Naftopidil

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 ;
PubChem CID	4418;
ChemSpider	4265 ;
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 ; Key:HRRBJVNMSRJFHQ-UHFFFAOYSA-N ;

Naftopidil (INN, marketed under the brand name Flivas) is a drug used in benign prostatic hyperplasia 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]

References

^ 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 from the original on 2024-07-08. Retrieved 2024-07-12.

[1] 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.

[2] 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

[3] 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.

[4] "Naftopidil". Pharmaceutical Substances. Thieme. Archived from the original on 2024-07-08. Retrieved 2024-07-12.

[1]

[2]

[3]

[4]

Synthesis

See also

References