4-(1,1-dioxo-1λ6,2-thiazinan-2-yl)(2H4)benzene-1-sulfonamide

• ChemBase ID: 178027
• Molecular Formular: C10H14N2O4S2
• Molecular Mass: 290.35916
• Monoisotopic Mass: 290.03949894
• SMILES: c1c(ccc(c1)N1S(=O)(=O)CCCC1)S(=O)(=O)N
• Canonical SMILES: O=S1(=O)CCCCN1c1ccc(cc1)S(=O)(=O)N
• InChI: InChI=1S/C10H14N2O4S2/c11-18(15,16)10-5-3-9(4-6-10)12-7-1-2-8-17(12,13)14/h3-6H,1-2,7-8H2,(H2,11,15,16)
• InChIKey: HMHVCUVYZFYAJI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(1,1-dioxo-1λ^6,2-thiazinan-2-yl)(^2H₄)benzene-1-sulfonamide
• IUPAC Traditional name: 4-(1,1-dioxo-1λ^6,2-thiazinan-2-yl)(^2H₄)benzenesulfonamide
• Synonyms: 4-(Tetrahydro-1,1-dioxido-2H-1,2-thiazin-2-yl)benzenesulfonamide-d4; 4-(Tetrahydro-2H-1,2-thiazin-2-yl)benzenesulfonamide-d4 S,S-Dioxide; 2-(p-Sulfamoylphenyl)-tetrahydro-2H-1,2-thiazine-d4 1,1-Dioxide; Bayer A 168-d4; Conadil-d4; Contravul-d4; Elisal-d4; Ospolot-d4; Riker 594-d4; Sulphenyltame-d4; Sulphenytame-d4; Sulphthiame-d4; Sulthiam-d4; Sulthiamine-d4; Sultiam-d4; Sultiame-d4; Trolone-d4; p-(Tetrahydro-2H-1,2-thiazin-2-yl)benzenesulfonamide-d4 Dioxide; Sulthiame-d4

Database IDs

• PubChem SID: 164233937
• PubChem CID: 71752302

CALCULATED PROPERTIES

• Acid pKa: 10.5486555
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.26592493
• LogD (pH = 7.4): -0.2661946
• Log P: -0.26592147
• Molar Refractivity: 67.4606 cm^3
• Polarizability: 27.679077 Å^3
• Polar Surface Area: 97.54 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - S789502

Labelled Sulthiame, a benzenesulfonamide derivative. Sulthiame acts as an inhibitor of the enzyme carbonic anhydrase. Sulthiame is used as an anticonvulsant in the treatment of benign and symptomatic focal epilepsy.

REFERENCES

• Green, J. et al.: Antiepilep. Drugs, 744 (1972)
• Inui, M.: Seish. Shin. Zas., 71, 114 (1972)
• Leniger, T. et al.: Epilepsia, 43, 469 (1972)