Contact us: +91 9550333722 040 - 40102781
Structured search
India
Choose your country
Different countries will display different contents
Try our best to find the right business for you.
My chemicalbook

Welcome back!

HomeProduct name listMethazolamide

Methazolamide

Synonym(s):N-(4-Methyl-2-sulfamoyl-Δ2-1,3,4-thiadiazolin-5-ylidene) acetamide;5-Acetylimino-4-methyl-·2-1,3,4-thiadiazoline-2-sulfonamide;Methazolamide;N-[5-(Aminosulfonyl)-3-methyl-1,3,4-thiadiazol-2(3H)-ylidene]acetamide;N-[5-(aminosulfonyl)-3-methyl-1,3,4-thiadiazol-2(3H)-ylidene]acetamide, Carbonic Anhydrase Inhibitor, Methazolamide, CAIX Inhibitor III

  • CAS NO.:554-57-4
  • Empirical Formula: C5H8N4O3S2
  • Molecular Weight: 236.27
  • MDL number: MFCD00083416
  • EINECS: 209-066-7
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-12-18 14:15:30
Methazolamide Structural

What is Methazolamide?

Absorption

Methazolamide is well absorbed from the gastrointestinal tract.

Toxicity

Electrolyte imbalance, development of an acidotic state, and central nervous system effects might be expected to occur in the case of an overdose.

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

The Uses of Methazolamide

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

The Uses of Methazolamide

CNS & respiratory stimulant

The Uses of Methazolamide

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.

Background

A carbonic anhydrase inhibitor that is used as a diuretic and in the treatment of glaucoma.

Indications

For treatment of chronic open-angle glaucoma and acute angle-closure glaucoma

What are the applications of Application

Methazolamide is a carbonic anhydrase inhibitor

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.

Pharmacokinetics

Methazolamide is topical carbonic anhydrase inhibitor. Methazolamide is indicated for the reduction of elevated intraocular pressure in patients with open-angle glaucoma or ocular hypertension who are insufficiently responsive to beta-blockers. Methazolamide is a sulfonamide derivative; however, it does not have any clinically significant antimicrobial properties. Although methazolamide achieves a high concentration in the cerebrospinal fluid, it is not-considered an effective anticonvulsant. Methazolamide has a weak and transient diuretic effect, therefore use results in an increase in urinary volume, with excretion of sodium, potassium and chloride.

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.

Metabolism

Not Available

Properties of Methazolamide

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)
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 information for Methazolamide

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
ghs
Health Hazard
GHS08
GHS Hazard Statements H351:Carcinogenicity
Precautionary Statement Codes P201:Obtain special instructions before use.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P308+P313:IF exposed or concerned: Get medical advice/attention.

Computed Descriptors for Methazolamide

InChIKey FLOSMHQXBMRNHR-QPJJXVBHSA-N

Related products of tetrahydrofuran

You may like

Statement: All products displayed on this website are only used for non medical purposes such as industrial applications or scientific research, and cannot be used for clinical diagnosis or treatment of humans or animals. They are not medicinal or edible.