Chemistry:Niaprazine

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Short description: Chemical compound
Niaprazine
Niaprazine.svg
Clinical data
Trade namesNopron
Other namesCERM-1709
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Oral
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Elimination half-life~4.5 hours
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
Chemical and physical data
FormulaC20H25FN4O
Molar mass356.445 g·mol−1
3D model (JSmol)

Niaprazine (INN) (brand name Nopron) is a sedative-hypnotic drug of the phenylpiperazine group.[1][2] It has been used in the treatment of sleep disturbances since the early 1970s in several European countries including France , Italy, and Luxembourg.[3][4] It is commonly used with children and adolescents on account of its favorable safety and tolerability profile and lack of abuse potential.[5][6][7][8][9][10]

Originally believed to act as an antihistamine and anticholinergic,[11] 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).[12] 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).[12]

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).[13][14] It is unclear what role, if any, pFPP plays in the clinical effects of niaprazine.[12] 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.[13]

References

  1. ↑ The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014. pp. 862–. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA862. 
  2. ↑ Sleep: physiology, investigations, and medicine. New York: Kluwer Academic/Plenum. 2003. ISBN 978-0-306-47406-4. https://books.google.com/books?id=IorPrIY6dOYC&q=niaprazine&pg=PA291. 
  3. ↑ Swiss Pharmaceutical Society (2000). Index Nominum 2000: International Drug Directory (Book with CD-ROM). Boca Raton: Medpharm Scientific Publishers. ISBN 978-3-88763-075-1. https://books.google.com/books?id=5GpcTQD_L2oC&q=niaprazine&pg=PA726. 
  4. ↑ Dictionary of Pharmacological Agents. Boca Raton: Chapman & Hall/CRC. 1996. ISBN 978-0-412-46630-4. https://books.google.com/books?id=A0THacd46ZsC&q=niaprazine&pg=PA1418. 
  5. ↑ "[Niaprazine in behavior disorders in children. Double-blind comparison with placebo]" (in it). La Pediatria Medica e Chirurgica: Medical and Surgical Pediatrics 9 (2): 185–7. 1987. PMID 2958783. 
  6. ↑ "[Niaprazine and side effects in pediatrics. Cooperative evaluation of French centers of pharmacovigilance]" (in fr). Thérapie 43 (4): 307–11. 1988. PMID 2903572. 
  7. ↑ "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 7 (6): 332–5. October 1991. doi:10.1007/bf00304832. PMID 1837245. 
  8. ↑ "Niaprazine vs chlordesmethyldiazepam in sleep disturbances in pediatric outpatients". Pharmacological Research 25 (Suppl 1): 83–4. 1992. doi:10.1016/1043-6618(92)90551-l. PMID 1354861. 
  9. ↑ "Insomnia in children: when are hypnotics indicated?". Paediatric Drugs 4 (6): 391–403. 2002. doi:10.2165/00128072-200204060-00006. PMID 12038875. https://dx.doi.org/10.2165%2F00128072-200204060-00006. 
  10. ↑ "Anxiolytics, hypnotics, and antidepressants dispensed to adolescents in a French region in 2002". Pharmacoepidemiology and Drug Safety 15 (7): 494–503. July 2006. doi:10.1002/pds.1258. PMID 16700077. 
  11. ↑ "[Some pharmacodynamical properties of niaprazine, a new antihistaminic agent]" (in fr). Thérapie 26 (6): 1203–9. 1971. PMID 4401719. 
  12. ↑ 12.0 12.1 12.2 "Molecular pharmacology of niaprazine". Progress in Neuro-psychopharmacology & Biological Psychiatry 12 (6): 989–1001. 1988. doi:10.1016/0278-5846(88)90093-0. PMID 2853885. 
  13. ↑ 13.0 13.1 "The effect of niaprazine on the turnover of 5-hydroxytryptamine in the rat brain". Neuropharmacology 21 (2): 163–9. February 1982. doi:10.1016/0028-3908(82)90157-5. PMID 6460945. 
  14. ↑ "Critical notes on the specificity of drugs in the study of metabolism and functions of brain monoamines". International Review of Neurobiology 29: 259–80. 1988. doi:10.1016/s0074-7742(08)60089-6. ISBN 9780123668295. PMID 3042665. https://books.google.com/books?id=Uf_BWXKXW2cC&q=niaprazine&pg=PA274. 



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