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Prestwick3_000509

Prestwick3_000509

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Also known as: 10457-90-6, Impromen, Bromoperidol, 4-(4-(4-bromophenyl)-4-hydroxypiperidin-1-yl)-1-(4-fluorophenyl)butan-1-one, 4-[4-(4-bromophenyl)-4-hydroxypiperidin-1-yl]-1-(4-fluorophenyl)butan-1-one, R 11333

Molecular Formula

C₂₁H₂₃BrFNO₂

Molecular Weight

420.3 g/mol

InChI Key

RKLNONIVDFXQRX-UHFFFAOYSA-N

FDA UNII

LYH6F7I22E

Bromperidol has been used in trials studying the treatment of Dementia, Depression, Schizophrenia, Anxiety Disorders, and Psychosomatic Disorders, among others.

1 2D Structure

Prestwick3_000509

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-[4-(4-bromophenyl)-4-hydroxypiperidin-1-yl]-1-(4-fluorophenyl)butan-1-one

2.1.2 InChI

InChI=1S/C21H23BrFNO2/c22-18-7-5-17(6-8-18)21(26)11-14-24(15-12-21)13-1-2-20(25)16-3-9-19(23)10-4-16/h3-10,26H,1-2,11-15H2

2.1.3 InChI Key

RKLNONIVDFXQRX-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1CN(CCC1(C2=CC=C(C=C2)Br)O)CCCC(=O)C3=CC=C(C=C3)F

2.2 Other Identifiers

2.2.1 UNII

LYH6F7I22E

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Bromoperidol

2. Bromperidol Hydrochloride

3. Bromperidol, 82br-labeled

4. C-c 2489-21

5. Impromen

6. R 11,333

7. Tesoprel

2.3.2 Depositor-Supplied Synonyms

1. 10457-90-6

2. Impromen

3. Bromoperidol

4. 4-(4-(4-bromophenyl)-4-hydroxypiperidin-1-yl)-1-(4-fluorophenyl)butan-1-one

5. 4-[4-(4-bromophenyl)-4-hydroxypiperidin-1-yl]-1-(4-fluorophenyl)butan-1-one

6. R 11333

7. Nsc-759275

8. 4-(4-(4-bromophenyl)-4-hydroxypiperidino)-4'-fluorobutyrophenone

9. 4-(4-(p-bromophenyl)-4-hydroxypiperidino)-4'-fluorobutyrophenone

10. R 11,333

11. Lyh6f7i22e

12. 4-[4-(4-bromophenyl)-4-hydroxy-1-piperidinyl]-1-(4-fluorophenyl)-1-butanone

13. Tesoprel

14. 1-butanone, 4-(4-(4-bromophenyl)-4-hydroxy-1-piperidinyl)-1-(4-fluorophenyl)-

15. 4-(4-(4-bromophenyl)-4-hydroxy-1-piperidinyl)-1-(4-fluorophenyl)-1-butanone

16. Ncgc00016692-01

17. Azurene

18. Cas-10457-90-6

19. Dsstox_cid_2690

20. 4-[4-(4-bromophenyl)-4-hydroxy-1-piperidyl]-1-(4-fluorophenyl)butan-1-one

21. Butyrophenone, 4-(4-(p-bromophenyl)-4-hydroxypiperidino)-4'-fluoro-

22. Dsstox_rid_76693

23. Dsstox_gsid_22690

24. R-11333

25. Bromperidolum

26. Bromperidolum [inn-latin]

27. 1-butanone, 4-[4-(4-bromophenyl)-4-hydroxy-1-piperidinyl]-1-(4-fluorophenyl)-

28. 4-[4-(p-bromophenyl)-4-hydroxypiperidino]-4'-fluorobutyrophenone;4-[4-(p-bromophenyl)-4-hydroxypiperidino]-4'-fluorobutyrophenone

29. Sr-05000001811

30. Einecs 233-943-3

31. Unii-lyh6f7i22e

32. Cc 2489

33. Brn 1552256

34. Impromen (tn)

35. Bromperidol [usan:inn:ban:jan]

36. Prestwick_781

37. Bromperidol [mi]

38. 4-(4-(p-bromophenyl)-4-hydroxypiperidinol)-4'-fluorobutyrophenone

39. Prestwick0_000509

40. Prestwick1_000509

41. Prestwick2_000509

42. Prestwick3_000509

43. Bromperidol [inn]

44. Bromperidol [jan]

45. Bromperidol [usan]

46. Bromperidol [mart.]

47. Schembl43755

48. Bromperidol [who-dd]

49. Bspbio_000437

50. 5-21-02-00382 (beilstein Handbook Reference)

51. Mls002153852

52. Chembl28218

53. Spbio_002358

54. Bromperidol (jan/usan/inn)

55. Bpbio1_000481

56. Dtxsid0022690

57. Bdbm81484

58. Chebi:31305

59. Bromperidol [ep Monograph]

60. Hms1569f19

61. Hms2093j06

62. Hms2096f19

63. Hms2230o05

64. Hms3370c12

65. Hms3713f19

66. Pharmakon1600-01505972

67. Zinc601270

68. Cas_2448

69. Hy-b0901

70. Nsc_2448

71. Tox21_110565

72. Nsc759275

73. Pdsp1_001125

74. Pdsp2_001109

75. Akos015914052

76. Tox21_110565_1

77. Ccg-213579

78. Db12401

79. Nsc 759275

80. Ncgc00016692-02

81. Ncgc00016692-05

82. Ncgc00179558-01

83. Smr001233211

84. Sbi-0206864.p001

85. Db-040551

86. Ft-0630383

87. D01101

88. A896205

89. L000662

90. R-11333r-11333

91. J-001195

92. Q4973749

93. Sr-05000001811-1

94. Sr-05000001811-3

95. Brd-k78643075-001-03-3

96. Brd-k78643075-001-06-6

97. Bromperidol Decanoate Impurity G [ep Impurity]

98. Bromperidol, European Pharmacopoeia (ep) Reference Standard

99. 1-butanone, 4-[4-(4-bromophenyl)-4-hydroxy-1-piperidyl]-1-(4-fluorophenyl)-

100. 4-[4-(4-bromo-phenyl)-4-hydroxy-piperidin-1-yl]-1-(4-fluoro-phenyl)-butan-1-one

101. 4-[4-(4-bromophenyl)-4-hydroxy-1-piperidyl]-1-(4-fluorophenyl)-butan-1-one

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₂₃BrFNO₂
Molecular Weight	420.3 g/mol
XLogP3	3.3
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	6
Exact Mass	419.08962 g/mol
Monoisotopic Mass	419.08962 g/mol
Topological Polar Surface Area	40.5 Å²
Heavy Atom Count	26
Formal Charge	0
Complexity	451
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 Pharmacology and Biochemistry

4.1 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.)

4.2 ATC Code

N05AD06

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

N05AD - Butyrophenone derivatives

N05AD06 - Bromperidol

4.3 Metabolism/Metabolites

Bromperidol has known human metabolites that include 4'-Fluorobutyrophenone and 4-(4-Bromophenyl)piperidin-4-ol.

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