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
• 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

Properties

• Product Name: Acetazolamide, ≥99%, powder
• biological source: synthetic
• Quality Segment: 200
• 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

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Codes: H315,H319
• Precautionary Statements: P264 - P280 - P302 + P352 - P305 + P351 + P338 - P332 + P313 - P337 + P313
• 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 (personal protective equipment): dust mask type N95 (US), Eyeshields, Gloves