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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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Methazolamide Suppliers

Hangzhou Aobo Baoling Pharmaceutical Co., Ltd.
Tel
4000-228211
Country
China
ProdList
3
Advantage
58
Wellman Pharmaceutical Group Limited
Tel
027-027-83778875 15807197853
Fax
027-83991220
Email
15807197853@163.com
Country
China
ProdList
4009
Advantage
58
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
Advantage
76
Chemsky(shanghai)International Co.,Ltd.
Tel
021-50135380
Email
shchemsky@sina.com
Country
China
ProdList
32321
Advantage
50
Syntechem Co.,Ltd
Tel
Fax
E-Mail Inquiry
Email
info@syntechem.com
Country
China
ProdList
12984
Advantage
57
Sinopharm Chemical Reagent Co,Ltd.
Tel
86-21-63210123
Fax
86-21-63290778 86-21-63218885
Email
sj_scrc@sinopharm.com
Country
China
ProdList
9815
Advantage
79
Hangzhou Yuhao Chemical Technology Co., Ltd
Tel
0571-82693216
Fax
+86-571-82880190
Email
info@yuhaochemical.com
Country
China
ProdList
9387
Advantage
52
Beijing Taiya Jie Technology Development Co., Ltd.
Tel
021-33690831-8001 13552411790
Fax
021-33690831
Email
postmaster@tyjchem.cn
Country
China
ProdList
1541
Advantage
55
Spectrum Chemical Manufacturing Corp.
Tel
021-021-021-67601398-809-809-809 15221380277
Fax
021-57711696
Email
marketing_china@spectrumchemical.com
Country
China
ProdList
9658
Advantage
60
Beijing HuaMeiHuLiBiological Chemical
Tel
010-56205725
Fax
010-65763397
Email
waley188@sohu.com
Country
China
ProdList
12335
Advantage
58
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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

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