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
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)
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)
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.
N-Bromosuccinimide Price
- Product number
- PHR3202
- Product name
- Methazolamide
- Purity
- pharmaceutical secondary standard, certified reference material
- Packaging
- 1G
- Price
- $173
- Updated
- 2024/03/01
- Product number
- 1406005
- Product name
- Methazolamide
- Purity
- United States Pharmacopeia (USP) Reference Standard
- Packaging
- 500mg
- Price
- $436
- Updated
- 2024/03/01
- Product number
- 23413
- Product name
- Methazolamide
- Purity
- ≥98%
- Packaging
- 500mg
- Price
- $46
- Updated
- 2024/03/01
- Product number
- 23413
- Product name
- Methazolamide
- Purity
- ≥98%
- Packaging
- 5 g
- Price
- $391
- Updated
- 2024/03/01
- Product number
- 23413
- Product name
- Methazolamide
- Purity
- ≥98%
- Packaging
- 10 g
- Price
- $689
- Updated
- 2024/03/01
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
- 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
- Product
- Methazolamide 554-57-4
- Price
- US $28.99/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 100KG
- Release date
- 2021-12-28
- Product
- Methazolamide 554-57-4
- Price
- US $22.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 20TONS
- Release date
- 2022-01-07