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

• ChemBase ID: 154060
• Molecular Formular: C21H24Cl2N4O2S
• Molecular Mass: 467.41186
• Monoisotopic Mass: 466.09970239
• SMILES: c1ccc2c(c1)c(ns2)N1CCN(CC1)CCc1cc2c(cc1Cl)NC(=O)C2.O.Cl
• Canonical SMILES: O=C1Nc2c(C1)cc(c(c2)Cl)CCN1CCN(CC1)c1nsc2c1cccc2.O.Cl
• InChI: InChI=1S/C21H21ClN4OS.ClH.H2O/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);1H;1H2
• InChIKey: ZCBZSCBNOOIHFP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-{2-[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]ethyl}-6-chloro-2,3-dihydro-1H-indol-2-one hydrate hydrochloride
• IUPAC Traditional name: ziprasidone hydrate hydrochloride
• Synonyms: CP-88059; Geodon; 5-[2-[4-(1,2-Benzisothiazol-3-yl)-1-piperazinyl]ethyl]-6-chloro-1,3-dihydro-2H-indol-2-one hydrochloride monohydrate; Ziprasidone hydrochloride monohydrate; 5-[2-[4-(1,2-Benzisothiazol-3-yl)-1-piperazinyl]ethyl]-6-chloro-1,3-dihydro-2H-indol-2-one Hydrochloride Monohydrate, CP-88059-1; Geodon Hydrochloride Hydrate; Ziprasidone Hydrochloride Monohydrate; 5-[2-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]ethyl]-6-chloro-1,3-dihydro-2H-indol-2-one 盐酸盐 一水合物; Ziprasidone 盐酸盐 一水合物

Database IDs

• CAS Number: 138982-67-9
• MDL Number: MFCD00921885
• PubChem SID: 162248199
• PubChem CID: 60853

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: 44.12495 Å^3
• Polar Surface Area: 48.47 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; DMSO: >10 mg/mL; H2O: insoluble
• Apperance: Pale Tan Powder; solid
• Melting Point: >300°C

Safety Information

• Storage Condition: -20°C Freezer
• German water hazard class: 3
• Storage Temperature: room temp

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C21H21ClN4OS · HCl · H2O

DETAILS

Sigma Aldrich - Z2777

Biochem/physiol Actions
Ziprasidone is an atypical antipsychotic; FDA approved for the treatment of schizophrenia.

Toronto Research Chemicals - Z485000

Combined serotonin (5HT2) and dopamine (D2) receptor antagonist. Used as an antipsychotic.

REFERENCES

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