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Merck

A6011

Acetazolamide

synthetic, ≥99%, carbonic anhydrase inhibitor, powder

Synonyme(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

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About This Item

Formule empirique (notation de Hill) :
C4H6N4O3S2
Numéro CAS:
59-66-5
Poids moléculaire :
222.25
NACRES:
NA.77
PubChem Substance ID:
57653866
UNSPSC Code:
12352202
EC Number:
200-440-5
MDL number:
MFCD00003105

Nom du produit

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)

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Catégories apparentées

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

Classe de stockage

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificats d'analyse (COA)

Lot/Batch Number
BCCN4957
BCCL6186
BCCK0066
BCCH8555
BCCF9805

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Consulter la Bibliothèque de documents

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)
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)
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
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
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