CAS 106516-24-9|Serlect|Sertindolum [inn-latin]|1-(2-{4-[5-chloro-1-(4-fluorophenyl)-1H-indol-3-yl]piperidin-1-yl}ethyl)imidazolidin-2-one|Serdolect|Sertindole|Sertindol [inn-spanish]|sertindole|1-[...

General Information

Structure

Molecular Formula

C₂₄H₂₆ClFN₄O

Molecular Mass

440.9408432

Exact Mass

440.17791737

Charge

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

Canonic Smiles

Clc1ccc2c(c1)c(cn2c1ccc(cc1)F)C1CCN(CC1)CCN1CCNC1=O

Isomeric Smiles

Clc1cc2c(C3CCN(CC3)CCN3CCNC3=O)cn(c2cc1)c1ccc(F)cc1

Calculated Properties

JChem

Acid pKa

14.3581505

H Acceptors

H Donor

LogD (pH = 5.5)

0.76146895

LogD (pH = 7.4)

2.5622704

Log P

3.7738

Molar Refractivity

131.7697

Polarizability

48.06371

Polar Surface Area

40.51

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

4.29

LOG S

-4.66

Solubility (Water)

9.63e-03 g/l

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

Synonyms

Sertindolum [inn-latin]SertindoleSertindol [inn-spanish]1-[2-[4-[5-chloro-1-(4-fluorophenyl)-1h-indol-3-yl]-1-piperidinyl]ethyl]-2-imidazolidinoneSertindoleSerdolectZerdol

Brand Name

SerlectSerdolect

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

Names and Identifiers

Registration numbers

CAS Number

MDL Number

PubChem CID

PubChem SID

Registration numbers

Properties

Product Information

Empirical Formula (Hill Notation)

C24H26ClFN4O

Purity

≥97.5% (HPLC)

Certificate of Analysis

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Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule 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approved; withdrawn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 It was first marketed in 1996 in several European countries before being withdrawn two years later because of numerous cardiac adverse effects.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]

Molecule Details

References

PubChem Literature

From Data Sources

• 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

• 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

• Perquin LN: Treatment with the new antipsychotic sertindole for late-occurring undesirable movement effects. Int Clin Psychopharmacol. 2005 Nov;20(6):335-8. Pubmed

• Karczewski, J., et al.: Biochem. Pharmacol., 77, 1602 (2008)

• Isoherranen, N., et al.: Chem. Res. Toxicol., 22, 294 (2008)

• Nourian, Z., et al.: Eur. J. Pharmacol., 596, 32 (2008)

• Goetghebeur, P., et al.: Psychopharmacol., 202, 287 (2008)

References

Bioactivity

PubChem BioAssay

Bioactivity