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

• ChemBase ID: 4385
• Molecular Formular: C26H26F2N2
• Molecular Mass: 404.4948464
• Monoisotopic Mass: 404.20640528
• SMILES: Fc1ccc(C(N2CCN(CC2)C/C=C/c2ccccc2)c2ccc(F)cc2)cc1
• Canonical SMILES: Fc1ccc(cc1)C(c1ccc(cc1)F)N1CCN(CC1)C/C=C/c1ccccc1
• 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+
• InChIKey: SMANXXCATUTDDT-QPJJXVBHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[bis(4-fluorophenyl)methyl]-4-[(2E)-3-phenylprop-2-en-1-yl]piperazine; 1-[bis(4-fluorophenyl)methyl]-4-(3-phenylprop-2-en-1-yl)piperazine
• IUPAC Traditional name: flunarizine; 1-[bis(4-fluorophenyl)methyl]-4-(3-phenylprop-2-en-1-yl)piperazine; 1-[bis(4-fluorophenyl)methyl]-4-[(2E)-3-phenylprop-2-en-1-yl]piperazine
• Brand Name: Sibelium; Novo-Flunarizine; Apo-flunarizine capsules; Vertix; Zinasen; Issium; Fluvert; Flufenal
• Synonyms: 1-[Bis(4-fluorophenyl)methyl]-4-[(2E)-3-phenyl-2-propen-1-yl]piperazine Hydrochloride; Dinaplex; Flugeral; Flunagen; Flunarl; Fluxarten; Gradient; Issium; Mondus; R 14950; Flunarizine Dihydrochloride; Flunarizinum [inn-latin]; Flunarizina [inn-spanish]; 1-(Bis(4-fluorophenyl)methyl)-4-cinnamylpiperazine; (E)-1-[Bis-(p-fluorophenyl)methyl]-4-cinnamylpiperazine; Flunarizine Hydrochloride; flunarizine dihydrochloride; Flunarizine; 1-[''bis''(4-fluorophenyl)methyl]-4-cinnamyl-piperazine; 1-[Bis(4-fluorophenyl)methyl]-4-(3-phenyl-2-propenyl)piperazine; 4',4''-Difluorocinnarizine; Flunarizine

Database IDs

• CAS Number: 52468-60-7; 30484-77-6
• PubChem SID: 160967817; 46507129
• PubChem CID: 941361
• ATC CODE: N07CA03
• CHEMBL: 30008
• Chemspider ID: 819216
• DrugBank ID: DB04841
• KEGG ID: D07971
• Unique Ingredient Identifier: R7PLA2DM0J
• Wikipedia Title: Flunarizine

CALCULATED PROPERTIES

JChem

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 4.0807085
• LogD (pH = 7.4): 5.754555
• Log P: 6.165795
• Molar Refractivity: 120.2976 cm^3
• Polarizability: 45.707912 Å^3
• Polar Surface Area: 6.48 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 5.3
• LOG S: -5.38
• Solubility (Water): 1.68e-03 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 188-190°C (dec.)

Safety Information

• Storage Condition: Refrigerator

Pharmacology Properties

• Mechanism of Action: Calcium channel blocker; Flunarizine is a selective calcium entry blocker with calmodulin binding properties and histamine H1 blocking activity

Product Information

• Application(s): 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.; It may help to reduce the severity and duration of attacks of paralysis associated with the more serious form of alternating hemiplegia.

DETAILS

DrugBank - DB04841

• Drug Groups: approved
• Description: 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.
• 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.
• Pharmacology: Flunarizine is a selective calcium entry blocker with calmodulin binding properties and histamine H1 blocking activity.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic, to two metabolites via N-dealylation and hydroxylation.
• Absorption: 85% following oral administration.
• Half Life: 18 days
• Protein Binding: 99% bound to plasma proteins
• External Links: Wikipedia

Toronto Research Chemicals - F455200

Calcium channel blocker; fluorinated derivative of Cinnarizine. Vasodilator (cerebral and peripheral).

REFERENCES

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• Holmes, B., et al.: Drugs, 27, 6 (1975)
• Ger. Pat., 1972, 2 220 242; CA, 78, 29815r, (synth)
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• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, FDD080