6356. Naftopidil
Nomenclature
CAS number: 57149-07-2
4-(2-Methoxyphenyl)-α-[(1-naphthalenyloxy)methyl]-1-piperazineethanol; RS-1-[4-(2-methoxyphenyl)-1-piperazinyl]-3-(1-naphthoxy)-2-propanol; 1-(2-methoxyphenyl)-4-[3-(naphth-1-yloxy)-2-hydroxypropyl]-piperazine; KT-611; Avishot (Kanebo); Flivas (Asahi). C24H28N2O3; mol wt 392.49.
C 73.44%, H 7.19%, N 7.14%, O 12.23%.
Description and references
α1-Adrenergic blocker and serotonin (5HT1A) receptor agonist. Prepn: E. C. Witte et al., DE 2408804; eidem, US 3997666 (1975, 1976 both to Boehringer Mann.). Clinical pharmacodynamics: R. Kirsten et al., Eur. J. Clin. Pharmacol. 46, 271 (1994). Clinical pharmacokinetics: M. J. G. Farthing et al., Postgrad. Med. J. 70, 363 (1994). HPLC determn in human plasma: G. Niebch et al., J. Chromatogr. 534, 247 (1990). Clinical evaluation in BPH: K. Yasuda et al., Prostate 25, 46 (1994). Review of pharmacology and clinical experience: H. M. Himmel, Cardiovasc. Drug Rev. 12, 32-47 (1994).
Properties
Crystals from isopropanol, mp 125-126°; also reported as colorless crystals, mp 125-129°. Insol in water. Partition coefficient (octanol/water): 75. LD50 in mice, rats (g/kg): 1.3, 6.4 orally (Himmel).Derivative
Dihydrochloride.Nomenclature
CAS number: 57149-08-3
C24H28N2O3.2HCl; mol wt 465.41.
C 61.94%, H 6.50%, N 6.02%, O 10.31%, Cl 15.24%.
Properties
Crystals from methanol/ethanol (1:2), mp 212-213°.Therapeutic Category
Antihypertensive; α-blocker in treatment of symptomatic benign prostate hypertrophy.
Keywords
α-Adrenergic Blocker; Antihypertensive