazobactam (VPT) Patient Safety Trial (VPS) |
| NCT00044746 | PHASE4 | COMPLETED | Study Evaluating the Safety and Efficacy of Piperacillin/Tazobactam and Ampicillin/Sulbactam in Patients With Diabetic Foot Infections |
| NCT00044928 | PHASE4 | COMPLETED | Study Evaluating Zosyn in Hospitalized Patients With Intra-abdominal Infection |
| NCT00703144 | PHASE4 | COMPLETED | Pharmacokinetics of Piperacillin/Tazobactam in Patients Treated by Continuous Renal Replacement Therapy |
| NCT00816790 | PHASE4 | TERMINATED | Standard Vs Adjusted Dosing of Piperacillin/Tazobactam in Acute Renal Failure and Septic Shock |
| NCT01760109 | PHASE4 | COMPLETED | Piperacillin Sodium and Sulbactam Sodium for Injection(2:1) for Treatment of Respiratory and Urinary System Infection |
| NCT02463747 | PHASE4 | UNKNOWN | Short vs Prolonged Antibiotic Treatment for Hospitalized Hemato-oncology Patients With Febrile Neutropenia |
| NCT02730624 | PHASE4 | COMPLETED | Piperacillin/Tazobactam in Critically Ill Patients With Severe Sepsis and Septic Shock |
| NCT02991937 | PHASE4 | COMPLETED | Comparison of Medical and Surgical Treatment of Uncomplicated Acute Appendicitis in Children |
| NCT03262142 | PHASE4 | TERMINATED | Targeted AntiBiotics for Chronic Pulmonary Diseases |
| NCT03289351 | PHASE4 | COMPLETED | Two Different Antibiotics Versus One Antibiotic for Pediatric Perforated Appendicitis |
| NCT03560232 | PHASE4 | TERMINATED | Noninferiority Comparison of Prophylactic Open Fracture Antimicrobial Regimens |
| NCT03891433 | PHASE4 | SUSPENDED | Piperacillin/Tazobactam Versus Carbapenems in Non-bacteremic UTI Due to -ESBL-producing Enterobacteriaceae |
| NCT04233996 | PHASE4 | UNKNOWN | Efficacy of Extended Infusion of β-lactam Antibiotics for the Treatment of Febrile Neutropenia in Hematologic Patients |
| NCT04895657 | PHASE4 | COMPLETED | Extended-infusion of Piperacillin-Tazobactam Versus Intermittent Infusion |
| NCT04948463 | PHASE4 | COMPLETED | Early Versus Late Stopping of Antibiotics in Children With Cancer and High-risk Febrile Neutropenia |
| NCT05355350 | PHASE4 | WITHDRAWN | PipEracillin/Tazobactam Versus mERoPENem for Treatment of AmpC Producing Blood Stream Infections |
| NCT05981079 | PHASE4 | UNKNOWN | Model-based Dose Versus Empirical Dose of Piperacillin/Tazobactam in Preterm Neonates With Late-onset Sepsis. |
| NCT02735707 | PHASE3 | RECRUITING | Randomized, Embedded, Multifactorial Adaptive Platform Trial for Community- Acquired Pneumonia |
| NCT05565222 | PHASE3 | RECRUITING | Piperacillin-tazobactam and Temocillin as Carbapenem-alternatives for the Treatment of Severe Infections Due to Extended-spectrum Beta-lactamase-Producing Gram-negative Enterobacteriaceae in the Intensive Care Unit |
| NCT00003805 | PHASE3 | COMPLETED | Prevention of Infection in Patients With Hematologic Cancer and Persistent Fever Caused by a Low White Blood Cell Count |
| NCT00044759 | PHASE3 | COMPLETED | Study Comparing the Safety and Efficacy of Piperacillin/Tazobactam to Cefepime in Patients With Hematologic Malignancy or Lymphoma |
| NCT00253955 | PHASE3 | COMPLETED | Study to Demonstrate the Clinical Efficacy of Levofloxacin in the Treatment of Pneumonia |
| NCT00402727 | PHASE3 | COMPLETED | Comparison of Sequential IV/PO Moxifloxacin With IV Piperacillin/Tazobactam Followed by PO Amoxicillin/Clavulanic Acid in Patients With a Complicated Skin and Skin Structure Infection |
| NCT01027832 | PHASE2/PHASE3 | UNKNOWN | Antibiotic Treatment in Ventilator Associated Tracheobronchitis (VAT) |
| NCT01370616 | PHASE3 | COMPLETED | Ertapenem Sodium (MK-0826) Versus Piperacillin/Tazobactam Sodium for the Treatment of Diabetic Foot Infections in Chinese Adults (MK-0826-061) |
| NCT01853982 | PHASE3 | TERMINATED | Study of Intravenous Ceftolozane/Tazobactam Compared to Piperacillin/Tazobactam in Ventilator-Associated Pneumonia |
| NCT02166476 | PHASE3 | COMPLETED | Efficacy/Safety of Meropenem-Vaborbactam Compared to Piperacillin-Tazobactam in Adults With cUTI and AP |
| NCT02473263 | PHASE3 | COMPLETED | Samu Save Sepsis: Early Goal Directed Therapy in Pre Hospital Care of Patients With Severe Sepsis and/or Septic Shock |
| NCT02493764 | PHASE3 | COMPLETED | Imipenem/Relebactam/Cilastatin Versus Piperacillin/Tazobactam for Treatment of Participants With Bacterial Pneumonia (MK-7655A-014) |
| NCT02753946 | PHASE2/PHASE3 | COMPLETED | Safety and Efficacy of ZTI-01 (IV Fosfomycin) vs Piperacillin/Tazobactam for Treatment cUTI/AP Infections |
| NCT02820987 | PHASE3 | COMPLETED | PK/PD of Extended-infusion Meropenem, Piperacillin-tazobactam and Cefepime in the Early Phase of Septic Shock |
| NCT03006679 | PHASE3 | WITHDRAWN | A Study of Meropenem-Vaborbactam Versus Piperacillin/Tazobactam in Participants With Hospital-Acquired and Ventilator-Associated Bacterial Pneumonia |
| NCT03269994 | PHASE3 | COMPLETED | Does Cefoxitin or Piperacillin-Tazobactam Prevent Postoperative Surgical Site Infections After Pancreatoduodenectomy? |
| NCT03687255 | PHASE3 | COMPLETED | Safety and Efficacy Study of Cefepime-AAI101 in the Treatment of Complicated Urinary Tract Infections |
| NCT04042077 | PHASE3 | TERMINATED | Delafloxacin IV and OS Administration Compared to Best Available Therapy in Patients With Surgical Site Infections |
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).