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Flunarizine

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ACTIVE PHARMA INGREDIENTS

13 API Suppliers, 6 CEP/COS, 5 EU WC, 4 KDMF, 1 NDC API, 10 Listed Suppliers, $ API Reference Price

13 API Suppliers
6 CEP/COS
5 EU WC
4 KDMF
1 NDC API
10 Listed Suppliers
$ API Reference Price

INTERMEDIATES

2 Intermediates Suppliers

2 Intermediates Suppliers

FINISHED DOSAGE FORMULATIONS

35 FDF Dossiers, 17 Europe, 1 Canada, 3 South Africa, 14 Listed Dossiers

35 FDF Dossiers
17 Europe
1 Canada
3 South Africa
14 Listed Dossiers

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1 NEWS #PharmaBuzz

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1 NEWS #PharmaBuzz

GLOBAL SALES INFORMATION

17 Finished Drug Prices

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17 Finished Drug Prices

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8 APIs, 2 FDF Dossiers

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8 APIs
2 FDF Dossiers

REF. STANDARDS & IMPURITIES

2 EDQM , 5 Others

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2 EDQM
5 Others

Synopsis

ACTIVE PHARMA INGREDIENTS

API Suppliers

USDMF

CEP/COS

JDMF

EU WC

KDMF

NDC API

VMF

Listed Suppliers

API REF. PRICE (USD/KG)

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API

FDF

FINISHED DOSAGE FORMULATIONS

FDF Dossiers

FDA Orange Book

Europe

Canada

Australia

South Africa

Listed Dossiers

0 DRUGS IN DEVELOPMENT

DRUG PRODUCT COMPOSITIONS

REF. STANDARDS OR IMPURITIES

EDQM

USP

Others

PATENTS & EXCLUSIVITIES

US Patents

US Exclusivities

Health Canada Patents

DIGITAL CONTENT

Data Compilation #PharmaFlow

Stock Recap #PipelineProspector

Weekly News Recap #Phispers

News #PharmaBuzz

GLOBAL SALES INFORMATION

US Medicaid (USD)

Annual Reports (USD Million)

Finished Drug Prices

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Chemistry

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Also known as: 52468-60-7, Sibelium, 1-(bis(4-fluorophenyl)methyl)-4-cinnamylpiperazine, Flunarizinum [inn-latin], Flunarizina [inn-spanish], 40218-96-0

Molecular Formula

C₂₆H₂₆F₂N₂

Molecular Weight

404.5 g/mol

InChI Key

SMANXXCATUTDDT-QPJJXVBHSA-N

FDA UNII

R7PLA2DM0J

Flunarizine is a selective calcium entry blocker with calmodulin binding properties and histamine H1 blocking activity. It is effective in the prophylaxis of migraine, occlusive peripheral vascular disease, vertigo of central and peripheral origin, and as an adjuvant in the therapy of epilepsy.

1 2D Structure

Flunarizine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-[bis(4-fluorophenyl)methyl]-4-[(E)-3-phenylprop-2-enyl]piperazine

2.1.2 InChI

InChI=1S/C26H26F2N2/c27-24-12-8-22(9-13-24)26(23-10-14-25(28)15-11-23)30-19-17-29(18-20-30)16-4-7-21-5-2-1-3-6-21/h1-15,26H,16-20H2/b7-4+

2.1.3 InChI Key

SMANXXCATUTDDT-QPJJXVBHSA-N

2.1.4 Canonical SMILES

C1CN(CCN1CC=CC2=CC=CC=C2)C(C3=CC=C(C=C3)F)C4=CC=C(C=C4)F

2.1.5 Isomeric SMILES

C1CN(CCN1C/C=C/C2=CC=CC=C2)C(C3=CC=C(C=C3)F)C4=CC=C(C=C4)F

2.2 Other Identifiers

2.2.1 UNII

R7PLA2DM0J

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Dihydrochloride, Flunarizine

2. Flunarizin

3. Flunarizine Dihydrochloride

4. Flunarizine Hydrochloride

5. Hydrochloride, Flunarizine

6. R 14950

7. R-14950

8. R14950

9. Sibelium

2.3.2 Depositor-Supplied Synonyms

1. 52468-60-7

2. Sibelium

3. 1-(bis(4-fluorophenyl)methyl)-4-cinnamylpiperazine

4. Flunarizinum [inn-latin]

5. Flunarizina [inn-spanish]

6. 40218-96-0

7. Flunarizine (inn)

8. (e)-1-(bis(4-fluorophenyl)methyl)-4-(3-phenyl-2-propenyl)piperazine

9. R7pla2dm0j

10. 1-[bis(4-fluorophenyl)methyl]-4-[(e)-3-phenylprop-2-enyl]piperazine

11. Chembl30008

12. (e)-1-[bis-(p-fluorophenyl)methyl]-4-cinnamylpiperazine

13. Piperazine, 1-(bis(4-fluorophenyl)methyl)-4-(3-phenyl-2-propenyl)-, (e)-

14. Flunarizine [inn]

15. 1-[bis(4-fluorophenyl)methyl]-4-[(2e)-3-phenylprop-2-en-1-yl]piperazine

16. Piperazine, 1-[bis(4-fluorophenyl)methyl]-4-(3-phenyl-2-propenyl)-, (e)-

17. Flunarizine [inn:ban]

18. Dsstox_cid_25616

19. Dsstox_rid_81005

20. Dsstox_gsid_45616

21. Flunarazine

22. Narzine

23. Sibelium (tn)

24. Cas-52468-60-7

25. Einecs 257-937-5

26. Unii-r7pla2dm0j

27. 1-[bis(4-fluorophenyl)methyl]-4-(3-phenylprop-2-enyl)piperazine

28. (e)-1-(bis-(p-fluorophenyl)methyl)-4-cinnamylpiperazine

29. Flunarizine2hcl

30. Ncgc00018102-06

31. Einecs 254-842-0

32. Flunarizine [mi]

33. Prestwick2_000312

34. Prestwick3_000312

35. Spectrum5_001570

36. Lopac0_000527

37. Schembl43440

38. Schembl43441

39. Bspbio_000304

40. Bspbio_001341

41. Bspbio_003096

42. Flunarizine [who-dd]

43. Bpbio1_000336

44. Dtxsid6045616

45. Bcbcmap01_000120

46. Chebi:92209

47. Cid_6365505

48. 1-[bis(4-fluorophenyl)methyl]-4-[(e)-cinnamyl]piperazine

49. Chebi:135652

50. Hms1361d03

51. Hms1791d03

52. Hms1989d03

53. Hms2089h21

54. Hy-b0358

55. Tox21_110825

56. Bdbm50017702

57. Piperazine, 1-(bis(4-fluorophenyl)methyl)-4-(3-phenyl-2-propenyl)-

58. Stl477617

59. Zinc19360739

60. 1-[bis(4-fluorophenyl)methyl]-4-[(2e)-3-phenyl-2-propenyl]piperazine

61. 4-((2e)-3-phenylprop-2-enyl)-1-[bis(4-fluorophenyl)methyl]piperazine

62. Akos015960783

63. Tox21_110825_1

64. Ac-1283

65. Ccg-204617

66. Db04841

67. Sdccgsbi-0050510.p004

68. Idi1_000043

69. Idi1_033811

70. Ncgc00018102-04

71. Ncgc00018102-05

72. Ncgc00018102-07

73. Ncgc00018102-08

74. Ncgc00018102-09

75. Ncgc00018102-10

76. Ncgc00018102-12

77. Ncgc00018102-24

78. Ncgc00024308-04

79. Ncgc00024308-05

80. Ncgc00024308-06

81. Ncgc00024308-07

82. As-75845

83. Sbi-0050510.p003

84. Cs-0013608

85. D07971

86. D93478

87. Ab00053586-15

88. Ab00053586_16

89. Ab00053586_17

90. A899896

91. Q416237

92. 1-[bis-(4-fluorophenyl)methyl]-4-cinnamylpiperazine

93. Brd-k12184470-300-01-8

94. Brd-k29582677-001-02-7

95. Brd-k29582677-300-05-6

96. Brd-k29582677-300-06-4

97. 1-[bis-(4-fluoro-phenyl)-methyl]-4-(3-phenyl-allyl)-piperazine

98. 1-[bis(4-fluorophenyl)methyl]-4-[(2z)-3-phenyl-2-propen-1-yl]piperazine

99. 1-[bis-(4-fluoro-phenyl)-methyl]-4-((e)-3-phenyl-allyl)-piperazine

100. Piperazine, 1-[bis(4-fluorophenyl)methyl]-4-[(2e)-3-phenyl-2-propenyl]-

101. 1-[bis-(4-fluoro-phenyl)-methyl]-4-(3-phenyl-allyl)-piperazine(flunarizine)

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₂₆H₂₆F₂N₂
Molecular Weight	404.5 g/mol
XLogP3	6
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	6
Exact Mass	404.20640516 g/mol
Monoisotopic Mass	404.20640516 g/mol
Topological Polar Surface Area	6.5 Å²
Heavy Atom Count	30
Formal Charge	0
Complexity	487
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Used in the prophylaxis of migraine, occlusive peripheral vascular disease, vertigo of central and peripheral origin, and as an adjuvant in the therapy of epilepsy.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Flunarizine is a selective calcium entry blocker with calmodulin binding properties and histamine H1 blocking activity.

5.2 MeSH Pharmacological Classification

Anticonvulsants

Drugs used to prevent SEIZURES or reduce their severity. (See all compounds classified as Anticonvulsants.)

Calcium Channel Blockers

A class of drugs that act by selective inhibition of calcium influx through cellular membranes. (See all compounds classified as Calcium Channel Blockers.)

Histamine H1 Antagonists

Drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine. Included here are the classical antihistaminics that antagonize or prevent the action of histamine mainly in immediate hypersensitivity. They act in the bronchi, capillaries, and some other smooth muscles, and are used to prevent or allay motion sickness, seasonal rhinitis, and allergic dermatitis and to induce somnolence. The effects of blocking central nervous system H1 receptors are not as well understood. (See all compounds classified as Histamine H1 Antagonists.)

Vasodilator Agents

Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)

5.3 ATC Code

N - Nervous system

N07 - Other nervous system drugs

N07C - Antivertigo preparations

N07CA - Antivertigo preparations

N07CA03 - Flunarizine

5.4 Absorption, Distribution and Excretion

Absorption

85% following oral administration.

5.5 Metabolism/Metabolites

Hepatic, to two metabolites via N-dealylation and hydroxylation.

Flunarizine has known human metabolites that include 1-[bis(4-fluorophenyl)methyl]piperazine, bis(4-fluorophenyl)methanone, and p-Hydroxyflunarizine.

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

5.6 Biological Half-Life

18 days

5.7 Mechanism of Action

Flunarizine inhibits the influx of extracellular calcium through myocardial and vascular membrane pores by physically plugging the channel. The decrease in intracellular calcium inhibits the contractile processes of smooth muscle cells, causing dilation of the coronary and systemic arteries, increased oxygen delivery to the myocardial tissue, decreased total peripheral resistance, decreased systemic blood pressure, and decreased afterload.

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API Reference Price

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