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
| 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) |
| InChI | InChI=1S/C5H8N4O3S2/c1-3(10)7-4-9(2)8-5(13-4)14(6,11)12/h1-2H3,(H2,6,11,12) |
| InChIKey | FLOSMHQXBMRNHR-QPJJXVBHSA-N |
| SMILES | C(N=C1N(C)N=C(S(N)(=O)=O)S1)(=O)C |
| CAS DataBase Reference | 554-57-4(CAS DataBase Reference) |
| FDA UNII | W733B0S9SD |
| NCI Drug Dictionary | methazolamide |
| ATC code | S01EC05 |
| 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) |
| UNSPSC Code | 41116107 |
| NACRES | NA.77 |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |   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 | |||||||||
| Hazardous Substances Data | 554-57-4(Hazardous Substances Data) | |||||||||
| NFPA 704 |
|
Methazolamide price More Price(28)
| 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 | $186 | 2025-07-31 | Buy |
| Sigma-Aldrich | 1406005 | Methazolamide United States Pharmacopeia (USP) Reference Standard | 554-57-4 | 500mg | $406 | 2025-07-31 | Buy |
| TCI Chemical | M3772 | Methazolamide | 554-57-4 | 100MG | $150 | 2025-07-31 | 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 |
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
Methazolamide is a carbonic anhydrase inhibitor. Methazolamide is used in the treatment of glaucoma.
Uses
CNS & respiratory stimulant
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.
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.
References
[1] MAREN T H. Carbonic anhydrase: chemistry, physiology, and inhibition.[J]. Physiological reviews, 1967, 47 4: 595-781. DOI: 10.1152/physrev.1967.47.4.595
[2] WILLIAM D. GRAY Charles E R. The anticonvulsant action of the carbonic anhydrase inhibitor methazolamide: Possible involvement of a noradrenergic mechanism[J]. European journal of pharmacology, 1974, 28 1: Pages 42-54. DOI: 10.1016/0014-2999(74)90110-1
[3] MINGCHANG LI. Methazolamide improves neurological behavior by inhibition of neuron apoptosis in subarachnoid hemorrhage mice[J]. Scientific Reports, 2016, 6 1. DOI: 10.1038/srep35055
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Nanjing ChemLin Chemical Industry Co., Ltd. | 025-83697070 | product@chemlin.com.cn | CHINA | 3009 | 60 |
| career henan chemical co | +86-0371-86658258 +8613203830695 | sales@coreychem.com | China | 29855 | 58 |
| Hubei Jusheng Technology Co.,Ltd. | 18871490254 | linda@hubeijusheng.com | CHINA | 28172 | 58 |
| Xiamen AmoyChem Co., Ltd | +86-86-5926051114 +8615060885618 | sales@amoychem.com | China | 6369 | 58 |
| HubeiwidelychemicaltechnologyCo.,Ltd | 18627774460 | faith@widelychemical.com | CHINA | 742 | 58 |
| CONIER CHEM AND PHARMA LIMITED | +8618523575427 | sales@conier.com | China | 49730 | 58 |
| TargetMol Chemicals Inc. | +1-781-999-5354; +17819995354 | marketing@targetmol.com | United States | 32430 | 58 |
| Hefei TNJ Chemical Industry Co.,Ltd. | +86-0551-65418671 +8618949823763 | sales@tnjchem.com | China | 34563 | 58 |
| Win-Win chemical CO., Limited | +86-0086-577-64498589 +86-15355981851 | sales@win-winchemical.com | China | 14447 | 58 |
| AFINE CHEMICALS LIMITED | +86-0571-85134551 | sales@afinechem.com | China | 15172 | 58 |
View Lastest Price from Methazolamide manufacturers
| Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
|---|---|---|---|---|---|---|---|---|
 |
2025-08-28 | Methazolamide
554-57-4
|
US $50.00 / mg | 99.77% | 10g | TargetMol Chemicals Inc. | ||
 |
2025-08-28 | Methazolamide
554-57-4
|
US $50.00 / mg | 99.77% | 10g | TargetMol Chemicals Inc. | ||
 |
2025-05-26 | 4-Methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
554-57-4
|
US $67.00 / kg | 1kg | 0.99 | 5000 tons | Hebei Fengjia New Material Co., Ltd |
-
- Methazolamide
554-57-4
- US $50.00 / mg
- 99.77%
- TargetMol Chemicals Inc.
-
- Methazolamide
554-57-4
- US $50.00 / mg
- 99.77%
- TargetMol Chemicals Inc.
-
- 4-Methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
554-57-4
- US $67.00 / kg
- 0.99
- Hebei Fengjia New Material Co., Ltd
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