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Naftopidil

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Chemical compound

Pharmaceutical compound

Naftopidil
Clinical data

Trade names	Flivas
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	none
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
IUPAC name 1-[4-(2-methoxyphenyl)piperazin-1-yl]-3-(1-naphthyloxy)propan-2-ol
CAS Number	57149-07-2^Y
PubChemCID	4418
ChemSpider	4265^Y
UNII	R9PHW59SFN
CompTox Dashboard(EPA)	DTXSID5045176
ECHA InfoCard	100.220.557
Chemical and physical data
Formula	C₂₄H₂₈N₂O₃
Molar mass	392.499 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES COC1=CC=CC=C1N2CCN(CC2)CC(COC3=CC=CC4=CC=CC=C43)O
InChI 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^Y Key:HRRBJVNMSRJFHQ-UHFFFAOYSA-N^Y

Naftopidil (INN, marketed under the brand nameFlivas) is a drug used inbenign prostatic hyperplasia which acts as aselective α₁-adrenergic receptor antagonist oralpha-1 blocker.^[1]

The reaction of1-naphthol (1) withepichlorohydrin (2) in the presence of alkali gives theepoxide (3).Alkylation of thepiperazine derivative (4) yields naftopidil.^[2]^[3]^[4]

^Sakai H, Igawa T, Onita T, Furukawa M, Hakariya T, Hayashi M, et al. (January 2011). "[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.PMID 21304253.
^US patent 3997666, Witte EC, Stach K, Thiel M, Sponer G, Roesch E, "1-[3-(Naphth-1-yloxy)-2-hydroxypropvl]-piperazine compounds and therapeutic compositions", issued 1976-12-14, assigned to Boehringer Mannheim GmbH
^Pujala B, Chakraborti AK (May 2007). "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.doi:10.1021/jo062674j.PMID 17411096.
^"Naftopidil".Pharmaceutical Substances. Thieme. Archived fromthe original on 2024-07-08. Retrieved2024-07-12.

Central

α₂-Adrenergic receptor agonists	Clonidine Guanabenz Guanfacine Guanoxabenz Methyldopa^# Tiamenidine^‡
Adrenergic release inhibitors	Bethanidine Bretylium Debrisoquine Guanadrel Guanazodine Guancydine Guanethidine Guanoclor Guanoxan
Imidazoline receptor agonists	Moxonidine Rilmenidine Tolonidine
Ganglion-blocking/nicotinic antagonists	Hexamethonium^‡ Mecamylamine Pentolinium Trimethaphan

Peripheral

Indirect

Monoamine oxidase inhibitors	Pargyline^‡
VMAT inhibitors	Bietaserpine Deserpidine Methoserpidine Reserpine Syrosingopine
Tyrosine hydroxylase inhibitors	Metirosine

Direct

α₁-Adrenergic receptor blockers	Doxazosin Ketanserin Indoramin Prazosin Trimazosin Urapidil
Non-selective α-adrenergic receptor blockers	Phentolamine

Serotonin receptor antagonists	Ketanserin Lidanserin
Endothelin receptor antagonists (for PHTooltip Pulmonary hypertension)	dual (Aprocitentan,Bosentan,Macitentan (+tadalafil),Riociguat) selective (Ambrisentan (+tadalafil),Sitaxentan,Sotatercept)