133024-36-9

Basic information

• Product Name: (naphthyl)hydroxy-naftopidil
• Synonyms: (naphthyl)hydroxy-naftopidil
• CAS NO: 133024-36-9
• Molecular Formula: C₂₄H₂₈N₂O₄
• Molecular Weight: 408.49012
• Mol File: 133024-36-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 647.6°Cat760mmHg
• Flash Point: 345.4°C
• Appearance: /
• Density: 1.239g/cm³
• Vapor Pressure: 1.18E-17mmHg at 25°C
• Refractive Index: 1.635
• CAS DataBase Reference: (naphthyl)hydroxy-naftopidil(CAS DataBase Reference)
• NIST Chemistry Reference: (naphthyl)hydroxy-naftopidil(133024-36-9)
• EPA Substance Registry System: (naphthyl)hydroxy-naftopidil(133024-36-9)

Safety Data

• Hazardous Substances Data: 133024-36-9(Hazardous Substances Data)

Usage

General Description

(naphthyl)hydroxy-naftopidil is a chemical compound that belongs to the class of naftopidil derivatives, which are primarily used as α1-adrenoceptor antagonists. This specific derivative contains a naphthyl and hydroxy group, and it acts as a selective α1D-adrenoceptor antagonist. It has been studied for its potential therapeutic effects in the treatment of conditions such as benign prostatic hyperplasia and lower urinary tract symptoms. Its mechanism of action involves blocking the α1-adrenoceptors in the smooth muscle of the prostate and bladder neck, leading to relaxation of the muscle and improvement in urinary symptoms. Research on (naphthyl)hydroxy-naftopidil continues to explore its potential in clinical applications.

InChI:InChI=1/C24H28N2O4/c1-29-24-9-5-4-8-21(24)26-14-12-25(13-15-26)16-18(27)17-30-23-11-10-22(28)19-6-2-3-7-20(19)23/h2-11,18,27-28H,12-17H2,1H3

Upstream product

• 57149-07-2 naftopidil 
• 35386-24-4 1-(2-Methoxyphenyl)piperazine 
• 133024-37-0 (+/-)-1-benzyloxy-4-(oxiranylmethoxy)naphthalene 
• 73661-06-0 1-Benzyloxy-4-hydroxynaphthalene 

Relevant articles and documents

Identification of HUHS190, a human naftopidil metabolite, as a novel anti-bladder cancer drug

We carried out structure-activity relationship study on anti-cancer effects of naftopidil (1) and its metabolites, resulted in identification of 1-(4-hydroxy-2-methoxyphenyl)piperazin-1-yl)-3-(naphthalen-1-yloxy) propan-2-ol (2, HUHS190), a major human metabolite of 1, which exhibited the most selective toxicities between against normal and cancer cells (Table 1). 2 was more hydrophilic compared to 1, was enough to be prepared in high concentration solution of more than 100 μM in saline for an intravesical instillation drug. Moreover, serum concentration of 2 was comparable to that of 1, an oral preparation drug, after oral administration at 32 mg/kg (Fig. 3). Both of 1 and 2 showed broad-spectrum anti-cancer activities in vitro, for example, 1 and 2 showed inhibitory activity IC50 = 21.1 μM and 17.2 μM for DU145, human prostate cancer cells, respectively, and IC50 = 18.5 μM and 10.5 μM for T24 cells, human bladder cancer cells. In this study, we estimated anticancer effects of 2 in a bladder cancer model after intravesical administration similar to clinical cases. A single intravesical administration of 2 exhibited the most potent inhibitory activities among the clinical drugs for bladder cancers, BCG and Pirarubicin, without obvious side effects and toxicity (Fig. 4). Thus, HUHS190 (2) can be effective for patients after post-TURBT therapy of bladder cancer without side effects, unlike the currently available clinical drugs.

Piperazine derivatives, uses thereof and pharmaceutical compositions containing them

The present invention provides compounds of the general formula: STR1 wherein R1 is a hydroxyl group or a methoxy radical, R2 is a hydrogen atom or a hyroxyl group and R3 is a hydrogen atom or a hydroxyl group, with the proviso that R2 and R3 are not simultaneously hydrogen atoms when R1 is a methoxy radical; and the pharmacologically acceptable salts thereof. The present invention also provides processes for the preparation of these compounds and pharmaceutical compositions containing them.