Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C5H8N4O3S2 |
| Molecular Weight | 236.272 |
| Optical Activity | UNSPECIFIED |
| 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 | |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 1 |
| Optical Activity | NONE |
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
PubMed
| Title | Date | PubMed |
|---|---|---|
| Treatment of essential tremor with methazolamide. | 1991 Oct |
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| Measuring drug concentrations using pulsatile microdialysis: theory and method development in vitro. | 2005 Apr 11 |
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| Expression of a novel carbonic anhydrase, CA XIII, in normal and neoplastic colorectal mucosa. | 2005 Apr 18 |
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| Proton-mediated feedback inhibition of presynaptic calcium channels at the cone photoreceptor synapse. | 2005 Apr 20 |
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| 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 |
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| Functional interaction of carbonic anhydrase and chloride/bicarbonate exchange in human platelets. | 2005 Nov |
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| Effects of low-dose methazolamide on the control of breathing in cats. | 2006 |
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| Carbonic anhydrase inhibitors: cloning and sulfonamide inhibition studies of a carboxyterminal truncated alpha-carbonic anhydrase from Helicobacter pylori. | 2006 Apr 15 |
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| Expression, purification, kinetic, and structural characterization of an alpha-class carbonic anhydrase from Aedes aegypti (AaCA1). | 2006 Aug |
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| [Diuretic therapy in heart failure]. | 2006 Jan-Feb |
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| Carbonic anhydrases and mucosal vanilloid receptors help mediate the hyperemic response to luminal CO2 in rat duodenum. | 2006 Jul |
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| Degradation and effects of the potential mosquito larvicides methazolamide and acetazolamide in sheepshead minnow (Cyprinodon variegatus). | 2006 Jul |
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| The carbonic anhydrase inhibitors methazolamide and acetazolamide have different effects on the hypoxic ventilatory response in the anaesthetized cat. | 2006 Jul 15 |
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| Epithelial carbonic anhydrases facilitate PCO2 and pH regulation in rat duodenal mucosa. | 2006 Jun 15 |
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| Mirtazapine in the treatment of essential tremor: an open-label, observer-blind study. | 2006 Mar |
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| Carbonic anhydrase inhibitors: DNA cloning and inhibition studies of the alpha-carbonic anhydrase from Helicobacter pylori, a new target for developing sulfonamide and sulfamate gastric drugs. | 2006 Mar 23 |
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| Topical dorzolamide for the treatment of cystoid macular edema in patients with retinitis pigmentosa. | 2006 May |
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| Inhibition profiling of human carbonic anhydrase II by high-throughput screening of structurally diverse, biologically active compounds. | 2006 Oct |
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| The development of topically acting carbonic anhydrase inhibitors as anti-glaucoma agents. | 2007 |
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| 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 |
|
| Statement on high-altitude illnesses. An Advisory Committee Statement (ACS). | 2007 Apr 1 |
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| Carbonic anhydrase inhibitors: cloning, characterization, and inhibition studies of the cytosolic isozyme III with sulfonamides. | 2007 Dec 1 |
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| Direct non-cyclooxygenase-2 targets of celecoxib and their potential relevance for cancer therapy. | 2007 Dec 3 |
|
| 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 |
|
| Topical inhibition of nasal carbonic anhydrase affects the CO2 detection threshold in rats. | 2007 Mar |
|
| The development of topically acting carbonic anhydrase inhibitors as antiglaucoma agents. | 2008 |
|
| The alpha and beta classes carbonic anhydrases from Helicobacter pylori as novel drug targets. | 2008 |
|
| CO2 chemosensing in rat oesophagus. | 2008 Dec |
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| Carbonic anhydrase II and alveolar fluid reabsorption during hypercapnia. | 2008 Jan |
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| Rational use of the fixed combination of dorzolamide - timolol in the management of raised intraocular pressure and glaucoma. | 2008 Jun |
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| Pharmacological impact on loop gain properties to prevent irregular breathing. | 2008 Mar |
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| Recent advances in pharmacotherapy of glaucoma. | 2008 Oct |
|
| Inhibitors of cytochrome c release with therapeutic potential for Huntington's disease. | 2008 Sep 17 |
|
| Acetazolamide reversibly inhibits water conduction by aquaporin-4. | 2009 Apr |
|
| Studies on bicarbonate transporters and carbonic anhydrase in porcine nonpigmented ciliary epithelium. | 2009 Apr |
|
| QSAR studies for the inhibition of the transmembrane carbonic anhydrase isozyme XIV with sulfonamides using PRECLAV software. | 2009 Apr |
|
| Molecular cloning, characterization, and inhibition studies of the Rv1284 beta-carbonic anhydrase from Mycobacterium tuberculosis with sulfonamides and a sulfamate. | 2009 Apr 23 |
|
| Functional coupling of the downregulated in adenoma Cl-/base exchanger DRA and the apical Na+/H+ exchangers NHE2 and NHE3. | 2009 Feb |
|
| Carbonic anhydrase inhibitors: inhibition of the beta-class enzyme from the yeast Saccharomyces cerevisiae with sulfonamides and sulfamates. | 2009 Feb 1 |
|
| 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 |
|
| Design of a carbonic anhydrase IX active-site mimic to screen inhibitors for possible anticancer properties. | 2009 Feb 17 |
|
| 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 |
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| 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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Tue Oct 22 00:41:15 UTC 2019
by
admin
on
Tue Oct 22 00:41:15 UTC 2019
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| Record UNII |
W733B0S9SD
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| Record Status |
Validated (UNII)
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LIVERTOX |
614
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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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554-57-4
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D008704
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SUB08843MIG
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METHAZOLAMIDE
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6828
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209-066-7
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M7304
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CHEMBL19
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882
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554-57-4
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DB00703
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554-57-4
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C61318
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554-57-4
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4100
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ACTIVE MOIETY |
| 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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