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

• ChemBase ID: 72648
• Molecular Formular: C10H17ClN2O4S3
• Molecular Mass: 360.90098
• Monoisotopic Mass: 360.00389771
• SMILES: C1[C@@H](S(=O)(=O)c2c([C@H]1NCC)cc(s2)S(=O)(=O)N)C.Cl
• Canonical SMILES: CCN[C@H]1C[C@H](C)S(=O)(=O)c2c1cc(s2)S(=O)(=O)N.Cl
• InChI: InChI=1S/C10H16N2O4S3.ClH/c1-3-12-8-4-6(2)18(13,14)10-7(8)5-9(17-10)19(11,15)16;/h5-6,8,12H,3-4H2,1-2H3,(H2,11,15,16);1H/t6-,8-;/m0./s1
• InChIKey: OSRUSFPMRGDLAG-QMGYSKNISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4S)-4-(ethylamino)-2-methyl-1,1-dioxo-2H,3H,4H-1λ^6,7-thieno[2,3-b][1λ^6]thiopyran-6-sulfonamide hydrochloride; (2S,4S)-4-(ethylamino)-2-methyl-1,1-dioxo-2H,3H,4H-1$l^{6},7-thieno[2,3-b][1$l^{6}]thiopyran-6-sulfonamide hydrochloride
• IUPAC Traditional name: (2S,4S)-4-(ethylamino)-2-methyl-1,1-dioxo-2H,3H,4H-1λ^6,7-thieno[2,3-b][1λ^6]thiopyran-6-sulfonamide hydrochloride; dorzolamide hydrochloride
• Synonyms: Dorzolamide Hydrochloride; Trusopt; Cosopt; Dorzolamide HCL

Database IDs

• CAS Number: 130693-82-2
• PubChem SID: 162037573
• PubChem CID: 6918132

CALCULATED PROPERTIES

• Acid pKa: 8.1842785
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -1.5705113
• LogD (pH = 7.4): -0.15743962
• Log P: -0.15111351
• Molar Refractivity: 72.4611 cm^3
• Polarizability: 30.45586 Å^3
• Polar Surface Area: 106.33 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: -20°C

Pharmacology Properties

• Target: carbonic anhydrase(CA)
• Mechanism of Action: Carbonic anhydrase inhibitor

Product Information

• Salt Data: HCl; Hydrochloride
• Application(s): Antiglaucoma agent

DETAILS

Selleck Chemicals - S1375

Research Area: Cancer
Biological Activity:
Dorzolamide HCl is a carbonic anhydrase inhibitor. It is an anti-glaucoma agent and topically applied in the form of eye drops. Dorzolamide HCl is used to lower increased intraocular pressure in open-angle glaucoma and ocular hypertension. [1]

REFERENCES

• http://en.wikipedia.org/wiki/Dorzolamide
• Eur. Pat., 1988, Merck, 296 879; CA, 110, 192805a, (synth, pharmacol)
• Wang, R.F. et al., Arch. Ophthalmol. (Chicago), 1990, 108, 511; 1991, 109, 1297, (pharmacol)
• Blacklock, T.J. et al., J.O.C., 1993, 58, 1672, (synth, pmr, cmr, ir, uv)
• Matuszewski, B.K. et al., Pharm. Res., 1994, 11, 449, (resoln)
• Quint, M.-P., Anal. Profiles Drug Subst., 1999, 26, 283-318, (rev)