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piperacillin

Trade name: pipracil

Small moleculeapproved

Approved

Dec 29, 1981

Piperacillin is a semisynthetic, broad-spectrum, ampicillin derived ureidopenicillin antibiotic which exerts bactericidal activity by inhibiting septum formation and cell wall synthesis of susceptible bacteria. Piperacillin sodium salt is used in combination with the β-lactamase inhibitor tazobactam sodium (ZOSYN®) for the treatment of patients with moderate to severe infections caused by susceptible bacteria. — NCATS

Clinical trial activity

106 trials · 167 clinical orgs · 26 marketing orgs

Phase 1
11
Phase 2
39
Phase 3
31
Phase 4
34

Earliest trial started Nov 1, 1997 (NCT00003805)

Timeline

1980s

  1. Dec 29, 1981

    Toyama — Earliest FDA Approval

  2. Dec 29, 1981

    Wyeth — NDA Secondary Org

  3. Dec 29, 1981

    Toyama — NDA Organization

  4. Dec 29, 1981

    American Home Products — NDA Secondary Org

  5. Oct 13, 1987

    American Home Products — Marketing Organization

1990s

  1. Oct 22, 1993

    Wyeth — Marketing Organization

  2. Jan 1, 1997

    Earliest Phase 3 Sponsor(trial)

  3. Feb 24, 1998

    Baxalta — NDA Secondary Org

2000s

  1. Jan 1, 2003

    Earliest Phase 2 Sponsor(trial)

  2. Nov 14, 2003

    Istituto Bio Ita Spa — Marketing Organization

  3. Jan 1, 2009

    Earliest Phase 1 Sponsor(trial)

  4. Sep 15, 2009

    Hospira — Marketing Organization

2010s

  1. Oct 21, 2010

    Sandoz — Marketing Organization

  2. Oct 21, 2010

    Novartis — Marketing Organization

  3. May 23, 2011

    Aurobindo Pharma — Marketing Organization

  4. May 23, 2011

    Eugia Pharma — Marketing Organization

  5. Aug 15, 2014

    Mylan — Marketing Organization

  6. Aug 15, 2014

    STERISCIENCE — Marketing Organization

  7. Aug 15, 2014

    ONESOURCE SPECIALTY — Marketing Organization

  8. Jan 13, 2017

    Apollo Hospitals, Chennai, India — Marketing Organization

  9. Jan 13, 2017

    Apollo Pharmacy — Marketing Organization

  10. Jan 13, 2017

    Provepharm Sas — Marketing Organization

  11. Jan 13, 2017

    Milla Pharms — Marketing Organization

  12. Mar 17, 2017

    Wockhardt — Marketing Organization

  13. Mar 17, 2017

    Apotex — Marketing Organization

  14. May 11, 2018

    Fresenius — Marketing Organization

  15. Aug 10, 2018

    Qilu Pharmaceutical Co., Ltd. — Marketing Organization

  16. Aug 10, 2018

    Shandong Lanjin Pharmaceuticals Co.,Ltd — Marketing Organization

  17. Jul 29, 2019

    Astral — Marketing Organization

2020s

  1. Feb 16, 2021

    Sagent Pharmaceuticals, Inc. — Marketing Organization

  2. Feb 16, 2021

    Nichi-Iko Pharmaceutical Co., Ltd. — Marketing Organization

  3. Apr 3, 2025

    B. Braun — NDA Secondary Org

Indications

Approved for

Studied for

Mechanism of action

Combination products

  • zosyn

    with tazobactam

    Also known as piperacillin and tazobactam

Approval history

  • approvedPriority reviewDec 29, 1981

Chemistry & pharmacology

Loading structure…

SMILES

CCN1CCN(C(=O)N[C@@H](C(=O)N[C@@H]2C(=O)N3[C@@H]2SC(C)(C)[C@@H]3C(=O)O)c2ccccc2)C(=O)C1=O
Mol. weight
517.56 g/mol
Lipinski Ro5
1 violation(s)
Rule of 3
No
Chirality
Single Stereoisomer
Inorganic
No
Polymer
No
Delivery
Parenteral
Availability
Prescription Only

Oral

No

Parenteral

Yes

Topical

No

Sources

Also known as

  • (2s,5r,6r)-6-{[(2r)-2-{[(4-ethyl-2,3-dioxopiperazin-1-yl)carbonyl]amino}-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
  • (2s,5r,6r)-6-{[(2r)-2-{[(4-ethyl-2,3-dioxopiperazin-1-yl)carbonyl]amino}-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
  • ahp brand of pipercillin sodium - tazobactam sodium
  • ceftolozane - tazobactam
  • ceftolozane, tazobactam drug combination
  • cl-227193
  • cl-227193
  • cl-307579
  • isipen
  • isipen
  • pentacillin
  • piperacil
  • piperacilina
  • piperacilina
  • piperacillin
  • piperacillin
  • piperacillin
  • piperacillin
  • piperacillin
  • piperacillin
  • piperacillin
  • piperacillin
  • piperacillina
  • piperacillin anhydrous
  • piperacillin anhydrous
  • pipéracilline
  • pipéracilline
  • piperacillin hydrate
  • piperacillin hydrate
  • piperacillin hydrate
  • piperacillin hydrate
  • piperacillin hydrate
  • piperacillin hydrate
  • piperacillin sodium
  • piperacillin sodium
  • piperacillin sodium
  • piperacillin sodium
  • piperacillin sodium salt
  • piperacillin - tazobactam
  • piperacillin-tazobactam combination product
  • piperacillin, tazobactam drug combination
  • piperacillinum
  • piperacillinum
  • pipercillin sodium - tazobactam sodium
  • pipracil
  • pipracil
  • pipracil
  • pipracil
  • pipril
  • pipril
  • t-1220
  • t-1220
  • tazocillin
  • tazocillin
  • tazocin
  • tazocin
  • tazocin
  • zerbaxa
  • zerbaxa
  • zerbaxa
  • zosyn

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT06954129Phase 4Oct 31, 2025University of Pennsylvania
NCT06712641Phase 4Jun 30, 2025Oslo Metropolitan University, University of Oslo
NCT06123169Phase 3Mar 31, 2024Rouen Normandy University
NCT06184659Phase 4Mar 1, 2024Scandinavian Critical Care Trials Group
NCT06293677Phase 4Mar 1, 2024University of Lausanne
NCT05943223Phase 2Jan 31, 2024McMaster University
NCT07096310Phase 1/Phase 2 (Phase 2)Jan 1, 2024Ain Shams University
NCT05753735Phase 2Dec 20, 2023Case Western Reserve University
NCT06422533N/ANov 7, 2023Government of Mexico
NCT05981079Phase 4Jul 31, 2023Hebei University, Liaocheng People's Hospital, Nanjing Medical University, Qingdao University, Shandong Province Qianfoshan Hospital, Shandong Provincial Hospital, Shandong University, Shengli Oilfield Central Hospital, Tai'an Central Hospital
NCT05565222Phase 3Jan 31, 2023Assistance Publique - Hôpitaux de Paris
NCT05355350Phase 4Jul 1, 2022Hebrew University, Technion University, Tel Aviv University
NCT05102162Phase 4Dec 31, 2021Food and Drug Administration, University of Florida
NCT05060419Phase 2Oct 8, 2021Fudan University, Qilu Pharmaceutical Co., Ltd.
NCT04816968Phase 1Sep 30, 2021Revert ONLUS, University of Milan
NCT04983901Phase 2Sep 14, 2021University of Texas at Houston
NCT04948463Phase 4Jul 31, 2021Murdoch University
NCT04394182N/AApr 21, 2020Clinica Virgen Milagrosa, Fundacion GenesisCare, Hospital Vithas Valencia Consuelo
NCT04276480N/AApr 1, 2020University of Bordeaux
NCT03990467N/ASep 30, 2019University of Lyon
Showing 20 of 106 trials
Page 1 / 6

Organizations

Research & Development (167)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
MerckFor profit7632001
PfizerFor profit7632000
WyethFor profit6032000
Tel Aviv UniversityAcademic/Hospital4222009
Ghent UniversityAcademic/Hospital3322010
University of QueenslandAcademic/Hospital3322014
University of Texas at HoustonAcademic/Hospital3312018
Ain Shams UniversityAcademic/Hospital2222018
AllecraFor profit2222013
BayerFor profit2112005
Duke UniversityAcademic/Hospital2222009
Fundación Pública AndaluzaAcademic/Hospital2212011
Government of MexicoGovernment2212017
Medpace, Inc.For profit2012016
Nanjing Medical UniversityAcademic/Hospital2122012
Ohio State UniversityAcademic/Hospital2122014
People's Liberation Army of ChinaGovernment2212012
Polyphor Ltd.For profit2212018
Prince of Songkla UniversityAcademic/Hospital2212014
Rhode Island HospitalAcademic/Hospital2122012
167 organizations
Page 1 / 9

Marketing (33)

OrganizationOrg typeRelationshipDate
American Home ProductsFor profitNDA2Dec 29, 1981
American Home ProductsFor profitMKTGOct 13, 1987
Apollo Hospitals, Chennai, IndiaAcademic/HospitalMKTGJan 13, 2017
Apollo PharmacyAcademic/HospitalMKTGJan 13, 2017
ApotexFor profitMKTGMar 17, 2017
AstralFor profitMKTGJul 29, 2019
Aurobindo PharmaFor profitMKTGMay 23, 2011
B. BraunFor profitNDA2Apr 3, 2025
BaxaltaFor profitNDA2Feb 24, 1998
Eugia PharmaFor profitMKTGMay 23, 2011
Eugia PharmaFor profitSYNOct 12, 2023
FreseniusFor profitMKTGMay 11, 2018
FreseniusFor profitSYNMay 11, 2018
HospiraFor profitMKTGSep 15, 2009
Istituto Bio Ita SpaFor profitMKTGNov 14, 2003
Milla PharmsFor profitMKTGJan 13, 2017
MylanFor profitMKTGAug 15, 2014
Nichi-Iko Pharmaceutical Co., Ltd.For profitMKTGFeb 16, 2021
NovartisFor profitMKTGOct 21, 2010
ONESOURCE SPECIALTYFor profitMKTGAug 15, 2014
Provepharm SasFor profitMKTGJan 13, 2017
Qilu Pharmaceutical Co., Ltd.For profitMKTGAug 10, 2018
Qilu Pharmaceutical Co., Ltd.For profitSYNAug 10, 2018
STERISCIENCEFor profitMKTGAug 15, 2014
STERISCIENCEFor profitSYNAug 15, 2014
Sagent Pharmaceuticals, Inc.For profitMKTGFeb 16, 2021
SandozFor profitMKTGOct 21, 2010
SandozFor profitSYNOct 29, 2014
Shandong Lanjin Pharmaceuticals Co.,LtdFor profitMKTGAug 10, 2018
ToyamaFor profitNDADec 29, 1981
WockhardtFor profitMKTGMar 17, 2017
WyethFor profitNDA2Dec 29, 1981
WyethFor profitMKTGOct 22, 1993