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cilastatin

Trade name: primaxin

Small moleculeapproved

Approved

Nov 26, 1985

PRIMAXIN® is a combination of cilastatin and imipenem. Cilastatin is a specific and reversible renal dehydropeptidase-I inhibitor. Imipenem is a penem antibacterial drug. Since the antibiotic, imipenem, is hydrolyzed by dehydropeptidase-I, which resides in the brush border of the renal tubule, cilastatin is administered with imipenem to block the metabolism and thus the inactivation of imipenem so that antibacterial levels of imipenem can be attained in the urine. However, cilastatin in and of itself does not have any antibacterial activity. It also prevents the metabolism of leukotriene D4 to leukotriene E4 through the inhibition of leukotriene D4 dipeptidase. — NCATS

Clinical trial activity

41 trials · 33 clinical orgs · 4 marketing orgs

Phase 1
9
Phase 2
26
Phase 3
15
Phase 4
6

Earliest trial started Dec 1, 1997 (NCT00236834)

Timeline

1980s

  1. Nov 26, 1985

    Merck — Earliest FDA Approval

  2. Nov 26, 1985

    Merck — NDA Secondary Org

  3. Nov 26, 1985

    Merck — NDA Organization

  4. 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 imipenem

    Also known as imipenem and cilastatin

  • recarbrio

    with relebactam, imipenem

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

Approval history

  • approvedPriority reviewNov 26, 1985

Chemistry & pharmacology

Loading structure…

SMILES

CC1(C)C[C@@H]1C(=O)N/C(=C\CCCCSC[C@H](N)C(=O)O)C(=O)O
Mol. weight
358.46 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

  • cilastatin
  • cilastatin
  • cilastatin
  • cilastatin
  • cilastatin
  • cilastatin
  • cilastatin
  • cilastatin
  • cilastatin
  • cilastatin
  • cilastatina
  • cilastatina
  • cilastatine
  • cilastatine
  • cilastatin, imipenem drug combination
  • cilastatin monosodium
  • cilastatin sodium
  • cilastatin sodium
  • cilastatin sodium
  • cilastatinum
  • cilastatinum
  • cilastin
  • imipenem - cilastatin
  • imipenem + cilastatin
  • imipenem-cilastatin
  • imipenem-cilastatin, sodium salt
  • (l)-7-(2-amino-2-carboxy-ethylsulfanyl)-2-[(2,2-dimethyl-cyclopropanecarbonyl)-amino]-hept-2-enoic acid
  • (l)-7-(2-amino-2-carboxy-ethylsulfanyl)-2-[(2,2-dimethyl-cyclopropanecarbonyl)-amino]-hept-2-enoic acid
  • mk 0787-mk 0791 mixture
  • mk 787-mk 791 mixture
  • mk-791
  • mk-791
  • primaxin
  • primaxin
  • primaxin
  • primaxin
  • thienam
  • thienam
  • tienam 500
  • (z)-7-((r)-2-amino-2-carboxy-ethylsulfanyl)-2-[((s)-2,2-dimethyl-cyclopropanecarbonyl)-amino]-hept-2-enoic acid
  • (z)-7-((r)-2-amino-2-carboxy-ethylsulfanyl)-2-[((s)-2,2-dimethyl-cyclopropanecarbonyl)-amino]-hept-2-enoic acid
  • zienam
  • (z)-(s)-6-carboxy-6-[(s)-2,2-dimethylcyclopropanecarboxamido]hex-5-enyl-l-cysteine
  • (z)-(s)-6-carboxy-6-[(s)-2,2-dimethylcyclopropanecarboxamido]hex-5-enyl-l-cysteine

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT07229040Phase 2Feb 21, 2025Hospital General Universitario Gregorio Marañon
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
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
NCT03969901Phase 2/Phase 3 (Phase 3)Oct 21, 2019Merck
NCT03894046Phase 3Apr 3, 2019Entasis Therapeutics
NCT03583333Phase 3Sep 18, 2018Merck
NCT03595189Phase 1Jun 19, 2018Autonomous University of Madrid, Spherium Biomed
NCT03445195Phase 2Jan 17, 2018Entasis Therapeutics, Medpace, Inc.
NCT03230916Phase 1Nov 6, 2017Merck
Showing 20 of 41 trials
Page 1 / 3

Organizations

Research & Development (33)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
MerckFor profit131042006
Sinovent Pty Ltd.For profit5522021
PfizerFor profit4332003
Entasis TherapeuticsFor profit3332016
Johnson and JohnsonFor profit3321997
AstraZenecaFor profit2222001
GlaxoSmithKlineFor profit2122011
Hengrui Therapeutics, Inc.For profit2222023
University of ConnecticutAcademic/Hospital2122020
Ain Shams UniversityAcademic/Hospital1112017
Autonomous University of MadridAcademic/Hospital1012018
Fonds NutsOhraAcademic/Hospital1012014
Free University of AmsterdamAcademic/Hospital1012014
Hartford HospitalAcademic/Hospital1112020
Heliopolis UniversityAcademic/Hospital1012017
Hospital General Universitario Gregorio MarañonAcademic/Hospital1112025
Indiana UniversityAcademic/Hospital1012022
Jiao Tong UniversityAcademic/Hospital1112011
Medpace, Inc.For profit1012018
Meiji Seika Pharma Co., Ltd.For profit1112023
33 organizations
Page 1 / 2

Marketing (7)

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