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SML0720

Sigma-Aldrich

Methazolamide

≥98% (HPLC)

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Synonym(s):
5-Acetylimino-4-methyl-·2-1,3,4-thiadiazoline-2-sulfonamide, N-(4-Methyl-2-sulfamoyl-Δ2-1,3,4-thiadiazolin-5-ylidene) acetamide, L 584601, N-[5-(Aminosulfonyl)-3-methyl-1,3,4-thiadiazol-2(3H)-ylidene]acetamide
Empirical Formula (Hill Notation):
C5H8N4O3S2
CAS Number:
554-57-4
Molecular Weight:
236.27
EC Number:
209-066-7
MDL number:
MFCD00083416
PubChem Substance ID:
329825590
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

storage condition

protect from light

color

white to beige

mp

208 °C (dec.) (lit.)

solubility

DMSO: 20 mg/mL, clear

storage temp.

2-8°C

SMILES string

CN1N=C(S\C1=N\C(C)=O)S(N)(=O)=O

InChI

1S/C5H8N4O3S2/c1-3(10)7-4-9(2)8-5(13-4)14(6,11)12/h1-2H3,(H2,6,11,12)/b7-4+

InChI key

FLOSMHQXBMRNHR-QPJJXVBHSA-N

Gene Information

human ... CA1(759) , CA2(760) , CA4(762) , CA7(766)

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Biochem/physiol Actions

Methazolamide has a plasma half-life of 14 hours in humans. Methazolamide has relatively good lipid solubility and low plasma protein binding ability. Thus, it diffuses into tissues and fluids much more readily than acetazolamide, another carbonic anhydrase inhibitor. Methazolamide has less side effects than acetazolamide.
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.

Other Notes

Light sensitive

Pictograms

Exclamation markHealth hazard
GHS07,GHS08

Signal Word

Warning

Hazard Statements

H302 + H312 + H332 - H351

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Carc. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

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The pharmacology of methazolamide in relation to the treatment of glaucoma.
Maren TH, et al.
Investigative Ophthalmology & Visual Science, 16(8), 730-742 (1977)
Ming-Tao Yang et al.
Psychopharmacology, 232(20), 3763-3772 (2015-08-01)
Dysregulation of noradrenergic and dopaminergic systems is involved in the pathology of attention deficit hyperactivity disorder (ADHD). Carbonic anhydrase (CA) has been reported to affect monoamine transmission in the central nervous system. The aim of this study is to investigate

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