Methazolamide Chemical Properties
- Melting point:208 °C (dec.)(lit.)
- Boiling point:402.0±28.0 °C(Predicted)
- Density 1.6625 (rough estimate)
- refractive index 1.6270 (estimate)
- storage temp. 2-8°C
- solubility DMSO: soluble20mg/mL, clear
- pka7.30(at 25℃)
- form White powder
- color white to beige
- Water Solubility 2.835g/L(25 ºC)
- CAS DataBase Reference554-57-4(CAS DataBase Reference)
- NIST Chemistry ReferenceMethazolamide(554-57-4)
- EPA Substance Registry SystemAcetamide, N-[5-(aminosulfonyl)-3-methyl-1,3,4-thiadiazol-2(3H)-ylidene]- (554-57-4)
Methazolamide Usage And Synthesis
- Chemical PropertiesWhite Solid
- OriginatorNeptazane ,Lederle,US,1959
- UsesMethazolamide is a carbonic anhydrase inhibitor. Methazolamide is used in the treatment of glaucoma.
- UsesCNS & respiratory stimulant
- UsesAction of this drug is similar to that of acetazolamide, and it is used for lowering intraocular pressure in treating wide-angle and secondary glaucoma, and before surgical intervention for severe wide-angle glaucoma.
- Manufacturing ProcessA suspension of 6 parts by weight of 5-acetylimino-4-methyl-2- benzylmercapto-δ2-1,3,4-thiadiazoline in 180 parts by volume of 33% aqueous acetic acid was chlorinated at 5°C for 30 minutes. The solid was filtered off, dried, and added portion-wise to 100 parts by volume of liquid ammonia. The ammonia was removed under a stream of dry nitrogen.
The residual solid was partially dissolved in 10 parts by volume of water, filtered, and acidified to give 5-acetylimino-4-methyl-δ2-1,3,4-thiadiazoline-2- sulfonamide. The product was purified by two recrystallizations from hot water.
- Therapeutic FunctionCarbonic anhydrase inhibitor
- Clinical UseMethazolamide is a derivative of acetazolamide in which one of the active hydrogens has been replaced by a methyl group. This decreases the polarity and permits a greater penetration into the ocular fluid, where it acts as a carbonic anhydrase inhibitor, reducing intraocular pressure. Its dose for glaucoma is 50 to 100 mg two to three times a day.
- Chemical SynthesisMethazolamide, N-(4-methyl-2-sulfamoyl-1,3,4-thiadiazol-5-yliden)
acetamide (21.2.3), is made by an intermediate product of acetazolamide synthesis—
2-acetylamino-5-mercapto-1,3,4-thadiazol (9.7.3). This is benzylated with benzylchloride at
the mercapto group, forming 2-acetylamino-5-benzylthio-1,3,4-thiadiazole (21.2.1). Further
methylation of the product with methyl iodide leads to the formation of N-(4-methyl-
2-benzylthio-1,3,4-thiadiazol-5-yliden)acetamide (21.2.2). Oxidation and simultaneous
chlorination of the resulting product with chlorine in an aqueous solution of acetic acid, and
reacting the resulting chlorosulfonic derivative with ammonia gives (21.2.3).
- Veterinary Drugs and TreatmentsOrally administered methazolamide is used for the medical treatment of glaucoma.
- Kresoxim-methyl 2,1,3-Benzothiadiazole Acetaminophen methyl hydrazonothiocarbamate Methazolamide Parathion-methyl Acetamide Thiophanate-methyl 2-Mercapto-5-methyl-1,3,4-thiadiazole Methyl Bensulfuron methyl Methylparaben N,N-Dimethylacetamide METHYL THIOPHENE-2-CARBOXYLATE Methyl acrylate Thioacetamide Methyl bromide
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