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Naftopidil

From Wikipedia, the free encyclopedia

Naftopidil
Clinical data
Trade namesFlivas
AHFS/Drugs.comInternational Drug Names
Routes of
administration
Oral
ATC code
  • none
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
  • 1-[4-(2-methoxyphenyl)piperazin-1-yl]-3-(1-naphthyloxy)propan-2-ol
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.220.557 Edit this at Wikidata
Chemical and physical data
FormulaC24H28N2O3
Molar mass392.499 g·mol−1
3D model (JSmol)
  • COC1=CC=CC=C1N2CCN(CC2)CC(COC3=CC=CC4=CC=CC=C43)O
  • 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 checkY
  • Key:HRRBJVNMSRJFHQ-UHFFFAOYSA-N checkY

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

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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

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References

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  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. Retrieved 2024-07-12.