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

• ChemBase ID: 162709
• Molecular Formular: C12H22ClN3O5S3
• Molecular Mass: 419.96818
• Monoisotopic Mass: 419.0410115
• SMILES: N1(C[C@@H](c2c(S1(=O)=O)sc(c2)S(=O)(=O)N)NCC)CCCOC.Cl
• Canonical SMILES: COCCCN1C[C@H](NCC)c2c(S1(=O)=O)sc(c2)S(=O)(=O)N.Cl
• InChI: InChI=1S/C12H21N3O5S3.ClH/c1-3-14-10-8-15(5-4-6-20-2)23(18,19)12-9(10)7-11(21-12)22(13,16)17;/h7,10,14H,3-6,8H2,1-2H3,(H2,13,16,17);1H/t10-;/m0./s1
• InChIKey: UGAMYTZPFRXCOG-PPHPATTJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R)-4-(ethylamino)-2-(3-methoxypropyl)-1,1-dioxo-2H,3H,4H-1λ^6,7,2-thieno[3,2-e][1λ^6,2]thiazine-6-sulfonamide hydrochloride
• IUPAC Traditional name: brinzolamide hydrochloride
• Synonyms: (4R)-4-(Ethylamino)-3,4-dihydro-2-(3-methoxypropyl)-2H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide 1,1-Dioxide Hydrochloride; AL-4682 Hydrochloride; Azopt Hydrochloride; Brinzolamide Hydrochloride

Database IDs

• CAS Number: 150937-43-2
• PubChem SID: 162256844
• PubChem CID: 11711447

CALCULATED PROPERTIES

• Acid pKa: 8.194564
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -1.7519147
• LogD (pH = 7.4): -0.5946276
• Log P: -0.67452025
• Molar Refractivity: 87.1995 cm^3
• Polarizability: 36.01203 Å^3
• Polar Surface Area: 118.8 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: Off-White to Yellow Solid
• Melting Point: 91-93°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - B677600

Carbonic anhydrase inhibitor. Antiglaucoma agent.

REFERENCES

• Silver, L.H., et al.: Am. J. Ophthalmol., 126, 400 (1998)
• Davies, N., et al.: Clin. Exp. Pharmacol. Physiol., 27, 558 (1998)
• Stave, J., et al.: Ophthalmologe, 99, 276 (1998)