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Details

Stereochemistry RACEMIC
Molecular Formula C24H28N2O3.2ClH
Molecular Weight 465.413
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NAFTOPIDIL DIHYDROCHLORIDE

SMILES

Cl.Cl.COC1=C(C=CC=C1)N2CCN(CC(O)COC3=CC=CC4=C3C=CC=C4)CC2

InChI

InChIKey=HZVCEQMJXMUXJF-UHFFFAOYSA-N
InChI=1S/C24H28N2O3.2ClH/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;2*1H

HIDE SMILES / InChI

Description

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 TargetPharmacologyConditionPotency
3.7 nM [Ki]
20.0 nM [Ki]
1.2 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Secondary
Unknown
Primary
Unknown

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
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.