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pyrimethamine

Trade name: daraprim

Small moleculeapproved

Approved

Jan 23, 1953

Pyrimethamine, sold under the trade name Daraprim, is one of the folic acid antagonists that is used as an antimalarial or with a sulfonamide to treat toxoplasmosis. In addition it was approved in Chemoprophylaxis of Malaria. However, resistance to pyrimethamine is prevalent worldwide. It is not suitable as a prophylactic agent for travelers to most areas. Pyrimethamine is well absorbed with peak levels occurring between 2 to 6 hours following administration. It is eliminated slowly and has a plasma half-life of approximately 96 hours. Pyrimethamine is 87% bound to human plasma proteins. Pyrimethamine acts by selectively inhibiting malarial dihydrofolate reductase-thymidylate synthase and the rationale for its therapeutic action is based on the differential requirement between host and parasite for nucleic acid precursors involved in growth. This activity is highly selective against plasmodia and Toxoplasma gondii. Pyrimethamine possesses blood schizonticidal and some tissue schizonticidal activity against malaria parasites of humans. The action of pyrimethamine against Toxoplasma gondii is greatly enhanced when used in conjunction with sulfonamides. — NCATS

Clinical trial activity

179 trials · 188 clinical orgs · 6 marketing orgs

Phase 1
29
Phase 2
76
Phase 3
65
Phase 4
34

Earliest trial started Apr 1, 1982 (NCT00294580)

Timeline

1950s

  1. Jan 23, 1953

    Vyera Pharmaceuticals — Earliest FDA Approval

  2. Jan 23, 1953

    Vyera Pharmaceuticals — NDA Secondary Org

  3. Jan 23, 1953

    Vyera Pharmaceuticals — NDA Organization

1980s

  1. Oct 28, 1981

    Roche — Marketing Organization

  2. Oct 28, 1981

    Roche — NDA Secondary Org

1990s

  1. Jan 1, 1999

    Earliest Phase 1 Sponsor(trial)

  2. Jan 1, 1999

    Earliest Phase 2 Sponsor(trial)

  3. Jan 1, 1999

    Earliest Phase 3 Sponsor(trial)

2020s

  1. Feb 28, 2020

    Cerovene — Marketing Organization

  2. Jul 27, 2021

    Alvogen — Marketing Organization

  3. Aug 13, 2021

    Teva — Marketing Organization

  4. Oct 25, 2022

    Aurobindo Pharma — Marketing Organization

Indications

Approved for

Studied for

Mechanism of action

Combination products

Approval history

  • approvedPriority reviewJan 23, 1953

Chemistry & pharmacology

Loading structure…

SMILES

CCC1=NC(N)=NC(N)=C1C2=CC=C(Cl)C=C2
Mol. weight
248.711 g/mol
Lipinski Ro5
Pass
Rule of 3
No
Chirality
Achiral Molecule
Inorganic
No
Polymer
No
Delivery
Oral
Availability
Prescription Only

Oral

Yes

Parenteral

No

Topical

No

Sources

Also known as

  • 2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidine
  • 2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidine
  • 2,4-diamino-5-chlorophenyl-6-ethylpyrimidine
  • 2,4-diamino-5-chlorophenyl-6-ethylpyrimidine
  • 2,4-diamino-5-(p-chlorophenyl)-6-ethylpyrimidine
  • 2,4-diamino-5-(p-chlorophenyl)-6-ethylpyrimidine
  • 5-(4'-chlorophenyl)-2,4-diamino-6-ethylpyrimidine
  • 5-(4'-chlorophenyl)-2,4-diamino-6-ethylpyrimidine
  • 5-(4-chlorophenyl)-6-ethyl-2,4-diaminopyrimidine
  • 5-(4-chlorophenyl)-6-ethyl-2,4-diaminopyrimidine
  • 5-(4-chlorophenyl)-6-ethyl-2,4-pyrimidinediamine
  • 5-(4-chlorophenyl)-6-ethyl-2,4-pyrimidinediamine
  • cd
  • cd
  • chloridin
  • chloridin
  • chloridin
  • chloridine
  • chloridine
  • chloridine
  • chloridyn
  • chloridyn
  • dapsone mixture with pyrimethamine
  • daraprim
  • daraprim
  • daraprim
  • daraprim
  • diaminopyritamin
  • diaminopyritamin
  • diaminopyritamin
  • ethylpyrimidine
  • ethylpyrimidine
  • gnf-pf-5586
  • gnf-pf-5586
  • malacide
  • malacide
  • maloprim
  • maloprim
  • pirimecidan
  • pirimetamin
  • pirimetamina
  • pirimetamina
  • primethamine
  • primethamine
  • pyrimethamin
  • pyrimethamine
  • pyrimethamine
  • pyrimethamine
  • pyrimethamine
  • pyrimethamine
  • pyrimethamine
  • pyrimethamine
  • pyrimethamine
  • pyrimethamine
  • pyrimethamine
  • pyrimethamine
  • pyrimethaminum
  • pyrimethaminum
  • pyrimethanine
  • tcmdc-123831
  • tcmdc-123831
  • tcmdc-125860
  • tcmdc-125860

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT06083688Phase 4Oct 31, 2024Kamuzu University of Health Sciences, University of Liverpool
NCT06182176N/AMay 27, 2024Kintampo Health Research Centre, Ghana, University of London
NCT06240520Phase 1/Phase 2 (Phase 2)Apr 30, 2024Erasmus University Rotterdam, ZonMw: The Netherlands Organisation for Health Research and Development
NCT06173206Phase 3Mar 15, 2024University of London
NCT06166498Phase 3Feb 15, 2024University of London
NCT05678348Early Phase 1 (Phase 1)Aug 3, 2023Washington University in St. Louis
NCT05946642Phase 3Jul 15, 2023Malaria Consortium
NCT05497063Phase 1Dec 31, 2022Emzor Pharmaceutical Industries Limited
NCT05426434Phase 3Aug 31, 2022Curtin University, Government of Papua New Guinea, Menzies School of Health Research, University of Liverpool, University of Melbourne
NCT05323721Phase 4Jun 1, 2022Government of Uganda, Malaria Consortium
NCT05081089Phase 2Oct 12, 2021Malaria Research and Training Center, Bamako, Mali, University of London
NCT04816461Phase 4Jul 31, 2021Institut et Haute école de la Santé, La Source
NCT04577469Phase 1Dec 31, 2020ACDIMA Biocenter, Emzor Pharmaceutical Industries Limited
NCT04336189Phase 3Jun 30, 2020Infectious Disease Institute, Kampala, Uganda, Makerere University, National Institutes of Health (NIH), University of California, San Francisco
NCT04319380Phase 3May 31, 2020Institut de Recherche en Sciences de la Santé, Direction Régionale de l'Ouest (IRSS-DRO), Institut et Haute école de la Santé, La Source, Malaria Research and Training Center, Bamako, Mali, University of London
NCT04235816Phase 3May 1, 2020Bill and Melinda Gates Foundation, Government of Sierra Leone, University of Barcelona, University of Sierra Leone
NCT04280692Phase 1/Phase 2 (Phase 2)Feb 29, 2020Kenya Medical Research Institute, Sanaria Inc., University of Heidelberg, University of Oxford, Wellcome Trust
NCT04189744Phase 3Dec 15, 2019University of London
NCT04160026Phase 4Nov 30, 2019Kenya Medical Research Institute, Kilimanjaro Christian Medical College, Tanzania, National Institute for Medical Research, Tanzania, University of Bergen, University of Liverpool, University of London, University of Malawi
NCT04086719Phase 1Sep 10, 2019Bristol-Myers Squibb
Showing 20 of 179 trials
Page 1 / 9

Organizations

Research & Development (188)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
University of LondonAcademic/Hospital564741982
National Institute of Allergy and Infectious Diseases (NIAID)Government171551999
Centers for Disease Control and Prevention (CDC)Government14932000
University of CopenhagenAcademic/Hospital10232002
World Health OrganizationGovernment10031995
University of BarcelonaAcademic/Hospital8631995
Bill and Melinda Gates FoundationAcademic/Hospital7042002
Cheikh Anta Diop University, SenegalAcademic/Hospital7142002
Government of FranceGovernment7232002
Kenya Medical Research InstituteAcademic/Hospital7142002
Malaria Research and Training Center, Bamako, MaliAcademic/Hospital7032005
University of California, San FranciscoAcademic/Hospital7732004
Institute of Tropical Medicine, BelgiumAcademic/Hospital6632003
Makerere UniversityAcademic/Hospital6122005
Medical Research Council, The GambiaGovernment6031982
Albert Schweitzer HospitalAcademic/Hospital5432002
Kilimanjaro Christian Medical College, TanzaniaAcademic/Hospital5042005
Medical Research CouncilGovernment5032003
Medical Research Council, South AfricaGovernment5012002
National Institute for Medical Research, TanzaniaGovernment5032004
188 organizations
Page 1 / 10

Marketing (8)

OrganizationOrg typeRelationshipDate
AlvogenFor profitMKTGJul 27, 2021
Aurobindo PharmaFor profitMKTGOct 25, 2022
CeroveneFor profitMKTGFeb 28, 2020
RocheFor profitMKTGOct 28, 1981
RocheFor profitNDA2Oct 28, 1981
TevaFor profitMKTGAug 13, 2021
Vyera PharmaceuticalsFor profitNDA2Jan 23, 1953
Vyera PharmaceuticalsFor profitNDAJan 23, 1953