Methazolamide

ChemicalBook > CAS DataBase List > Methazolamide

Product Name: 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
Formula Weight: 236.27
MOL File: 554-57-4.mol

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Methazolamide Property

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

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Safety

Hazard Codes: Xn
Risk Statements: 20/21/22-40
Safety Statements: 22-36
WGK Germany: 3
RTECS: AC6350000
HS Code: 2935904000
Hazardous Substances Data: 554-57-4(Hazardous Substances Data)

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H351Suspected of causing cancer

Precautionary statements

P201Obtain special instructions before use.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P308+P313IF exposed or concerned: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: PHR3202
Product name: Methazolamide
Purity: pharmaceutical secondary standard, certified reference material
Packaging: 1G
Price: $173
Updated: 2024/03/01

Sigma-Aldrich

Product number: 1406005
Product name: Methazolamide
Purity: United States Pharmacopeia (USP) Reference Standard
Packaging: 500mg
Price: $436
Updated: 2024/03/01

Cayman Chemical

Product number: 23413
Product name: Methazolamide
Purity: ≥98%
Packaging: 500mg
Price: $46
Updated: 2024/03/01

Cayman Chemical

Product number: 23413
Product name: Methazolamide
Purity: ≥98%
Packaging: 5 g
Price: $391
Updated: 2024/03/01

Cayman Chemical

Product number: 23413
Product name: Methazolamide
Purity: ≥98%
Packaging: 10 g
Price: $689
Updated: 2024/03/01

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Methazolamide Chemical Properties,Usage,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

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

Uses

CNS & respiratory stimulant

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).

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

Hebei Fengjia New Material Co., Ltd

Product: 4-Methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid 554-57-4
Price: US $67.00/kg
Min. Order: 1kg
Purity: 0.99
Supply Ability: 5000 tons
Release date: 2024-08-22

Hong Kong Tiansheng New Material Trading Co., Ltd

Product: Methazolamide 554-57-4
Price: US $28.99/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 100KG
Release date: 2021-12-28

Hong Kong Tiansheng New Material Trading Co., Ltd

Product: Methazolamide 554-57-4
Price: US $22.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 20TONS
Release date: 2022-01-07

554-57-4, MethazolamideRelated Search:

N,N-Dimethylacetamide Kresoxim-methyl 2,1,3-Benzothiadiazole Acetaminophen Bensulfuron methyl Methylparaben METHYL THIOPHENE-2-CARBOXYLATE Methyl acrylate Thioacetamide Acetamide Thiophanate-methyl 2-Mercapto-5-methyl-1,3,4-thiadiazole Methyl Methyl bromide Parathion-methyl methyl hydrazonothiocarbamate Methazolamide

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%

Carbonic Anhydrase IX Inhibitor III, Methazolamide - CAS 554-57-4 - Calbiochem

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

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

Methazolamide, 10 mM in DMSO

554-57-4

554-47-4

C5H2N4O3S2D6

C5H8N4O3S2

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