Naftopidil

An orally administered α₁-adrenergic receptor antagonist used to improve lower urinary tract symptoms associated with benign prostatic hyperplasia (BPH), particularly in Japan and several Asian countries. Naftopidil relaxes smooth muscle in the prostate, bladder neck, and lower urinary tract, reducing urinary outflow resistance and improving voiding symptoms. Its preferential activity at α₁D receptors may also contribute to the improvement of urinary storage symptoms, including urgency and increased frequency

Compound Structure

CAS Number: 57149-07-2

Molecular Mass: 392.5 g/mol

Formula: C24H28N2O3

Smiles: COc1ccccc1N1CCN(CC(O)COc2cccc3ccccc23)CC1

Synonymes:

Bioactivity: α₁-Adrenergic receptor antagonist with preferential affinity for α₁D and α₁A receptor subtypes; urinary tract smooth muscle relaxant

Solubility in Different Solvents

Solvent Temperature [K] Crystal form Solubility [mg/mL] Reference
Acetone 273.15 - 17.54 [111]
Acetone 278.15 - 21.87 [111]
Acetone 283.15 - 26.2 [111]
Acetone 288.15 - 31.33 [111]
Acetone 293.15 - 36.34 [111]
Acetone 298.15 - 41.79 [111]
Acetone 303.15 - 47.52 [111]
Acetone 308.15 - 54.02 [111]
Acetone 313.15 - 61.81 [111]
Acetonitrile 273.15 - 8.677 [111]
Acetonitrile 278.15 - 10.13 [111]
Acetonitrile 283.15 - 11.84 [111]
Acetonitrile 288.15 - 13.7 [111]
Acetonitrile 293.15 - 15.62 [111]
Acetonitrile 298.15 - 18.17 [111]
Acetonitrile 303.15 - 20.68 [111]
Acetonitrile 308.15 - 23.57 [111]
Acetonitrile 313.15 - 27.13 [111]
Dimethyl sulfoxide 293.15 - 160.8 [110]
Dimethyl sulfoxide 298.15 - 183.9 [110]
Dimethyl sulfoxide 303.15 - 208.7 [110]
Dimethyl sulfoxide 308.15 - 236.7 [110]
Dimethyl sulfoxide 313.15 - 266.7 [110]
Dimethyl sulfoxide 318.15 - 300.4 [110]
Dimethyl sulfoxide 323.15 - 337.3 [110]
Dimethyl sulfoxide 328.15 - 378.0 [110]
Ethanol 273.15 - 5.622 [111]
Ethanol 278.15 - 6.537 [111]
Ethanol 283.15 - 7.606 [111]
Ethanol 288.15 - 9.618 [110]
Ethanol 288.15 - 8.872 [111]
Ethanol 293.15 - 11.0 [110]
Ethanol 293.15 - 10.25 [111]
Ethanol 298.15 - 12.71 [110]
Ethanol 298.15 - 11.74 [111]
Ethanol 303.15 - 14.41 [110]
Ethanol 303.15 - 13.17 [111]
Ethanol 308.15 - 16.18 [110]
Ethanol 308.15 - 15.21 [111]
Ethanol 313.15 - 18.25 [110]
Ethanol 313.15 - 17.52 [111]
Ethanol 318.15 - 20.61 [110]
Ethanol 323.15 - 23.17 [110]
Ethanol 328.15 - 25.76 [110]
Ethyl acetate 273.15 - 18.11 [111]
Ethyl acetate 278.15 - 20.69 [111]
Ethyl acetate 283.15 - 23.93 [111]
Ethyl acetate 288.15 - 27.25 [111]
Ethyl acetate 293.15 - 31.04 [111]
Ethyl acetate 298.15 - 35.0 [111]
Ethyl acetate 303.15 - 39.91 [111]
Ethyl acetate 308.15 - 44.63 [111]
Ethyl acetate 313.15 - 49.78 [111]
Isopropanol 288.15 - 3.686 [110]
Isopropanol 293.15 - 4.247 [110]
Isopropanol 298.15 - 4.897 [110]
Isopropanol 303.15 - 5.634 [110]
Isopropanol 308.15 - 6.408 [110]
Isopropanol 313.15 - 7.29 [110]
Isopropanol 318.15 - 8.239 [110]
Isopropanol 323.15 - 9.246 [110]
Isopropanol 328.15 - 10.53 [110]
Methanol 273.15 - 5.56 [111]
Methanol 278.15 - 6.277 [111]
Methanol 283.15 - 7.054 [111]
Methanol 288.15 - 8.018 [111]
Methanol 293.15 - 8.942 [111]
Methanol 298.15 - 10.02 [111]
Methanol 303.15 - 11.27 [111]
Methanol 308.15 - 12.71 [111]
Methanol 313.15 - 14.17 [111]
Toluene 273.15 - 20.26 [111]
Toluene 278.15 - 23.9 [111]
Toluene 283.15 - 27.34 [111]
Toluene 288.15 - 31.7 [111]
Toluene 293.15 - 36.47 [111]
Toluene 298.15 - 41.91 [111]
Toluene 303.15 - 47.85 [111]
Toluene 308.15 - 54.87 [111]
Toluene 313.15 - 62.36 [111]
Water 288.15 - 0.045 [110]
Water 293.15 - 0.05846 [110]
Water 298.15 - 0.0752 [110]
Water 303.15 - 0.096 [110]
Water 308.15 - 0.1224 [110]
Water 313.15 - 0.1525 [110]
Water 318.15 - 0.191 [110]
Water 323.15 - 0.2349 [110]
Water 328.15 - 0.2934 [110]

Molecule 3D descriptors

Descriptor Value
PMI1 1390.1370
PMI2 9223.1039
PMI3 9475.8224
NPR1 0.1467
NPR2 0.9733
RadiusOfGyration 5.0588
InertialShapeFactor 0.0007
Eccentricity 0.9892
Asphericity 0.6284
SpherocityIndex 0.2095
PBF 1.1242