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Pipamperone

Pipamperone

Synopsis, Chemistry

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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

Pipamperone

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 Formula	C₂₁H₃₀FN₃O₂
Molecular Weight	375.5 g/mol
XLogP3	2
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	7
Exact Mass	375.23220537 g/mol
Monoisotopic Mass	375.23220537 g/mol
Topological Polar Surface Area	66.6 Å²
Heavy Atom Count	27
Formal Charge	0
Complexity	506
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

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.