Methazolamide

Methazolamide Basic information
Product Name:Methazolamide
Synonyms:2-acetylimino-3-methyl-delta(sup4)-1,3,4-thiadiazoline-5-sulfonamide;2-Acetylimino-3-methyl-delta4-1,3,4-thiadiazoline-5-sulfonamide;5-acetylimino-4-methyl-delta(sup2)-1,3,4-thiadiazoline-2-sulfonamide;CL 8490;N-[5-(Aminosulfonyl)-3-methyl-1,3,4-thiadiazol-2(3H)-ylidene]acetamide;N-(3-methyl-5-sulfamoyl-1,3,4-thiadiazol-2-ylidene)acetamide;N-(3-methyl-5-sulfamoyl-1,3,4-thiadiazol-2-ylidene)ethanamide;Methazolamide (500 mg)
CAS:554-57-4
MF:C5H8N4O3S2
MW:236.27
EINECS:209-066-7
Product Categories:VANDID;Other APIs;Heterocycles;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds
Mol File:554-57-4.mol
Methazolamide Structure
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)
InChIKeyFLOSMHQXBMRNHR-QPJJXVBHSA-N
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)
Safety Information
Hazard Codes Xn
Risk Statements 20/21/22-40
Safety Statements 22-36
WGK Germany 3
RTECS AC6350000
HS Code 2935904000
Hazardous Substances Data554-57-4(Hazardous Substances Data)
MSDS Information
ProviderLanguage
SigmaAldrich English
Methazolamide Usage And Synthesis
DescriptionMethazolamide is a carbonic anhydrase inhibitor (IC50 = 130 nM). It reduces intraocular pressure and cerebrospinal fluid flow in a rat model of glaucoma. Methazolamide reduces electroshock-induced seizures in rats with an ED50 value of 19.2 mg/kg. It also inhibits production of reactive oxygen species (ROS) in a primary cortical neuron (PCN) cellular model of subarachnoid hemorrhage (SAH) and reduces cerebral edema in a mouse model of SAH. Methazolamide is larvicidal, with a larvicidal concentration (LC50) value of 724 ppm, but has no activity when administered in the diet to adult A. aegypti. Formulations containing methazolamide have been used for the treatment of glaucoma.
Chemical PropertiesWhite Solid
OriginatorNeptazane ,Lederle,US,1959
UsesMethazolamide is a carbonic anhydrase inhibitor. Methazolamide is used in the treatment of glaucoma.
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.
UsesCNS & respiratory stimulant
DefinitionChEBI: Methazolamide is a member of thiadiazoles and a sulfonamide.
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
Biochem/physiol ActionsMethazolamide is a cell-permeable and potent carbonic anhydrase (CA) inhibitor that is used in the treatment of glaucoma. Methazolamide is an insulin sensitizer that reduces hepatic glucose generation in animal models.
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.
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?a 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).

Synthesis_554-57-4

Veterinary Drugs and TreatmentsOrally administered methazolamide is used for the medical treatment of glaucoma.
Methazolamide Preparation Products And Raw materials
Raw materialsAmmonia-->Chlorine
Methylparaben Methyl methyl hydrazonothiocarbamate 2-Mercapto-5-methyl-1,3,4-thiadiazole Acetaminophen Bensulfuron methyl Parathion-methyl Acetamide Methazolamide Kresoxim-methyl 2,1,3-Benzothiadiazole Thiophanate-methyl Thioacetamide Methyl acrylate N,N-Dimethylacetamide Methyl bromide METHYL THIOPHENE-2-CARBOXYLATE

Email:[email protected] [email protected]
Copyright © 2024 Mywellwork.com All rights reserved.