methazolamide

Trade name: neptazane

Small moleculeapproved

Approved

Jan 26, 1959

Methazolamide is topical carbonic anhydrase inhibitor. Methazolamide is indicated for the reduction of elevated intraocular pressure in patients with open-angle glaucoma or ocular hypertension who are insufficiently responsive to beta-blockers. Methazolamide is a sulfonamide derivative; however, it does not have any clinically significant antimicrobial properties. Although methazolamide achieves a high concentration in the cerebrospinal fluid, it is not-considered an effective anticonvulsant. Methazolamide has a weak and transient diuretic effect, therefore use results in an increase in urinary volume, with excretion of sodium, potassium and chloride. Methazolamide is a potent inhibitor of carbonic anhydrase. Inhibition of carbonic anhydrase in the ciliary processes of the eye decreases aqueous humor secretion, presumably by slowing the formation of bicarbonate ions with subsequent reduction in sodium and fluid transport. Methazolamide is used for treatment of chronic open-angle glaucoma and acute angle-closure glaucoma. — NCATS

Clinical trial activity

9 trials · 13 clinical orgs · 14 marketing orgs

Phase 1
2
Phase 2
3
Phase 3
1
Phase 4
5

Earliest trial started Jul 1, 2004 (NCT00257829)

Timeline

1950s

  1. Jan 26, 1959

    Lederle — Earliest FDA Approval

  2. Jan 26, 1959

    Lederle — NDA Organization

  3. Jan 26, 1959

    American Cyanamid — NDA Secondary Org

1990s

  1. Jun 30, 1993

    Ani Pharmaceuticals — Marketing Organization

  2. Jun 30, 1993

    Sandoz — Marketing Organization

  3. Jun 30, 1993

    Chartwell Pharmaceuticals — Marketing Organization

  4. Jan 27, 1994

    Mikart — Marketing Organization

  5. Jan 27, 1994

    ANDA Repository — Marketing Organization

  6. Aug 28, 1996

    Invatech — Marketing Organization

  7. Aug 28, 1996

    Athem — Marketing Organization

2000s

  1. Jan 1, 2004

    Earliest Phase 2 Sponsor(trial)

2010s

  1. Jan 1, 2011

    Earliest Phase 1 Sponsor(trial)

  2. Jan 1, 2014

    Earliest Phase 3 Sponsor(trial)

  3. Oct 5, 2018

    Bausch & Lomb — Marketing Organization

  4. Oct 5, 2018

    Micro Labs Ltd India — Marketing Organization

  5. Oct 5, 2018

    Bausch Health Companies — Marketing Organization

2020s

  1. Oct 18, 2022

    Precision Dose — Marketing Organization

  2. Feb 9, 2026

    Ajanta Pharma Ltd — Marketing Organization

Indications

Mechanism of action

Approval history

  • approvedJan 26, 1959

Chemistry & pharmacology

Loading structure…

SMILES

CN1N=C(S\C1=N\C(C)=O)S(N)(=O)=O
Mol. weight
236.272 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

  • metazolamida
  • metazolamida
  • metazolamide
  • methazolamid
  • methazolamid
  • methazolamide
  • methazolamide
  • methazolamide
  • methazolamide
  • methazolamide
  • methazolamide
  • methazolamide
  • methazolamide
  • methazolamide
  • méthazolamide
  • méthazolamide
  • methazolamidum
  • methazolamidum
  • methenamide
  • methenamide
  • methenamide
  • neptazane
  • neptazane
  • neptazane
  • neptazane
  • neptazaneat
  • neptazaneat
  • neptazaneat
  • n-methylacetazolamide
  • n-methylacetazolamide
  • n-methylacetazolamide
  • n-methylacetazolamide
  • n-methylacetazolamide
  • n-methylacetazolamide

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT05575180Phase 4Apr 30, 2023University of Waterloo, Wilderness Medical Society
NCT05498103Phase 4Jan 1, 2023University of Colorado, Denver
NCT02758470Phase 4Nov 1, 2016University of British Columbia
NCT02760121Phase 4May 1, 2016University of British Columbia
NCT02463357Phase 4Aug 1, 2015Alma College, University of Colorado, University of Colorado, Denver
NCT02390284Phase 3Sep 1, 2014National Eye Institute (NEI), University of Miami
NCT01702025Phase 1/Phase 2 (Phase 2)Jun 1, 2012Colorado State University, Defense Advanced Research Projects Agency, University of Colorado, Denver
NCT01587027Phase 1Dec 1, 2011Defense Advanced Research Projects Agency, Poudre Valley Health System, University of Colorado, Denver
NCT00257829Phase 2Jul 1, 2004Chao Family Comprehensive Cancer Center, University of California, Irvine
Showing 9 of 9 trials
Page 1 / 1

Organizations

Research & Development (13)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
University of Colorado, DenverAcademic/Hospital4232011
Defense Advanced Research Projects AgencyGovernment2022011
University of British ColumbiaAcademic/Hospital2212016
Alma CollegeAcademic/Hospital1012015
Chao Family Comprehensive Cancer CenterAcademic/Hospital1012004
Colorado State UniversityAcademic/Hospital1112012
National Eye Institute (NEI)Government1012014
Poudre Valley Health SystemAcademic/Hospital1112011
University of California, IrvineAcademic/Hospital1112004
University of ColoradoAcademic/Hospital1012015
University of MiamiAcademic/Hospital1112014
University of WaterlooAcademic/Hospital1112023
Wilderness Medical SocietyAcademic/Hospital1012023
13 organizations
Page 1 / 1

Marketing (16)

OrganizationOrg typeRelationshipDate
ANDA RepositoryFor profitMKTGJan 27, 1994
Ajanta Pharma LtdFor profitMKTGFeb 9, 2026
American CyanamidFor profitNDA2Jan 26, 1959
Ani PharmaceuticalsFor profitMKTGJun 30, 1993
Ani PharmaceuticalsFor profitSYNJun 30, 1993
Ani PharmaceuticalsFor profitSYNJul 17, 1997
AthemFor profitMKTGAug 28, 1996
Bausch & LombFor profitMKTGOct 5, 2018
Bausch Health CompaniesFor profitMKTGOct 5, 2018
Chartwell PharmaceuticalsFor profitMKTGJun 30, 1993
InvatechFor profitMKTGAug 28, 1996
LederleFor profitNDAJan 26, 1959
Micro Labs Ltd IndiaFor profitMKTGOct 5, 2018
MikartFor profitMKTGJan 27, 1994
Precision DoseFor profitMKTGOct 18, 2022
SandozFor profitMKTGJun 30, 1993