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    Sertindole

    ACTIVE PHARMA INGREDIENTS

    FINISHED DOSAGE FORMULATIONS

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    2D Structure
    Also known as: 106516-24-9, Serlect, Serdolect, Sertindol, Lu 23-174, Sertindolum
    Molecular Formula
    C24H26ClFN4O
    Molecular Weight
    440.9  g/mol
    InChI Key
    GZKLJWGUPQBVJQ-UHFFFAOYSA-N
    FDA UNII
    GVV4Z879SP
    Sertindole, a neuroleptic, is one of the newer antipsychotic medications available. Serdolect 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 It was first marketed in 1996 in several European countries before being withdrawn two years later because of numerous cardiac adverse effects.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.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    1-[2-[4-[5-chloro-1-(4-fluorophenyl)indol-3-yl]piperidin-1-yl]ethyl]imidazolidin-2-one
    2.1.2 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)
    2.1.3 InChI Key
    GZKLJWGUPQBVJQ-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C1CN(CCC1C2=CN(C3=C2C=C(C=C3)Cl)C4=CC=C(C=C4)F)CCN5CCNC5=O
    2.2 Other Identifiers
    2.2.1 UNII
    GVV4Z879SP
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 1-(2-(4-(5-chloro-1-(4-fluorophenyl)-1h-indol-3-yl)-1-piperidinyl)ethyl)-2-imidazolidinone

    2. Lu 23-174

    3. Lu-23-174

    4. Serdolect

    5. Serlect

    6. Sertindole Hydrochloride

    2.3.2 Depositor-Supplied Synonyms

    1. 106516-24-9

    2. Serlect

    3. Serdolect

    4. Sertindol

    5. Lu 23-174

    6. Sertindolum

    7. Sertindol [inn-spanish]

    8. Sertindolum [inn-latin]

    9. Zerdol

    10. Lu-23-174

    11. 1-[2-[4-[5-chloro-1-(4-fluorophenyl)indol-3-yl]piperidin-1-yl]ethyl]imidazolidin-2-one

    12. 1-(2-{4-[5-chloro-1-(4-fluorophenyl)-1h-indol-3-yl]piperidin-1-yl}ethyl)imidazolidin-2-one

    13. Gvv4z879sp

    14. Chembl12713

    15. Chebi:9122

    16. 1-(2-(4-(5-chloro-1-(p-fluorophenyl)indol-3-yl)piperidino)ethyl)-2-imidazolidinone

    17. 1-[2-[4-[5-chloro-1-(4-fluorophenyl)-indol-3-yl]-1-piperidyl]ethyl]imidazolidin-2-one

    18. Ncgc00181782-01

    19. Ncgc00181782-02

    20. 1-(2-(4-(5-chloro-1-(4-fluorophenyl)-1h-indol-3-yl)piperidin-1-yl)ethyl)imidazolidin-2-one

    21. 1-[2-[4-[5-chloro-1-(4-fluorophenyl)-1h-indol-3-yl]-1-piperidinyl]ethyl]-2-imidazolidinone

    22. 2-imidazolidinone, 1-(2-(4-(5-chloro-1-(4-fluorophenyl)-1h-indol-3-yl)-1-piperidinyl)ethyl)-

    23. Dsstox_cid_28893

    24. Dsstox_rid_83161

    25. Dsstox_gsid_48967

    26. 1-(2-{4-[5-chloro-1-(p-fluorophenyl)indol-3-yl]piperidino}ethyl)-2-imidazolidinone

    27. 2-imidazolidinone, 1-[2-[4-[5-chloro-1-(4-fluorophenyl)-1h-indol-3-yl]-1-piperidinyl]ethyl]-

    28. Serlect (tn)

    29. Cas-106516-24-9

    30. Sertindole (usan/inn)

    31. Unii-gvv4z879sp

    32. Sertindole [usan:inn:ban]

    33. 1-(2-(4-[5-chloro-1-(4-fluoro-phenyl)-1h-indol-3-yl]-piperidin-1-yl)-ethyl)-imidazolidin-2-one

    34. 1-(2-{4-[5-chloro-1-(4-fluoro-phenyl)-1h-indol-3-yl]-piperidin-1-yl}-ethyl)-imidazolidin-2-one

    35. 1-(2-{4-[5-chloro-1-(4-fluorophenyl)-1h-indol-3-yl]-1-piperidinyl}ethyl)-2-imidazolidinone

    36. Mfcd00867749

    37. 1-(2-(4-(5-chloro-1-(4-fluorophenyl)-1h-indole-3-yl)-1-piperidinyl)ethyl)-2-imidazolidinone

    38. Sertindole [mi]

    39. Sertindole [inn]

    40. Sertindole [usan]

    41. Sertindole [vandf]

    42. Gtpl98

    43. S-1991

    44. Sertindole [mart.]

    45. Sertindole [who-dd]

    46. Mls003899237

    47. Schembl112092

    48. Dtxsid6048967

    49. Ex-a883

    50. Hms3713p22

    51. Zinc538337

    52. Bcp27121

    53. Sertindole, >=97.5% (hplc)

    54. Tox21_113408

    55. Tox21_113421

    56. Bdbm50001786

    57. Pdsp1_001561

    58. Pdsp2_001545

    59. Akos015962616

    60. Tox21_113421_1

    61. Ccg-220640

    62. Db06144

    63. 5-chloro-1-(4-fluorophenyl)-3-[1-[2-(2-imidazolidinon-1-yl)ethyl]-4-piperidyl]-1h-indole

    64. Ncgc00181782-03

    65. Ac-32937

    66. As-56243

    67. Hy-14543

    68. Smr002204118

    69. Ft-0674562

    70. S0942

    71. C07567

    72. D00561

    73. L001396

    74. Q418050

    75. Sr-01000872708

    76. J-001604

    77. Sr-01000872708-1

    78. 5-chloro-1-(4'-fluorophenyl)-3-(1-(2-(2imidazolidinon-1-yl)ethyl)-4-piperidyl)-1h-indole

    79. 5-chloro-1-(4'-fluorophenyl)-3-(1-(2-imidazolidinon-1-ylethyl)-4-piperidyl)-1h-indole

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 440.9 g/mol
    Molecular Formula C24H26ClFN4O
    XLogP34.1
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count5
    Exact Mass440.1779173 g/mol
    Monoisotopic Mass440.1779173 g/mol
    Topological Polar Surface Area40.5 Ų
    Heavy Atom Count31
    Formal Charge0
    Complexity623
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Used in the treatment of schizophrenia.

    5 Pharmacology and Biochemistry
    5.1 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).

    5.2 MeSH Pharmacological Classification

    Antipsychotic Agents

    Agents that control agitated psychotic behavior, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect. They are used in SCHIZOPHRENIA; senile dementia; transient psychosis following surgery; or MYOCARDIAL INFARCTION; etc. These drugs are often referred to as neuroleptics alluding to the tendency to produce neurological side effects, but not all antipsychotics are likely to produce such effects. Many of these drugs may also be effective against nausea, emesis, and pruritus. (See all compounds classified as Antipsychotic Agents.)

    5.3 ATC Code

    N - Nervous system

    N05 - Psycholeptics

    N05A - Antipsychotics

    N05AE - Indole derivatives

    N05AE03 - Sertindole

    5.4 Absorption, Distribution and Excretion

    Absorption

    Orally available.

    5.5 Metabolism/Metabolites

    Hepatic. Sertindole is metabolized by cytochrome P450 isoenzymes CYP 2D6 and CYP 3A4.

    Sertindole has known human metabolites that include 1-[2-[4-[5-Chloro-1-(4-fluorophenyl)indol-3-yl]piperidin-1-yl]ethyl]-4-hydroxyimidazolidin-2-one and 5-Chloro-1-(4-fluorophenyl)-3-(piperidin-4-yl)-1H-indole.

    S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

    5.6 Biological Half-Life

    3 days

    5.7 Mechanism of Action

    Sertindole is an antipsychotic drug with affinity for dopamine D2, serotonin 5-HT2A and 5-HT2C, and alpha1-adrenoreceptors. Preclinical studies suggest that sertindole acts preferentially on limbic and cortical dopaminergic neurons and clinical trials have confirmed that sertindole is effective at a low dopamine D2 occupancy level.