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 It was first marketed in 1996 in several European countries before being withdrawn two years later because of numerous cardiac adverse effects.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


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ABOUT THIS PAGE

Sertindole Manufacturers

A Sertindole manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Sertindole, including repackagers and relabelers. The FDA regulates Sertindole manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Sertindole API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

Sertindole Suppliers

A Sertindole supplier is an individual or a company that provides Sertindole active pharmaceutical ingredient (API) or Sertindole finished formulations upon request. The Sertindole suppliers may include Sertindole API manufacturers, exporters, distributors and traders.

click here to find a list of Sertindole suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Sertindole USDMF

A Sertindole DMF (Drug Master File) is a document detailing the whole manufacturing process of Sertindole active pharmaceutical ingredient (API) in detail. Different forms of Sertindole DMFs exist exist since differing nations have different regulations, such as Sertindole USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A Sertindole DMF submitted to regulatory agencies in the US is known as a USDMF. Sertindole USDMF includes data on Sertindole's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Sertindole USDMF is kept confidential to protect the manufacturer’s intellectual property.

click here to find a list of Sertindole suppliers with USDMF on PharmaCompass.

Sertindole GMP

Sertindole Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Sertindole GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Sertindole GMP manufacturer or Sertindole GMP API supplier for your needs.

Sertindole CoA

A Sertindole CoA (Certificate of Analysis) is a formal document that attests to Sertindole's compliance with Sertindole specifications and serves as a tool for batch-level quality control.

Sertindole CoA mostly includes findings from lab analyses of a specific batch. For each Sertindole CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Sertindole may be tested according to a variety of international standards, such as European Pharmacopoeia (Sertindole EP), Sertindole JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Sertindole USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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