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Atlas / Drug / Methazolamide

Methazolamide

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Also known as L-584601MetazolamidaMethenamideNeptazaneNeptazaneatNSC-758426VVP-808VVP808metazolamideSID11112413SID26747005SID855821SID56422398SID144204015MethazolamideÊMethazolamideÂC0165010US10172837

Summary

Methazolamide (CHEMBL19) is an approved small molecule (ATC S01EC05) targeting CA1, CA14, and CA4; indicated across 5 conditions including open-angle glaucoma and glaucoma.

At a glance

  • Status: Approved (max clinical phase 4)
  • Modality: Small molecule
  • ATC class: S01EC05
  • Targets: 5 (CA1, CA14, CA4…)
  • Indications: 5 conditions
  • Clinical trials: 10
  • Chemistry: 236.3 Da · C5H8N4O3S2

Identifiers

Drug identity and classification

FieldValue
ChEMBL IDCHEMBL19
NameMethazolamide
TypeSmall molecule
Max phase4
FDA approvedno
PubChem CID4100
ATCS01EC05
Molecular formulaC5H8N4O3S2
Molecular weight236.3
InChIKeyFLOSMHQXBMRNHR-UHFFFAOYSA-N

SMILES: CC(=O)N=C1N(N=C(S1)S(=O)(=O)N)C

IUPAC name: N-(3-methyl-5-sulfamoyl-1,3,4-thiadiazol-2-ylidene)acetamide

Also known as: L-584601, Metazolamida, Methazolamide, Methenamide, Neptazane, Neptazaneat, NSC-758426, VVP-808, VVP808, methazolamide, metazolamide, SID11112413

Patent coverage: 44 distinct patent families (65 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

GeneTargetActionpAffinityCancer dependencyUniProt
CA1carbonic anhydrase 1Inhibition7.480%P00915
CA14carbonic anhydrase 14Inhibition7.570%Q9ULX7
CA4carbonic anhydrase 4Inhibition7.620.3%P22748
CA12carbonic anhydrase 12Inhibition8.470.2%O43570
CA7carbonic anhydrase 7Inhibition8.681.6%P43166

Broader ChEMBL bioactivity targets: 29 (assay-derived). Sample: Microtubule-associated protein tau, 4’-phosphopantetheinyl transferase ffp, 15-hydroxyprostaglandin dehydrogenase [NAD(+)], Carbonic anhydrase 2, Carbonic anhydrase, Carbonic anhydrase V, Carbonic anhydrase 13, Carbonic anhydrase 7, Carbonic anhydrase 1, Carbonic anhydrase 4.

Bioactivity

ChEMBL activities: 376 potent at pChembl ≥ 5 of 386 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

TargetpChemblTypeValueUnitActivity ID
CA99.6IC500.25nMCHEMBL_ACT_12679163
CA38.96Ki1.1nMCHEMBL_ACT_2056539
CA78.68Ki2.1nMCHEMBL_ACT_13407602
CA78.68Ki2.1nMCHEMBL_ACT_13440687
CA78.68Ki2.1nMCHEMBL_ACT_1435541
CA78.68Ki2.1nMCHEMBL_ACT_1780574
CA78.68Ki2.1nMCHEMBL_ACT_2056573
CA78.68Ki2.1nMCHEMBL_ACT_2159092
CA78.68Ki2.1nMCHEMBL_ACT_2287530
CA78.68Ki2.1nMCHEMBL_ACT_2491996
CA78.68Ki2.1nMCHEMBL_ACT_25934073
CA78.68Ki2.1nMCHEMBL_ACT_6262809
CA5A8.6Ki2.5nMCHEMBL_ACT_1520946
CA128.47Ki3.4nMCHEMBL_ACT_13440645
CA128.47Ki3.4nMCHEMBL_ACT_13888961
CA128.47Ki3.4nMCHEMBL_ACT_13910696
CA128.47Ki3.4nMCHEMBL_ACT_1420983
CA128.47Ki3.4nMCHEMBL_ACT_1424987
CA128.47Ki3.4nMCHEMBL_ACT_1426023
CA128.47Ki3.4nMCHEMBL_ACT_14711143
CA128.47Ki3.4nMCHEMBL_ACT_1522136
CA128.47Ki3.4nMCHEMBL_ACT_15239158
CA128.47Ki3.4nMCHEMBL_ACT_1666724
CA128.47Ki3.4nMCHEMBL_ACT_1767379
CA128.47Ki3.4nMCHEMBL_ACT_1780576
CA128.47Ki3.4nMCHEMBL_ACT_18364812
CA128.47Ki3.4nMCHEMBL_ACT_19201951
CA128.47Ki3.4nMCHEMBL_ACT_1946646
CA128.47Ki3.4nMCHEMBL_ACT_2056587
CA128.47Ki3.4nMCHEMBL_ACT_2090966

Target pathways

Aggregated over 5 target gene(s): CA1, CA14, CA4, CA12, CA7.

Top Reactome pathways

12 total, by targets touching each:

PathwayTargetsGenes
Metabolism5CA1, CA12, CA14, CA4, CA7
Reversible hydration of carbon dioxide5CA1, CA12, CA14, CA4, CA7
Erythrocytes take up carbon dioxide and release oxygen2CA1, CA4
Erythrocytes take up oxygen and release carbon dioxide2CA1, CA4
O2/CO2 exchange in erythrocytes2CA1, CA4
Transport of small molecules2CA1, CA4
Cytokine Signaling in Immune system1CA1
Immune System1CA1
Interleukin-12 family signaling1CA1
Signaling by Interleukins1CA1
Gene and protein expression by JAK-STAT signaling after Interleukin-12 stimulation1CA1
Interleukin-12 signaling1CA1

Dominant GO biological processes

GO termTargets
response to fructose1
bicarbonate transport1
estrous cycle1
chloride ion homeostasis1
positive regulation of synaptic transmission, GABAergic1
obsolete positive regulation of cellular pH reduction1
regulation of intracellular pH1
neuron cellular homeostasis1
regulation of chloride transport1

Indications & clinical

Indications

5 indications (2 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

IndicationTrial phaseMONDOEFO
open-angle glaucoma4MONDO:0005338EFO:0004190
glaucoma4MONDO:0005041MONDO:0005041
essential tremor2MONDO:0003233EFO:0003108
altitude sickness1MONDO:0006625EFO:1000782

1 further indication record had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 10.

Phase distribution

PhaseTrials
PHASE45
PHASE22
PHASE31
PHASE1/PHASE21
PHASE11

Top trials by phase / activity

NCTPhaseStatusTitle
NCT05498103PHASE4ACTIVE_NOT_RECRUITINGUse of Methazolamide to Lower Intraocular Pressure
NCT02463357PHASE4COMPLETEDThree New Ideas to Protect Special Forces From the Stress of High Altitude
NCT02758470PHASE4COMPLETEDMuscle Fatigue and Carbonic Anhydrase Inhibitors
NCT02760121PHASE4COMPLETEDAZ, MZ, and the Pulmonary System Response to Hypoxia
NCT05575180PHASE4COMPLETEDEffect of Acetazolamide and Methazolamide on Hypoxic Exercise Performance
NCT02390284PHASE3TERMINATEDStop Retinal Ganglion Cell Dysfunction Study
NCT00257829PHASE2WITHDRAWNImproving Tumor Oxygenation in Cervical Cancer
NCT01702025PHASE1/PHASE2COMPLETEDRapid Acclimatization to Hypoxia at Altitude
NCT06312800PHASE2WITHDRAWNAcamprosate and Methazolamide for Essential Tremor
NCT01587027PHASE1COMPLETEDSafety Evaluation of Aminophylline and Methazolamide

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline, but PharmGKB curates 2 clinical and 14 variant annotation(s) for this drug (gene-keyed; see PharmGKB).

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

92 molecules share ≥1 primary target. Top 60 by shared-target count:

MoleculeSourceStatusShared targets
ACETAMINOPHENChEMBL + PubChemPhase 4 (approved)CA1, CA12, CA14, CA4, CA7
ACETAZOLAMIDEChEMBL + PubChemPhase 4 (approved)CA1, CA12, CA14, CA4, CA7
CELECOXIBChEMBL + PubChemPhase 4 (approved)CA1, CA12, CA14, CA4, CA7
CHLORTHALIDONEChEMBL + PubChemPhase 4 (approved)CA1, CA12, CA14, CA4, CA7
COUMARINChEMBL + PubChemPhase 4 (approved)CA1, CA12, CA14, CA4, CA7
DICHLORPHENAMIDEChEMBL + PubChemPhase 4 (approved)CA1, CA12, CA14, CA4, CA7
DOBUTAMINEChEMBL + PubChemPhase 4 (approved)CA1, CA12, CA14, CA4, CA7
FUROSEMIDEChEMBL + PubChemPhase 4 (approved)CA1, CA12, CA14, CA4, CA7
LACOSAMIDEChEMBL + PubChemPhase 4 (approved)CA1, CA12, CA14, CA4, CA7
SALICYLIC ACIDChEMBL + PubChemPhase 4 (approved)CA1, CA12, CA14, CA4, CA7
BORTEZOMIBChEMBLPhase 4 (approved)CA1, CA12, CA14, CA4, CA7
BRINZOLAMIDEChEMBLPhase 4 (approved)CA1, CA12, CA14, CA4, CA7
DORZOLAMIDEChEMBLPhase 4 (approved)CA1, CA12, CA14, CA4, CA7
ETHOXZOLAMIDEChEMBLPhase 4 (approved)CA1, CA12, CA14, CA4, CA7
FAMOTIDINEChEMBLPhase 4 (approved)CA1, CA12, CA14, CA4, CA7
IMATINIBChEMBLPhase 4 (approved)CA1, CA12, CA14, CA4, CA7
INDAPAMIDEChEMBLPhase 4 (approved)CA1, CA12, CA14, CA4, CA7
LEVETIRACETAMChEMBLPhase 4 (approved)CA1, CA12, CA14, CA4, CA7
MAFENIDEChEMBLPhase 4 (approved)CA1, CA12, CA14, CA4, CA7
NILOTINIBChEMBLPhase 4 (approved)CA1, CA12, CA14, CA4, CA7
SULFANILAMIDEChEMBLPhase 4 (approved)CA1, CA12, CA14, CA4, CA7
TOPIRAMATEChEMBLPhase 4 (approved)CA1, CA12, CA14, CA4, CA7
TRICHLORMETHIAZIDEChEMBLPhase 4 (approved)CA1, CA12, CA14, CA4, CA7
TRIENTINEChEMBLPhase 4 (approved)CA1, CA12, CA14, CA4, CA7
VALDECOXIBChEMBLPhase 4 (approved)CA1, CA12, CA14, CA4, CA7
VERALIPRIDEChEMBLPhase 4 (approved)CA1, CA12, CA14, CA4, CA7
ZONISAMIDEChEMBLPhase 4 (approved)CA1, CA12, CA14, CA4, CA7
CAFFEIC ACIDChEMBLPhase 3CA1, CA12, CA14, CA4, CA7
CURCUMINChEMBLPhase 3CA1, CA12, CA14, CA4, CA7
QUERCETINChEMBLPhase 3CA1, CA12, CA14, CA4, CA7
RESVERATROLChEMBLPhase 3CA1, CA12, CA14, CA4, CA7
SACCHARINChEMBLPhase 3CA1, CA12, CA14, CA4, CA7
SPERMIDINEChEMBLPhase 3CA1, CA12, CA14, CA4, CA7
COUMAPHOSChEMBLPhase 2CA1, CA12, CA14, CA4, CA7
ELLAGIC ACIDChEMBLPhase 2CA1, CA12, CA14, CA4, CA7
GALLIC ACIDChEMBLPhase 2CA1, CA12, CA14, CA4, CA7
IROSUSTATChEMBLPhase 2CA1, CA12, CA14, CA4, CA7
PCI-27483ChEMBLPhase 2CA1, CA12, CA14, CA4, CA7
SONEPIPRAZOLEChEMBLPhase 2CA1, CA12, CA14, CA4, CA7
HYDROQUINONEChEMBLPhase 4 (approved)CA1, CA12, CA14, CA4
PHENOLChEMBLPhase 4 (approved)CA1, CA12, CA14, CA4
PYRITHIONE ZINCChEMBLPhase 4 (approved)CA12, CA14, CA4, CA7
THIMEROSALChEMBLPhase 3CA12, CA14, CA4, CA7
CARZENIDEChEMBLPhase 2CA1, CA12, CA14, CA7
INDISULAMChEMBLPhase 2CA1, CA12, CA14, CA7
SULFASUCCINAMIDEChEMBLPhase 2CA1, CA12, CA14, CA4
SULPIRIDEChEMBLPhase 4 (approved)CA1, CA12, CA7
P-TOLUENESULFONAMIDEChEMBLPhase 3CA1, CA12, CA7
DAIDZEINChEMBLPhase 2CA12, CA4, CA7
DITIOCARBChEMBLPhase 2CA1, CA12, CA4
ISOQUERCETINChEMBLPhase 2CA12, CA4, CA7
LUTEOLINChEMBLPhase 2CA12, CA4, CA7
SODIUM CYCLAMATEChEMBLPhase 2CA12, CA14, CA7
SildenafilPubChemApprovedCA14, CA4, CA7
HYDROCHLOROTHIAZIDEChEMBL + PubChemPhase 4 (approved)CA1, CA14
PAZOPANIBChEMBL + PubChemPhase 4 (approved)CA1, CA12
SODIUMChEMBLPhase 4 (approved)CA1, CA4
SULTHIAMEChEMBLPhase 4 (approved)CA1, CA7
ZOLEDRONIC ACIDChEMBLPhase 4 (approved)CA12, CA14
PRITELIVIRChEMBLPhase 3CA1, CA12

About this page

Generated deterministically by Sugi Atlas from primary biomedical databases via BioBTree. Every record on this page traces to a primary source.

Generated
Atlas version
v1.1.2
BioBTree
v2.0.2

Sources 30

This page pulls from 30 datasets indexed by BioBTree:

chebichembl_activitychembl_moleculechembl_targetcivic_evidenceclingen_dosageclinical_trialsdepmapefoensemblentrezgogoparentgtopdbgtopdb_interactiongtopdb_ligandhgncmeshmondomsigdbpatent_compoundpharmgkbpharmgkb_guidelinepubchempubchem_activityreactomereactomeparentrefseqtranscriptuniprot