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Merck
CN

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

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About This Item

Empirical Formula (Hill Notation):
C5H8N4O3S2
CAS Number:
554-57-4
Molecular Weight:
236.27
UNSPSC Code:
12352200
MDL number:
MFCD00083416

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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

assay

≥99% (HPLC)

form

powder

potency

20 nM Ki

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze, protect from light

color

white

solubility

DMSO: 50 mg/mL

General description

A cell-permeable thiadiazolylsulfonamide derivative that acts as a carbonic anhydrase (CA) inhibitor (Ki = 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

Preparation Note

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

Disclaimer

Toxicity: Standard Handling (A)

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Warning

Hazard Classifications

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

Storage Class

11 - Combustible Solids

wgk

WGK 3

Regulatory Information

新产品
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