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Details

Stereochemistry RACEMIC
Molecular Formula C24H28N2O3
Molecular Weight 392.4907
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NAFTOPIDIL

SMILES

COC1=C(C=CC=C1)N2CCN(CC(O)COC3=CC=CC4=C3C=CC=C4)CC2

InChI

InChIKey=HRRBJVNMSRJFHQ-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C24H28N2O3
Molecular Weight 392.4907
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment: description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/23554846 http://www.ncbi.nlm.nih.gov/pubmed/19233432

Naftopidil (INN, marketed under the brand name Flivas) is a drug used in benign prostatic hypertrophy which acts as a selective alpha1-adrenergic receptor antagonist, has been used for the treatment of benign prostatic obstruction and benign prostatic hyperplasia (BPH) associated lower urinary tract symptoms (LUTS). The Japanese Ministry of Health, Labor and Welfare approved naftopidil for treating men with BPH in 1996. Although well-designed, randomized studies are warranted to confirm the long-term outcomes and effector/target of naftopidil, the α1A-antagonist naftopidil, which also blocks α1D-adrenoceptor, improves voiding symptoms, and may also be useful for the management of men with storage symptoms represented by nocturia, retrieving their quality of life impaired by BPH-associated LUTS. The selective alpha1D-blocker naftopidil can significantly facilitate spontaneous passage of distal ureteral stones with few side effects, providing a new choice for medical expulsive therapy.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P35348|||B0ZBD9|||Q6RUJ8
Gene ID: 148.0
Gene Symbol: ADRA1A
Target Organism: Homo sapiens (Human)
3.7 nM [Ki]
Target ID: P35368
Gene ID: 147.0
Gene Symbol: ADRA1B
Target Organism: Homo sapiens (Human)
20.0 nM [Ki]
Target ID: P25100
Gene ID: 146.0
Gene Symbol: ADRA1D
Target Organism: Homo sapiens (Human)
1.2 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Secondary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
[The clinical efficacy of Naftopidil tablet in the treatment of benign prostatic hyperplasia].
2002
Differential actions of naftopidil, doxazosin and nifedipine on platelet thromboxane generation and platelet-derived growth factor efflux in vitro.
2002 Aug-Sep
alpha-Adrenoceptor antagonists in the treatment of benign prostate hyperplasia.
2002 Jul
Effects of intrathecal injection of tamsulosin and naftopidil, alpha-1A and 1D adrenergic receptor antagonists, on bladder activity in rats.
2003 Apr
Single-blind, randomized controlled study of the clinical and urodynamic effects of an alpha-blocker (naftopidil) and phytotherapy (eviprostat) in the treatment of benign prostatic hyperplasia.
2005 Sep
Improvement of bladder storage function by alpha1-blocker depends on the suppression of C-fiber afferent activity in rats.
2006
Comparison of two alpha1-adrenoceptor antagonists, naftopidil and tamsulosin hydrochloride, in the treatment of lower urinary tract symptoms with benign prostatic hyperplasia: a randomized crossover study.
2006 Apr
[The study of the in vivo-in vitro correlation of the naftopidil sustained-release tablet in dog].
2006 Aug
[Effects of silodosin (KMD-3213) on phenylephrine-induced increase in intraurethral pressure and blood pressure in rats--study of the selectivity for lower urinary tract].
2006 Mar
[Alpha1-adrenoceptor subtype selectivity and organ specificity of silodosin (KMD-3213)].
2006 Mar
[Latest frontiers in pharmacotherapy for benign prostatic hyperplasia].
2006 Mar
[Alpha1-adrenoceptor subtypes and alpha1-adrenoceptor antagonists].
2006 Mar
Ejaculatory disorder caused by alpha-1 adrenoceptor antagonists is not retrograde ejaculation but a loss of seminal emission.
2006 Oct
Naftopidil monotherapy vs naftopidil and an anticholinergic agent combined therapy for storage symptoms associated with benign prostatic hyperplasia: A prospective randomized controlled study.
2006 Oct
Search for new alpha1a-adrenoceptor-selective antagonist for treating lower urinary tract symptoms associated with benign prostatic hyperplasia.
2007 Apr
Crossover comparison study on the therapeutic effects of tamsulosin hydrochloride and naftopidil in lower urinary tract symptoms associated with benign prostatic hyperplasia.
2007 Feb
Zinc(II) perchlorate hexahydrate catalyzed opening of epoxide ring by amines: applications to synthesis of (RS)/(R)-propranolols and (RS)/(R)/(S)-naftopidils.
2007 May 11
Clinical effect of alpha 1D/A adrenoceptor inhibitor naftopidil on benign prostatic hyperplasia: an international prostate symptom score and King's Health Questionnaire assessment.
2008 Aug
Naftopidil versus tamsulosin hydrochloride for lower urinary tract symptoms associated with benign prostatic hyperplasia with special reference to the storage symptom: a prospective randomized controlled study.
2008 Dec
[Clinical evaluation of supplemental administration of flavoxate hydrochloride in benign prostatic hyperplasia patients with nocturia resistant to an alpha1-adrenoceptor blocker].
2008 Mar
Expression of alpha1-adrenoceptor subtype mRNA as a predictor of the efficacy of subtype selective alpha1-adrenoceptor antagonists in the management of benign prostatic hyperplasia.
2008 Mar
[Evaluation of supplemental administration of Eviprostat in patients with benign prostatic hyperplasia with persistent symptoms following treatment with alpha1-adrenoceptor blocker].
2008 May
Spontaneous regression of an asymptomatic meningioma associated with discontinuation of progesterone agonist administration.
2008 May
[Effectiveness and safety of naftopidil for benign prostatic hyperplasia patients with overactive bladder symptoms].
2008 Oct
1,3-Dioxolane-based ligands as rigid analogues of naftopidil: structure-affinity/activity relationships at alpha1 and 5-HT1A receptors.
2009 Mar
Naftopidil for the treatment of lower urinary tract symptoms compatible with benign prostatic hyperplasia.
2009 Oct 7
The add-on effect of solifenacin for patients with remaining overactive bladder after treatment with tamsulosin for lower urinary tract symptoms suggestive of benign prostatic obstruction.
2010
A prospective, randomized, controlled, multicenter study of naftopidil for treatment of male lower urinary tract symptoms associated with benign prostatic hyperplasia: 75 mg once daily in the evening compared to 25 mg thrice daily.
2010
[Efficacy of naftopidil for nocturia and consequent sleep disturbance in patients with benign prostatic hyperplasia].
2010 Apr
Functional alpha-1B adrenergic receptors on human epicardial coronary artery endothelial cells.
2010 Dec
Facilitation of expulsion of ureteral stones by addition of α1-blockers to conservative therapy.
2010 Dec
Clinical effect of naftopidil on the quality of life of patients with lower urinary tract symptoms suggestive of benign prostatic hyperplasia: a prospective study.
2010 Jun
Patents

Patents

Sample Use Guides

50 or 75 mg/day in Japanese men in clinical practice. For men in the US or European countries, the optimal dose is estimated to be higher
Route of Administration: Oral
In Vitro Use Guide
Naftopidil has growth inhibitory effect in androgen-sensitive and -insensitive human prostate cancer cell lines. The concentrations causing 50% inhibition (IC50) of cancer cell growth were 22.2 +/- 4.0 microM in androgen-sensitive LNCaP cells and 33.2 +/- 1.1 microM in androgen-insensitive PC-3 cells.
Substance Class Chemical
Created
by admin
on Wed Jul 05 23:20:14 UTC 2023
Edited
by admin
on Wed Jul 05 23:20:14 UTC 2023
Record UNII
R9PHW59SFN
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NAFTOPIDIL
INN   JAN   MART.   MI   WHO-DD  
INN  
Official Name English
naftopidil [INN]
Common Name English
FLIVAS
Brand Name English
NSC-759293
Code English
NAFTOPIDIL [MART.]
Common Name English
NAFTOPIDIL [JAN]
Common Name English
Naftopidil [WHO-DD]
Common Name English
(±)-4-(O-METHOXYPHENYL)-.ALPHA.-((1-NAPHTHYLOXY)METHYL)-1-PIPERAZINEETHANOL
Common Name English
NAFTOPIDIL [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29713
Created by admin on Wed Jul 05 23:20:14 UTC 2023 , Edited by admin on Wed Jul 05 23:20:14 UTC 2023
NCI_THESAURUS C1327
Created by admin on Wed Jul 05 23:20:14 UTC 2023 , Edited by admin on Wed Jul 05 23:20:14 UTC 2023
Code System Code Type Description
MERCK INDEX
M7710
Created by admin on Wed Jul 05 23:20:14 UTC 2023 , Edited by admin on Wed Jul 05 23:20:14 UTC 2023
PRIMARY Merck Index
SMS_ID
100000091565
Created by admin on Wed Jul 05 23:20:14 UTC 2023 , Edited by admin on Wed Jul 05 23:20:14 UTC 2023
PRIMARY
EPA CompTox
DTXSID5045176
Created by admin on Wed Jul 05 23:20:14 UTC 2023 , Edited by admin on Wed Jul 05 23:20:14 UTC 2023
PRIMARY
INN
5589
Created by admin on Wed Jul 05 23:20:14 UTC 2023 , Edited by admin on Wed Jul 05 23:20:14 UTC 2023
PRIMARY
MESH
C064357
Created by admin on Wed Jul 05 23:20:14 UTC 2023 , Edited by admin on Wed Jul 05 23:20:14 UTC 2023
PRIMARY
EVMPD
SUB09132MIG
Created by admin on Wed Jul 05 23:20:14 UTC 2023 , Edited by admin on Wed Jul 05 23:20:14 UTC 2023
PRIMARY
DRUG CENTRAL
1873
Created by admin on Wed Jul 05 23:20:14 UTC 2023 , Edited by admin on Wed Jul 05 23:20:14 UTC 2023
PRIMARY
FDA UNII
R9PHW59SFN
Created by admin on Wed Jul 05 23:20:14 UTC 2023 , Edited by admin on Wed Jul 05 23:20:14 UTC 2023
PRIMARY
DRUG BANK
DB12092
Created by admin on Wed Jul 05 23:20:14 UTC 2023 , Edited by admin on Wed Jul 05 23:20:14 UTC 2023
PRIMARY
WIKIPEDIA
NAFTOPIDIL
Created by admin on Wed Jul 05 23:20:14 UTC 2023 , Edited by admin on Wed Jul 05 23:20:14 UTC 2023
PRIMARY
CAS
57149-07-2
Created by admin on Wed Jul 05 23:20:14 UTC 2023 , Edited by admin on Wed Jul 05 23:20:14 UTC 2023
PRIMARY
NCI_THESAURUS
C72927
Created by admin on Wed Jul 05 23:20:14 UTC 2023 , Edited by admin on Wed Jul 05 23:20:14 UTC 2023
PRIMARY
PUBCHEM
4418
Created by admin on Wed Jul 05 23:20:14 UTC 2023 , Edited by admin on Wed Jul 05 23:20:14 UTC 2023
PRIMARY
ChEMBL
CHEMBL142635
Created by admin on Wed Jul 05 23:20:14 UTC 2023 , Edited by admin on Wed Jul 05 23:20:14 UTC 2023
PRIMARY
NSC
759293
Created by admin on Wed Jul 05 23:20:14 UTC 2023 , Edited by admin on Wed Jul 05 23:20:14 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
Ki
Related Record Type Details
ACTIVE MOIETY