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Details

Stereochemistry RACEMIC
Molecular Formula C24H28N2O3
Molecular Weight 392.4916
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NAFTOPIDIL

SMILES

COc1ccccc1N2CCN(CC2)CC(COc3cccc4ccccc43)O

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

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
Vascular alpha1-adrenoceptor subtype selectivity and alpha1-blocker-induced orthostatic hypotension.
1998 May
The use of modified simplex method to optimize the room temperature phosphorescence variables in the determination of an antihypertensive drug.
2002 Jun 10
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
Short-term efficacy and long-term compliance/treatment failure of the alpha1 blocker naftopidil for patients with lower urinary tract symptoms suggestive of benign prostatic hyperplasia.
2007
Search for new alpha1a-adrenoceptor-selective antagonist for treating lower urinary tract symptoms associated with benign prostatic hyperplasia.
2007 Apr
Effects of propiverine and naftopidil on the urinary ATP level and bladder activity after bladder stimulation in rats.
2007 Dec 18
Crossover comparison study on the therapeutic effects of tamsulosin hydrochloride and naftopidil in lower urinary tract symptoms associated with benign prostatic hyperplasia.
2007 Feb
[Giant prostate carcinoma treated effectively with endocrine therapy: case report].
2007 Feb
[The effectiveness of naftopidil in patients with benign prostatic hyperplasia evaluated by QOL index].
2007 Jan
Incidence of intraoperative floppy iris syndrome in patients on either systemic or topical alpha(1)-adrenoceptor antagonist.
2007 Jan
[Design, synthesis and vasorelaxant activity of R, S-1-(substituted phenyl)-4-[3-(naphtha-1-yl-oxy)-2-hydroxypropyl]-piperazine derivatives].
2007 Jul
[A comparative study assessing clinical effects of naftopidil and tamsulosin hydrochloride on benign prostatic hyperplasia with overactive bladder].
2007 Jul
[Comparison of different drugs on the treatment of benign prostate hyperplasia].
2007 Jul 15
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
Change of expression levels of alpha1-adrenoceptor subtypes by administration of alpha1d-adrenoceptor-subtype-selective antagonist naftopidil in benign prostate hyperplasia patients.
2007 Sep 1
Differential effects of prazosin and naftopidil on pelvic blood flow and nitric oxide synthase levels in spontaneously hypertensive rats.
2008
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
Alpha antagonists and intraoperative floppy iris syndrome: A spectrum.
2008 Dec
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
In vivo study on the effects of alpha1-adrenoceptor antagonists on intraurethral pressure in the prostatic urethra and intraluminal pressure in the vas deferens in male dogs.
2008 Feb 2
Naftopidil, a selective alpha-1 adrenoceptor antagonist, inhibits growth of human prostate cancer cells by G1 cell cycle arrest.
2008 Jan 15
[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
Effect of naftopidil on nocturia after failure of tamsulosin.
2008 Nov
[Effectiveness and safety of naftopidil for benign prostatic hyperplasia patients with overactive bladder symptoms].
2008 Oct
Alpha-adrenoceptor blockade modifies neurally induced atrial arrhythmias.
2008 Oct
Ejaculatory disorders caused by alpha-1 blockers for patients with lower urinary tract symptoms suggestive of benign prostatic hyperplasia: comparison of naftopidil and tamsulosin in a randomized multicenter study.
2009
Naftopidil and propiverine hydrochloride for treatment of male lower urinary tract symptoms suggestive of benign prostatic hyperplasia and concomitant overactive bladder: a prospective randomized controlled study.
2009
Usefulness of naftopidil for dysuria in benign prostatic hyperplasia and its optimal dose--comparison between 75 and 50 mg.
2009
Role of alpha1-adrenergic receptors in detrusor overactivity induced by cold stress in conscious rats.
2009
Efficacy of selective alpha1D-blocker naftopidil as medical expulsive therapy for distal ureteral stones.
2009 Apr
Mechanical function and gene expression of alpha(1)-adrenoceptor subtypes in dog intravesical ureter.
2009 Aug
Clinical efficacy of naftopidil on lower urinary tract symptoms after radical prostatectomy.
2009 Mar
1,3-Dioxolane-based ligands as rigid analogues of naftopidil: structure-affinity/activity relationships at alpha1 and 5-HT1A receptors.
2009 Mar
Prostate growth inhibition by subtype-selective alpha(1)-adrenoceptor antagonist naftopidil in benign prostatic hyperplasia.
2009 Oct 1
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
[Effects of alpha1 adrenoceptor antagonist, naftopidil, on non-bacterial chronic pelvic pain syndrome in patients with lower urinary tract syndrome: evaluation of its efficacy using NIH-CPSI after 4-week treatment].
2010 Apr
[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
Long-term treatment and prognostic factors of alpha 1-blockers for lower urinary tract symptoms associated with benign prostatic hyperplasia: a pilot study comparing naftopidil and tamsulosin hydrochloride.
2010 Feb
Effects of silodosin and naftopidil on the distal ureter and cardiovascular system in anesthetized dogs: comparison of potential medications for distal ureteral stone passage.
2010 Jan
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
Re: Efficacy of selective alpha1D-blocker naftopidil as medical expulsive therapy for distal ureteral stones. X. Sun, L. He, W. Ge and J. Lv. J Urol 2009; 181: 1716-1720.
2010 Mar
[A randomized controlled study comparing clinical effects of naftopidil and tamsulosin on benign prostatic hyperplasia].
2010 Sep
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.
Name Type Language
NAFTOPIDIL
INN   JAN   MART.   MI   WHO-DD  
INN  
Official Name English
NAFTOPIDIL [WHO-DD]
Common 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
(+/-)-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 Fri Jun 25 21:52:41 UTC 2021 , Edited by admin on Fri Jun 25 21:52:41 UTC 2021
NCI_THESAURUS C1327
Created by admin on Fri Jun 25 21:52:41 UTC 2021 , Edited by admin on Fri Jun 25 21:52:41 UTC 2021
Code System Code Type Description
MERCK INDEX
M7710
Created by admin on Fri Jun 25 21:52:41 UTC 2021 , Edited by admin on Fri Jun 25 21:52:41 UTC 2021
PRIMARY Merck Index
EPA CompTox
57149-07-2
Created by admin on Fri Jun 25 21:52:41 UTC 2021 , Edited by admin on Fri Jun 25 21:52:41 UTC 2021
PRIMARY
INN
5589
Created by admin on Fri Jun 25 21:52:41 UTC 2021 , Edited by admin on Fri Jun 25 21:52:41 UTC 2021
PRIMARY
MESH
C064357
Created by admin on Fri Jun 25 21:52:41 UTC 2021 , Edited by admin on Fri Jun 25 21:52:41 UTC 2021
PRIMARY
EVMPD
SUB09132MIG
Created by admin on Fri Jun 25 21:52:41 UTC 2021 , Edited by admin on Fri Jun 25 21:52:41 UTC 2021
PRIMARY
DRUG CENTRAL
1873
Created by admin on Fri Jun 25 21:52:41 UTC 2021 , Edited by admin on Fri Jun 25 21:52:41 UTC 2021
PRIMARY
FDA UNII
R9PHW59SFN
Created by admin on Fri Jun 25 21:52:41 UTC 2021 , Edited by admin on Fri Jun 25 21:52:41 UTC 2021
PRIMARY
DRUG BANK
DB12092
Created by admin on Fri Jun 25 21:52:41 UTC 2021 , Edited by admin on Fri Jun 25 21:52:41 UTC 2021
PRIMARY
WIKIPEDIA
NAFTOPIDIL
Created by admin on Fri Jun 25 21:52:41 UTC 2021 , Edited by admin on Fri Jun 25 21:52:41 UTC 2021
PRIMARY
CAS
57149-07-2
Created by admin on Fri Jun 25 21:52:41 UTC 2021 , Edited by admin on Fri Jun 25 21:52:41 UTC 2021
PRIMARY
NCI_THESAURUS
C72927
Created by admin on Fri Jun 25 21:52:41 UTC 2021 , Edited by admin on Fri Jun 25 21:52:41 UTC 2021
PRIMARY
PUBCHEM
4418
Created by admin on Fri Jun 25 21:52:41 UTC 2021 , Edited by admin on Fri Jun 25 21:52:41 UTC 2021
PRIMARY
ChEMBL
CHEMBL142635
Created by admin on Fri Jun 25 21:52:41 UTC 2021 , Edited by admin on Fri Jun 25 21:52:41 UTC 2021
PRIMARY