5-{2-[4-(1,2-benzothiazol-3-yl)(2H8)piperazin-1-yl]ethyl}-6-chloro-2,3-dihydro-1H-indol-2-one

• ChemBase ID: 179640
• Molecular Formular: C21H21ClN4OS
• Molecular Mass: 412.93564
• Monoisotopic Mass: 412.11245999
• SMILES: c1c2c(cc(c1Cl)CCN1CCN(CC1)c1nsc3c1cccc3)CC(=O)N2
• Canonical SMILES: O=C1Nc2c(C1)cc(c(c2)Cl)CCN1CCN(CC1)c1nsc2c1cccc2
• InChI: InChI=1S/C21H21ClN4OS/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)28-24-21/h1-4,11,13H,5-10,12H2,(H,23,27)
• InChIKey: MVWVFYHBGMAFLY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-{2-[4-(1,2-benzothiazol-3-yl)(^2H₈)piperazin-1-yl]ethyl}-6-chloro-2,3-dihydro-1H-indol-2-one
• IUPAC Traditional name: 5-{2-[4-(1,2-benzothiazol-3-yl)(^2H₈)piperazin-1-yl]ethyl}-6-chloro-1,3-dihydroindol-2-one
• Synonyms: 5-[2-[4-(1,2-Benzisothiazol-3yl)-1-(piperazinyl-d8)]ethyl]-6-chloro-1,3-dihydro-2H-indol-2-one; Ziprasidone-d8

Database IDs

• PubChem SID: 164235550
• PubChem CID: 25216238

CALCULATED PROPERTIES

• Acid pKa: 13.181678
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.7102394
• LogD (pH = 7.4): 4.1316934
• Log P: 4.3040466
• Molar Refractivity: 116.7248 cm^3
• Polarizability: 44.12406 Å^3
• Polar Surface Area: 48.47 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol (Slightly)
• Apperance: Tan to Light Brown Solid
• Melting Point: 213-215°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - Z485002

Labelled Ziprasidone, which is used as an antipsychotic. Combined serotonin (5HT2) and dopamine (D2) receptor antagonist.

REFERENCES

• Bench, C.J., et al.: Psychopharmacology, 112, 308 (1993)
• Goldstein, J.M., et al.: Exp. Opin. Invest. Drugs, 4, 291 (1995)