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Blonanserin

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Chemistry

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Also known as: 132810-10-7, Lonasen, Ad-5423, Blonanserin [inn], Ad 5423, 2-(4-ethylpiperazin-1-yl)-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine

Molecular Formula

C₂₃H₃₀FN₃

Molecular Weight

367.5 g/mol

InChI Key

XVGOZDAJGBALKS-UHFFFAOYSA-N

FDA UNII

AQ316B4F8C

Blonanserin is an atypical antipsychotic approved in Japan in January, 2008. It offers improved tolerability as it lacks side effects such as extrapyramidal symptoms, excessive sedation, or hypotension. As a second-generation (atypical) antipsychotic, it is significantly more efficacious in the treatment of the negative symptoms of schizophrenia compared to first-generation (typical) antipsychotics.

1 2D Structure

Blonanserin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-(4-ethylpiperazin-1-yl)-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine

2.1.2 InChI

InChI=1S/C23H30FN3/c1-2-26-13-15-27(16-14-26)23-17-21(18-9-11-19(24)12-10-18)20-7-5-3-4-6-8-22(20)25-23/h9-12,17H,2-8,13-16H2,1H3

2.1.3 InChI Key

XVGOZDAJGBALKS-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CCN1CCN(CC1)C2=NC3=C(CCCCCC3)C(=C2)C4=CC=C(C=C4)F

2.2 Other Identifiers

2.2.1 UNII

AQ316B4F8C

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2-(4-ethyl-1-piperazinyl)-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta(b)pyridine

2. Ad 5423

3. Ad-5423

4. Ad5423

5. Cycloocta(b)pyridine, 2-(4-ethyl-1-piperazinyl)-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydro-

6. Lonasen

2.3.2 Depositor-Supplied Synonyms

1. 132810-10-7

2. Lonasen

3. Ad-5423

4. Blonanserin [inn]

5. Ad 5423

6. 2-(4-ethylpiperazin-1-yl)-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine

7. Blonanserin (lonasen)

8. 2-(4-ethyl-1-piperazinyl)-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta(b)pyridine

9. Aq316b4f8c

10. Chembl178803

11. 132810-10-7 (free Base)

12. 2-(4-ethyl-1-piperazinyl)-4-(p-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta(b)pyridine

13. Ncgc00183858-01

14. 2-(4-ethyl-1-piperazinyl)-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine

15. Cycloocta(b)pyridine, 2-(4-ethyl-1-piperazinyl)-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydro-

16. 2-(4-ethylpiperazin-1-yl)-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine.

17. Blonanserin (jan/inn)

18. Unii-aq316b4f8c

19. 2-(4-ethylpiperazin-1-yl)-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta(b)pyridine

20. Cycloocta[b]pyridine, 2-(4-ethyl-1-piperazinyl)-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydro-

21. Ad5423

22. Blonanserin [mi]

23. Blonanserin [jan]

24. Blonanserin(ad-5423)

25. Blonanserin [mart.]

26. Dsstox_cid_28716

27. Dsstox_rid_82985

28. Dsstox_gsid_48790

29. Blonanserin [who-dd]

30. Schembl119669

31. Gtpl7670

32. Dtxsid7048790

33. Blonanserin, >=98% (hplc)

34. Chebi:31296

35. Amy8830

36. Ex-a663

37. Hms3740e13

38. Zinc597434

39. Bcp04236

40. Dsp-5423

41. Tox21_113267

42. Bdbm50160807

43. Mfcd00893838

44. Pdsp1_000720

45. Pdsp2_000710

46. S2112

47. Akos005145823

48. Ac-1599

49. Db09223

50. Sb17396

51. Cycloocta(b)pyridine, 2-(4-ethyl-1-piperazinyl)-4-(1-fluorophenyl)-5,6,7,8,9,10-hexahydro-

52. As-11421

53. Hy-13575

54. A8384

55. B4565

56. Cas-132810-10-7

57. Ft-0663415

58. Ad-5423;ad5423;ad 5423

59. D01176

60. Ab01565798_02

61. 810b107

62. L001392

63. Sr-01000945256

64. Q4927426

65. Sr-01000945256-1

66. 4-(4-fluoro-phenyl)-2-(4-propyl-piperazin-1-yl)-5,6,7,8,9,10-hexahydro-cycloocta[b]pyridine

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₃H₃₀FN₃
Molecular Weight	367.5 g/mol
XLogP3	5.5
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	3
Exact Mass	367.24237613 g/mol
Monoisotopic Mass	367.24237613 g/mol
Topological Polar Surface Area	19.4 Å²
Heavy Atom Count	27
Formal Charge	0
Complexity	443
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 for the treatment of schizophrenia.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Blonanserin antagonizes dopamine and serotonin receptors to reduce symptoms of schizophrenia.

5.2 Absorption, Distribution and Excretion

Absorption

Blonanserin has a Tmax of 1.5 h and a bioavailablity of 55%. Tmax has been observed to be prolonged and relative bioavailability increased when administered with food.

Route of Elimination

57% of blonanserin is excreted in the urine and 30% in the feces. Only 5% of the drug in the feces is the parent drug with no parent drug excreted through the urine.

Volume of Distribution

Blonanserin has a Vc of 9500 L and a Vt of 8560 L for a total Vd of 18060 L.

Clearance

Blonanserin has a clearance of 1230 L/h.

5.3 Metabolism/Metabolites

Blonanserin is mainly metabolized by CYP3A4. It undergoes hydoxylation of the cyclooctane ring as well as N-oxidation and N-deethylation of the piperazine ring. The N-deethylated and hydroxylated metabolites are active but to a lesser degree than the parent drug.

5.4 Biological Half-Life

Blonanserin has a half life of elimination of 10.7-16.2 h.

5.5 Mechanism of Action

Blonanserin binds to and inhibits dopamine receptors D2 and D3 as well as the serotonin receptor 5-HT2A with high affinity. Blonanserin has low affinity for other dopamine and serotonin receptors as well as muscarinic, adrenergic, and histamine receptors. This reduces dopaminergic and serotonergic neurotransmission which is thought to produce a reduction in positive and negative symptoms of schizophrenia respectively.

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