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 ;
	(verify)

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

Thieme ChemDrug Synthesis:^[2] Patent:^[3] ~94%:^[4]

The reaction of 1-Naphthol [90-15-3] (1) with Epichlorohydrin [106-89-8] (2) in the presence of alkali led to 2-[(1-Naphthyloxy)Methyl]Oxirane [2461-42-9] (3). Further addition of 1-(2-Methoxyphenyl)Piperazine [35386-24-4] (4) completed the synthesis of naftopidil (5).

References

^ 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 (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. 57 (1): 7–13. PMID 21304253.
^ Prous, J., Castañer, J. (1987). "Naftopidil". Drugs of the Future. 12 (1): 31. doi:10.1358/dof.1987.012.01.51182.
^ Ernst-Christian Witte, Kurt Stach, Max Thiel, Gisbert Sponer, Egon Roesch, U.S. patent 3,997,666 (1976 to Boehringer Mannheim G.M.B.H.); CA, 83, 179122e
^ Shivani, 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. J Org Chem. 2007 May 11;72(10):3713-22. doi: 10.1021/jo062674j. Epub 2007 Apr 6. PMID: 17411096.

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[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 (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. 57 (1): 7–13. PMID 21304253.

[2] Prous, J., Castañer, J. (1987). "Naftopidil". Drugs of the Future. 12 (1): 31. doi:10.1358/dof.1987.012.01.51182.

[3] Ernst-Christian Witte, Kurt Stach, Max Thiel, Gisbert Sponer, Egon Roesch, U.S. patent 3,997,666 (1976 to Boehringer Mannheim G.M.B.H.); CA, 83, 179122e

[4] Shivani, 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. J Org Chem. 2007 May 11;72(10):3713-22. doi: 10.1021/jo062674j. Epub 2007 Apr 6. PMID: 17411096.

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[2]

[3]

[4]

Naftopidil

Synthesis

See also

References