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imipenem

Trade name: primaxin

Small moleculeapproved

Approved

Jun 1, 1985

Imipenem is a beta-lactam antibiotic belongings to the subgroup of carbapenems. Imipenem has a broad spectrum of activity against aerobic and anaerobic Gram positive as well as Gram negative bacteria. It is particularly important for its activity against Pseudomonas aeruginosa and the Enterococcus species. Imipenem is rapidly degraded by the renal enzyme dehydropeptidase when administered alone, and is always co-administered with cilastatin to prevent this inactivation. The bactericidal activity of imipenem results from the inhibition of cell wall synthesis. Its greatest affinity is for penicillin binding proteins (PBPs) 1A, 1B, 2, 4, 5 and 6 of Escherichia coli, and 1A, 1B, 2, 4 and 5 of Pseudomonas aeruginosa. The lethal effect is related to binding to PBP 2 and PBP 1B. Imipenem is marketed under the brand name Primaxin. PRIMAXIN I.M. (Imipenem and Cilastatin for Injectable Suspension) is a formulation of imipenem (a thienamycin antibiotic) and cilastatin sodium (the inhibitor of the renal dipeptidase, dehydropeptidase I). PRIMAXIN I.M. is a potent broad spectrum antibacterial agent for intramuscular administration. — NCATS

Clinical trial activity

71 trials · 70 clinical orgs · 4 marketing orgs

Phase 1
11
Phase 2
26
Phase 3
20
Phase 4
22

Earliest trial started Dec 1, 1997 (NCT00236834)

Timeline

1980s

  1. Jun 1, 1985

    Earliest FDA Approval

  2. Nov 26, 1985

    Merck — First NDA Organization

  3. Nov 26, 1985

    Merck — NDA Organization

  4. Nov 26, 1985

    Merck — NDA Secondary Org

  5. Jan 8, 1987

    Merck — Marketing Organization

1990s

  1. Jan 1, 1997

    Earliest Phase 3 Sponsor(trial)

2000s

  1. Jan 1, 2007

    Earliest Phase 2 Sponsor(trial)

2010s

  1. Jan 1, 2011

    Merck — Earliest Phase 1 Sponsor(trial)

  2. Nov 16, 2011

    Hospira — Marketing Organization

  3. Dec 21, 2011

    ACS Dobfar — Marketing Organization

  4. Dec 12, 2019

    Hq Speciality Pharma — Marketing Organization

Indications

Approved for

Studied for

Mechanism of action

Combination products

  • primaxin

    with cilastatin

    Also known as imipenem and cilastatin

  • recarbrio

    with cilastatin, relebactam

    Also known as imipenem, cilastatin and relebactam, imipenem/cilastatin/relebactam

Approval history

  • approvedJun 1, 1985

Chemistry & pharmacology

Loading structure…

SMILES

C[C@@H](O)[C@H]1C(=O)N2C(C(=O)O)=C(SCCNC=N)C[C@H]12
Mol. weight
299.35 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

Also known as

  • (5r,6s)-3-(2-formimidoylamino-ethylsulfanyl)-6-((r)-1-hydroxy-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid
  • (5r,6s)-3-(2-formimidoylamino-ethylsulfanyl)-6-((r)-1-hydroxy-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid
  • (5r,6s)-3-((2-(formimidoylamino)ethyl)thio)-6-((r)-1-hydroxyethyl)-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid
  • (5r,6s)-3-((2-(formimidoylamino)ethyl)thio)-6-((r)-1-hydroxyethyl)-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid
  • (5r,6s)-6-((r)-1-hydroxyethyl)-3-(2-(iminomethylamino)ethylthio)-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carbonsaeure
  • (5r,6s)-6-((r)-1-hydroxyethyl)-3-(2-(iminomethylamino)ethylthio)-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carbonsaeure
  • carbapenem
  • carbapenem
  • carbepenem
  • imipemide
  • imipemide
  • imipemide
  • imipenem
  • imipenem
  • imipenem
  • imipenem
  • imipenem
  • imipenem
  • imipenem
  • imipenem
  • imipenem
  • imipenem
  • imipenem anhydrous
  • imipenem anhydrous
  • imipenem + cilastatin
  • imipenem hydrate
  • imipenem hydrate
  • imipenem hydrate
  • imipenemum
  • imipenemum
  • imipenen
  • mk0787
  • mk0787
  • mk-0787
  • mk-0787
  • n-formimidoylthienamycin
  • n-formimidoylthienamycin
  • n-formimidoyl thienamycin
  • n-formimidoyl thienamycin
  • tienamycin

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT06569056Phase 3Sep 25, 2024Hengrui Therapeutics, Inc.
NCT06144060Phase 2Dec 31, 2023Hengrui Therapeutics, Inc.
NCT06059846Phase 3Nov 30, 2023GlaxoSmithKline, Spero Therapeutics
NCT05887908Phase 3May 23, 2023Meiji Seika Pharma Co., Ltd.
NCT05561764Phase 4Dec 31, 2022Indiana University, Merck, Q2 solutions, The University of Texas, Dallas, University of Connecticut, University of Pittsburgh
NCT05204368Phase 3Mar 31, 2022Sinovent Pty Ltd.
NCT05204563Phase 3Mar 31, 2022Sinovent Pty Ltd.
NCT05146154Phase 4Jan 31, 2022Merck, University of Illinois at Chicago
NCT04983901Phase 2Sep 14, 2021University of Texas at Houston
NCT04785924Phase 4Jun 7, 2021Merck, University of Florida
NCT04802863Phase 1Mar 25, 2021Sinovent Pty Ltd.
NCT04801043Phase 1Mar 2, 2021Sinovent Pty Ltd.
NCT04787562Phase 1Feb 25, 2021Sinovent Pty Ltd.
NCT04493151Phase 1Sep 1, 2020Hartford Hospital, Merck, University of Connecticut
NCT04482569Phase 1Jul 10, 2020Sinovent Pty Ltd.
NCT04310930Phase 2/Phase 3 (Phase 3)Mar 31, 2020Cystic Fibrosis Foundation, Erasmus University Rotterdam, Government of Australia, Griffith University, James Cook University Hospital, Middlesbrough, UK, Monash University, Murdoch University, Newcastle University, South Australian Health and Medical Research Institute, University of Copenhagen, University of Manitoba, University of Melbourne, University of Paris, University of Queensland
NCT04147221Phase 1Jan 31, 2020Merck, University of Connecticut
NCT04208763N/ADec 20, 2019Institute of Liver and Biliary Sciences, India
NCT03969901Phase 2/Phase 3 (Phase 3)Oct 21, 2019Merck
NCT03894046Phase 3Apr 3, 2019Entasis Therapeutics
Showing 20 of 71 trials
Page 1 / 4

Organizations

Research & Development (70)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
MerckFor profit181042006
Sinovent Pty Ltd.For profit6622020
Prince of Songkla UniversityAcademic/Hospital5512008
PfizerFor profit4332003
Entasis TherapeuticsFor profit3332016
Institute of Liver and Biliary Sciences, IndiaAcademic/Hospital3312012
Johnson and JohnsonFor profit3321997
University of ConnecticutAcademic/Hospital3222020
University of ParisAcademic/Hospital3232009
Ain Shams UniversityAcademic/Hospital2222016
AstraZenecaFor profit2222001
GlaxoSmithKlineFor profit2122011
Hengrui Therapeutics, Inc.For profit2222023
University of LorraineAcademic/Hospital2222016
Central South UniversityAcademic/Hospital1112018
Cystic Fibrosis FoundationAcademic/Hospital1012020
Erasmus University RotterdamAcademic/Hospital1012020
Fonds NutsOhraAcademic/Hospital1012014
Free University of AmsterdamAcademic/Hospital1012014
Fundación Pública AndaluzaAcademic/Hospital1112016
70 organizations
Page 1 / 4

Marketing (7)

OrganizationOrg typeRelationshipDate
ACS DobfarFor profitMKTGDec 21, 2011
HospiraFor profitMKTGNov 16, 2011
Hq Speciality PharmaFor profitMKTGDec 12, 2019
MerckFor profitNDANov 26, 1985
MerckFor profitNDA2Nov 26, 1985
MerckFor profitSYNJul 16, 2019
MerckFor profitMKTGJan 8, 1987