| Identification | More | [Name]
Naftopidil dihydrochloride | [CAS]
57149-07-2 | [Synonyms]
NAFTOPIDIL
(+-)-1-(4-(2-methoxyphenyl)piperazinyl)-3-(1-naphthyloxy)propan-2-ol
4-(2-methoxyphenyl)-alpha-((1-naphthalenyloxy)methyl)-1-pioerazineethano
4-(2-methoxyphenyl)-alpha-((1-naphthalenyloxy)methyl)-1-pioerazineethanol
kt-611
NAFTOPIDIL DIHYDROCHLORIDE (KT-611) A1 A DRENOCEPTOR ANTAG
NafTopIDi1
Avishot
Flivas
Naftopidil Dihydrochloride See: N213501
rac-4-(2-Methoxyphenyl)-a-[(1-naphthalenyloxy)methyl]-1-piperazineethanol Dihydrochloride
4-(2-Methoxyphenyl)-a-[(1-naphthalenyloxy)methyl]-1-piperazineethanol,
4-(2-methoxyphenyl)-α-[(1-naphthalenyloxy)methyl]-1-piperazineethanol dihydrochloride
1-Piperazineethanol, 4-(2-methoxyphenyl)-a-[(1-naphthalenyloxy)methyl]-(9CI)
3-[4-(2-Methoxyphenyl)piperazinyl]-1-naphthyloxypropan-2-ol
Naftopidil and intermediates
4-(2-Methoxyphenyl)-alpha-[(1-naphthalenyloxy)methyl]-1-piperazineethanol dihydrochloride
Naftopidil dihydrochloride
rac-4-(2-Methoxyphenyl)-α-[(1-naphthalenyloxy)methyl]-1-piperazineethanol Dihydrochloride
4-(2-Methoxyphenyl)-α-[(1-naphthalenyloxy)methyl]-1-piperazineethanol, | [EINECS(EC#)]
692-531-5 | [Molecular Formula]
C24H28N2O3 | [MDL Number]
MFCD00242741 | [Molecular Weight]
392.49 | [MOL File]
57149-07-2.mol |
| Chemical Properties | Back Directory | [Appearance]
Off-White Solid | [Melting point ]
127 °C | [Boiling point ]
517.2°C (rough estimate) | [density ]
1.1592 (rough estimate) | [refractive index ]
1.6300 (estimate) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
methanol: >10 mg/mL
| [form ]
solid
| [pka]
14.01±0.20(Predicted) | [color ]
white
| [Usage]
A a-1-Adrenergic receptor antagonist, antihypertensive | [Merck ]
6356 | [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 | [SMILES]
C12C=CC=CC1=CC=CC=2OCC(O)CN1CCN(C2C=CC=CC=2OC)CC1 | [CAS DataBase Reference]
57149-07-2(CAS DataBase Reference) |
| Safety Data | Back Directory | [RIDADR ]
3077 | [WGK Germany ]
3
| [RTECS ]
TL9336500
| [HS Code ]
29335990 | [Toxicity]
LD50 in mice, rats (g/kg): 1.3, 6.4 orally (Himmel) |
| Hazard Information | Back Directory | [Description]
Naftopidil was launched in Japan for the treatment of dysuria
associated with benign prostatic hypertrophy (BPH). It can be prepared by a two
step route starting with α-naphthol. Naftopidil is a potent postsynaptic-selective
alpha-l-antagonist with a slightly higher affinity for the human prostatic than for
the aortic alpha-adrenoceptor. It also shows a 5-HT1A agonistic effect, as well
as a weak calcium antagonistic activity, but no alpha-2 or beta-adrenoreceptor
affinity. In experiments with rats or rabbits, Naftopidil was shown to be more
potent and selective for the urodynamic effect than the hypotensive effect.
Aromatic or aliphatic hydroxylation are the major routes of metabolism,
producing metabolites with a profile similar to the parent compound. | [Chemical Properties]
Off-White Solid | [Originator]
Boehringer Mannheim (Germany) | [Uses]
A α-1-Adrenergic receptor antagonist, antihypertensive. | [Uses]
antihypertensive, alpha-blocker, 5HT1a agonist | [Definition]
ChEBI: Naftopidil is a member of piperazines. | [Brand name]
Avishot;Flivas | [Biological Activity]
An α 1 -adrenoceptor antagonist with only weak antagonism at post-junctional α 2 receptors; a potent, persistent antihypertensive and vasodilator. | [Synthesis]
The general procedure for the synthesis of 1-(4-(2-methoxyphenyl)piperazin-1-yl)-3-(naphthalen-1-yloxy)propan-2-ol from 3-(1-naphthyloxy)-1,2-epoxypropane and 1-(2-methoxyphenyl)piperazine was as follows: with reference to the synthesis of Example 1 (RS)-naphthalenophenedil (HUHS1001), to a solution of 2-((1-naphthyloxy)methyl) ethylene oxide (100 mg, 0.50 mmol) to a solution of 2-(2-methoxyphenyl)piperazine (95 μL, 0.60 mmol) in ethanol (1 mL). The reaction mixture was stirred at room temperature for 1 hour. Subsequently, the reaction mixture was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to afford (RS)-naphthodil (199 mg, 100% yield). The structure of the product was confirmed by 1H-NMR (400 MHz, CDCl3) and ESI-HRMS (cation, sodium formate).1H-NMR data were as follows: δ 2.72-2.76 (m, 4H), 2.92-2.95 (m, 2H), 3.09-3.18 (m, 4H), 3.87 (s, 3H), 4.16 (dd, J = 9.6 and 5.0 Hz, 1H), 4.24 (dd, J = 9.6 and 5.0 Hz, 1H), 4.28-4.34 (m, 1H), 6.84 (d, J = 7.8 Hz, 1H), 6.87 (d, J = 7.8 Hz, 1H), 6.91-6.98 (m, 2H), 7.00-7.04 (m, 1H), 7.39 (t , J = 8.2 Hz, 1H), 7.44 (d, J = 8.2 Hz, 1H), 7.47-7.51 (m, 2H), 7.79-7.81 (m, 1H), 8.26-8.29 (m, 1H).ESI-HRMS (cation, sodium formate) Calculated value: C24H29N2O3 ([M + H]+) m/z 393.2173 , measured value 393.2148. | [References]
[1] Patent: US2015/353473, 2015, A1. Location in patent: Paragraph 0179-0181
[2] Patent: JP6041303, 2016, B2. Location in patent: Paragraph 0064-0066
[3] Journal of Organic Chemistry, 2007, vol. 72, # 10, p. 3713 - 3722
[4] Patent: US3997666, 1976, A |
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