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trimethoprim

Small moleculeapproved

Approved

Jan 1, 1962

Trimethoprim (TMP) is an antibiotic is used for the treatment of initial episodes of uncomplicated urinary tract infections due to susceptible strains of the following organisms: Escherichia coli, Proteus mirabilis, Klebsiella pneumoniae, Enterobacter species, and coagulase-negative Staphylococcus species, including S. saprophyticus. Cultures and susceptibility tests should be performed to determine the susceptibility of the bacteria to trimethoprim. Therapy may be initiated prior to obtaining the results of these tests. Trimethoprim is rapidly absorbed following oral administration. It exists in the blood as unbound, protein-bound, and metabolized forms. Ten to twenty percent of trimethoprim is metabolized, primarily in the liver; the remainder is excreted unchanged in the urine. The principal metabolites of trimethoprim are the 1- and 3-oxides and the 3'- and 4'-hydroxy derivatives. The free form is considered to be the therapeutically active form. Approximately 44% of trimethoprim is bound to plasma proteins. Trimethoprim blocks the production of tetrahydrofolic acid from dihydrofolic acid by binding to and reversibly inhibiting the required enzyme, dihydrofolate reductase. This binding is very much stronger for the bacterial enzyme than for the corresponding mammalian enzyme — NCATS

Clinical trial activity

173 trials · 247 clinical orgs · 56 marketing orgs

Phase 1
21
Phase 2
79
Phase 3
50
Phase 4
34

Earliest trial started Jun 1, 1993 (NCT00002524)

Timeline

1960s

  1. Jan 1, 1962

    Burroughs Wellcome — Earliest FDA Approval

  2. Jan 1, 1962

    Burroughs Wellcome — NDA Organization

1970s

  1. Jul 30, 1973

    Monarch Pharmaceuticals — NDA Secondary Org

  2. Jul 30, 1973

    Sun Pharmaceuticals — NDA Secondary Org

1980s

  1. May 30, 1980

    Roche — NDA Secondary Org

  2. May 19, 1981

    Teva — Marketing Organization

  3. May 19, 1981

    Teva — NDA Secondary Org

  4. Jun 23, 1981

    Sun Pharmaceuticals — Marketing Organization

  5. May 19, 1982

    Fosun — Marketing Organization

  6. May 19, 1982

    Fosun — NDA Secondary Org

  7. Jul 30, 1982

    Mayne Pharma — NDA Secondary Org

  8. Jul 30, 1982

    Dr. Reddy's Laboratories — Marketing Organization

  9. Jul 30, 1982

    Dr. Reddy's Laboratories — NDA Secondary Org

  10. Jan 7, 1983

    Pharmaceutical Associates — Marketing Organization

  11. Jan 7, 1983

    Pharmaceutical Associates — NDA Secondary Org

  12. May 9, 1983

    Watson Pharmaceuticals — Marketing Organization

  13. May 9, 1983

    Watson Pharmaceuticals — NDA Secondary Org

  14. Nov 14, 1984

    Mutual Pharmaceutical — Marketing Organization

  15. Feb 15, 1985

    Novel Anti-Infective Technologies, LLC — Marketing Organization

  16. Jun 24, 1985

    Superpharm — Marketing Organization

  17. Sep 10, 1985

    Pliva — Marketing Organization

  18. Sep 19, 1985

    Heritage Pharma — Marketing Organization

  19. Oct 29, 1985

    Ani Pharmaceuticals — Marketing Organization

  20. Nov 13, 1986

    AiPing Pharm Inc — Marketing Organization

  21. Apr 30, 1987

    West-Ward Pharmaceutical — Marketing Organization

  22. Apr 30, 1987

    Hikma — Marketing Organization

  23. May 23, 1988

    Naska Pharmacal — Marketing Organization

  24. Oct 20, 1988

    Allergan — NDA Secondary Org

  25. Oct 20, 1988

    SmithKline Beckman — NDA Secondary Org

1990s

  1. Aug 30, 1991

    Roxane Laboratories — Marketing Organization

  2. Aug 30, 1991

    Boehringer Ingelheim — Marketing Organization

  3. Sep 11, 1992

    Hospira — Marketing Organization

  4. Jan 1, 1993

    Earliest Phase 2 Sponsor(trial)

  5. Jun 23, 1995

    Allegis Pharma — NDA Secondary Org

  6. Jun 23, 1995

    PANGAEA — Marketing Organization

  7. Jan 1, 1997

    Earliest Phase 3 Sponsor(trial)

  8. Feb 14, 1997

    Bausch & Lomb — Marketing Organization

  9. Dec 29, 1997

    Hi Tech Pharmaceuticals — Marketing Organization

  10. Apr 13, 1998

    Sandoz — Marketing Organization

  11. Apr 13, 1998

    Novartis — Marketing Organization

  12. Dec 17, 1998

    Akorn, Inc. — Marketing Organization

  13. Dec 17, 1998

    Epic Pharma Llc — Marketing Organization

  14. Jan 1, 1999

    Earliest Phase 1 Sponsor(trial)

2000s

  1. Jun 26, 2001

    Able Laboratories — Marketing Organization

  2. Jun 26, 2001

    Able Laboratories — NDA Secondary Org

  3. Jan 27, 2005

    Amneal Pharmaceuticals — Marketing Organization

  4. Oct 7, 2005

    VistaPharm, Inc. — Marketing Organization

  5. Nov 13, 2006

    Prasco LLC — Marketing Organization

  6. Jan 24, 2007

    Lannett Company, Inc. — Marketing Organization

  7. Jan 25, 2007

    Chartwell Pharmaceuticals — Marketing Organization

2010s

  1. Feb 16, 2010

    Aurobindo Pharma — Marketing Organization

  2. Dec 22, 2010

    Glenmark Pharmaceuticals — Marketing Organization

  3. Aug 30, 2017

    Mylan — Marketing Organization

  4. Aug 30, 2017

    PHARMOBEDIENT — Marketing Organization

  5. Jun 26, 2019

    Somerset Pharmaceuticals — Marketing Organization

  6. Jun 26, 2019

    ANDA Repository — Marketing Organization

2020s

  1. Jan 5, 2021

    Lupin — Marketing Organization

  2. Feb 8, 2022

    Novitium Pharma — Marketing Organization

Indications

Approved for

Studied for

Mechanism of action

Combination products

  • polytrim

    with polymyxin b sulfate

  • septra

    with sulfamethoxazole

    Also known as bactrim, bactrim ds, bactrim pediatric, cotrim, cotrim d.s, septra ds, septra grape, sulfamethoprim, sulfamethoprim-ds, sulfamethoxazole and trimethoprim double strength, sulfamethoxazole and trimethoprim single strength, sulfatrim, sulfatrim-ds, sulfatrim pediatric, sulfatrim-ss, trimeth/sulfa

Approval history

  • approvedJan 1, 1962

Chemistry & pharmacology

Loading structure…

SMILES

COc1cc(Cc2cnc(N)nc2N)cc(OC)c1OC.COc1cc(Cc2cnc(N)nc2N)cc(OC)c1OC.O=S(=O)(O)O
Mol. weight
678.73 g/mol
Lipinski Ro5
Pass
Rule of 3
No
Chirality
Achiral Molecule
Inorganic
No
Polymer
No
Delivery
Topical
Availability
Prescription Only

Oral

No

Parenteral

No

Topical

Yes

Sources

Also known as

  • 2,4-diamino-5-(3,4,5-trimethoxybenzyl)pyrimidine
  • 2,4-diamino-5-(3,4,5-trimethoxybenzyl)pyrimidine
  • 5-[(3,4,5-trimethoxyphenyl)methyl]-2,4-pyrimidinediamine
  • 5-[(3,4,5-trimethoxyphenyl)methyl]-2,4-pyrimidinediamine
  • aminobenzene
  • aminobenzene
  • aminophen
  • aminophen
  • anilin
  • anilin
  • anilina
  • anilina
  • aniline
  • aniline
  • aniline
  • aniline
  • aniline, (13)c-labeled cpd
  • aniline, (14)c-labeled cpd
  • aniline, 15n-labeled cpd
  • aniline, 2-(13)c-labeled cpd
  • aniline, 3-(13)c-labeled cpd
  • aniline, 3h-labeled cpd
  • aniline, 4-(13)c-labeled cpd
  • aniline aluminium salt
  • aniline, conjugate acid
  • aniline dihydrofluoride
  • aniline diphosphate (1:1)
  • aniline diphosphate (3:1)
  • aniline diphosphate (4:1)
  • aniline hydrobromide
  • aniline hydrochloride
  • aniline hydrochloride-(14)c-labeled cpd
  • aniline hydrochloride-(15)n-labeled cpd
  • aniline hydrofluoride
  • aniline hydrogen iodide
  • aniline, ion(1+)
  • aniline, magnesium (1:1) salt
  • aniline, monolithium salt
  • aniline monosulfate
  • aniline nitrate
  • aniline oil
  • aniline oil
  • aniline perchlorate
  • aniline phosphate (1:1)
  • aniline phosphate (1:2)
  • aniline phosphate (2:1)
  • aniline phosphonate (1:1)
  • aniline, sodium salt
  • aniline sulfate
  • aniline sulfate (2:1)
  • aniline sulfate (2:1), (14)c-labeled cpd
  • anilinum
  • anilinum
  • bactrim
  • bactrim
  • benzenamine
  • benzenamine
  • benzenamine
  • benzeneamine
  • benzeneamine
  • bw-5672
  • bw-5672
  • bw-56-72
  • bw-56-72
  • bw-72u
  • bw-72u
  • fentanyl impurity f
  • fentanyl impurity f
  • huile d'aniline
  • huile d'aniline
  • ipral
  • ipral
  • kyanol
  • kyanol
  • ledatrim
  • monotrim
  • monotrim
  • phenylamine
  • phenylamine
  • polytrim
  • polytrim
  • primsol
  • primsol
  • proloprim
  • proloprim
  • proloprin
  • septra
  • septra
  • syraprim
  • syraprim
  • tcmdc-125538
  • tcmdc-125538
  • tiempe
  • tiempe
  • trimethioprim
  • trimethoprim
  • trimethoprim
  • trimethoprim
  • trimethoprim
  • trimethoprim
  • trimethoprim
  • trimethoprim
  • trimethoprim
  • trimethoprim
  • trimethoprim
  • trimethoprim
  • triméthoprime
  • triméthoprime
  • trimethoprim hcl
  • trimethoprim hcl
  • trimethoprim hcl
  • trimethoprim hydrochloride
  • trimethoprim hydrochloride
  • trimethoprim hydrochloride
  • trimethoprim hydrochloride
  • trimethoprim specified impurity k
  • trimethoprim specified impurity k
  • trimethoprim sulfate
  • trimethoprim sulfate
  • trimethoprim sulfate
  • trimethoprimum
  • trimethoprimum
  • trimetoprim
  • trimetoprima
  • trimetoprima
  • trimogal
  • trimogal
  • trimopan
  • trimopan
  • trimopan
  • trimpex
  • trimpex
  • trimpex 200
  • trimpex 200
  • triprimix 200

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT06841705Phase 2Jul 15, 2025Harvard University, Takeda
NCT06982105Phase 4May 20, 2025Indiana University
NCT07202078Phase 2/Phase 3 (Phase 3)May 7, 2025Monash University
NCT07202091Phase 2/Phase 3 (Phase 3)May 6, 2025Monash University
NCT07202052Phase 2/Phase 3 (Phase 3)May 6, 2025Monash University
NCT06536374Phase 2Nov 30, 2024University of Texas, San Antonio
NCT06499233Phase 4Jul 20, 2024Huazhong University of Science and Technology
NCT06336824Phase 3Jun 28, 2024Clinical Research Centre, Malaysia, Government of Malaysia
NCT05823467N/AJun 26, 2023University of Alberta
NCT05678621Phase 2/Phase 3 (Phase 3)Jan 31, 2023Monash University
NCT05224401Phase 3Jan 10, 2023Lund University
NCT05418777Phase 1/Phase 2 (Phase 2)Sep 28, 2022Oakland University
NCT05268120N/AJul 25, 2022Leiden University
NCT05488340Phase 2/Phase 3 (Phase 3)Jul 13, 2022Locus Biosciences, Parexel
NCT05398679Phase 4Jun 1, 2022University of Barcelona
NCT05302531Phase 1Apr 4, 2022Fresenius, Société Francophone Nutrition Clinique et Métabolisme, University of Lorraine
NCT05199324Phase 3Apr 1, 2022Changi General Hospital, Melbourne Health, Nanyang Technological University, National University of Singapore, Ng Teng Fong General Hospital, Rush University, Sengkang General Hospital, Singapore Clinical Research Institute, Singapore General Hospital, Sungkyunkwan University, University of London, University of Malaya, University of Queensland
NCT05274672Phase 4Mar 1, 2022Baylor Scott and White, Baylor University, Yeshiva University
NCT05100654N/AOct 30, 2021Loyola University, University of Chicago
NCT04851015Phase 3Jun 30, 2021McGill University
Showing 20 of 173 trials
Page 1 / 9

Organizations

Research & Development (247)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
National Institute of Allergy and Infectious Diseases (NIAID)Government272151999
National Cancer Institute (NCI)Government7221993
University of California, San FranciscoAcademic/Hospital7542004
University of WashingtonAcademic/Hospital7332002
Harvard UniversityAcademic/Hospital6442001
Baylor UniversityAcademic/Hospital5332007
Glaxo WellcomeFor profit5031999
National Institutes of Health (NIH)Government5041999
University of PennsylvaniaAcademic/Hospital5442006
Johns Hopkins UniversityAcademic/Hospital4232007
Monash UniversityAcademic/Hospital4412023
The University of Texas, DallasAcademic/Hospital4132005
Thomas Jefferson UniversityAcademic/Hospital4132007
University of ChicagoAcademic/Hospital4232006
University of North Carolina at Chapel HillAcademic/Hospital4222006
Instituto Nacional de Ciencias Medicas y Nutricion Salvador ZubiranGovernment3312013
Jacobus PharmaceuticalFor profit3131999
Kenya Medical Research InstituteAcademic/Hospital3032002
Loyola UniversityAcademic/Hospital3121994
Makerere UniversityAcademic/Hospital3112007
247 organizations
Page 1 / 13

Marketing (75)

OrganizationOrg typeRelationshipDate
ANDA RepositoryFor profitMKTGJun 26, 2019
Able LaboratoriesFor profitMKTGJun 26, 2001
Able LaboratoriesFor profitNDA2Jun 26, 2001
AbraxisFor profitMKTG—
AiPing Pharm IncFor profitMKTGNov 13, 1986
Akorn, Inc.For profitMKTGDec 17, 1998
Akorn, Inc.For profitSYNDec 29, 1997
Allegis PharmaFor profitNDA2Jun 23, 1995
AllerganFor profitNDA2Oct 20, 1988
AlpharmaFor profitMKTG—
Amneal PharmaceuticalsFor profitMKTGJan 27, 2005
Ani PharmaceuticalsFor profitMKTGOct 29, 1985
Ani PharmaceuticalsFor profitSYNOct 29, 1985
Athenex, Inc.For profitMKTG—
Aurobindo PharmaFor profitMKTGFeb 16, 2010
Bausch & LombFor profitMKTGFeb 14, 1997
Bausch & LombFor profitSYNFeb 14, 1997
Bedford PharmaceuticalsFor profitMKTG—
Boehringer IngelheimFor profitMKTGAug 30, 1991
Burroughs WellcomeFor profitNDAJan 1, 1962
Chartwell PharmaceuticalsFor profitMKTGJan 25, 2007
Chartwell PharmaceuticalsFor profitSYNJan 24, 2007
Dr. Reddy's LaboratoriesFor profitMKTGJul 30, 1982
Dr. Reddy's LaboratoriesFor profitNDA2Jul 30, 1982
Epic Pharma LlcFor profitMKTGDec 17, 1998
FosunFor profitMKTGMay 19, 1982
FosunFor profitNDA2May 19, 1982
Glenmark PharmaceuticalsFor profitMKTGDec 22, 2010
Glenmark PharmaceuticalsFor profitSYNDec 22, 2010
Heather PharmaFor profitNDA2—
Heritage PharmaFor profitSYNSep 19, 1985
Heritage PharmaFor profitMKTGSep 19, 1985
Hi Tech PharmaceuticalsFor profitMKTGDec 29, 1997
HikmaFor profitMKTGApr 30, 1987
HospiraFor profitMKTGSep 11, 1992
InterpharmFor profitMKTG—
Lannett Company, Inc.For profitMKTGJan 24, 2007
LupinFor profitMKTGJan 5, 2021
LupinFor profitSYNJan 5, 2021
Mayne PharmaFor profitNDA2Jul 30, 1982
Monarch PharmaceuticalsFor profitNDA2Jul 30, 1973
Mutual PharmaceuticalFor profitMKTGNov 14, 1984
MylanFor profitMKTGAug 30, 2017
Naska PharmacalFor profitMKTGMay 23, 1988
NovartisFor profitMKTGApr 13, 1998
Novel Anti-Infective Technologies, LLCFor profitMKTGFeb 15, 1985
Novitium PharmaFor profitMKTGFeb 8, 2022
PANGAEAFor profitMKTGJun 23, 1995
PHARMOBEDIENTFor profitMKTGAug 30, 2017
Pharmaceutical AssociatesFor profitMKTGJan 7, 1983
Pharmaceutical AssociatesFor profitNDA2Jan 7, 1983
PlivaFor profitMKTGSep 10, 1985
Prasco LLCFor profitMKTGNov 13, 2006
RocheFor profitNDA2May 30, 1980
Roxane LaboratoriesFor profitMKTGAug 30, 1991
SandozFor profitMKTGApr 13, 1998
SandozFor profitSYNApr 13, 1998
ShionogiFor profitMKTG—
SmithKline BeckmanFor profitNDA2Oct 20, 1988
Somerset PharmaceuticalsFor profitMKTGJun 26, 2019
Somerset PharmaceuticalsFor profitSYNJun 26, 2019
Soremartec Italia S.r.l.For profitMKTG—
Sun PharmaceuticalsFor profitMKTGJun 23, 1981
Sun PharmaceuticalsFor profitSYNJul 30, 1973
Sun PharmaceuticalsFor profitNDA2Jul 30, 1973
SuperpharmFor profitMKTGJun 24, 1985
TevaFor profitMKTGMay 19, 1981
TevaFor profitSYNSep 19, 1985
TevaFor profitSYNOct 31, 1991
TevaFor profitNDA2May 19, 1981
Upsher-Smith LaboratoriesFor profitMKTG—
VistaPharm, Inc.For profitMKTGOct 7, 2005
Watson PharmaceuticalsFor profitMKTGMay 9, 1983
Watson PharmaceuticalsFor profitNDA2May 9, 1983
West-Ward PharmaceuticalFor profitMKTGApr 30, 1987