methazolamide ๐Ÿถ Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
1741 554-57-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • N-Methylacetazolamide
  • metazolamide
  • methazolamide
  • neptazane
  • neptazaneat
  • methenamide
A carbonic anhydrase inhibitor that is used as a diuretic and in the treatment of glaucoma.
  • Molecular weight: 236.26
  • Formula: C5H8N4O3S2
  • CLOGP: 0.09
  • LIPINSKI: 0
  • HAC: 7
  • HDO: 1
  • TPSA: 105.19
  • ALOGS: -2.13
  • ROTB: 1

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.20 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 3 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.70 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 61 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 21.16 ยตM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD

Approvals:

DateAgencyCompanyOrphan
Jan. 26, 1959 FDA LEDERLE

FDA Adverse Event Reporting System (Female)

None

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Nerve degeneration 78.89 72.74 11 517 197 34956206

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Nerve degeneration 81.75 51.02 11 651 280 79743446
Renal neoplasm 60.52 51.02 11 651 1997 79741729
Abdominal rigidity 55.80 51.02 11 651 3077 79740649
Renal mass 54.94 51.02 11 651 3329 79740397

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC S01EC05 SENSORY ORGANS
OPHTHALMOLOGICALS
ANTIGLAUCOMA PREPARATIONS AND MIOTICS
Carbonic anhydrase inhibitors
MeSH PA D002257 Carbonic Anhydrase Inhibitors
MeSH PA D004232 Diuretics
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D045283 Natriuretic Agents

Drug Use | Suggest Off label Use Form| |View source of the data|

DiseaseRelationSNOMED_IDDOID
Open-angle glaucoma indication 84494001 DOID:1067
Secondary glaucoma indication 95717004
Angle-closure glaucoma indication 392291006 DOID:13550
Malignant glaucoma off-label use 10100008
Renal tubular acidosis contraindication 1776003 DOID:14219
Respiratory acidosis contraindication 12326000
Hyperkalemia contraindication 14140009
Metabolic acidosis, normal anion gap, acidifying salts contraindication 18104000
Diabetes mellitus type 2 contraindication 44054006 DOID:9352
Diabetes mellitus type 1 contraindication 46635009 DOID:9744
Acute nephropathy contraindication 58574008
Hepatic failure contraindication 59927004
Decreased respiratory function contraindication 80954004
Hyponatremia contraindication 89627008
Gout contraindication 90560007 DOID:13189
Kidney disease contraindication 90708001 DOID:557
Disease of blood AND/OR blood-forming organ contraindication 191124002 DOID:74
Disease of liver contraindication 235856003 DOID:409
Disorder of electrolytes contraindication 237840007
Primary adrenocortical insufficiency contraindication 373662000
Recurrent Calcium Renal Calculi contraindication




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 7.28 acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Carbonic anhydrase 4 Enzyme INHIBITOR Ki 6.62 CHEMBL CHEMBL
Carbonic anhydrase 7 Enzyme INHIBITOR Ki 8.68 CHEMBL CHEMBL
Carbonic anhydrase 1 Enzyme INHIBITOR Ki 7.85 CHEMBL CHEMBL
Carbonic anhydrase 2 Enzyme INHIBITOR Ki 8.05 CHEMBL CHEMBL
Carbonic anhydrase 5B, mitochondrial Enzyme Ki 7.21 CHEMBL
Carbonic anhydrase 3 Enzyme Ki 8.96 CHEMBL
Carbonic anhydrase 6 Enzyme Ki 8 CHEMBL
Carbonic anhydrase 14 Enzyme Ki 7.37 CHEMBL
Carbonic anhydrase 13 Enzyme Ki 7.72 CHEMBL
Carbonic anhydrase Enzyme IC50 7.70 CHEMBL
Carbonic anhydrase V Enzyme Ki 8.60 CHEMBL
Carbonic anhydrase 9 Enzyme Ki 7.57 CHEMBL
Carbonic anhydrase 12 Enzyme Ki 8.47 CHEMBL
Carbonic anhydrase 5A, mitochondrial Enzyme Ki 7.19 CHEMBL
Carbonic anhydrase Enzyme Ki 6.77 CHEMBL
Carbonic anhydrase 13 Enzyme Ki 7.72 CHEMBL
Carbonic anhydrase 4 Enzyme Ki 7.44 CHEMBL
Carbonic anhydrase Enzyme Ki 6.85 CHEMBL
Carbonic anhydrase Enzyme Ki 4.49 CHEMBL
Carbonic anhydrase 15 Enzyme Ki 7.19 CHEMBL
Carbonic anhydrase Enzyme Ki 6.92 CHEMBL
Carbonic anhydrase Enzyme Ki 7.85 CHEMBL
Probable transmembrane carbonic anhydrase (Carbonate dehydratase) (Carbonic dehydratase); Transmembrane carbonic anhydrase Enzyme Ki 6.25 CHEMBL
Carbonic anhydrase Enzyme Ki 6.93 CHEMBL
Alpha carbonic anhydrase Enzyme Ki 7.67 CHEMBL
Carbonic anhydrase Enzyme Ki 6.88 CHEMBL
Carbonic anhydrase 2 Enzyme Ki 7.20 CHEMBL
Astrosclerin-3 Enzyme Ki 6.49 CHEMBL
Beta-carbonic anhydrase 1 Enzyme Ki 6.11 CHEMBL
Delta carbonic anhydrase Unclassified Ki 6.77 CHEMBL
Carbonic anhydrase 2 Enzyme Ki 6.18 CHEMBL
Carbonic anhydrase Enzyme Ki 6.74 CHEMBL
Carbonic anhydrase, alpha family Unclassified Ki 7.58 CHEMBL
Carbonate dehydratase Enzyme Ki 8.09 CHEMBL

External reference:

IDSource
4017906 VUID
N0000146257 NUI
D00655 KEGG_DRUG
4017906 VANDF
C0025631 UMLSCUI
CHEBI:6822 CHEBI
MZM PDB_CHEM_ID
CHEMBL19 ChEMBL_ID
DB00703 DRUGBANK_ID
D008704 MESH_DESCRIPTOR_UI
4100 PUBCHEM_CID
6828 IUPHAR_LIGAND_ID
882 INN_ID
W733B0S9SD UNII
218699 RXNORM
2252 MMSL
5067 MMSL
921 MMSL
d00640 MMSL
002289 NDDF
392575007 SNOMEDCT_US
53052005 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
methazolamide HUMAN PRESCRIPTION DRUG LABEL 1 0574-0790 TABLET 25 mg ORAL ANDA 21 sections
methazolamide HUMAN PRESCRIPTION DRUG LABEL 1 0574-0791 TABLET 50 mg ORAL ANDA 21 sections
Methazolamide HUMAN PRESCRIPTION DRUG LABEL 1 24208-022 TABLET 25 mg ORAL ANDA 19 sections
Methazolamide HUMAN PRESCRIPTION DRUG LABEL 1 24208-023 TABLET 50 mg ORAL ANDA 19 sections
METHAZOLAMIDE HUMAN PRESCRIPTION DRUG LABEL 1 42571-239 TABLET 25 mg ORAL ANDA 19 sections
METHAZOLAMIDE HUMAN PRESCRIPTION DRUG LABEL 1 42571-240 TABLET 50 mg ORAL ANDA 19 sections
methazolamide HUMAN PRESCRIPTION DRUG LABEL 1 50090-3233 TABLET 50 mg ORAL ANDA 21 sections
Methazolamide HUMAN PRESCRIPTION DRUG LABEL 1 51224-024 TABLET 25 mg ORAL ANDA 21 sections
Methazolamide HUMAN PRESCRIPTION DRUG LABEL 1 51224-124 TABLET 50 mg ORAL ANDA 21 sections
Methazolamide HUMAN PRESCRIPTION DRUG LABEL 1 51407-026 TABLET 25 mg ORAL ANDA 19 sections
Methazolamide HUMAN PRESCRIPTION DRUG LABEL 1 51407-027 TABLET 50 mg ORAL ANDA 19 sections
METHAZOLAMIDE HUMAN PRESCRIPTION DRUG LABEL 1 54868-2996 TABLET 50 mg ORAL ANDA 22 sections
methazolamide HUMAN PRESCRIPTION DRUG LABEL 1 55806-020 TABLET 50 mg ORAL ANDA 20 sections
methazolamide HUMAN PRESCRIPTION DRUG LABEL 1 55806-020 TABLET 50 mg ORAL ANDA 20 sections
methazolamide HUMAN PRESCRIPTION DRUG LABEL 1 55806-021 TABLET 25 mg ORAL ANDA 20 sections
methazolamide HUMAN PRESCRIPTION DRUG LABEL 1 55806-021 TABLET 25 mg ORAL ANDA 20 sections
Methazolamide HUMAN PRESCRIPTION DRUG LABEL 1 62559-240 TABLET 25 mg ORAL ANDA 19 sections
Methazolamide HUMAN PRESCRIPTION DRUG LABEL 1 62559-241 TABLET 50 mg ORAL ANDA 19 sections
Methazolamide HUMAN PRESCRIPTION DRUG LABEL 1 63629-1958 TABLET 25 mg ORAL ANDA 19 sections
Methazolamide HUMAN PRESCRIPTION DRUG LABEL 1 63629-1958 TABLET 25 mg ORAL ANDA 19 sections
Methazolamide HUMAN PRESCRIPTION DRUG LABEL 1 63629-1986 TABLET 25 mg ORAL ANDA 19 sections
Methazolamide HUMAN PRESCRIPTION DRUG LABEL 1 63629-1986 TABLET 25 mg ORAL ANDA 19 sections
Methazolamide HUMAN PRESCRIPTION DRUG LABEL 1 63629-1987 TABLET 50 mg ORAL ANDA 19 sections
Methazolamide HUMAN PRESCRIPTION DRUG LABEL 1 63629-1987 TABLET 50 mg ORAL ANDA 19 sections
Methazolamide HUMAN PRESCRIPTION DRUG LABEL 1 68151-3110 TABLET 50 mg ORAL ANDA 21 sections
Methazolamide HUMAN PRESCRIPTION DRUG LABEL 1 68682-022 TABLET 25 mg ORAL ANDA 19 sections
Methazolamide HUMAN PRESCRIPTION DRUG LABEL 1 68682-023 TABLET 50 mg ORAL ANDA 19 sections