Skip to Content
Merck

A6011

Acetazolamide

synthetic, ≥99%, carbonic anhydrase inhibitor, powder

Synonym(s):

5-Acetamido-1,3,4-thiadiazole-2-sulfonamide, N-(5-Sulfamoyl-1,3,4-thiadiazol-2-yl)acetamide, N-(5-[Aminosulfonyl]-1,3,4-thiadiazol-2-yl)acetamide

Sign In to View Organizational & Contract Pricing.

Select a Size

About This Item

Empirical Formula (Hill Notation):
C4H6N4O3S2
CAS Number:
59-66-5
Molecular Weight:
222.25
NACRES:
NA.77
PubChem Substance ID:
57653866
UNSPSC Code:
12352202
EC Number:
200-440-5
MDL number:
MFCD00003105

Key Documents

View All Documentation
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

Product Name

Acetazolamide, ≥99%, powder

InChI key

BZKPWHYZMXOIDC-UHFFFAOYSA-N

InChI

1S/C4H6N4O3S2/c1-2(9)6-3-7-8-4(12-3)13(5,10)11/h1H3,(H2,5,10,11)(H,6,7,9)

SMILES string

CC(=O)Nc1nnc(s1)S(N)(=O)=O

biological source

synthetic

assay

≥99%

form

powder

pKa 

7.2

mp

258-259 °C

solubility

1 M NH4OH: 50 mg/mL, DMSO: soluble, methanol and ethanol: slightly soluble

Quality Level

200

Gene Information

human ... CA1(759), CA12(771), CA14(23632), CA2(760), CA3(761), CA4(762), CA5A(763), CA5B(11238), CA9(768)
mouse ... Car13(71934), Car5a(12352)
rat ... Car2(54231), Car4(29242)

Looking for similar products? Visit Product Comparison Guide

Application

Acetazolamide has been used:
  • to study its protective effect on steatotic liver grafts against cold ischemia reperfusion injury{49)
  • to determine its ability to bind isolated porcine retinal pigment epithelium (RPE) melanin by cassette dosing and rapid equilibrium dialysis inserts
  • to validate the in vitro gastrulation model of P19C5 stem cells for developmental toxicity screening assays
  • to study its inhibitory effect on melanogenesis through enzyme kinetic, in vitro, in vivo and in silico analyses in zebrafish and in A375 human melanoma cells

Carbonic anhydrase inhibitor; increases cerebral blood flow.

Biochem/physiol Actions

Acetazolamide is a member of sulfonamide drug family. It as an ability to inhibit the activity of carbonic anhydrase. It rapidly increases cerebral blood flow (CBF) and is used as an investigative tool in CBF studies. Acetazolamide acts as a therapeutic agent for epilepsy, glaucoma and pseudotumor cerebri.
Inhibits water permeability of membranes by interacting with aquaporins

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

Substances Subject to be Indicated Names

ishl_indicated

Substances Subject to be Notified Names

ishl_notified

A6011-100G: + A6011-25G: + A6011-250G: + A6011-VAR: + A6011-BULK: + A6011-10G:

jan

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
BCCF9805
BCCD4223
BCCC4390
BCCC3407
BCCC3406

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Gianfranco Bazzu et al.
Analytical chemistry, 81(6), 2235-2241 (2009-02-19)
A miniaturized biotelemetric device for the amperometric detection of brain tissue oxygen is presented. The new system, derived from a previous design, has been coupled with a carbon microsensor for the real-time detection of dissolved O(2) in the striatum of
Effect of acetazolamide on cerebral blood flow and cerebral metabolic rate for oxygen.
Vorstrup S, et al.
The Journal of Clinical Investigation, 74(5), 1634-1639 (1984)
Acetazolamide inhibits the level of tyrosinase and melanin: an enzyme kinetic, in vitro, in vivo, and in silico studies
Abbas Q, et al.
Chemistry and Biodiversity, 14(9), e1700117-e1700117 (2017)
Maria Skytte Torring et al.
Investigative ophthalmology & visual science, 50(1), 345-351 (2008-09-02)
Carbonic anhydrase inhibitors reduce intraocular pressure, which may protect the optic nerve from ischemia. However, carbonic anhydrase inhibitors have also been shown to dilate the blood vessels in the retina and the optic nerve head. The purpose of the present
Lorenzo Biancalana et al.
Dalton transactions (Cambridge, England : 2003), 47(28), 9367-9384 (2018-06-29)
The carbonic anhydrase inhibitor acetazolamide (AcmH2) reacted with [(η6-p-cymene)RuCl(μ-Cl)]2 to afford [(η6-p-cymene)RuCl2(κN-AcmH2)], 1A, in near-quantitative yield. In methanol, 1A exists in equilibrium with 1B, being probably a coordination isomer, as established by VT 1H-EXSY NMR spectroscopy. DFT calculations pointed to
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service