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Prestwick2_000906

Prestwick2_000906

Synopsis, Chemistry

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Also known as: Redeptin, Imap, 1841-19-6, Fluspirilen, Mcn-jr-6218, Fluspirilenum [inn-latin]

Molecular Formula

C₂₉H₃₁F₂N₃O

Molecular Weight

475.6 g/mol

InChI Key

QOYHHIBFXOOADH-UHFFFAOYSA-N

FDA UNII

C5QA4GLR9M

A long-acting injectable antipsychotic agent used for chronic schizophrenia.

1 2D Structure

Prestwick2_000906

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

8-[4,4-bis(4-fluorophenyl)butyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one

2.1.2 InChI

InChI=1S/C29H31F2N3O/c30-24-12-8-22(9-13-24)27(23-10-14-25(31)15-11-23)7-4-18-33-19-16-29(17-20-33)28(35)32-21-34(29)26-5-2-1-3-6-26/h1-3,5-6,8-15,27H,4,7,16-21H2,(H,32,35)

2.1.3 InChI Key

QOYHHIBFXOOADH-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1CN(CCC12C(=O)NCN2C3=CC=CC=C3)CCCC(C4=CC=C(C=C4)F)C5=CC=C(C=C5)F

2.2 Other Identifiers

2.2.1 UNII

C5QA4GLR9M

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Beta, Fluspirilen

2. Fluspi

3. Fluspirilen Beta

4. Fluspirilen Lindo

5. Imap

6. Kivat

7. Redeptin

8. Spirodiflamine

2.3.2 Depositor-Supplied Synonyms

1. Redeptin

2. Imap

3. 1841-19-6

4. Fluspirilen

5. Mcn-jr-6218

6. Fluspirilenum [inn-latin]

7. Fluspirileno [inn-spanish]

8. R 6218

9. 8-[4,4-bis(4-fluorophenyl)butyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one

10. Fluspiriline

11. R 6218;redeptin

12. R-6218

13. C5qa4glr9m

14. 1-phenyl-4-oxo-8-(4,4-bis(4-fluorophenyl)butyl)-1,3,8-triazaspiro(4,5)decane

15. 8-(4,4-bis(p-fluorophenyl)butyl)-1-phenyl-1,3,8-triazaspiro-(4.5)decan-4-one

16. Chembl46516

17. 1,3,8-triazaspiro(4.5)decan-4-one, 8-(4,4-bis(4-fluorophenyl)butyl)-1-phenyl-

18. Ncgc00015424-04

19. Ncgc00015424-11

20. Fluspirileno

21. Fluspirilenum

22. Cas-1841-19-6

23. 1,3,8-triazaspiro[4.5]decan-4-one, 8-[4,4-bis(4-fluorophenyl)butyl]-1-phenyl-

24. Dsstox_cid_25152

25. Dsstox_rid_80706

26. Dsstox_gsid_45152

27. Fluspirilene [usan:inn:ban]

28. Smr000058304

29. Imap (tn)

30. Lopac-f-100

31. Sr-01000075385

32. Einecs 217-418-6

33. Unii-c5qa4glr9m

34. Fluspirilene (usan/inn)

35. Spiropiperidine Analogue, 1

36. Brn 0633853

37. 8-(4,4-bis(4-fluorophenyl)butyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one

38. Prestwick0_000906

39. Prestwick1_000906

40. Prestwick2_000906

41. Prestwick3_000906

42. Fluspirilene [mi]

43. F-100

44. Fluspirilene [inn]

45. Gtpl85

46. 8-[4,4-bis(4-fluorophenyl)butyl]-4-phenyl-2,4,8-triazaspiro[4.5]decan-1-one

47. Fluspirilene [usan]

48. Cid_3396

49. Lopac0_000518

50. Oprea1_804941

51. Schembl42082

52. Bspbio_000752

53. Bspbio_001343

54. Fluspirilene [mart.]

55. 5-26-04-00097 (beilstein Handbook Reference)

56. Mls000069357

57. Mls001333730

58. Fluspirilene [who-dd]

59. Spbio_002951

60. Mcn-jr 6218

61. Bpbio1_000828

62. Dtxsid7045152

63. Bdbm26948

64. Chebi:93369

65. Tqp0727

66. Hms1570f14

67. Hms1791d05

68. Hms1989d05

69. Hms2089c15

70. Hms2097f14

71. Hms2233b20

72. Hms3261h17

73. Hms3372h20

74. Hms3402d05

75. Hms3714f14

76. Zinc537755

77. Fluspirilene [ep Monograph]

78. Bcp09254

79. Fluspirilene (r 6218; Redeptin)

80. Hy-b1655

81. Tox21_110142

82. Tox21_500518

83. Nsc772296

84. Akos015969747

85. Tox21_110142_1

86. Ccg-204608

87. Db04842

88. Lp00518

89. Nsc-772296

90. Sdccgsbi-0050501.p002

91. 1,3,8-triazaspiro[4.5]decan-4-one, 8-[4,4-bis(p-fluorophenyl)butyl]-1-phenyl-

92. Ncgc00015424-01

93. Ncgc00015424-02

94. Ncgc00015424-03

95. Ncgc00015424-05

96. Ncgc00015424-06

97. Ncgc00015424-07

98. Ncgc00015424-08

99. Ncgc00015424-09

100. Ncgc00015424-10

101. Ncgc00015424-15

102. Ncgc00016595-01

103. Ncgc00093913-01

104. Ncgc00093913-02

105. Ncgc00093913-03

106. Ncgc00093913-04

107. Ncgc00093913-05

108. Ncgc00261203-01

109. As-16749

110. Ab00513956

111. Cs-0013609

112. Eu-0100518

113. Ft-0668770

114. D02629

115. Ab00513956-10

116. L001195

117. Q408300

118. J-011797

119. Sr-01000075385-1

120. Sr-01000075385-5

121. Brd-k77947974-001-04-9

122. Ethyl1-(tert-butyl)-4,5-dioxopyrrolidine-3-carboxylate

123. Fluspirilene, European Pharmacopoeia (ep) Reference Standard

124. 8-(4,4-bis(p-fluorophenyl)butyl)-1-phenyl-1,3,8-triazaspiro(4,5)decan-4-one

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₂₉H₃₁F₂N₃O
Molecular Weight	475.6 g/mol
XLogP3	5.6
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	7
Exact Mass	475.24351894 g/mol
Monoisotopic Mass	475.24351894 g/mol
Topological Polar Surface Area	35.6 Å²
Heavy Atom Count	35
Formal Charge	0
Complexity	653
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

Fluspirilene is a relatively long-acting injectable depot antipsychotic drug used for schizophrenia. Fluspirilene does not differ greatly from other depot antipsychotics (fluphenazine decanoate, fluphenazine enathate, perphenazine onanthat, pipotiazine undecylenate) with respect to treatment efficacy, response or tolerability. Outcomes suggest that fluspirilene does not differ significantly from oral antipsychotics or in different weekly regimens, although much cannot be inferred because of the shortage of trials.

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.)

Dopamine Antagonists

Drugs that bind to but do not activate DOPAMINE RECEPTORS, thereby blocking the actions of dopamine or exogenous agonists. Many drugs used in the treatment of psychotic disorders (ANTIPSYCHOTIC AGENTS) are dopamine antagonists, although their therapeutic effects may be due to long-term adjustments of the brain rather than to the acute effects of blocking dopamine receptors. Dopamine antagonists have been used for several other clinical purposes including as ANTIEMETICS, in the treatment of Tourette syndrome, and for hiccup. Dopamine receptor blockade is associated with NEUROLEPTIC MALIGNANT SYNDROME. (See all compounds classified as Dopamine Antagonists.)

5.3 ATC Code

N05AG01

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

N - Nervous system

N05 - Psycholeptics

N05A - Antipsychotics

N05AG - Diphenylbutylpiperidine derivatives

N05AG01 - Fluspirilene