1-(2-{4-[5-chloro-1-(4-fluorophenyl)-1H-indol-3-yl]piperidin-1-yl}ethyl)imidazolidin-2-one

• ChemBase ID: 4414
• Molecular Formular: C24H26ClFN4O
• Molecular Mass: 440.9408432
• Monoisotopic Mass: 440.17791737
• SMILES: Clc1cc2c(C3CCN(CC3)CCN3CCNC3=O)cn(c2cc1)c1ccc(F)cc1
• Canonical SMILES: Clc1ccc2c(c1)c(cn2c1ccc(cc1)F)C1CCN(CC1)CCN1CCNC1=O
• InChI: InChI=1S/C24H26ClFN4O/c25-18-1-6-23-21(15-18)22(16-30(23)20-4-2-19(26)3-5-20)17-7-10-28(11-8-17)13-14-29-12-9-27-24(29)31/h1-6,15-17H,7-14H2,(H,27,31)
• InChIKey: GZKLJWGUPQBVJQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(2-{4-[5-chloro-1-(4-fluorophenyl)-1H-indol-3-yl]piperidin-1-yl}ethyl)imidazolidin-2-one
• IUPAC Traditional name: sertindole
• Brand Name: Serdolect; Serlect
• Synonyms: 1-[2-[4-[5-chloro-1-(4-fluorophenyl)-1h-indol-3-yl]-1-piperidinyl]ethyl]-2-imidazolidinone; Sertindole; Sertindol [inn-spanish]; Sertindolum [inn-latin]; Sertindole; Serdolect; Zerdol

Database IDs

• CAS Number: 106516-24-9
• MDL Number: MFCD00867749
• PubChem SID: 46504717; 160967846
• PubChem CID: 60149

CALCULATED PROPERTIES

JChem

• LogD (pH = 7.4): 2.5622704
• Log P: 3.7738
• Molar Refractivity: 131.7697 cm^3
• Polarizability: 48.06371 Å^3
• Polar Surface Area: 40.51 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true
• Acid pKa: 14.3581505
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.76146895

ALOGPS 2.1

• Log P: 4.29
• LOG S: -4.66
• Solubility (Water): 9.63e-03 g/l

PROPERTIES

Physical Property

• Solubility: DMSO; DMSO: >10 mg/mL; H2O: <2 mg/mL; Methanol
• Apperance: off-white solid; Off-White to Pale Yellow Solid
• Melting Point: 150-152°C

Safety Information

• Storage Condition: Refrigerator
• RTECS: NJ0621100
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335-H413
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.5% (HPLC)
• Empirical Formula (Hill Notation): C24H26ClFN4O

DETAILS

DrugBank - DB06144

• Drug Groups: approved; withdrawn
• Description: Sertindole, a neuroleptic, is one of the newer antipsychotic medications available. Serdolect is developed by the Danish pharmaceutical company H. Lundbeck. Like the other atypical antipsychotics, it has activity at dopamine and serotonin receptors in the brain. It is used in the treatment of schizophrenia. It is classified chemically as a phenylindole derivative. It was first marketed in 1996 in several European countries before being withdrawn two years later because of numerous cardiac adverse effects. It has once again been approved and should soon be available on the French and Australian market.
• Indication: Used in the treatment of schizophrenia.
• Pharmacology: Sertindole is an atypical antipsychotic at least as effective as haloperidol and risperidone in the treatment of neuroleptic-responsive schizophrenia. Sertindole improves negative symptoms, and is also effective for the treatment of neuroleptic-resistant schizophrenia. Sertindole is generally well tolerated and is associated with a low rate of extrapyramidal symptoms (EPS).
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic. Sertindole is metabolized by cytochrome P450 isoenzymes CYP 2D6 and CYP 3A4.
• Absorption: Orally available.
• Half Life: 3 days
• References: Kane JM, Tamminga CA: Sertindole (Serdolect): preclinical and clinical findings of a new atypical antipsychotic. Expert Opin Investig Drugs. 1997 Nov;6(11):1729-41. [Pubmed] ; Lewis R, Bagnall AM, Leitner M: Sertindole for schizophrenia. Cochrane Database Syst Rev. 2005 Jul 20;(3):CD001715. [Pubmed] ; Perquin LN: Treatment with the new antipsychotic sertindole for late-occurring undesirable movement effects. Int Clin Psychopharmacol. 2005 Nov;20(6):335-8. [Pubmed] ; Murdoch D, Keating GM: Sertindole : a review of its use in schizophrenia. CNS Drugs. 2006;20(3):233-55. [Pubmed] ; Sertindole: new drug. Another "atypical" neuroleptic; QT prolongation. Prescrire Int. 2007 Apr;16(88):59-62. [Pubmed] ; Lindstrom E, Levander S: Sertindole: efficacy and safety in schizophrenia. Expert Opin Pharmacother. 2006 Sep;7(13):1825-34. [Pubmed] ; Hertel P: Comparing sertindole to other new generation antipsychotics on preferential dopamine output in limbic versus striatal projection regions: mechanism of action. Synapse. 2006 Dec 1;60(7):543-52. [Pubmed]
• External Links: Wikipedia

Sigma Aldrich - S8072

Biochem/physiol Actions
Sertindole is a 5-HT2 serotonin and D2 dopamine receptor antagonist and antipsychotic.

Toronto Research Chemicals - S279500

Antipsychotic used in the treatment of schizophrenia.

REFERENCES

• Lindstrom E, Levander S: Sertindole: efficacy and safety in schizophrenia. Expert Opin Pharmacother. 2006 Sep;7(13):1825-34. Pubmed
• Hertel P: Comparing sertindole to other new generation antipsychotics on preferential dopamine output in limbic versus striatal projection regions: mechanism of action. Synapse. 2006 Dec 1;60(7):543-52. Pubmed
• Kane JM, Tamminga CA: Sertindole (Serdolect): preclinical and clinical findings of a new atypical antipsychotic. Expert Opin Investig Drugs. 1997 Nov;6(11):1729-41. Pubmed
• Lewis R, Bagnall AM, Leitner M: Sertindole for schizophrenia. Cochrane Database Syst Rev. 2005 Jul 20;(3):CD001715. Pubmed
• Perquin LN: Treatment with the new antipsychotic sertindole for late-occurring undesirable movement effects. Int Clin Psychopharmacol. 2005 Nov;20(6):335-8. Pubmed
• Murdoch D, Keating GM: Sertindole : a review of its use in schizophrenia. CNS Drugs. 2006;20(3):233-55. Pubmed
• Sertindole: new drug. Another "atypical" neuroleptic; QT prolongation. Prescrire Int. 2007 Apr;16(88):59-62. Pubmed
• Nourian, Z., et al.: Eur. J. Pharmacol., 596, 32 (2008)
• Karczewski, J., et al.: Biochem. Pharmacol., 77, 1602 (2008)
• Isoherranen, N., et al.: Chem. Res. Toxicol., 22, 294 (2008)
• Goetghebeur, P., et al.: Psychopharmacol., 202, 287 (2008)