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A6011 Sigma-Aldrich

Acetazolamide

≥99%, powder

Synonym: 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

  • CAS Number 59-66-5

  • Empirical Formula (Hill Notation) C4H6N4O3S2

  • Molecular Weight 222.25

  •  EC Number 200-440-5

  •  MDL number MFCD00003105

  •  PubChem Substance ID 57653866

  •  NACRES NA.77

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Properties

Related Categories A to C, Biochemicals and Reagents, Carbonic anhydrase, Enzyme Inhibitors, Enzyme Inhibitors by Enzyme,
Quality Level   200
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)

Description

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

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. A6011.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Safety & Documentation

Safety Information

Symbol 
Signal word 
Warning-Warning
Hazard statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 2
RTECS 
AC8225000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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