N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)acetamide

• ChemBase ID: 698
• Molecular Formular: C4H6N4O3S2
• Molecular Mass: 222.24544
• Monoisotopic Mass: 221.98813207
• SMILES: S(=O)(=O)(N)c1sc(NC(=O)C)nn1
• Canonical SMILES: CC(=O)Nc1nnc(s1)S(=O)(=O)N
• InChI: 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)
• InChIKey: BZKPWHYZMXOIDC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)acetamide
• IUPAC Traditional name: acetazolamide
• Brand Name: Acetamox; Acetazolam; Ak-Zol; Apo-Acetazolamide; Atenezol; Cidamex; Dazamide; Defiltran; Dehydratin; Diacarb; Diakarb; Diamox; Diamox Sequels; Didoc; Diluran; Diuramid; Diureticum-Holzinger; Diuriwas; Diutazol; Donmox; Duiramid; Edemox; Eumicton; Fonurit; Glaupax; Glupax; Natrionex; Nephramid; Nephramide; Phonurit; Sk-Acetazolamide; Storzolamide; Vetamox
• Synonyms: 2-ACETAMINO-1,3,4-THIADIAZOLE-5-SULFONAMIDE; N-(5-Sulfamoyl-1,3,4-thiadiazol-2-yl)acetamide; Acetazolamide; N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)acetamide; Acetamidothiadiazolesulfonamide; Acetazolamid; Acetazolamide Sodium; Acetazolamine; Acetazoleamide; Acetozalamide; Carbonic Anhydrase Inhibitor 6063; Acetazolamide; N-[5-Sulfamoyl-1,3,4-thiadiazol-2-yl]acetamide; 5-Acetamido-1,3,4-thiadiazole-2-sulfonamide; N-(5-[Aminosulfonyl]-1,3,4-thiadiazol-2-yl)acetamide; N-[5-Aminosulfonyl)-1,3,4-thiadiazol-2-yl]acetamide; Acetamox; Atenezol; Defiltran; Diamox; Didoc; 乙酰唑胺

Database IDs

• CAS Number: 59-66-5
• EC Number: 200-440-5
• MDL Number: MFCD00003105
• Beilstein Number: 212994
• Merck Index: 1453
• PubChem SID: 24278144; 160964161; 46504493
• PubChem CID: 1986

CALCULATED PROPERTIES

JChem

• Acid pKa: 6.9279256
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -1.0535402
• LogD (pH = 7.4): -1.5116225
• Log P: -1.039467
• Molar Refractivity: 47.3567 cm^3
• Polarizability: 17.841074 Å^3
• Polar Surface Area: 115.04 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.39
• LOG S: -1.9
• Solubility (Water): 2.79e+00 g/l

PROPERTIES

Physical Property

• Solubility: 0.98 mg/mL at 30 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]; 1 M NH4OH: soluble50 mg/mL; DMSO; DMSO: soluble; methanol and ethanol: slightly soluble
• Apperance: powder; White Solid
• Melting Point: 249 - 251°C; 258-259; 270-275°C; ca 255°C dec.
• Hydrophobicity(logP): -0.26 [HANSCH,C ET AL. (1995)]; -1.922
• pKa: 7.2

Safety Information

• Storage Condition: Refrigerator; Room Temperature (15-30°C), Desiccate
• RTECS: AC8225000
• European Hazard Symbols: Toxic (T); Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 36/38; 61; R:36/37/38
• Safety Statements: 26; 53-36-45; S:20-25-26-37/39
• TSCA Listed: 是
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319; H360-H303
• GHS Precautionary statements: P281-P201-P312-P308+P313-P405-P501A; P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

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

Product Information

• Purity: ≥99%; 95%; 99%

DETAILS

MP Biomedicals - 05212363

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02154171

(N-[5-Sulfamoyl-1,3,4-thiadiazol- 2-yl]acetamide) Crystalline

DrugBank - DB00819

• Drug Groups: approved
• Description: One of the carbonic anhydrase inhibitors that is sometimes effective against absence seizures. It is sometimes useful also as an adjunct in the treatment of tonic-clonic, myoclonic, and atonic seizures, particularly in women whose seizures occur or are exacerbated at specific times in the menstrual cycle. However, its usefulness is transient often because of rapid development of tolerance. Its antiepileptic effect may be due to its inhibitory effect on brain carbonic anhydrase, which leads to an increased transneuronal chloride gradient, increased chloride current, and increased inhibition. (From Smith and Reynard, Textbook of Pharmacology, 1991, p337)
• Indication: For adjunctive treatment of: edema due to congestive heart failure; drug-induced edema; centrencephalic epilepsies; chronic simple (open-angle) glaucoma
• Pharmacology: Acetazolamide is a potent carbonic anhydrase inhibitor, effective in the control of fluid secretion, in the treatment of certain convulsive disorders and in the promotion of diuresis in instances of abnormal fluid retention. Acetazolamide is not a mercurial diuretic. Rather, it is a nonbacteriostatic sulfonamide possessing a chemical structure and pharmacological activity distinctly different from the bacteriostatic sulfonamides.
• Affected Organisms: Humans and other mammals
• Half Life: 3 to 9 hours
• Protein Binding: 98%
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - A6011

Application
Carbonic anhydrase inhibitor; increases cerebral blood flow.
Biochem/physiol Actions
Inhibits water permeability of membranes by interacting with aquaporins1,2
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.

Toronto Research Chemicals - A161500

Carbonic anhydrase inhibitor. Diuretic.

REFERENCES

• Vitale, R., et al.: J. Med. Chem., 52, 5990 (2009)
• Bell, H., et al.: Am. J. Physiol., 297, R370 (2009)
• Maresca, A., et al.: Bioorg. Med. Chem. Lett., 19, 4929 (2009)
• Liu, Y., et al.: Anal. Bioanal. Chem., 395, 591 (2009)