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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
Vascular alpha1-adrenoceptor subtype selectivity and alpha1-blocker-induced orthostatic hypotension.
1998 May
Direct determination of naftopidil by non-protected fluid room temperature phosphorescence.
2001 Feb
Determination of carvedilol in human cardiac tissue by high-performance liquid chromatography.
2001 Mar
Effects of intrathecal injection of tamsulosin and naftopidil, alpha-1A and -1D adrenergic receptor antagonists, on bladder activity in rats.
2002 Aug 2
Flow injection chemiluminescence determination of naftopidil based on potassium permanganate oxidation in the presence of formaldehyde or formic acid.
2005 Feb
In vivo studies on the effects of alpha1-adrenoceptor antagonists on pupil diameter and urethral tone in rabbits.
2006 Feb
[Clinical application of alpha1 adrenoceptor antagonist Naftopidil to the treatment of chronic non-bacterial prostatitis].
2006 Mar
[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 subtypes and alpha1-adrenoceptor antagonists].
2006 Mar
Emerging drug therapies for benign prostatic hyperplasia.
2006 Mar
Ejaculatory disorder caused by alpha-1 adrenoceptor antagonists is not retrograde ejaculation but a loss of seminal emission.
2006 Oct
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
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
Naftopidil, a selective alpha-1 adrenoceptor antagonist, inhibits growth of human prostate cancer cells by G1 cell cycle arrest.
2008 Jan 15
[Effectiveness and safety of naftopidil for benign prostatic hyperplasia patients with overactive bladder symptoms].
2008 Oct
Usefulness of naftopidil for dysuria in benign prostatic hyperplasia and its optimal dose--comparison between 75 and 50 mg.
2009
[The clinical efficacy and safety of naftopidil 75 mg on benign prostatic hyperplasia patients with moderate or severe urinary disturbance].
2009 Apr
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
1,3-Dioxolane-based ligands as rigid analogues of naftopidil: structure-affinity/activity relationships at alpha1 and 5-HT1A receptors.
2009 Mar
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
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
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
[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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:51:51 UTC 2023
Edited
by admin
on Fri Dec 15 15:51:51 UTC 2023
Record UNII
R9PHW59SFN
Record Status Validated (UNII)
Record Version
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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 Fri Dec 15 15:51:51 UTC 2023 , Edited by admin on Fri Dec 15 15:51:51 UTC 2023
NCI_THESAURUS C1327
Created by admin on Fri Dec 15 15:51:51 UTC 2023 , Edited by admin on Fri Dec 15 15:51:51 UTC 2023
Code System Code Type Description
MERCK INDEX
m7710
Created by admin on Fri Dec 15 15:51:51 UTC 2023 , Edited by admin on Fri Dec 15 15:51:51 UTC 2023
PRIMARY Merck Index
SMS_ID
100000091565
Created by admin on Fri Dec 15 15:51:51 UTC 2023 , Edited by admin on Fri Dec 15 15:51:51 UTC 2023
PRIMARY
EPA CompTox
DTXSID5045176
Created by admin on Fri Dec 15 15:51:51 UTC 2023 , Edited by admin on Fri Dec 15 15:51:51 UTC 2023
PRIMARY
INN
5589
Created by admin on Fri Dec 15 15:51:51 UTC 2023 , Edited by admin on Fri Dec 15 15:51:51 UTC 2023
PRIMARY
MESH
C064357
Created by admin on Fri Dec 15 15:51:51 UTC 2023 , Edited by admin on Fri Dec 15 15:51:51 UTC 2023
PRIMARY
EVMPD
SUB09132MIG
Created by admin on Fri Dec 15 15:51:51 UTC 2023 , Edited by admin on Fri Dec 15 15:51:51 UTC 2023
PRIMARY
DRUG CENTRAL
1873
Created by admin on Fri Dec 15 15:51:51 UTC 2023 , Edited by admin on Fri Dec 15 15:51:51 UTC 2023
PRIMARY
FDA UNII
R9PHW59SFN
Created by admin on Fri Dec 15 15:51:51 UTC 2023 , Edited by admin on Fri Dec 15 15:51:51 UTC 2023
PRIMARY
DRUG BANK
DB12092
Created by admin on Fri Dec 15 15:51:51 UTC 2023 , Edited by admin on Fri Dec 15 15:51:51 UTC 2023
PRIMARY
WIKIPEDIA
NAFTOPIDIL
Created by admin on Fri Dec 15 15:51:51 UTC 2023 , Edited by admin on Fri Dec 15 15:51:51 UTC 2023
PRIMARY
CAS
57149-07-2
Created by admin on Fri Dec 15 15:51:51 UTC 2023 , Edited by admin on Fri Dec 15 15:51:51 UTC 2023
PRIMARY
NCI_THESAURUS
C72927
Created by admin on Fri Dec 15 15:51:51 UTC 2023 , Edited by admin on Fri Dec 15 15:51:51 UTC 2023
PRIMARY
PUBCHEM
4418
Created by admin on Fri Dec 15 15:51:51 UTC 2023 , Edited by admin on Fri Dec 15 15:51:51 UTC 2023
PRIMARY
ChEMBL
CHEMBL142635
Created by admin on Fri Dec 15 15:51:51 UTC 2023 , Edited by admin on Fri Dec 15 15:51:51 UTC 2023
PRIMARY
NSC
759293
Created by admin on Fri Dec 15 15:51:51 UTC 2023 , Edited by admin on Fri Dec 15 15:51:51 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
Ki
Related Record Type Details
ACTIVE MOIETY