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=CC=CC=C1N2CCN(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 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
44 μg/L |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
NAFTOPIDIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
179.5 μg/L |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
NAFTOPIDIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
114.3 μg/L |
75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered: |
NAFTOPIDIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
88.9 μg/L |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
NAFTOPIDIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
71.1 μg × h/L |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
NAFTOPIDIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
342.6 μg × h/L |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
NAFTOPIDIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
298.3 μg × h/L |
75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered: |
NAFTOPIDIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
178.7 μg × h/L |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
NAFTOPIDIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
3 h |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
NAFTOPIDIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
10.1 h |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
NAFTOPIDIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
9 h |
75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered: |
NAFTOPIDIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
6.9 h |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
NAFTOPIDIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
3.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8016009/ |
5 mg single, intravenous dose: 5 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
NAFTOPIDIL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
3.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8016009/ |
5 mg single, intravenous dose: 5 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
NAFTOPIDIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
16.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8016009/ |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
NAFTOPIDIL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
5.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8016009/ |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
NAFTOPIDIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
75 mg 1 times / day multiple, oral Studied dose Dose: 75 mg, 1 times / day Route: oral Route: multiple Dose: 75 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: |
Disc. AE: Orthostatic hypotension, Dizziness... AEs leading to discontinuation/dose reduction: Orthostatic hypotension (1 pt) Sources: Dizziness (1 pt) Palpitation (1 pt) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Dizziness | 1 pt Disc. AE |
75 mg 1 times / day multiple, oral Studied dose Dose: 75 mg, 1 times / day Route: oral Route: multiple Dose: 75 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: |
| Orthostatic hypotension | 1 pt Disc. AE |
75 mg 1 times / day multiple, oral Studied dose Dose: 75 mg, 1 times / day Route: oral Route: multiple Dose: 75 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: |
| Palpitation | 1 pt Disc. AE |
75 mg 1 times / day multiple, oral Studied dose Dose: 75 mg, 1 times / day Route: oral Route: multiple Dose: 75 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Functional alpha-1B adrenergic receptors on human epicardial coronary artery endothelial cells. | 2010-12 |
|
| Facilitation of expulsion of ureteral stones by addition of α1-blockers to conservative therapy. | 2010-12 |
|
| [A randomized controlled study comparing clinical effects of naftopidil and tamsulosin on benign prostatic hyperplasia]. | 2010-09 |
|
| Clinical effect of naftopidil on the quality of life of patients with lower urinary tract symptoms suggestive of benign prostatic hyperplasia: a prospective study. | 2010-06 |
|
| [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]. | 2010-04 |
|
| [Efficacy of naftopidil for nocturia and consequent sleep disturbance in patients with benign prostatic hyperplasia]. | 2010-04 |
|
| 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. | 2010-03 |
|
| 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. | 2010-02 |
|
| Effects of silodosin and naftopidil on the distal ureter and cardiovascular system in anesthetized dogs: comparison of potential medications for distal ureteral stone passage. | 2010-01 |
|
| 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 |
|
| Naftopidil for the treatment of lower urinary tract symptoms compatible with benign prostatic hyperplasia. | 2009-10-07 |
|
| Prostate growth inhibition by subtype-selective alpha(1)-adrenoceptor antagonist naftopidil in benign prostatic hyperplasia. | 2009-10-01 |
|
| Mechanical function and gene expression of alpha(1)-adrenoceptor subtypes in dog intravesical ureter. | 2009-08 |
|
| [The clinical efficacy and safety of naftopidil 75 mg on benign prostatic hyperplasia patients with moderate or severe urinary disturbance]. | 2009-04 |
|
| Efficacy of selective alpha1D-blocker naftopidil as medical expulsive therapy for distal ureteral stones. | 2009-04 |
|
| Clinical efficacy of naftopidil on lower urinary tract symptoms after radical prostatectomy. | 2009-03 |
|
| 1,3-Dioxolane-based ligands as rigid analogues of naftopidil: structure-affinity/activity relationships at alpha1 and 5-HT1A receptors. | 2009-03 |
|
| 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 |
|
| Alpha antagonists and intraoperative floppy iris syndrome: A spectrum. | 2008-12 |
|
| 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. | 2008-12 |
|
| Effect of naftopidil on nocturia after failure of tamsulosin. | 2008-11 |
|
| [Effectiveness and safety of naftopidil for benign prostatic hyperplasia patients with overactive bladder symptoms]. | 2008-10 |
|
| Alpha-adrenoceptor blockade modifies neurally induced atrial arrhythmias. | 2008-10 |
|
| Clinical effect of alpha 1D/A adrenoceptor inhibitor naftopidil on benign prostatic hyperplasia: an international prostate symptom score and King's Health Questionnaire assessment. | 2008-08 |
|
| [Evaluation of supplemental administration of Eviprostat in patients with benign prostatic hyperplasia with persistent symptoms following treatment with alpha1-adrenoceptor blocker]. | 2008-05 |
|
| Spontaneous regression of an asymptomatic meningioma associated with discontinuation of progesterone agonist administration. | 2008-05 |
|
| [Clinical evaluation of supplemental administration of flavoxate hydrochloride in benign prostatic hyperplasia patients with nocturia resistant to an alpha1-adrenoceptor blocker]. | 2008-03 |
|
| 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. | 2008-03 |
|
| 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. | 2008-02-02 |
|
| Naftopidil, a selective alpha-1 adrenoceptor antagonist, inhibits growth of human prostate cancer cells by G1 cell cycle arrest. | 2008-01-15 |
|
| Differential effects of prazosin and naftopidil on pelvic blood flow and nitric oxide synthase levels in spontaneously hypertensive rats. | 2008 |
|
| Effects of propiverine and naftopidil on the urinary ATP level and bladder activity after bladder stimulation in rats. | 2007-12-18 |
|
| Change of expression levels of alpha1-adrenoceptor subtypes by administration of alpha1d-adrenoceptor-subtype-selective antagonist naftopidil in benign prostate hyperplasia patients. | 2007-09-01 |
|
| [Comparison of different drugs on the treatment of benign prostate hyperplasia]. | 2007-07-15 |
|
| [Design, synthesis and vasorelaxant activity of R, S-1-(substituted phenyl)-4-[3-(naphtha-1-yl-oxy)-2-hydroxypropyl]-piperazine derivatives]. | 2007-07 |
|
| [A comparative study assessing clinical effects of naftopidil and tamsulosin hydrochloride on benign prostatic hyperplasia with overactive bladder]. | 2007-07 |
|
| Zinc(II) perchlorate hexahydrate catalyzed opening of epoxide ring by amines: applications to synthesis of (RS)/(R)-propranolols and (RS)/(R)/(S)-naftopidils. | 2007-05-11 |
|
| Search for new alpha1a-adrenoceptor-selective antagonist for treating lower urinary tract symptoms associated with benign prostatic hyperplasia. | 2007-04 |
|
| Crossover comparison study on the therapeutic effects of tamsulosin hydrochloride and naftopidil in lower urinary tract symptoms associated with benign prostatic hyperplasia. | 2007-02 |
|
| [Giant prostate carcinoma treated effectively with endocrine therapy: case report]. | 2007-02 |
|
| [The effectiveness of naftopidil in patients with benign prostatic hyperplasia evaluated by QOL index]. | 2007-01 |
|
| Incidence of intraoperative floppy iris syndrome in patients on either systemic or topical alpha(1)-adrenoceptor antagonist. | 2007-01 |
|
| 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 |
|
| Ejaculatory disorder caused by alpha-1 adrenoceptor antagonists is not retrograde ejaculation but a loss of seminal emission. | 2006-10 |
|
| The use of modified simplex method to optimize the room temperature phosphorescence variables in the determination of an antihypertensive drug. | 2002-06-10 |
|
| Vascular alpha1-adrenoceptor subtype selectivity and alpha1-blocker-induced orthostatic hypotension. | 1998-05 |
Patents
Sample Use Guides
50 or 75 mg/day in Japanese men in clinical practice. For men in the US or Europeancountries, 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
by
admin
on
Edited
Mon Mar 31 18:11:18 GMT 2025
by
admin
on
Mon Mar 31 18:11:18 GMT 2025
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| Record UNII |
R9PHW59SFN
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| Record Status |
Validated (UNII)
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| Record Version |
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NCI_THESAURUS |
C29713
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NCI_THESAURUS |
C1327
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TARGET -> INHIBITOR |
Ki
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ACTIVE MOIETY |
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