Methazolamide

Base Information

• Chemical Name: Methazolamide
• CAS No.: 554-57-4
• Molecular Formula: C5H8N4O3S2
• Molecular Weight: 236.276
• Hs Code.: 2935904000
• European Community (EC) Number: 209-066-7
• NSC Number: 758426
• UNII: W733B0S9SD,DA43GW06P1
• DSSTox Substance ID: DTXSID1023281,DTXSID50901331
• Nikkaji Number: J2.070B
• Wikipedia: Methazolamide
• Wikidata: Q1149099,Q27276292,Q106029850
• NCI Thesaurus Code: C61318
• RXCUI: 6826
• Pharos Ligand ID: 41TQ31ACADZW,41TU5XRHJCRY
• Metabolomics Workbench ID: 67471
• ChEMBL ID: CHEMBL19,CHEMBL288100,CHEMBL1335656
• Mol file: 554-57-4.mol

Synonyms:Methazolamide;N Methylacetazolamide;N-Methylacetazolamide

Chemical Property of Methazolamide

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 208 ºC (dec.)
• Refractive Index: 1.737
• Boiling Point: 402°Cat760mmHg
• PKA: 7.30(at 25℃)
• Flash Point: 196.9°C
• PSA: 144.03000
• Density: 1.79g/cm³
• LogP: 0.35730
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble20mg/mL, clear
• Water Solubility.: 2.835g/L(25 oC)
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 236.00378248
• Heavy Atom Count: 14
• Complexity: 419

Purity/Quality:

99.5% ^*data from raw suppliers

Methazolamide ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 20/21/22-40
• Safety Statements: 22-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)N=C1N(N=C(S1)S(=O)(=O)N)C
• Recent ClinicalTrials: Use of Methazolamide to Lower Intraocular Pressure
• Description: Methazolamide 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.
• Uses: Methazolamide is a carbonic anhydrase inhibitor. Methazolamide is used in the treatment of glaucoma. CNS & respiratory stimulant Action 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.
• 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.

Technology Process of Methazolamide

There total 2 articles about Methazolamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

5-acetylimino-4-methyl-4,5-dihydro-[1,3,4]thiadiazole-2-sulfonyl chloride (114224-34-9) → methazolamide (554-57-4)

Guidance literature:

With ammonia;

DOI:10.1021/ja01599a033

Reference yield:

→ methazolamide (554-57-4)

Guidance literature:

With water; chlorine; iron(III) chloride; Behandeln des Reaktionsprodukts mit fluessigem NH₃;

Reference yield:

cobalt(II) nitrate hexahydrate + methazolamide (554-57-4) → {Co(2-methyl-2-amino-4-iminopentane)2(NH3)2}(NO3)3*2H2O + {Co(methazolamidate)(2-methyl-2-amino-4-iminopentane)2(NH3)}(NO3)2*2H2O

Guidance literature:

With NH₃; acetone; air; In acetone; dissolving of methazolamide in acetone at 50°C; heating at 80°C; addn. of Co(NO3)2*6H2O with stirring; cooling to 50°C and dropwise addn. of concd. NH3; standing at room temp.; mechanism discussed;; crystn. on cooling within 2-3 days; crystals of the methazolamidate complex were separated from the solid (Co(C6H14N2)2(NH3)2)(NO3)3*2H2O, washed and dried over silica gel in a vac. desiccator; elem. anal.;;

DOI:10.1016/S0020-1693(00)87358-2

upstream raw materials:

5-acetylimino-4-methyl-4,5-dihydro-[1,3,4]thiadiazole-2-sulfonyl chloride