3-{4-[2-(6-chloro-2-oxo-2,3-dihydro-1H-indol-5-yl)ethyl]piperazin-1-yl}-1λ6,2-benzothiazole-1,1-dione hydrochloride

• ChemBase ID: 179641
• Molecular Formular: C21H22Cl2N4O3S
• Molecular Mass: 481.39538
• Monoisotopic Mass: 480.07896694
• SMILES: c1c2c(cc(c1Cl)CCN1CCN(CC1)C1=NS(=O)(=O)c3c1cccc3)CC(=O)N2.Cl
• Canonical SMILES: O=C1Nc2c(C1)cc(c(c2)Cl)CCN1CCN(CC1)C1=NS(=O)(=O)c2c1cccc2.Cl
• InChI: InChI=1S/C21H21ClN4O3S.ClH/c22-17-13-18-15(12-20(27)23-18)11-14(17)5-6-25-7-9-26(10-8-25)21-16-3-1-2-4-19(16)30(28,29)24-21;/h1-4,11,13H,5-10,12H2,(H,23,27);1H
• InChIKey: DXWJYEYNMAVTKL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{4-[2-(6-chloro-2-oxo-2,3-dihydro-1H-indol-5-yl)ethyl]piperazin-1-yl}-1λ^6,2-benzothiazole-1,1-dione hydrochloride
• IUPAC Traditional name: 3-{4-[2-(6-chloro-2-oxo-1,3-dihydroindol-5-yl)ethyl]piperazin-1-yl}-1λ^6,2-benzothiazole-1,1-dione hydrochloride
• Synonyms: 6-Chloro-5-[2-[4-(1,1-dioxido-1,2-benzisothiazol-3-yl)-1-piperazinyl]ethyl]-1,3-dihydro-2H-indol-2-one Hydrochloride; Ziprasidone Sulfone Hydrochloride

Database IDs

• PubChem SID: 164235551
• PubChem CID: 71753022

CALCULATED PROPERTIES

• Acid pKa: 13.181678
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 2.0673916
• LogD (pH = 7.4): 2.1677842
• Log P: 2.169227
• Molar Refractivity: 118.1922 cm^3
• Polarizability: 44.846912 Å^3
• Polar Surface Area: 82.08 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Pale Purple Solid
• Melting Point: 143-146°C

Safety Information

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

DETAILS

Toronto Research Chemicals - Z485010

A metabolite of Ziprasidone (Z485000).

REFERENCES

• Huang, M., et al.: Clin. Pharmacol. Ther., 54, 257 (1993)
• Prakash, C., et al.: Drug Metab. Dispos., 25, 206 (1993)
• Brosen, K., et al.: Eur. J. Clin. Pharmacol., 44, 349 (1993)