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    Pipamperone

    ACTIVE PHARMA INGREDIENTS

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    2D Structure
    Also known as: Floropipamide, 1893-33-0, Dipiperon, Dipiperone, Dipiperal, Piperonyl
    Molecular Formula
    C21H30FN3O2
    Molecular Weight
    375.5  g/mol
    InChI Key
    AXKPFOAXAHJUAG-UHFFFAOYSA-N
    FDA UNII
    5402501F0W
    Pipamperone is a typical antipsychotic of the butyrophenone family used in the treatment of schizophrenia. It was developed by Janssen Pharmaceutica in 1961 and started its first round of clinical trials in 1963. In an effort to improve [haloperidol]'s pharmacological effects, Janssen discovered that pipamperone, an agent whose pharmacological profile was distinct from haloperidol and all other known antipsychotic drugs at this time, had significant anti-tryptamine activity. Some studies suggest pipamperone was the first atypical antipsychotic. Interestingly, when [risperidone] was created, Janssen suggested it was a more potent version of pipamperone. Synthesized in the year 1984, risperidones pharmacological properties were similar to pipamperones in that both block more serotonin more potently than dopamine.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    1-[4-(4-fluorophenyl)-4-oxobutyl]-4-piperidin-1-ylpiperidine-4-carboxamide
    2.1.2 InChI
    InChI=1S/C21H30FN3O2/c22-18-8-6-17(7-9-18)19(26)5-4-12-24-15-10-21(11-16-24,20(23)27)25-13-2-1-3-14-25/h6-9H,1-5,10-16H2,(H2,23,27)
    2.1.3 InChI Key
    AXKPFOAXAHJUAG-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C1CCN(CC1)C2(CCN(CC2)CCCC(=O)C3=CC=C(C=C3)F)C(=O)N
    2.2 Other Identifiers
    2.2.1 UNII
    5402501F0W
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 1'-(3-(4-fluorobenzoyl)propyl)-(1,4'-bipiperidine) -4'-carboxamide

    2. Dipiperon

    3. Pipamperon-neuraxpharm

    4. Pipamperone Dihydrochloride

    5. R 3345

    2.3.2 Depositor-Supplied Synonyms

    1. Floropipamide

    2. 1893-33-0

    3. Dipiperon

    4. Dipiperone

    5. Dipiperal

    6. Piperonyl

    7. Piperonil

    8. R 3345

    9. Pipamperona

    10. Pipamperonum

    11. Pipamperone Hydrochloride

    12. Mcn-jr-3345

    13. Pipaneperone

    14. Pipamperone Free Base

    15. Pipamperone Dihydrochloride Approx. 99

    16. Nsc-759178

    17. 1'-(3-(p-fluorobenzoyl)propyl)-(1,4'-bipiperidine)-4'-carboxamide

    18. (1,4'-bipiperidine)-4'-carboxamide, 1'-(3-(p-fluorobenzoyl)propyl)-

    19. Chebi:78549

    20. 1893-33-0 (free Base)

    21. 4'-fluoro-4-(4-n-piperidino-4-carbamidopiperidino)butyrophenone

    22. P-fluoro-gamma-(4-piperidino-4-carbamoylpiperidino)butyrophenone

    23. R-3345

    24. Carpiperone

    25. Fluoropipamide

    26. [1,4'-bipiperidine]-4'-carboxamide, 1'-[4-(4-fluorophenyl)-4-oxobutyl]-

    27. 1-[4-(4-fluorophenyl)-4-oxobutyl]-4-piperidin-1-ylpiperidine-4-carboxamide

    28. Floropipamide; Mcn-jr 3345; R 3345

    29. 5402501f0w

    30. 1'-[4-(4-fluorophenyl)-4-oxobutyl]-1,4'-bipiperidine-4'-carboxamide

    31. (1,4'-bipiperidine)-4'-carboxamide, 1'-(4-(4-fluorophenyl)-4-oxobutyl)-

    32. Pipamperon

    33. 1'-(4-(4-fluorophenyl)-4-oxobutyl)-[1,4'-bipiperidine]-4'-carboxamide

    34. Pipamperonum [inn-latin]

    35. Pipamperona [inn-spanish]

    36. Pipamperone [usan:inn:ban]

    37. Ccris 9071

    38. Ncgc00165864-02

    39. Brn 0496532

    40. 1'-(4-(4-fluorophenyl)-4-oxobutyl)-1,4'-bipiperidine-4'-carboxamide

    41. 1'-[4-(4-fluorophenyl)-4-oxobutyl]-[1,4'-bipiperidine]-4'-carboxamide

    42. Unii-5402501f0w

    43. Propitan (salt/mix)

    44. Isonipacotamide, 1-(3-(p-fluorobenzoyl)propyl)-4-piperidino-

    45. Pipamperone [mi]

    46. Pipamperone [inn]

    47. Pipamperone (usan/inn)

    48. Pipamperone [usan]

    49. Gtpl92

    50. Schembl2412

    51. Pipamperone [mart.]

    52. Pipamperone [who-dd]

    53. 5-22-13-00536 (beilstein Handbook Reference)

    54. Mcn-jr 3345

    55. Chembl440294

    56. Dtxsid8048369

    57. Bdbm81483

    58. Hms3264g14

    59. Pharmakon1600-01505690

    60. Nsc_4830

    61. 1'-(3-(p-fluorobenzoyl)propyl)(1,4'-bipiperidine)-4'-carboxamide

    62. Mfcd00242979

    63. Nsc759178

    64. Pdsp1_001560

    65. Pdsp2_001544

    66. Zinc21297287

    67. Ccg-213514

    68. Db09286

    69. Nsc 759178

    70. Ncgc00165864-01

    71. Ac-32938

    72. Pipamperonedihydrochlorideapprox.99

    73. Cas_1893-33-0

    74. Sbi-0206899.p001

    75. Hy-100703

    76. Cs-0020023

    77. P2315

    78. D02622

    79. Ab01563106_01

    80. A929272

    81. L000727

    82. Q415118

    83. Sr-05000001930

    84. Sr-05000001930-1

    85. Brd-k26801045-001-01-1

    86. Isonipecotamide, 1-(3-(p-fluorobenzoyl)propyl)-4-piperidino-

    87. P-fluoro-.gamma.-(4-piperidino-4-carbamoylpiperidino)butyrophenone

    88. 1,4'-bipiperidine)-4'-carboxamide, 1'-(4-(4-fluorophenyl)-4-oxobutyl)-

    89. 1-(4-fluorophenyl)-4-(4-piperidino-4-carbamoylpiperidino)-1-butanone

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 375.5 g/mol
    Molecular Formula C21H30FN3O2
    XLogP32
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count7
    Exact Mass375.23220537 g/mol
    Monoisotopic Mass375.23220537 g/mol
    Topological Polar Surface Area66.6 Ų
    Heavy Atom Count27
    Formal Charge0
    Complexity506
    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

    Treatment of chronic psychoses and states of aggressiveness of various origins.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Pipamperone is an antipsychotic medication that has sedative effects, which may be beneficial in the management of agitation and disordered sleep. Pipamperone, showing antidopaminergic and anti-serotonergic properties, has been noted for its anti- agitation effects and for its ability to normalize sleep rhythms in psychiatric patients. One study showed that pipamperone increased the expression of D4 (dopaminergic) receptors, explaining its helpfulness in decreasing positive psychotic symptoms, such as delusions and hallucinations.

    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.)

    Serotonin Antagonists

    Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or SEROTONIN RECEPTOR AGONISTS. (See all compounds classified as Serotonin Antagonists.)

    5.3 ATC Code

    N05AD05

    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

    N05AD05 - Pipamperone

    5.4 Absorption, Distribution and Excretion

    Route of Elimination

    Mainly via the kidneys

    5.5 Metabolism/Metabolites

    Pipamperone is metabolised in the liver.

    5.6 Biological Half-Life

    17-26h

    5.7 Mechanism of Action

    Pipamperone binds mainly to 5-HT2A receptors, with a nearly equal affinity to D4 receptors and a moderate affinity for 5-HT2C, D2, D3, 1- and 2B-adrenoceptors. This drug is a selective 5-HT2A, D1 and D4 antagonist. Extrapyramidal adverse effects also appear to be limited in pipamperone treatment compared to traditional antipsychotic medications due to its high receptor selectivity. Pipamperone has a 15-fold higher affinity for D4 than D2 receptors. It has been suggested that D4 receptors may play a role in the modulation of GABAergic neuronal activity by dopamine.