215902-M

Carbonic Anhydrase IX Inhibitor III, Methazolamide

The Carbonic Anhydrase IX Inhibitor III, Methazolamide, also referenced under CAS 554-57-4, controls the biological activity of Carbonic Anhydrase IX.

• Synonym(s): Carbonic Anhydrase IX Inhibitor III, Methazolamide, N-[5-(aminosulfonyl)-3-methyl-1,3,4-thiadiazol-2(3H)-ylidene]acetamide, Carbonic Anhydrase Inhibitor, Methazolamide, CAIX Inhibitor III
• Empirical Formula (Hill Notation): C₅H₈N₄O₃S₂
• CAS Number: 554-57-4
• Molecular Weight: 236.27
• MDL number: MFCD00083416
• UNSPSC Code: 12352200

Properties

• assay: ≥99% (HPLC)
• form: powder
• potency: 20 nM K_i
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze; protect from light
• color: white
• solubility: DMSO: 50 mg/mL
• storage temp.: 2-8°C
• InChI: 1S/C5H8N4O3S2/c1-3(10)7-4-9(2)8-5(13-4)14(6,11)12/h1-2H3,(H2,6,11,12)
• InChI key: FLOSMHQXBMRNHR-UHFFFAOYSA-N

Description

General description

A cell-permeable thiadiazolylsulfonamide derivative that acts as a carbonic anhydrase (CA) inhibitor (K_i = 20 nM) with anti-glaucoma, anti-diabetic, and potential anti-neoplastic activity. May induce death in hypoxic tumor cells by inhibiting tumor-associated CAIX in maintaining an acidic tumor microenvironment, and blocking CAIX-dependent resistance to chemotherapy in these tumors. Shown to enhance insulin sensitivity and reduce HbA1c levels in diabetic rodent models in a dose-dependent manner. Shown to reduce oxygen and glucose-deprived cell death in primary cerebrocortical neurons by diminishing the release of cytochrome c and dissipating the mitochondrial membrane potential gradient.

Biochem/physiol Actions

Primary Target
carbonic anhydrase

Warning

Toxicity: Standard Handling (A)

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Other Notes

Maren, T., et al. 1977. Invest Ophthalmol Vis Sci.16, 730.
Chegwidden, W. R. and Spencer, I. M. 1995. Inflammopharmacology.3, 231.
Wang, X., et al. 2009. Stroke.40, 1877.
Konstantopoulos, N., et al. 2012. Diabetes.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Safety Information

• pictograms: GHS08,GHS07
• signalword: Warning
• hcodes: H302 + H312 + H332,H351
• pcodes: P202 - P280 - P301 + P312 - P302 + P352 + P312 - P304 + P340 + P312 - P308 + P313
• Hazard Classifications: Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Carc. 2
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3