(4R)-4-amino-2-(3-methoxypropyl)-1,1-dioxo-2H,3H,4H-1λ6,7,2-thieno[3,2-e][1λ6,2]thiazine-6-sulfonamide

• ChemBase ID: 166171
• Molecular Formular: C10H17N3O5S3
• Molecular Mass: 355.45408
• Monoisotopic Mass: 355.03303366
• SMILES: N1(C[C@@H](c2c(S1(=O)=O)sc(c2)S(=O)(=O)N)N)CCCOC
• Canonical SMILES: COCCCN1C[C@H](N)c2c(S1(=O)=O)sc(c2)S(=O)(=O)N
• InChI: InChI=1S/C10H17N3O5S3/c1-18-4-2-3-13-6-8(11)7-5-9(20(12,14)15)19-10(7)21(13,16)17/h5,8H,2-4,6,11H2,1H3,(H2,12,14,15)/t8-/m0/s1
• InChIKey: MVBJPOIMDXIBKC-QMMMGPOBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R)-4-amino-2-(3-methoxypropyl)-1,1-dioxo-2H,3H,4H-1λ^6,7,2-thieno[3,2-e][1λ^6,2]thiazine-6-sulfonamide
• IUPAC Traditional name: (4R)-4-amino-2-(3-methoxypropyl)-1,1-dioxo-3H,4H-1λ^6,7,2-thieno[3,2-e][1λ^6,2]thiazine-6-sulfonamide
• Synonyms: (4R)-4-Amino-3,4-dihydro-2-(3-methoxypropyl)-2H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide 1,1-Dioxide; AL 8520; N-Desethyl Brinzolamide

Database IDs

• CAS Number: 404034-55-5
• PubChem SID: 162260304
• PubChem CID: 10021113

CALCULATED PROPERTIES

• Acid pKa: 8.248398
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -3.0291858
• LogD (pH = 7.4): -1.5523721
• Log P: -1.5017134
• Molar Refractivity: 77.6763 cm^3
• Polarizability: 32.37697 Å^3
• Polar Surface Area: 132.79 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D288900

Brinzolamide derivative; a carbonic anhydrase inhibitor as antiglaucoma agent.

REFERENCES

• Maren, T., et al.: Mol. Pharmacol., 44, 901 (1993)
• Baird, T., et al.: Biochemistry, 36, 2669 (1993)
• Chen, H., et al.: Bioorg. Med. Chem., 8, 957 (1993)