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
| 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 | ( + / - ) |
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 |
|---|---|---|
| [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
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.
| Substance Class |
Chemical
Created
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| Record UNII |
R9PHW59SFN
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Validated (UNII)
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TARGET -> INHIBITOR |
Ki
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ACTIVE MOIETY |
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