Surf Wiki
Save to docs
general/alpha-1-blockers

From Surf Wiki (app.surf) — the open knowledge base

Niaprazine

Sedative-hypnotic medication

Sedative-hypnotic medication

| Drugs.com =

| elimination_half-life = ~4.5 hours

Niaprazine (INN; brand name Nopron) is a sedative-hypnotic drug of the phenylpiperazine group. It has been used in the treatment of sleep disturbances since the early 1970s in several European countries including France, Italy, and Luxembourg. It is commonly used with children and adolescents on account of its favorable safety and tolerability profile and lack of abuse potential.

Originally believed to act as an antihistamine and anticholinergic, niaprazine was later discovered to have low or no binding affinity for the H1 and mACh receptors (Ki = 1 μM), and was instead found to act as a potent and selective 5-HT2A and α1-adrenergic receptor antagonist (Ki = 75 nM and 86 nM, respectively). It possesses low or no affinity for the 5-HT1A, 5-HT2B, D2, and β-adrenergic, as well as at SERT and VMAT (Ki = all 1 μM), but it does have some affinity for the α2-adrenergic receptor (Ki = 730 nM).

Niaprazine has been shown to metabolize to the compound para-fluorophenylpiperazine (pFPP) in a similar manner to how trazodone and nefazodone metabolize to meta-chlorophenylpiperazine (mCPP). It is unclear what role, if any, pFPP plays in the clinical effects of niaprazine. However, from animal studies it is known that pFPP, unlike niaprazine, does not produce sedative effects, and instead exerts a behavioral profile indicative of serotonergic activation.

Synthesis

:[[File:Niaprazine synthesis.svg|upright=2|class=skin-invert-image]]

A Mannich reaction using 4-fluorophenylpiperazine (1), 1,3,5-trioxane (2) and acetone gives the ketone (4). Reaction with hydroxylamine produces the oxime, (5), which is reduced with lithium aluminium hydride to give the amine (6). Amide formation with nicotinic acid (7), activated as its acid chloride, yields nilaprazine.

References

References

  1. (14 November 2014). "The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies". Springer.
  2. (2003). "Sleep: physiology, investigations, and medicine". Kluwer Academic/Plenum.
  3. Swiss Pharmaceutical Society. (2000). "Index Nominum 2000: International Drug Directory (Book with CD-ROM)". Medpharm Scientific Publishers.
  4. (1996). "Dictionary of Pharmacological Agents". Chapman & Hall/CRC.
  5. (1987). "[Niaprazine in behavior disorders in children. Double-blind comparison with placebo]". La Pediatria Medica e Chirurgica: Medical and Surgical Pediatrics.
  6. (1988). "[Niaprazine and side effects in pediatrics. Cooperative evaluation of French centers of pharmacovigilance]". Thérapie.
  7. (October 1991). "The effect of niaprazine on some common sleep disorders in children. A double-blind clinical trial by means of continuous home-videorecorded sleep". Child's Nervous System.
  8. (1992). "Niaprazine vs chlordesmethyldiazepam in sleep disturbances in pediatric outpatients". Pharmacological Research.
  9. (2002). "Insomnia in children: when are hypnotics indicated?". Paediatric Drugs.
  10. (July 2006). "Anxiolytics, hypnotics, and antidepressants dispensed to adolescents in a French region in 2002". Pharmacoepidemiology and Drug Safety.
  11. (1971). "[Some pharmacodynamical properties of niaprazine, a new antihistaminic agent]". Thérapie.
  12. (1988). "Molecular pharmacology of niaprazine". Progress in Neuro-psychopharmacology & Biological Psychiatry.
  13. (February 1982). "The effect of niaprazine on the turnover of 5-hydroxytryptamine in the rat brain". Neuropharmacology.
  14. (1988). "Critical Notes on the Specificity of Drugs in the Study of Metabolism and Functions of Brain Monoamines".
  15. "Butyl-piperazine derivatives".
  16. "Niaprazine". Thieme.
Info: Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

alpha-1-blockers alpha-2-blockers 4-fluorophenyl-compounds hypnotics nicotinamides phenylpiperazines sedatives
Want to explore this topic further?

Ask Mako anything about Niaprazine — get instant answers, deeper analysis, and related topics.

Research with Mako

Free with your Surf account

Content sourced from Wikipedia, available under CC BY-SA 4.0.

This content may have been generated or modified by AI. CloudSurf Software LLC is not responsible for the accuracy, completeness, or reliability of AI-generated content. Always verify important information from primary sources.

Report