Sertindole (CHEM020183)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 06:53:25 UTC
Update Date2016-11-09 01:16:09 UTC
Accession NumberCHEM020183
Identification
Common NameSertindole
ClassSmall Molecule
DescriptionSertindole, a neuroleptic, is one of the newer antipsychotic medications available. Sertindole is developed by the Danish pharmaceutical company H. Lundbeck. It is a phenylindole derivative used in the treatment of schizophrenia. It was first marketed in 1996 in several European countries before being withdrawn two years later because of numerous cardiac adverse effects.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.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
1-[2-[4-[5-Chloro-1-(4-fluorophenyl)-indol-3-yl]-1-piperidyl]ethyl]imidazolidin-2-oneChEBI
SerdolectChEBI
SerLectChEBI
SertindolChEBI
SertindolumChEBI
Sertindole hydrochlorideHMDB
1-(2-(4-(5-Chloro-1-(4-fluorophenyl)-1H-indol-3-yl)-1-piperidinyl)ethyl)-2-imidazolidinoneHMDB
Chemical FormulaC24H26ClFN4O
Average Molecular Mass440.941 g/mol
Monoisotopic Mass440.178 g/mol
CAS Registry Number106516-24-9
IUPAC Name1-(2-{4-[5-chloro-1-(4-fluorophenyl)-1H-indol-3-yl]piperidin-1-yl}ethyl)imidazolidin-2-one
Traditional Namesertindole
SMILESFC1=CC=C(C=C1)N1C=C(C2CCN(CCN3CCNC3=O)CC2)C2=C1C=CC(Cl)=C2
InChI IdentifierInChI=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)
InChI KeyGZKLJWGUPQBVJQ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenylpyrroles. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrrole ring through a CC or CN bond.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrroles
Sub ClassSubstituted pyrroles
Direct ParentPhenylpyrroles
Alternative Parents
Substituents
  • 1-phenylpyrrole
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Fluorobenzene
  • Halobenzene
  • Aralkylamine
  • Aryl chloride
  • Aryl fluoride
  • Aryl halide
  • Monocyclic benzene moiety
  • Imidazolidinone
  • Piperidine
  • Benzenoid
  • Heteroaromatic compound
  • Imidazolidine
  • Urea
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carbonic acid derivative
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organohalogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organochloride
  • Organofluoride
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0096 g/LALOGPS
logP4.29ALOGPS
logP3.77ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)14.36ChemAxon
pKa (Strongest Basic)8.59ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area40.51 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity131.77 m³·mol⁻¹ChemAxon
Polarizability47.17 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9316000000-4bb52e2e5e8e2a9184d6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-1102900000-e335eb6b5c8c8eef4ad5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bt9-9608100000-46bf4f0a0cb438e48d2dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05n3-9102000000-c2f828835f177b419d84Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-2002900000-d0dc328638ffb9d02e6eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000f-9006500000-81edac274ee530e66a04Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-f6bff0a5529034a8c762Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000900000-b94ed5b6a2bb56ffd763Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0306900000-ea94866f94a9c7569ff8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-074r-9417200000-c67920dfb0cb81309e4aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000900000-1eb0a7d6abf1ae0f18beSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0019-8006900000-ac9fbc1ceebafe4be96eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9002000000-7ad68bf9c03599f52b43Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB06144
HMDB IDHMDB0015618
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkSertindole
Chemspider ID54229
ChEBI ID9122
PubChem Compound ID60149
Kegg Compound IDC07567
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. 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.
2. Lewis R, Bagnall AM, Leitner M: Sertindole for schizophrenia. Cochrane Database Syst Rev. 2005 Jul 20;(3):CD001715.
3. Perquin LN: Treatment with the new antipsychotic sertindole for late-occurring undesirable movement effects. Int Clin Psychopharmacol. 2005 Nov;20(6):335-8.
4. Murdoch D, Keating GM: Sertindole : a review of its use in schizophrenia. CNS Drugs. 2006;20(3):233-55.
5. Lindstrom E, Levander S: Sertindole: efficacy and safety in schizophrenia. Expert Opin Pharmacother. 2006 Sep;7(13):1825-34.
6. 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.
7. Authors unspecified: Sertindole: new drug. Another "atypical" neuroleptic; QT prolongation. Prescrire Int. 2007 Apr;16(88):59-62.
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=15461313
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=15989577
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=16317317
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=16529528
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=18484920
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=21080854
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=23432404
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=9694935