Naftopidil Explained

Naftopidil (INN, marketed under the brand name Flivas) is a drug used in benign prostatic hypertrophy which acts as a selective α₁-adrenergic receptor antagonist or alpha-1 blocker.^[1]

Synthesis

The reaction of 1-naphthol (1) with epichlorohydrin (2) in the presence of alkali gives the epoxide (3). Alkylation of the piperazine derivative (4) yields naftopidil.^{[2] [3] [4]}

See also

• Urapidil

Notes and References

1. Sakai H, Igawa T, Onita T, Furukawa M, Hakariya T, Hayashi M, Matsuya F, Shida Y, Nishimura N, Yogi Y, Tsurusaki T, Takehara K, Nomata K, Shiraishi K, Shono T, Aoki D, Kanetake H . [Efficacy of naftopidil in patients with overactive bladder associated with benign prostatic hyperplasia: prospective randomized controlled study to compare differences in efficacy between morning and evening medication] . Hinyokika Kiyo. Acta Urologica Japonica . 57 . 1 . 7–13 . January 2011 . 21304253 .
2. US . 3997666 . Witte EC, Stach K, Thiel M, Sponer G, Roesch E. 1-[3-(Naphth-1-yloxy)-2-hydroxypropvl]-piperazine compounds and therapeutic compositions ]. patent . 1976-12-14 . 1975-01-28 . Boehringer Mannheim GmbH .
3. Pujala B, Chakraborti AK . Zinc(II) perchlorate hexahydrate catalyzed opening of epoxide ring by amines: applications to synthesis of (RS)/(R)-propranolols and (RS)/(R)/(S)-naftopidils . The Journal of Organic Chemistry . 72 . 10 . 3713–3722 . May 2007 . 17411096 . 10.1021/jo062674j .
4. Web site: Naftopidil . Pharmaceutical Substances . Thieme . 2024-07-12.