6-chloro-1,1-dioxo-3-[(prop-2-en-1-ylsulfanyl)methyl]-3,4-dihydro-2H-1λ6,2,4-benzothiadiazine-7-sulfonamide

• ChemBase ID: 159746
• Molecular Formular: C11H14ClN3O4S3
• Molecular Mass: 383.89456
• Monoisotopic Mass: 382.98349662
• SMILES: c1(c(cc2c(c1)NC(NS2(=O)=O)CSCC=C)S(=O)(=O)N)Cl
• Canonical SMILES: C=CCSCC1Nc2cc(Cl)c(cc2S(=O)(=O)N1)S(=O)(=O)N
• InChI: InChI=1S/C11H14ClN3O4S3/c1-2-3-20-6-11-14-8-4-7(12)9(21(13,16)17)5-10(8)22(18,19)15-11/h2,4-5,11,14-15H,1,3,6H2,(H2,13,16,17)
• InChIKey: VGLGVJVUHYTIIU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-chloro-1,1-dioxo-3-[(prop-2-en-1-ylsulfanyl)methyl]-3,4-dihydro-2H-1λ^6,2,4-benzothiadiazine-7-sulfonamide
• IUPAC Traditional name: althiazide
• Synonyms: 6-Chloro-3,4-dihydro-3-[(2-propen-1-ylthio)methyl]-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-Dioxide; 3-[(Allylthio)methyl]-6-chloro-3,4-dihydro-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-Dioxide; Althizide; Altizid; Altizide; Althiazide

Database IDs

• CAS Number: 5588-16-9
• PubChem SID: 162253881
• PubChem CID: 2122

CALCULATED PROPERTIES

• Acid pKa: 9.051268
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 0.83119017
• LogD (pH = 7.4): 0.8227282
• Log P: 0.8312989
• Molar Refractivity: 89.4859 cm^3
• Polarizability: 35.409878 Å^3
• Polar Surface Area: 118.36 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 200-202°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - A575775

Diuretic and antihypertensive.

REFERENCES

• Twagirumukiza, M., et al.: Trop. Med. Int. Health, 15, 350 (2010)
• Gohil, V., et al.: Nat. Biotechnol., 28, 249 (2010)
• Peters, R., et al.: Anal. Bioanal. Chem., 396, 2583 (2010)