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A6011

Sigma-Aldrich

Acetazolamide

≥99%, 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

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About This Item

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

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

SMILES string

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

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)

InChI key

BZKPWHYZMXOIDC-UHFFFAOYSA-N

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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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

Signal Word

Warning

Hazard Statements

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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)
Karine Auré et al.
Neurology, 81(21), 1810-1818 (2013-10-25)
To report that homoplasmic deleterious mutations in the mitochondrial DNA MT-ATP6/8 genes may be responsible for acute episodes of limb weakness mimicking periodic paralysis due to channelopathies and dramatically responding to acetazolamide. Mitochondrial DNA sequencing and restriction PCR, oxidative phosphorylation
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