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Sertindole

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Chemistry

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 It was first marketed in 1996 in several European countries before being withdrawn two years later because of numerous cardiac adverse effects.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

Sertindole

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 Formula	C₂₄H₂₆ClFN₄O
Molecular Weight	440.9 g/mol
XLogP3	4.1
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	5
Exact Mass	440.1779173 g/mol
Monoisotopic Mass	440.1779173 g/mol
Topological Polar Surface Area	40.5 Å²
Heavy Atom Count	31
Formal Charge	0
Complexity	623
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.

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