methazolamide
Trade name: neptazane
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
Earliest trial started Jul 1, 2004 (NCT00257829)
Timeline
1950s
- Jan 26, 1959
Lederle — Earliest FDA Approval
- Jan 26, 1959
Lederle — NDA Organization
- Jan 26, 1959
American Cyanamid — NDA Secondary Org
1990s
- Jun 30, 1993
Ani Pharmaceuticals — Marketing Organization
- Jun 30, 1993
Sandoz — Marketing Organization
- Jun 30, 1993
Chartwell Pharmaceuticals — Marketing Organization
- Jan 27, 1994
Mikart — Marketing Organization
- Jan 27, 1994
ANDA Repository — Marketing Organization
- Aug 28, 1996
Invatech — Marketing Organization
- Aug 28, 1996
Athem — Marketing Organization
2000s
- Jan 1, 2004
Earliest Phase 2 Sponsor(trial)
2010s
- Jan 1, 2011
Earliest Phase 1 Sponsor(trial)
- Jan 1, 2014
Earliest Phase 3 Sponsor(trial)
- Oct 5, 2018
Bausch & Lomb — Marketing Organization
- Oct 5, 2018
Micro Labs Ltd India — Marketing Organization
- Oct 5, 2018
Bausch Health Companies — Marketing Organization
2020s
- Oct 18, 2022
Precision Dose — Marketing Organization
- Feb 9, 2026
Ajanta Pharma Ltd — Marketing Organization
Indications
Mechanism of action
- Carbonic anhydrase VIIINHIBITOR
CA7 inhibitor
- Carbonic anhydrase IINHIBITOR
CA1 inhibitor
- Carbonic anhydrase IVINHIBITOR
CA4 inhibitor
- Carbonic anhydrase IIINHIBITOR
CA2 inhibitor
Approval history
- approvedJan 26, 1959
Chemistry & pharmacology
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
- WikipediaMethazolamide ↗
- NCATSW733B0S9SD ↗
- ChEMBLCHEMBL19 ↗
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 ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT05575180 | Phase 4 | Apr 30, 2023 | University of Waterloo, Wilderness Medical Society |
| NCT05498103 | Phase 4 | Jan 1, 2023 | University of Colorado, Denver |
| NCT02758470 | Phase 4 | Nov 1, 2016 | University of British Columbia |
| NCT02760121 | Phase 4 | May 1, 2016 | University of British Columbia |
| NCT02463357 | Phase 4 | Aug 1, 2015 | Alma College, University of Colorado, University of Colorado, Denver |
| NCT02390284 | Phase 3 | Sep 1, 2014 | National Eye Institute (NEI), University of Miami |
| NCT01702025 | Phase 1/Phase 2 (Phase 2) | Jun 1, 2012 | Colorado State University, Defense Advanced Research Projects Agency, University of Colorado, Denver |
| NCT01587027 | Phase 1 | Dec 1, 2011 | Defense Advanced Research Projects Agency, Poudre Valley Health System, University of Colorado, Denver |
| NCT00257829 | Phase 2 | Jul 1, 2004 | Chao Family Comprehensive Cancer Center, University of California, Irvine |
Organizations
Research & Development (13)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| University of Colorado, Denver | Academic/Hospital | 4 | 2 | 3 | 2011 |
| Defense Advanced Research Projects Agency | Government | 2 | 0 | 2 | 2011 |
| University of British Columbia | Academic/Hospital | 2 | 2 | 1 | 2016 |
| Alma College | Academic/Hospital | 1 | 0 | 1 | 2015 |
| Chao Family Comprehensive Cancer Center | Academic/Hospital | 1 | 0 | 1 | 2004 |
| Colorado State University | Academic/Hospital | 1 | 1 | 1 | 2012 |
| National Eye Institute (NEI) | Government | 1 | 0 | 1 | 2014 |
| Poudre Valley Health System | Academic/Hospital | 1 | 1 | 1 | 2011 |
| University of California, Irvine | Academic/Hospital | 1 | 1 | 1 | 2004 |
| University of Colorado | Academic/Hospital | 1 | 0 | 1 | 2015 |
| University of Miami | Academic/Hospital | 1 | 1 | 1 | 2014 |
| University of Waterloo | Academic/Hospital | 1 | 1 | 1 | 2023 |
| Wilderness Medical Society | Academic/Hospital | 1 | 0 | 1 | 2023 |
Marketing (16)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| ANDA Repository | For profit | MKTG | Jan 27, 1994 |
| Ajanta Pharma Ltd | For profit | MKTG | Feb 9, 2026 |
| American Cyanamid | For profit | NDA2 | Jan 26, 1959 |
| Ani Pharmaceuticals | For profit | MKTG | Jun 30, 1993 |
| Ani Pharmaceuticals | For profit | SYN | Jun 30, 1993 |
| Ani Pharmaceuticals | For profit | SYN | Jul 17, 1997 |
| Athem | For profit | MKTG | Aug 28, 1996 |
| Bausch & Lomb | For profit | MKTG | Oct 5, 2018 |
| Bausch Health Companies | For profit | MKTG | Oct 5, 2018 |
| Chartwell Pharmaceuticals | For profit | MKTG | Jun 30, 1993 |
| Invatech | For profit | MKTG | Aug 28, 1996 |
| Lederle | For profit | NDA | Jan 26, 1959 |
| Micro Labs Ltd India | For profit | MKTG | Oct 5, 2018 |
| Mikart | For profit | MKTG | Jan 27, 1994 |
| Precision Dose | For profit | MKTG | Oct 18, 2022 |
| Sandoz | For profit | MKTG | Jun 30, 1993 |