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57149-07-2 分子结构
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1-[4-(2-methoxyphenyl)piperazin-1-yl]-3-(naphthalen-1-yloxy)propan-2-ol dihydrochloride

ChemBase编号:72654
分子式:C24H30Cl2N2O3
平均质量:465.4126
单一同位素质量:464.16334819
SMILES和InChIs

SMILES:
c1(c2c(ccc1)cccc2)OCC(CN1CCN(CC1)c1ccccc1OC)O.Cl.Cl
Canonical SMILES:
COc1ccccc1N1CCN(CC1)CC(COc1cccc2c1cccc2)O.Cl.Cl
InChI:
InChI=1S/C24H28N2O3.2ClH/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;2*1H
InChIKey:
HZVCEQMJXMUXJF-UHFFFAOYSA-N

引用这个纪录

CBID:72654 http://www.chembase.cn/molecule-72654.html

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
1-[4-(2-methoxyphenyl)piperazin-1-yl]-3-(naphthalen-1-yloxy)propan-2-ol dihydrochloride
IUPAC传统名
flivas dihydrochloride
别名
Flivas
KT-611
BM-15275
Avishot
Naftopidil Dihydrochloride
CAS号
57149-07-2
57149-08-3
PubChem SID
162037579
PubChem CID
11957660

数据来源

数据来源

所有数据来源 商品来源 非商品来源
数据来源 数据ID
PubChem 11957660 external link

理论计算性质

理论计算性质

JChem
Acid pKa 14.078878  质子受体
质子供体 LogD (pH = 5.5) 1.9296913 
LogD (pH = 7.4) 3.4984076  Log P 3.7739294 
摩尔折射率 115.9648 cm3 极化性 46.108505 Å3
极化表面积 45.17 Å2 可自由旋转的化学键
里宾斯基五规则 true 

分子性质

分子性质

安全信息 药理学性质 产品相关信息 生物活性(PubChem)
保存条件
-20°C expand 查看数据来源
Room Temperature (15-30°C) expand 查看数据来源
RTECS编号
TL9336500 expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
作用靶点
adrenergic receptor expand 查看数据来源
成盐信息
Dihydrochloride expand 查看数据来源
质检报告
下载链接 expand 查看数据来源

详细说明

详细说明

MP Biomedicals MP Biomedicals Selleck Chemicals Selleck Chemicals
MP Biomedicals -  02193688 external link
Dihydrochloride
An α1 -adrenoceptor antagonist.
Selleck Chemicals -  S1387 external link
Research Area
Description Cardiovascular Disease
Biological Activity
Description Naftopidil DiHCl is a selective 5-HT1A and α1-adrenergic receptor antagonist with IC50 of 0.1 μM and 0.2 μM, respectively.
Targets 5-HT1A receptor α1-adrenergic receptor
IC50 0.1 μM 0.2 μM [1]
In Vitro Naftopidil diHCl possesses 5-HT1A agonistic properties in addition to being an α1-adrenoceptor antagonist. [1] Naftopidil has growth inhibitory effect in androgen-sensitive and -insensitive human prostate cancer cell lines. Naftopidil inhibits the growth of androgen-sensitive LNCaP cells and androgen-insensitive PC-3 cells with IC50 of 22.2 μM and 33.2 μM, respectively. Cell growth inhibition by Naftopidil is due to the arrest of the G1 cell cycle. Expressions of p27kip1 and p21cip1 are significantly increased in LNCaP cells treated with Naftopidil. In PC-3 cells, Naftopidil induces p21cip1 but not p27kip1. [2] Naftopidil produces a concentration-dependent inhibition of collagen-induced Ca2+ mobilization, maximum inhibition (22.9%) occurring with 40 μM Naftopidil. The adrenaline-induced rise in [Ca2+]i is inhibited dose dependently by Naftopidil. [3] Naftopidil is significantly more effective than tamsulosin in relieving nocturia. [4] Naftopidil induces G(1) cell-cycle arrest in both PCa cells and PrSC. In Naftopidil-treated PrSC, total interleukin-6 protein is significantly reduced with increased suppression of cell proliferation. [5]
In Vivo Oral administration of Naftopidil to nude mice inhibits the growth of PC-3 tumors as compared to vehicle-treated controls. Naftopidil improves bladder capacity and relaxed voiding via inhibition of afferent nerve activity. [2] Naftopidil (0.1 μg–30 μg) transiently abolishes isovolumetric rhythmic bladder contraction. The amplitude of bladder contraction is decreased by intrathecal injection of naftopidil (3 μg–30 μg). [6] Naftopidil selectively inhibits the phenylephrine-induced increase in prostatic pressure compared with mean blood pressure in the anesthetized dog model. [7]
Clinical Trials
Features Higher selectivity for the -1A and -1D subtypes.
Protocol
Cell Assay [2]
Cell Lines LNCaP and PC-3 cell lines
Concentrations 20 μM, 40 μM
Incubation Time 24 hours
Methods Cell cycle analysis is performed by flow cytometry. Cells are treated with either 20 μM Naftopidil (LNCaP), 40 μM Naftopidil (PC-3) or vehicle (0.1% DMSO) for 24 hours, then trypsinized and washed once with phosphate-buffer saline (PBS), fixed in 70% ethanol and stored at 4 °C for subsequent cell cycle analysis. Fixed cells are washed with PBS and incubated with PBS containing 20 μg/mL RNaseA and 0.3% NP-40 for 30 minutes at 37 °C, then stained with 50 μg/mL propidium iodide (PI) for 30 minutes at 4 °C in the dark. The DNA content of 1 × 106 stained cells is analyzed on a FACS Caliburflow cytometer. The fractions of cells in the G0/G1, S and G2/M phases are calculated using Cell Quest software.
Animal Study [2]
Animal Models Athymic nude mice bearing PC-3 cells
Formulation 0.5% carboxymethylcellulose
Doses 10 mL/kg/day
Administration Orally
References
[1] Borbe HO, et al. Eur J Pharmacol, 1991, 205(1), 105-107.
[2] Kanda H, et al. Int J Cancer, 2008, 122(2), 444-451.
[3] Alarayyed NA, et al. Br J Clin Pharmacol, 1997, 43(4), 415-420.
[4] Nishino Y, et al. BJU Int, 2006, 97(4), 747-751.
[5] Hori Y, et al. Cancer Prev Res (Phila), 2011, 4(1), 87-96.
[6] Sugaya K, et al. Neurosci Lett, 2002, 328(1), 74-76.
[7] Takei R, et al. Jpn J Pharmacol, 1999, 79(4), 447-454.

专利

专利

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