554-57-4 Usage
Originator
Neptazane ,Lederle,US,1959
Manufacturing Process
A 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.
Biochem/physiol Actions
Methazolamide 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 Use
Methazolamide is a derivative of acetazolamide in which one of the active hydrogens has been replaced by a methyl group.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.
Synthesis
Methazolamide, 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 Treatments
Orally administered methazolamide is used for the medical treatment
of glaucoma.
Check Digit Verification of cas no
The CAS Registry Mumber 554-57-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,5 and 4 respectively; the second part has 2 digits, 5 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 554-57:
(5*5)+(4*5)+(3*4)+(2*5)+(1*7)=74
74 % 10 = 4
So 554-57-4 is a valid CAS Registry Number.
InChI:InChI=1/C5H8N4O3S2/c1-3(10)7-4-9(2)8-5(13-4)14(6,11)12/h1-2H3,(H2,6,11,12)/b7-4+
