(2S,4S)-4-amino-2-methyl-1,1-dioxo-2H,3H,4H-1λ6,7-thieno[2,3-b][1λ6]thiopyran-6-sulfonamide

• ChemBase ID: 165553
• Molecular Formular: C8H12N2O4S3
• Molecular Mass: 296.38688
• Monoisotopic Mass: 295.99591987
• SMILES: [C@@H]1(C[C@H](N)c2c(S1(=O)=O)sc(c2)S(=O)(=O)N)C
• Canonical SMILES: N[C@H]1C[C@H](C)S(=O)(=O)c2c1cc(s2)S(=O)(=O)N
• InChI: InChI=1S/C8H12N2O4S3/c1-4-2-6(9)5-3-7(17(10,13)14)15-8(5)16(4,11)12/h3-4,6H,2,9H2,1H3,(H2,10,13,14)/t4-,6-/m0/s1
• InChIKey: HVURBRAECUMAHY-NJGYIYPDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4S)-4-amino-2-methyl-1,1-dioxo-2H,3H,4H-1λ^6,7-thieno[2,3-b][1λ^6]thiopyran-6-sulfonamide
• IUPAC Traditional name: (2S,4S)-4-amino-2-methyl-1,1-dioxo-2H,3H,4H-1λ^6,7-thieno[2,3-b][1λ^6]thiopyran-6-sulfonamide
• Synonyms: (4S-trans)-4-Amino-5,6-dihydro-6-methyl-4H-thieno[2,3-b]thiopyran-2-sulfonamide 7,7-Dioxide; N-Deethyl Dorzolamide

Database IDs

• CAS Number: 154154-90-2
• PubChem SID: 162259686
• PubChem CID: 3074858

CALCULATED PROPERTIES

• Acid pKa: 8.260162
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -2.6730025
• LogD (pH = 7.4): -1.1163005
• Log P: -1.0081693
• Molar Refractivity: 62.9379 cm^3
• Polarizability: 26.819658 Å^3
• Polar Surface Area: 120.32 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D228550

A metabolite of Dorzolamide (D535100) in human plasma.

REFERENCES

• Matuszewski, B., et al.: Pharm. Res., 11, 449 (1994)
• Chavez, C., et al.: J. Pharm. Biomed. Anal., 13, 1179 (1994)
• Zagrobelny, J., et al.: J. Pharm. Biomed. Anal., 13, 1215 (1994)