1-[4-(2-methoxyphenyl)piperazin-1-yl]-3-(naphthalen-1-yloxy)propan-2-ol

• ChemBase ID: 72842
• Molecular Formular: C24H28N2O3
• Molecular Mass: 392.49072
• Monoisotopic Mass: 392.20999277
• SMILES: c1(c2c(ccc1)cccc2)OCC(CN1CCN(CC1)c1ccccc1OC)O
• Canonical SMILES: COc1ccccc1N1CCN(CC1)CC(COc1cccc2c1cccc2)O
• InChI: InChI=1S/C24H28N2O3/c1-28-24-11-5-4-10-22(24)26-15-13-25(14-16-26)17-20(27)18-29-23-12-6-8-19-7-2-3-9-21(19)23/h2-12,20,27H,13-18H2,1H3
• InChIKey: HRRBJVNMSRJFHQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[4-(2-methoxyphenyl)piperazin-1-yl]-3-(naphthalen-1-yloxy)propan-2-ol
• IUPAC Traditional name: 1-[4-(2-methoxyphenyl)piperazin-1-yl]-3-(naphthalen-1-yloxy)propan-2-ol; naftopidil; flivas
• Synonyms: 4-(2-Methoxyphenyl)-α-[(1-naphthalenyloxy)methyl]-1-piperazineethanol; Naftopil; (+/-)-Naftopidil; rac-4-(2-Methoxyphenyl)-α-[(1-naphthalenyloxy)methyl]-1-piperazineethanol Dihydrochloride; Flivas; KT 611; Naftopidil DihydrochlorideSee: N213501; Naftopidil; 1-(4-(2-methoxyphenyl)piperazin-1-yl)-3-(naphthalen-1-yloxy)propan-2-ol; Flivas; KT-611; BM-15275; Avishot; Naftopidil

Database IDs

• CAS Number: 57419-08-3; 57149-07-2; 57149-08-3
• PubChem SID: 162037763
• PubChem CID: 4418

CALCULATED PROPERTIES

• Acid pKa: 14.078878
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 1.9296913
• LogD (pH = 7.4): 3.4984076
• Log P: 3.7739294
• Molar Refractivity: 115.9648 cm^3
• Polarizability: 46.108505 Å^3
• Polar Surface Area: 45.17 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Dimethyl Sulfoxide; DMSO; Methanol
• Apperance: Off-White Solid; White Solid
• Melting Point: 116-118°C; 125-126°C

Safety Information

• Storage Condition: -20°C; -20°C Freezer

Pharmacology Properties

• Mechanism of Action: alpha-1 Adrenoceptor and calcium antagonist; Vasodilator

Product Information

• Salt Data: Free Base
• Application(s): Antihypertensive agent; Used for the treatment of dysuria associated with benign prostatic hypertrophy; Vasodilator, mediates contraction of prostatic smooth muscle

DETAILS

Selleck Chemicals - S2126

Research Area: Cardiovascular Disease
Biological Activity:
Naftopidil (Flivas) is a selective α1-adrenergic receptor antagonist or alpha blocker with a Ki of 58.3 nM. Naftopidil (Flivas) is an antihypertensive agent. [1] Naftopidil (Flivas) binds specifically to alpha 1-adrenoceptors. The Ki values are 58.3 nM for naftopidil, 0.43 nM for prazosin, and 197 nM for urapidil. The affinities of naftopidil to alpha 2- and beta-adrenoceptor sites are very low (> 6,000 and > 2,500 nM). Naftopidil relaxes aortic strips precontracted with norepinephrine concentration-dependently, and naftopidil (Flivas) shifts the concentration-response curve of norepinephrine in a parallel manner to the right. The pA2 values are 7.10 for naftopidil, 8.85 for prazosin, and 6.25 for urapidil. [2]References on Naftopidil (Flivas)[1] http://en.wikipedia.org/wiki/Naftopidil, , [2] J Cardiovasc Pharmacol., 1992 Dec, 20(6):1006-13.

Toronto Research Chemicals - N213500

A α-1-Adrenergic receptor antagonist, antihypertensive.

Toronto Research Chemicals - N213501

Naftopidil is an α-1-adrenergic receptor antagonist. Naftopidil is used as an antihypertensive.

REFERENCES

• http://en.wikipedia.org/wiki/Naftopidil
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• Kirsten, et al.: Eur. J. Clin. Pharmacol., 46, 271 (1994)
• Farthing, M.J.G., et al.: Postgrad. Med. J., 70, 363 (1994)
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