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methimazole

Trade name: tapazole

Small moleculeapproved

Approved

Jun 21, 1950

Methimazole (also known as Tapazole or Thiamazole or MMI) is an antithyroid drug. Methimazole binds to thyroid peroxidase and thereby inhibits the conversion of iodide to iodine. Thyroid peroxidase normally converts iodide to iodine (via hydrogen peroxide as a cofactor) and also catalyzes the incorporation of the resulting iodide molecule onto both the 3 and/or 5 positions of the phenol rings of tyrosines found in thyroglobulin. Thyroglobulin is degraded to produce thyroxine (T4) and tri-iodothyronine (T3), which are the main hormones produced by the thyroid gland. So methimazole effectively inhibits the production of new thyroid hormones. Methimazole is used for the treatment of hyperthyroidism, goiter, Graves disease and psoriasis. — NCATS

Clinical trial activity

21 trials · 25 clinical orgs · 18 marketing orgs

Phase 1
3
Phase 2
8
Phase 3
3
Phase 4
6

Earliest trial started Jun 1, 1995 (NCT00001421)

Timeline

1950s

  1. Jun 21, 1950

    King Pharmaceuticals — Earliest FDA Approval

  2. Jun 21, 1950

    King Pharmaceuticals — NDA Secondary Org

  3. Jun 21, 1950

    King Pharmaceuticals — NDA Organization

1990s

  1. Jan 1, 1995

    Earliest Phase 2 Sponsor(trial)

2000s

  1. Mar 29, 2000

    Mylan — Marketing Organization

  2. Mar 31, 2000

    King Pharmaceuticals — Marketing Organization

  3. Mar 27, 2001

    Chartwell Pharmaceuticals — Marketing Organization

  4. Mar 27, 2001

    CASI Pharmaceuticals, Inc. — Marketing Organization

  5. Jan 1, 2003

    Earliest Phase 1 Sponsor(trial)

  6. Feb 18, 2005

    Eci Pharmaceuticals Llc — Marketing Organization

  7. Feb 18, 2005

    TTY Biopharm — Marketing Organization

  8. Feb 18, 2005

    Aderis — Marketing Organization

  9. Feb 18, 2005

    AiPing Pharm Inc — Marketing Organization

  10. Feb 18, 2005

    Baheal Pharmaceutical — Marketing Organization

  11. Jul 12, 2005

    Schwarz Pharma — Marketing Organization

  12. Sep 25, 2007

    Sun Pharmaceuticals — Marketing Organization

  13. Dec 14, 2007

    Heritage Pharma — Marketing Organization

2010s

  1. Mar 7, 2012

    Rising Pharmaceuticals — Marketing Organization

  2. Mar 7, 2012

    ANDA Repository — Marketing Organization

  3. Jan 1, 2019

    Earliest Phase 3 Sponsor(trial)

2020s

  1. May 24, 2023

    Macleods Pharmaceuticals, Ltd — Marketing Organization

  2. May 24, 2023

    Neogen — Marketing Organization

  3. Sep 25, 2023

    Bionpharma Inc — Marketing Organization

  4. Feb 5, 2025

    Square Pharmaceuticals — Marketing Organization

Indications

Approved for

Studied for

Mechanism of action

Approval history

  • approvedPriority reviewJun 21, 1950

Chemistry & pharmacology

Loading structure…

SMILES

CN1C=CNC1=S
Mol. weight
114.169 g/mol
Lipinski Ro5
Pass
Rule of 3
Yes
Chirality
Achiral Molecule
Inorganic
No
Polymer
No
Delivery
Oral
Availability
Prescription Only

Oral

Yes

Parenteral

No

Topical

No

Sources

Also known as

  • 1-methyl-1,3-dihydro-2h-imidazole-2-thione
  • 1-methyl-1,3-dihydro-2h-imidazole-2-thione
  • 1-methylimidazole-2(3h)-thione
  • 1-methylimidazole-2(3h)-thione
  • danantizol
  • danantizol
  • favistan
  • favistan
  • favistan
  • mercazolyl
  • mercazolyl
  • methimazole
  • methimazole
  • methimazole
  • methimazole
  • methimazole
  • methimazole
  • methimazole
  • methimazole
  • methimazole
  • methimazole
  • methylimidazolethiol
  • methymazol
  • mmi-467
  • strumazol
  • strumazol
  • tapazole
  • tapazole
  • tapazole
  • tapazole
  • tapazole
  • thacapzol
  • thacapzol
  • thiamazol
  • thiamazol
  • thiamazole
  • thiamazole
  • thiamazole
  • thiamazole
  • thiamazole
  • thiamazole
  • thiamazolum
  • thiamazolum
  • thycapzol
  • thymidazol
  • thymidazole
  • thyrozol
  • tiamazol
  • tiamazol
  • usaf el-30
  • usaf el-30

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT05607407Phase 2Jan 31, 2024Case Western Reserve University, University of Rochester
NCT06240455Phase 2Jan 11, 2024Worg Biotherapeutics Inc.
NCT06068179Phase 2/Phase 3 (Phase 3)Oct 8, 2023Xiamen University
NCT05017610Early Phase 1 (Phase 1)Dec 31, 2021Emory University
NCT04776993Phase 3Dec 1, 2021University of Pisa
NCT04346901Phase 1Aug 1, 2019University of Indonesia
NCT05118542Phase 3Jan 1, 2019University of Indonesia
NCT05461820Phase 4May 1, 2018Nanjing Medical University
NCT03064542N/AJun 1, 2017Agency for Science, Technology and Research, Nanyang Technological University, National University of Singapore
NCT02654041Phase 2Mar 1, 2016Musli Thyropeutics Ltd., Tel Aviv University
NCT02727738N/AJan 1, 2014University of Pisa
NCT01849861Phase 4Sep 1, 2011Conselho Nacional de Desenvolvimento Científico e Tecnológico, Federal University of Rio de Janeiro
NCT01560299N/AFeb 1, 2010Mashhad University of Medical Sciences
NCT01093118Phase 2Sep 1, 2009J&S Studies Inc., Oregon Medical Research Center, Radiant Research, Talima Therapeutics, Inc.
NCT01893450N/AJun 1, 2008Instituto Nacional de Ciencias Medicas y Nutricion Salvador Zubiran
NCT01458600Phase 4Sep 1, 2006Karolinska Institute, Region Skane
NCT00917241Phase 4Jun 1, 2004Nanjing Medical University
NCT00150111Phase 1/Phase 2 (Phase 2)Jun 1, 2003University of Southern Denmark
NCT00150137Phase 4Jan 1, 2003University of Southern Denmark
NCT00150124Phase 4Jan 1, 2003University of Southern Denmark
Showing 20 of 21 trials
Page 1 / 2

Organizations

Research & Development (25)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
University of Southern DenmarkAcademic/Hospital3322003
Nanjing Medical UniversityAcademic/Hospital2212004
University of IndonesiaAcademic/Hospital2222019
University of PisaAcademic/Hospital2222014
Agency for Science, Technology and ResearchGovernment1012017
Case Western Reserve UniversityAcademic/Hospital1112024
Conselho Nacional de Desenvolvimento Científico e TecnológicoGovernment1012011
Emory UniversityAcademic/Hospital1112021
Federal University of Rio de JaneiroAcademic/Hospital1112011
Instituto Nacional de Ciencias Medicas y Nutricion Salvador ZubiranGovernment1112008
J&S Studies Inc.For profit1012009
Karolinska InstituteAcademic/Hospital1012006
Mashhad University of Medical SciencesAcademic/Hospital1112010
Musli Thyropeutics Ltd.For profit1112016
Nanyang Technological UniversityAcademic/Hospital1012017
National Institute of Arthritis and Musculoskeletal and Skin Diseases (NIAMS)Government1111995
National University of SingaporeAcademic/Hospital1112017
Oregon Medical Research CenterFor profit1012009
Radiant ResearchAcademic/Hospital1012009
Region SkaneGovernment1112006
25 organizations
Page 1 / 2

Marketing (23)

OrganizationOrg typeRelationshipDate
ANDA RepositoryFor profitMKTGMar 7, 2012
AderisFor profitMKTGFeb 18, 2005
AiPing Pharm IncFor profitMKTGFeb 18, 2005
AiPing Pharm IncFor profitSYNFeb 18, 2005
Baheal PharmaceuticalFor profitMKTGFeb 18, 2005
Bionpharma IncFor profitMKTGSep 25, 2023
Bionpharma IncFor profitSYNSep 25, 2023
CASI Pharmaceuticals, Inc.For profitMKTGMar 27, 2001
Chartwell PharmaceuticalsFor profitMKTGMar 27, 2001
Eci Pharmaceuticals LlcFor profitMKTGFeb 18, 2005
Heritage PharmaFor profitMKTGDec 14, 2007
King PharmaceuticalsFor profitNDA2Jun 21, 1950
King PharmaceuticalsFor profitMKTGMar 31, 2000
King PharmaceuticalsFor profitNDAJun 21, 1950
Macleods Pharmaceuticals, LtdFor profitMKTGMay 24, 2023
MylanFor profitMKTGMar 29, 2000
NeogenFor profitMKTGMay 24, 2023
Rising PharmaceuticalsFor profitMKTGMar 7, 2012
Rising PharmaceuticalsFor profitSYNMar 7, 2012
Schwarz PharmaFor profitMKTGJul 12, 2005
Square PharmaceuticalsFor profitMKTGFeb 5, 2025
Sun PharmaceuticalsFor profitMKTGSep 25, 2007
TTY BiopharmFor profitMKTGFeb 18, 2005