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

• ChemBase ID: 126635
• Molecular Formular: C22H25ClN2OS
• Molecular Mass: 400.9647
• Monoisotopic Mass: 400.13761211
• SMILES: Clc1cc2/C(=C/CCN3CCN(CCO)CC3)/c3c(Sc2cc1)cccc3
• Canonical SMILES: OCCN1CCN(CC1)CC/C=C/1\c2ccccc2Sc2c1cc(Cl)cc2
• InChI: InChI=1S/C22H25ClN2OS/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/h1-2,4-8,16,26H,3,9-15H2
• InChIKey: WFPIAZLQTJBIFN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{4-[3-(2-chloro-9H-thioxanthen-9-ylidene)propyl]piperazin-1-yl}ethan-1-ol
• IUPAC Traditional name: clopenthixol
• Synonyms: Clopenthixol; Zuclopenthixol

Database IDs

• CAS Number: 53772-83-1; 982-24-1
• PubChem SID: 162220965
• PubChem CID: 12454; 5372683; 5311507
• CHEBI ID: 51364
• ATC CODE: N05AF05; N05AF02
• CHEMBL: 53904
• Chemspider ID: 11945; 4470984
• DrugBank ID: DB01624
• KEGG ID: D03556; D02613
• Unique Ingredient Identifier: 47ISU063SG; FLE878A8ZI
• Wikipedia Title: Clopenthixol; Zuclopenthixol

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: 5
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Admin Routes: Oral; Oral, IM
• Bioavailability: 49% (oral)
• Excretion: Feces
• Half Life: 20 hours (oral), 19 days (IM)
• Metabolism: Hepatic (CYP2D6-mediated)
• Protein Bound: 98%
• Legal Status: Rx-only
• Pregnancy Category: C