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
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
DescriptionCurator'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
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.
CNS Activity
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
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
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Secondary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Vascular alpha1-adrenoceptor subtype selectivity and alpha1-blocker-induced orthostatic hypotension. | 1998 May |
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| The use of modified simplex method to optimize the room temperature phosphorescence variables in the determination of an antihypertensive drug. | 2002 Jun 10 |
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| Ejaculatory disorder caused by alpha-1 adrenoceptor antagonists is not retrograde ejaculation but a loss of seminal emission. | 2006 Oct |
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| 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 |
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| Search for new alpha1a-adrenoceptor-selective antagonist for treating lower urinary tract symptoms associated with benign prostatic hyperplasia. | 2007 Apr |
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| Effects of propiverine and naftopidil on the urinary ATP level and bladder activity after bladder stimulation in rats. | 2007 Dec 18 |
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| Crossover comparison study on the therapeutic effects of tamsulosin hydrochloride and naftopidil in lower urinary tract symptoms associated with benign prostatic hyperplasia. | 2007 Feb |
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| [Giant prostate carcinoma treated effectively with endocrine therapy: case report]. | 2007 Feb |
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| [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 |
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| [Comparison of different drugs on the treatment of benign prostate hyperplasia]. | 2007 Jul 15 |
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| 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 |
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| 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 |
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| 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 |
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| 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 |
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| 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 |
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| Spontaneous regression of an asymptomatic meningioma associated with discontinuation of progesterone agonist administration. | 2008 May |
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| Effect of naftopidil on nocturia after failure of tamsulosin. | 2008 Nov |
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| [Effectiveness and safety of naftopidil for benign prostatic hyperplasia patients with overactive bladder symptoms]. | 2008 Oct |
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| Alpha-adrenoceptor blockade modifies neurally induced atrial arrhythmias. | 2008 Oct |
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| 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 |
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| 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 |
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| [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 |
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| Clinical efficacy of naftopidil on lower urinary tract symptoms after radical prostatectomy. | 2009 Mar |
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| 1,3-Dioxolane-based ligands as rigid analogues of naftopidil: structure-affinity/activity relationships at alpha1 and 5-HT1A receptors. | 2009 Mar |
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| Prostate growth inhibition by subtype-selective alpha(1)-adrenoceptor antagonist naftopidil in benign prostatic hyperplasia. | 2009 Oct 1 |
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| Naftopidil for the treatment of lower urinary tract symptoms compatible with benign prostatic hyperplasia. | 2009 Oct 7 |
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| 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 |
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| 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 |
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| 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
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
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.
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NCI_THESAURUS |
C29713
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C1327
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m7710
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100000091565
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NAFTOPIDIL
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ACTIVE MOIETY
