2-(4-{3-[(9E)-2-chloro-9H-thioxanthen-9-ylidene]propyl}piperazin-1-yl)ethan-1-ol; butanedioic acid

• ChemBase ID: 164898
• Molecular Formular: C26H31ClN2O5S
• Molecular Mass: 519.05274
• Monoisotopic Mass: 518.16422078
• SMILES: c1(ccc2c(c1)/C(=C/CCN1CCN(CC1)CCO)/c1c(S2)cccc1)Cl.C(CC(=O)O)C(=O)O
• Canonical SMILES: OC(=O)CCC(=O)O.OCCN1CCN(CC1)CC/C=C/1\c2ccccc2Sc2c1cc(Cl)cc2
• InChI: InChI=1S/C22H25ClN2OS.C4H6O4/c23-17-7-8-22-20(16-17)18(19-4-1-2-6-21(19)27-22)5-3-9-24-10-12-25(13-11-24)14-15-26;5-3(6)1-2-4(7)8/h1-2,4-8,16,26H,3,9-15H2;1-2H2,(H,5,6)(H,7,8)/b18-5+
• InChIKey: KUEAHHOXAMWWOW-RZFZGDDESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(4-{3-[(9E)-2-chloro-9H-thioxanthen-9-ylidene]propyl}piperazin-1-yl)ethan-1-ol; butanedioic acid
• IUPAC Traditional name: clopenthixol; succinic acid
• Synonyms: 4-[(3E)-3-(2-Chloro-9H-thioxanthen-9-ylidene)propyl]-1-piperazineethanol Succinate Salt; (E)-Clopenthixol Succinate Salt; β-Clopenthixol Succinate Salt; trans-Clopenthixol Succinate Salt

Database IDs

• PubChem SID: 162259032
• PubChem CID: 71314943

CALCULATED PROPERTIES

• Acid pKa: 15.593099
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.396457
• LogD (pH = 7.4): 3.1579008
• Log P: 4.222984
• Molar Refractivity: 127.0003 cm^3
• Polarizability: 45.285892 Å^3
• Polar Surface Area: 26.71 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C587190

The trans isomer of Clopenthixol, which exhibits similar pharmacological properties with its cis-isomer, Zuclopenthixol, less anti-dopaminergic effects.

REFERENCES

• Leysen, J., et al.: Psychopharmacol., 110, 27 (1993)
• Pajeva, I., et al.: J. Med. Chem., 41, 1815 (1993)
• Varga, A., et al.: Anticancer Res., 21, 2709 (1993)