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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:03 UTC
HMDB IDHMDB0015618
Secondary Accession Numbers
  • HMDB15618
Metabolite Identification
Common NameSertindole
DescriptionSertindole, 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 It was first marketed in 1996 in several European countries before being withdrawn two years later because of numerous cardiac adverse effects.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.
Structure
Data?1582753316
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 Weight440.941
Monoisotopic Molecular Weight440.177917386
IUPAC Name1-(2-{4-[5-chloro-1-(4-fluorophenyl)-1H-indol-3-yl]piperidin-1-yl}ethyl)imidazolidin-2-one
Traditional Namesertindole
CAS Registry Number106516-24-9
SMILES
FC1=CC=C(C=C1)N1C=C(C2CCN(CCN3CCNC3=O)CC2)C2=C1C=CC(Cl)=C2
InChI Identifier
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)
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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0096 g/LNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+202.75530932474
DeepCCS[M-H]-200.39730932474
DeepCCS[M-2H]-234.64530932474
DeepCCS[M+Na]+209.87330932474
AllCCS[M+H]+203.032859911
AllCCS[M+H-H2O]+200.832859911
AllCCS[M+NH4]+205.032859911
AllCCS[M+Na]+205.632859911
AllCCS[M-H]-200.532859911
AllCCS[M+Na-2H]-200.732859911
AllCCS[M+HCOO]-201.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
SertindoleFC1=CC=C(C=C1)N1C=C(C2CCN(CCN3CCNC3=O)CC2)C2=C1C=CC(Cl)=C24908.7Standard polar33892256
SertindoleFC1=CC=C(C=C1)N1C=C(C2CCN(CCN3CCNC3=O)CC2)C2=C1C=CC(Cl)=C23882.9Standard non polar33892256
SertindoleFC1=CC=C(C=C1)N1C=C(C2CCN(CCN3CCNC3=O)CC2)C2=C1C=CC(Cl)=C24088.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Sertindole,1TMS,isomer #1C[Si](C)(C)N1CCN(CCN2CCC(C3=CN(C4=CC=C(F)C=C4)C4=CC=C(Cl)C=C34)CC2)C1=O3747.3Semi standard non polar33892256
Sertindole,1TMS,isomer #1C[Si](C)(C)N1CCN(CCN2CCC(C3=CN(C4=CC=C(F)C=C4)C4=CC=C(Cl)C=C34)CC2)C1=O3670.5Standard non polar33892256
Sertindole,1TMS,isomer #1C[Si](C)(C)N1CCN(CCN2CCC(C3=CN(C4=CC=C(F)C=C4)C4=CC=C(Cl)C=C34)CC2)C1=O4787.5Standard polar33892256
Sertindole,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CCN(CCN2CCC(C3=CN(C4=CC=C(F)C=C4)C4=CC=C(Cl)C=C34)CC2)C1=O3951.6Semi standard non polar33892256
Sertindole,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CCN(CCN2CCC(C3=CN(C4=CC=C(F)C=C4)C4=CC=C(Cl)C=C34)CC2)C1=O3857.6Standard non polar33892256
Sertindole,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CCN(CCN2CCC(C3=CN(C4=CC=C(F)C=C4)C4=CC=C(Cl)C=C34)CC2)C1=O4840.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Sertindole GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9316000000-4bb52e2e5e8e2a9184d62017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sertindole GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sertindole GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sertindole 10V, Positive-QTOFsplash10-0006-1102900000-e335eb6b5c8c8eef4ad52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sertindole 20V, Positive-QTOFsplash10-0bt9-9608100000-46bf4f0a0cb438e48d2d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sertindole 40V, Positive-QTOFsplash10-05n3-9102000000-c2f828835f177b419d842016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sertindole 10V, Negative-QTOFsplash10-000i-2002900000-d0dc328638ffb9d02e6e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sertindole 20V, Negative-QTOFsplash10-000f-9006500000-81edac274ee530e66a042016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sertindole 40V, Negative-QTOFsplash10-0006-9000000000-f6bff0a5529034a8c7622016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sertindole 10V, Positive-QTOFsplash10-0006-0000900000-b94ed5b6a2bb56ffd7632021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sertindole 20V, Positive-QTOFsplash10-0006-0306900000-ea94866f94a9c7569ff82021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sertindole 40V, Positive-QTOFsplash10-074r-9417200000-c67920dfb0cb81309e4a2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sertindole 10V, Negative-QTOFsplash10-000i-0000900000-1eb0a7d6abf1ae0f18be2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sertindole 20V, Negative-QTOFsplash10-0019-8006900000-ac9fbc1ceebafe4be96e2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sertindole 40V, Negative-QTOFsplash10-001i-9002000000-7ad68bf9c03599f52b432021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB06144 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB06144 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB06144
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID54229
KEGG Compound IDC07567
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSertindole
METLIN IDNot Available
PubChem Compound60149
PDB IDNot Available
ChEBI ID9122
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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:16952163 ]
  2. Lindstrom E, Levander S: Sertindole: efficacy and safety in schizophrenia. Expert Opin Pharmacother. 2006 Sep;7(13):1825-34. [PubMed:16925508 ]
  3. 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:15989577 ]
  4. Lewis R, Bagnall AM, Leitner M: Sertindole for schizophrenia. Cochrane Database Syst Rev. 2005 Jul 20;(3):CD001715. [PubMed:16034864 ]
  5. Perquin LN: Treatment with the new antipsychotic sertindole for late-occurring undesirable movement effects. Int Clin Psychopharmacol. 2005 Nov;20(6):335-8. [PubMed:16192844 ]
  6. Murdoch D, Keating GM: Sertindole : a review of its use in schizophrenia. CNS Drugs. 2006;20(3):233-55. [PubMed:16529528 ]
  7. Authors unspecified: Sertindole: new drug. Another "atypical" neuroleptic; QT prolongation. Prescrire Int. 2007 Apr;16(88):59-62. [PubMed:17458045 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
Gene Name:
DRD2
Uniprot ID:
P14416
Molecular weight:
50618.9
References
  1. Lindstrom E, Levander S: Sertindole: efficacy and safety in schizophrenia. Expert Opin Pharmacother. 2006 Sep;7(13):1825-34. [PubMed:16925508 ]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  3. Mork A, Witten LM, Arnt J: Effect of sertindole on extracellular dopamine, acetylcholine, and glutamate in the medial prefrontal cortex of conscious rats: a comparison with risperidone and exploration of mechanisms involved. Psychopharmacology (Berl). 2009 Sep;206(1):39-49. doi: 10.1007/s00213-009-1578-4. Epub 2009 Jun 9. [PubMed:19506838 ]
  4. Seeman P: Dopamine D2(High) receptors moderately elevated by sertindole. Synapse. 2008 May;62(5):389-93. doi: 10.1002/syn.20498. [PubMed:18293356 ]
  5. Cincotta SL, Rodefer JS: Emerging role of sertindole in the management of schizophrenia. Neuropsychiatr Dis Treat. 2010 Sep 7;6:429-41. [PubMed:20856607 ]
General function:
Involved in ion channel activity
Specific function:
Pore-forming (alpha) subunit of voltage-gated inwardly rectifying potassium channel. Channel properties are modulated by cAMP and subunit assembly. Mediates the rapidly activating component of the delayed rectifying potassium current in heart (IKr). Isoform 3 has no channel activity by itself, but modulates channel characteristics when associated with isoform 1
Gene Name:
KCNH2
Uniprot ID:
Q12809
Molecular weight:
126653.5
References
  1. Rampe D, Murawsky MK, Grau J, Lewis EW: The antipsychotic agent sertindole is a high affinity antagonist of the human cardiac potassium channel HERG. J Pharmacol Exp Ther. 1998 Aug;286(2):788-93. [PubMed:9694935 ]
  2. Kang J, Chen XL, Rampe D: The antipsychotic drugs sertindole and pimozide block erg3, a human brain K(+) channel. Biochem Biophys Res Commun. 2001 Aug 24;286(3):499-504. [PubMed:11511086 ]
  3. Tang W, Kang J, Wu X, Rampe D, Wang L, Shen H, Li Z, Dunnington D, Garyantes T: Development and evaluation of high throughput functional assay methods for HERG potassium channel. J Biomol Screen. 2001 Oct;6(5):325-31. [PubMed:11689132 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. This receptor is involved in tracheal smooth muscle contraction, bronchoconstriction, and control of aldosterone production
Gene Name:
HTR2A
Uniprot ID:
P28223
Molecular weight:
52602.6
References
  1. Lindstrom E, Levander S: Sertindole: efficacy and safety in schizophrenia. Expert Opin Pharmacother. 2006 Sep;7(13):1825-34. [PubMed:16925508 ]
  2. Schreiber R, Brocco M, Millan MJ: Blockade of the discriminative stimulus effects of DOI by MDL 100,907 and the 'atypical' antipsychotics, clozapine and risperidone. Eur J Pharmacol. 1994 Oct 13;264(1):99-102. [PubMed:7530204 ]
  3. Hietala J, Kuonnamaki M, Palvimaki EP, Laakso A, Majasuo H, Syvalahti E: Sertindole is a serotonin 5-HT2c inverse agonist and decreases agonist but not antagonist binding to 5-HT2c receptors after chronic treatment. Psychopharmacology (Berl). 2001 Sep;157(2):180-7. [PubMed:11594443 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system
Gene Name:
HTR2C
Uniprot ID:
P28335
Molecular weight:
51820.7
References
  1. Lindstrom E, Levander S: Sertindole: efficacy and safety in schizophrenia. Expert Opin Pharmacother. 2006 Sep;7(13):1825-34. [PubMed:16925508 ]
  2. Hietala J, Kuonnamaki M, Palvimaki EP, Laakso A, Majasuo H, Syvalahti E: Sertindole is a serotonin 5-HT2c inverse agonist and decreases agonist but not antagonist binding to 5-HT2c receptors after chronic treatment. Psychopharmacology (Berl). 2001 Sep;157(2):180-7. [PubMed:11594443 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that stimulate adenylate cyclase. It has a high affinity for tricyclic psychotropic drugs
Gene Name:
HTR6
Uniprot ID:
P50406
Molecular weight:
46953.6
References
  1. Pouzet B, Didriksen M, Arnt J: Effects of the 5-HT(6) receptor antagonist, SB-271046, in animal models for schizophrenia. Pharmacol Biochem Behav. 2002 Apr;71(4):635-43. [PubMed:11888555 ]
  2. Mork A, Witten LM, Arnt J: Effect of sertindole on extracellular dopamine, acetylcholine, and glutamate in the medial prefrontal cortex of conscious rats: a comparison with risperidone and exploration of mechanisms involved. Psychopharmacology (Berl). 2009 Sep;206(1):39-49. doi: 10.1007/s00213-009-1578-4. Epub 2009 Jun 9. [PubMed:19506838 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins
Gene Name:
ADRA1A
Uniprot ID:
P35348
Molecular weight:
51486.0
References
  1. Lindstrom E, Levander S: Sertindole: efficacy and safety in schizophrenia. Expert Opin Pharmacother. 2006 Sep;7(13):1825-34. [PubMed:16925508 ]
  2. Hietala J, Kuonnamaki M, Palvimaki EP, Laakso A, Majasuo H, Syvalahti E: Sertindole is a serotonin 5-HT2c inverse agonist and decreases agonist but not antagonist binding to 5-HT2c receptors after chronic treatment. Psychopharmacology (Berl). 2001 Sep;157(2):180-7. [PubMed:11594443 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system
Gene Name:
ADRA1B
Uniprot ID:
P35368
Molecular weight:
56835.4
References
  1. Lindstrom E, Levander S: Sertindole: efficacy and safety in schizophrenia. Expert Opin Pharmacother. 2006 Sep;7(13):1825-34. [PubMed:16925508 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This alpha-adrenergic receptor mediates its effect through the influx of extracellular calcium
Gene Name:
ADRA1D
Uniprot ID:
P25100
Molecular weight:
60462.2
References
  1. Lindstrom E, Levander S: Sertindole: efficacy and safety in schizophrenia. Expert Opin Pharmacother. 2006 Sep;7(13):1825-34. [PubMed:16925508 ]