Details
Stereochemistry | ACHIRAL |
Molecular Formula | C5H8N4O3S2 |
Molecular Weight | 236.272 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1N=C(S\C1=N\C(C)=O)S(N)(=O)=O
InChI
InChIKey=FLOSMHQXBMRNHR-QPJJXVBHSA-N
InChI=1S/C5H8N4O3S2/c1-3(10)7-4-9(2)8-5(13-4)14(6,11)12/h1-2H3,(H2,6,11,12)/b7-4+
Molecular Formula | C5H8N4O3S2 |
Molecular Weight | 236.272 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Optical Activity | NONE |
DescriptionSources: http://www.drugbank.ca/drugs/DB00703Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/pro/methazolamide.html
Sources: http://www.drugbank.ca/drugs/DB00703
Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/pro/methazolamide.html
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.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL261 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23965175 |
50.0 nM [Ki] | ||
Target ID: CHEMBL205 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23965175 |
14.0 nM [Ki] | ||
Target ID: CHEMBL3594 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23965175 |
27.0 nM [Ki] | ||
Target ID: CHEMBL3242 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23965175 |
3.4 nM [Ki] | ||
Target ID: CHEMBL2326 Sources: http://www.drugbank.ca/drugs/DB00703 |
2.1 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Methazolamide Approved Useindicated in the treatment of ocular conditions where lowering intraocular pressure is likely to be of therapeutic benefit, such as chronic open-angle glaucoma, secondary glaucoma, and preoperatively in acute angle-closure glaucoma where lowering the intraocular pressure is desired before surgery. Launch Date1993 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.5 μg/mL |
25 mg 2 times / day multiple, oral dose: 25 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
METHAZOLAMIDE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
5.1 μg/mL |
50 mg 2 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
METHAZOLAMIDE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
10.7 μg/mL |
100 mg 2 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
METHAZOLAMIDE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1130 μg × min/mL |
25 mg 2 times / day multiple, oral dose: 25 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
METHAZOLAMIDE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
2571 μg × min/mL |
50 mg 2 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
METHAZOLAMIDE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
5418 μg × min/mL |
100 mg 2 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
METHAZOLAMIDE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
14 h |
steady-state, oral |
METHAZOLAMIDE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
45% |
25 mg 2 times / day multiple, oral dose: 25 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
METHAZOLAMIDE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://dmd.aspetjournals.org/content/38/2/347 Page: 348.0 |
no |
PubMed
Title | Date | PubMed |
---|---|---|
Treatment of essential tremor with methazolamide. | 1991 Oct |
|
Carbonic anhydrase inhibitors are specific openers of skeletal muscle BK channel of K+-deficient rats. | 2004 Apr |
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Carbonic anhydrase inhibitors. Inhibition of the prokariotic beta and gamma-class enzymes from Archaea with sulfonamides. | 2004 Dec 20 |
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Carbonic anhydrase inhibitors: N-(p-sulfamoylphenyl)-alpha-D-glycopyranosylamines as topically acting antiglaucoma agents in hypertensive rabbits. | 2004 Jan 5 |
|
Carbonic anhydrase inhibitors: E7070, a sulfonamide anticancer agent, potently inhibits cytosolic isozymes I and II, and transmembrane, tumor-associated isozyme IX. | 2004 Jan 5 |
|
Carbonic anhydrase inhibitors: the first QSAR study on inhibition of tumor-associated isoenzyme IX with aromatic and heterocyclic sulfonamides. | 2004 Jun 21 |
|
Alkalization of larval mosquito midgut and the role of carbonic anhydrase in different species of mosquitoes. | 2004 Mar |
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Interactions of human organic anion transporters with diuretics. | 2004 Mar |
|
Carbonic anhydrase inhibitors: aromatic and heterocyclic sulfonamides incorporating adamantyl moieties with strong anticonvulsant activity. | 2004 May 15 |
|
HCO3- secretion in the esophageal submucosal glands. | 2005 Apr |
|
Measuring drug concentrations using pulsatile microdialysis: theory and method development in vitro. | 2005 Apr 11 |
|
Expression of a novel carbonic anhydrase, CA XIII, in normal and neoplastic colorectal mucosa. | 2005 Apr 18 |
|
Proton-mediated feedback inhibition of presynaptic calcium channels at the cone photoreceptor synapse. | 2005 Apr 20 |
|
Carbonic anhydrase inhibitors. Inhibition of the membrane-bound human and bovine isozymes IV with sulfonamides. | 2005 Feb 15 |
|
Carbonic anhydrase inhibitors. Inhibition of the human cytosolic isozyme VII with aromatic and heterocyclic sulfonamides. | 2005 Feb 15 |
|
Stimulation of renal sulfate secretion by metabolic acidosis requires Na+/H+ exchange induction and carbonic anhydrase. | 2005 Jul |
|
Rat adrenal chromaffin cells are neonatal CO2 sensors. | 2005 Jul 13 |
|
Mechanism of augmented duodenal HCO(3)(-) secretion after elevation of luminal CO(2). | 2005 Mar |
|
Carbonic anhydrase inhibitors. Zonisamide is an effective inhibitor of the cytosolic isozyme II and mitochondrial isozyme V: solution and X-ray crystallographic studies. | 2005 May 2 |
|
Functional interaction of carbonic anhydrase and chloride/bicarbonate exchange in human platelets. | 2005 Nov |
|
Carbonic anhydrase inhibitors: inhibition of cytosolic/tumor-associated carbonic anhydrase isozymes I, II, and IX with benzo[b]thiophene 1,1-dioxide sulfonamides. | 2005 Nov 1 |
|
Carbonic anhydrase in the adult mosquito midgut. | 2005 Sep |
|
Carbonic anhydrase inhibitors: inhibition of the transmembrane isozyme XIV with sulfonamides. | 2005 Sep 1 |
|
Effects of low-dose methazolamide on the control of breathing in cats. | 2006 |
|
Expression, purification, kinetic, and structural characterization of an alpha-class carbonic anhydrase from Aedes aegypti (AaCA1). | 2006 Aug |
|
Carbonic anhydrase inhibitors ameliorate the symptoms of hypokalaemic periodic paralysis in rats by opening the muscular Ca2+-activated-K+ channels. | 2006 Jan |
|
[Diuretic therapy in heart failure]. | 2006 Jan-Feb |
|
Carbonic anhydrases and mucosal vanilloid receptors help mediate the hyperemic response to luminal CO2 in rat duodenum. | 2006 Jul |
|
Degradation and effects of the potential mosquito larvicides methazolamide and acetazolamide in sheepshead minnow (Cyprinodon variegatus). | 2006 Jul |
|
The carbonic anhydrase inhibitors methazolamide and acetazolamide have different effects on the hypoxic ventilatory response in the anaesthetized cat. | 2006 Jul 15 |
|
Epithelial carbonic anhydrases facilitate PCO2 and pH regulation in rat duodenal mucosa. | 2006 Jun 15 |
|
Mirtazapine in the treatment of essential tremor: an open-label, observer-blind study. | 2006 Mar |
|
Inhibition profiling of human carbonic anhydrase II by high-throughput screening of structurally diverse, biologically active compounds. | 2006 Oct |
|
The development of topically acting carbonic anhydrase inhibitors as anti-glaucoma agents. | 2007 |
|
Inhibition of hypoxia-induced calcium responses in pulmonary arterial smooth muscle by acetazolamide is independent of carbonic anhydrase inhibition. | 2007 Apr |
|
PAT-1 (Slc26a6) is the predominant apical membrane Cl-/HCO3- exchanger in the upper villous epithelium of the murine duodenum. | 2007 Apr |
|
Carbonic anhydrase inhibition prevents and reverts cardiomyocyte hypertrophy. | 2007 Feb 15 |
|
Carbonic anhydrase inhibitors. DNA cloning, characterization, and inhibition studies of the human secretory isoform VI, a new target for sulfonamide and sulfamate inhibitors. | 2007 Jan 25 |
|
The alpha and beta classes carbonic anhydrases from Helicobacter pylori as novel drug targets. | 2008 |
|
Rational use of the fixed combination of dorzolamide - timolol in the management of raised intraocular pressure and glaucoma. | 2008 Jun |
|
Recent advances in pharmacotherapy of glaucoma. | 2008 Oct |
|
Molecular cloning, characterization, and inhibition studies of the Rv1284 beta-carbonic anhydrase from Mycobacterium tuberculosis with sulfonamides and a sulfamate. | 2009 Apr 23 |
|
Carbonic anhydrase inhibitors. Comparison of chlorthalidone, indapamide, trichloromethiazide, and furosemide X-ray crystal structures in adducts with isozyme II, when several water molecules make the difference. | 2009 Feb 1 |
|
Carbonic anhydrase inhibitors. Inhibition and homology modeling studies of the fungal beta-carbonic anhydrase from Candida albicans with sulfonamides. | 2009 Jul 1 |
|
Carbonic anhydrase inhibitors. Inhibition studies of a coral secretory isoform by sulfonamides. | 2009 Jul 15 |
|
Titration calorimetry standards and the precision of isothermal titration calorimetry data. | 2009 Jun 18 |
|
Methazolamide and melatonin inhibit mitochondrial cytochrome C release and are neuroprotective in experimental models of ischemic injury. | 2009 May |
|
Carbonic anhydrase inhibitors. Cloning, characterization, and inhibition studies of a new beta-carbonic anhydrase from Mycobacterium tuberculosis. | 2009 May 14 |
|
Evaluation of the therapeutic potential of carbonic anhydrase inhibitors in two animal models of dystrophin deficient muscular dystrophy. | 2009 Nov 1 |
|
Methazolamide does not impair respiratory work performance in anesthetized rabbits. | 2009 Sep |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/methazolamide.html
Usual Adult Dose for Glaucoma
50 to 100 mg orally 2 or 3 times a day
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14764447
Methazolamide (0.1 mM) inhibited acid-induced [CO(2)](t) increase in mice.
Substance Class |
Chemical
Created
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on
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Record UNII |
W733B0S9SD
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Validated (UNII)
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LIVERTOX |
NBK548664
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NCI_THESAURUS |
C29577
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QS01EC05
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S01EC05
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NCI_THESAURUS |
C448
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D008704
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METHAZOLAMIDE
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m7304
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CHEMBL19
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3269
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DB00703
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6826
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Methazolamide
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554-57-4
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100000081410
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C61318
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TRANSPORTER -> INHIBITOR | |||
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BINDING
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Volume of Distribution | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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