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Methazolamide

CAS No.
554-57-4
Chemical Name:
Methazolamide
Synonyms
CL 8490;Neptaza;L 584601;Naptazane;Neptazane;Methenamide;Neptazaneat;Methazolamid;Mathazolamide;METHAZOLAMIDE
CBNumber:
CB6150374
Molecular Formula:
C5H8N4O3S2
Molecular Weight:
236.27
MDL Number:
MFCD00083416
MOL File:
554-57-4.mol
MSDS File:
SDS
Last updated:2023-06-08 09:02:53

Methazolamide 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
pka 7.30(at 25℃)
form White powder
color white to beige
Water Solubility 2.835g/L(25 ºC)
InChIKey FLOSMHQXBMRNHR-QPJJXVBHSA-N
CAS DataBase Reference 554-57-4(CAS DataBase Reference)
FDA UNII W733B0S9SD
NIST Chemistry Reference Methazolamide(554-57-4)
NCI Drug Dictionary methazolamide
ATC code S01EC05
EPA Substance Registry System Acetamide, N-[5-(aminosulfonyl)-3-methyl-1,3,4-thiadiazol-2(3H)-ylidene]- (554-57-4)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS07,GHS08
Signal word  Warning
Hazard statements  H302+H312+H332-H351
Precautionary statements  P201-P280-P301+P312-P302+P352+P312-P304+P340+P312-P308+P313
Hazard Codes  Xn
Risk Statements  20/21/22-40
Safety Statements  22-36
WGK Germany  3
RTECS  AC6350000
HS Code  2935904000
NFPA 704
0
3 0

Methazolamide price More Price(27)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich PHR3202 Methazolamide pharmaceutical secondary standard, certified reference material 554-57-4 1G $173 2024-03-01 Buy
Sigma-Aldrich 1406005 Methazolamide United States Pharmacopeia (USP) Reference Standard 554-57-4 500mg $436 2024-03-01 Buy
Cayman Chemical 23413 Methazolamide ≥98% 554-57-4 500mg $46 2024-03-01 Buy
Cayman Chemical 23413 Methazolamide ≥98% 554-57-4 5 g $391 2024-03-01 Buy
Cayman Chemical 23413 Methazolamide ≥98% 554-57-4 10 g $689 2024-03-01 Buy
Product number Packaging Price Buy
PHR3202 1G $173 Buy
1406005 500mg $436 Buy
23413 500mg $46 Buy
23413 5 g $391 Buy
23413 10 g $689 Buy

Methazolamide Chemical Properties,Uses,Production

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.

Chemical Properties

White Solid

Originator

Neptazane ,Lederle,US,1959

Uses

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.

Uses

CNS & respiratory stimulant

Uses

Methazolamide is a carbonic anhydrase inhibitor. Methazolamide is used in the treatment of glaucoma.

Definition

ChEBI: Methazolamide is a member of thiadiazoles and a sulfonamide.

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.

Therapeutic Function

Carbonic anhydrase inhibitor

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?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 Treatments

Orally administered methazolamide is used for the medical treatment of glaucoma.

Methazolamide Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Methazolamide manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Methazolamide pictures 2023-02-13 Methazolamide
554-57-4
US $9.00 / kg 1kg 99% 50MT Hebei baicao biology science and technology co., ltd
Methazolamide pictures 2022-08-13 Methazolamide
554-57-4
US $100.00 / kg 1kg 99% 5000 Ton Hebei Duling International Trade Co. LTD
Methazolamide pictures 2022-02-25 Methazolamide
554-57-4
US $28.99 / KG 1KG 99% 100KG Hong Kong Tiansheng New Material Trading Co., Ltd
  • Methazolamide pictures
  • Methazolamide
    554-57-4
  • US $9.00 / kg
  • 99%
  • Hebei baicao biology science and technology co., ltd
  • Methazolamide pictures
  • Methazolamide
    554-57-4
  • US $100.00 / kg
  • 99%
  • Hebei Duling International Trade Co. LTD
  • Methazolamide pictures
  • Methazolamide
    554-57-4
  • US $28.99 / KG
  • 99%
  • Hong Kong Tiansheng New Material Trading Co., Ltd

Methazolamide Spectrum

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) MethazolaMide, USP 5-AcetyliMino-4-Methyl-Δ2-1,3,4-thiadiazoline-2-sulfonaMide L 584601 Neptaza n-(4-methyl-2-sulfamoyl-△2-1,3,4-thiadiazolin-5-ylidene) acetamide N-[(2E)-5-(Aminosulfonyl)-3-methyl-1,3,4-thiadiazol-2(3H)-ylidene]acetamide (E)-N-(3-Methyl-5-sulfaMoyl-1,3,4-thiadiazol-2(3H)-ylidene)acetaMide Methazolamide≥ 98% (HPLC) Carbonic Anhydrase IX Inhibitor III, Methazolamide Mathazolamide Methazolamide, >=99% 5-Acetylimino-4-methyl-delta2-1,3,4-thiadiazoline-2-sulfonamide Acetamide, N-(4-methyl-2-sulfamoyl-delta2-1,3,4-thiadiazolin-5-ylidene)- Acetamide, N-[5-(aminosulfonyl)-3-methyl-1,3,4-thiadiazol-2(3H)-ylidene]- Methenamide N-((2Z)-5-(Aminosulfonyl)-3-methyl-1,3,4-thiadiazol-2(3H)-ylidene)acetamide n-(4-methyl-2-sulfamoyl-delta(2)-1,3,4-thiadiazolin-5-ylidene)-acetamid n-(4-methyl-2-sulfamoyl-delta(sup2)-1,3,4-thiadiazolin-5-ylidene)-acetamid N-(4-Methyl-2-sulfamoyl-delta2-1,3,4-thiadiazolin-5-ylidene)acetamide n-(5-(aminosulfonyl)-3-methyl-1,3,4-thiadiazol-2(3h)-ylidene)-acetamid Naptazane Neptazane Neptazaneat METHAZOLAMIDE N-[4-METHYL-2-SULFAMOYL-DELTA2-1,3,4-THIADIAZOLIN-5-YLIDENE] ACETAMIDE N-(3-Methyl-5-sulfamoyl-3H-[1,3,4]thiadiazol-2-ylidene)-acetamide Carbonic Anhydrase IX Inhibitor III, Methazolamide - CAS 554-57-4 - Calbiochem Methazolamide USP/EP/BP N-(3-Methyl-5-sulfamoyl-1,3,4-thiadiazol-2(3H)-ylidene)acetamide MethazolamideQ: What is Methazolamide Q: What is the CAS Number of Methazolamide Q: What is the storage condition of Methazolamide Q: What are the applications of Methazolamide Methazolamide (1406005) Methazolamid 554-57-4 554-47-4 C5H2N4O3S2D6 C5H8N4O3S2 Analytical Standards Analytical Chromatography Product Catalog Alphabetic META - METH VANDID Other APIs Heterocycles Inhibitors Intermediates & Fine Chemicals Pharmaceuticals Sulfur & Selenium Compounds