N-(3-methyl-5-sulfamoyl-2,3-dihydro-1,3,4-thiadiazol-2-ylidene)acetamide

• ChemBase ID: 156502
• Molecular Formular: C5H8N4O3S2
• Molecular Mass: 236.27202
• Monoisotopic Mass: 236.00378214
• SMILES: CC(=O)/N=c/1\n(nc(s1)S(=O)(=O)N)C
• Canonical SMILES: CC(=O)/N=c\1/sc(nn1C)S(=O)(=O)N
• InChI: InChI=1S/C5H8N4O3S2/c1-3(10)7-4-9(2)8-5(13-4)14(6,11)12/h1-2H3,(H2,6,11,12)
• InChIKey: FLOSMHQXBMRNHR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(3-methyl-5-sulfamoyl-2,3-dihydro-1,3,4-thiadiazol-2-ylidene)acetamide; N-[(2E)-3-methyl-5-sulfamoyl-2,3-dihydro-1,3,4-thiadiazol-2-ylidene]acetamide
• IUPAC Traditional name: methazolamide; N-[(2E)-3-methyl-5-sulfamoyl-1,3,4-thiadiazol-2-ylidene]acetamide
• Synonyms: N-(4-Methyl-2-sulfamoyl-Δ2-1,3,4-thiadiazolin-5-ylidene) acetamide; Methazolamide; N-[5-(aminosulfonyl)-3-methyl-1,3,4-thiadiazol-2(3H)-ylidene]acetamide; 5-Acetylimino-4-methyl-Δ2-1,3,4-thiadiazoline-2-sulfonamide; L 584601; N-(4-Methyl-2-sulfamoyl-Δ2-1,3,4-thiadiazolin-5-ylidene)acetamide; Methenamide; Neptazane; Neptazaneat; Methazolamide; N-(4-甲基-2-氨基磺酰基-Δ2-1,3,4-噻二唑-5-亚基)乙酰胺; 醋甲唑胺

Database IDs

• CAS Number: 554-57-4
• EC Number: 209-066-7
• MDL Number: MFCD00083416
• PubChem SID: 162250640; 24896908
• PubChem CID: 4100

CALCULATED PROPERTIES

• Acid pKa: 7.2084455
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): -0.6008814
• LogD (pH = 7.4): -0.9298447
• Log P: -0.59343314
• Molar Refractivity: 51.2971 cm^3
• Polarizability: 20.541395 Å^3
• Polar Surface Area: 105.19 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 201-203°C; 208 °C (dec.)(lit.)

Safety Information

• Storage Condition: Refrigerator
• RTECS: AC6350000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22-40
• Safety Statements: 22-36
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H332-H351
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Target: Carbonic Anhydrase
• Gene Information: human ... CA1(759), CA2(760), CA9(768)

Product Information

• Grade: analytical standard, for drug analysis; VETRANAL™, analytical standard
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C5H8N4O3S2

DETAILS

Sigma Aldrich - 37011

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - M226020

Methazolamide is a carbonic anhydrase inhibitor. Methazolamide is used in the treatment of glaucoma.

REFERENCES

• Iyer, G.R. et al.: J. Pharmac. Biomed. Anal., 16, 1021 (1998)
• Maren, T. H. et al.: Invest. Ophthamol. Vis. Sci., 16, 730 (1998)