57149-07-2

Basic information

• Product Name: Naftopidil dihydrochloride
• Synonyms: (+-)-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;NAFTOPIDIL DIHYDROCHLORIDE (KT-611) A1 A DRENOCEPTOR ANTAG;NafTopIDi1;Avishot
• CAS NO: 57149-07-2
• Molecular Formula: C₂₄H₂₈N₂O₃
• Molecular Weight: 392.49
• EINECS: 1308068-626-2
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Adrenoceptor;AVISHOT
• Mol File: 57149-07-2.mol
• Article Data: 9

Chemical Properties

• Melting Point: 127 °C
• Boiling Point: 517.2°C (rough estimate)
• Flash Point: 318.3 °C
• Appearance: white/solid
• Density: 1.1592 (rough estimate)
• Vapor Pressure: 2.22E-15mmHg at 25°C
• Refractive Index: 1.6300 (estimate)
• Storage Temp.: Store at RT
• Solubility: methanol: >10 mg/mL
• PKA: 14.01±0.20(Predicted)
• Water Solubility: methanol: >10 mg/mL
• Merck: 14,6356
• CAS DataBase Reference: Naftopidil dihydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Naftopidil dihydrochloride(57149-07-2)
• EPA Substance Registry System: Naftopidil dihydrochloride(57149-07-2)

Safety Data

• RIDADR: 3077
• WGK Germany: 3
• RTECS: TL9336500
• Hazardous Substances Data: 57149-07-2(Hazardous Substances Data)

Usage

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

Uses

Different sources of media describe the Uses of 57149-07-2 differently. You can refer to the following data:
1. Naftopidil is an α-1-adrenergic receptor antagonist. Naftopidil is used as an antihypertensive.
2. A α-1-Adrenergic receptor antagonist, antihypertensive.
3. antihypertensive, alpha-blocker, 5HT1a agonist

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.

InChI:InChI=1/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

Upstream product

• 90-15-3 α-naphthol 
• 1164469-60-6 (2RS)-1-[4-(2-methoxyphenyl)piperazin-1-yl]-3-(naphthalene-1-yloxy)propan-2-ol monohydrochloride 
• 35386-24-4 1-(2-Methoxyphenyl)piperazine 
• 106-89-8 epichlorohydrin 
• 90-04-0 2-methoxy-phenylamine 
• 2461-42-9 3-(1-naphthyloxy)-1,2-epoxypropane 

Downstream Products

• 133347-36-1 O-desmethyl-naftopidil 
• 133024-36-9 (naphthyl)hydroxy-naftopidil 
• 133024-35-8 (phenyl)hydroxy-naftopidil 
• 117067-06-8 3-<4-(2-Methoxyphenyl)piperazinyl>-1,2-propandiol 
• 127931-15-1 (R)-(+)-1-<4-(2-Methoxyphenyl)-1-piperazinyl>-3-(1-naphthyloxy)-2-propanol 
• 127931-16-2 (S)-(-)-1-<4-(2-Methoxyphenyl)-1-piperazinyl>-3-(1-naphthyloxy)-2-propanol 

Relevant articles and documents

NAFTOPIDIL MONOHYDROCHLORIDE DIHYDRATE AND USE THEREOF FOR PREPARATION OF NAFTOPIDIL

PROBLEM TO BE SOLVED: To provide an intermediate that is useful for the preparation of naftopidil (Naftopidil, (2RS)-1-[4-(2-methoxyphenyl)piperazin-1-yl]-3-(naphthalene-1-yloxy)propan-2-ol), and a method for preparing naftopidil using the same. SOLUTION: By freeing naftopidil monohydrochloride dihydrate, naftopidil can be obtained in high yield and high purity. In particular, a purity of 99.99% can be achieved without repeating purification operation such as recrystallization multiple times. SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2021,JPOandINPIT

New anticancer agent

PROBLEM TO BE SOLVED: To provide a compound having excellent anticancer activity equal to or greater than that of naftopidil.SOLUTION: This invention relates to a compound represented by formula (I), where the definition of each symbol is as described in

THERAPY FOR COMPLICATIONS OF DIABETES

A method for enhancing glycemic control and/or insulin sensitivity in a human subject having diabetic nephropathy and/or metabolic syndrome comprises administering to the subject a selective endothelin A (ETA) receptor antagonist in a glycemic control and/or insulin sensitivity enhancing effective amount. A method for treating a complex of comorbidities in an elderly diabetic human subject comprises administering to the subject a selective ETA receptor antagonist in combination or as adjunctive therapy with at least one additional agent that is (i) other than a selective ETA receptor antagonist and (ii) effective in treatment of diabetes and/or at least one of said comorbidities other than hypertension. A therapeutic combination useful in such a method comprises a selective ETA receptor antagonist and at least one antidiabetic, anti-obesity or antidyslipidemic agent other than a selective ETA receptor antagonist.