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Wikipedia

Niaprazine

January 20, 2023

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]

Niaprazine
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
  • N-{4-[4-(4-fluorophenyl)piperazin- 1-yl]butan- 2-yl}pyridine- 3-carboxamide
CAS Number
  • 27367-90-4
PubChem CID
  • 71919
ChemSpider
  • 64930
UNII
  • R2H3YN6E3L
KEGG
  • D07333
ECHA InfoCard100.044.014
Chemical and physical data
FormulaC20H25FN4O
Molar mass356.445 g·mol−1
3D model (JSmol)
  • Interactive image
  • Fc3ccc(N2CCN(CCC(NC(=O)c1cccnc1)C)CC2)cc3
  • InChI=1S/C20H25FN4O/c1-16(23-20(26)17-3-2-9-22-15-17)8-10-24-11-13-25(14-12-24)19-6-4-18(21)5-7-19/h2-7,9,15-16H,8,10-14H2,1H3,(H,23,26)
  • Key:RSKQGBFMNPDPLR-UHFFFAOYSA-N

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. ^ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 862–. ISBN 978-1-4757-2085-3.
  2. ^ Kent A, Billiard M (2003). Sleep: physiology, investigations, and medicine. New York: Kluwer Academic/Plenum. ISBN 978-0-306-47406-4.
  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.
  4. ^ Triggle DJ (1996). Dictionary of Pharmacological Agents. Boca Raton: Chapman & Hall/CRC. ISBN 978-0-412-46630-4.
  5. ^ Franzoni E, Masoni P, Mambelli M, Marzano P, Donati C (1987). "[Niaprazine in behavior disorders in children. Double-blind comparison with placebo]". La Pediatria Medica e Chirurgica: Medical and Surgical Pediatrics (in Italian). 9 (2): 185–7. PMID 2958783.
  6. ^ Bodiou C, Bavoux F (1988). "[Niaprazine and side effects in pediatrics. Cooperative evaluation of French centers of pharmacovigilance]". Thérapie (in French). 43 (4): 307–11. PMID 2903572.
  7. ^ Ottaviano S, Giannotti F, Cortesi F (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. 7 (6): 332–5. doi:10.1007/bf00304832. PMID 1837245. S2CID 35908448.
  8. ^ Montanari G, Schiaulini P, Covre A, Steffan A, Furlanut M (1992). "Niaprazine vs chlordesmethyldiazepam in sleep disturbances in pediatric outpatients". Pharmacological Research. 25 Suppl 1: 83–4. doi:10.1016/1043-6618(92)90551-l. PMID 1354861.
  9. ^ Younus M, Labellarte MJ (2002). "Insomnia in children: when are hypnotics indicated?". Paediatric Drugs. 4 (6): 391–403. doi:10.2165/00128072-200204060-00006. PMID 12038875. S2CID 33340367.
  10. ^ Mancini J, Thirion X, Masut A, et al. (July 2006). "Anxiolytics, hypnotics, and antidepressants dispensed to adolescents in a French region in 2002". Pharmacoepidemiology and Drug Safety. 15 (7): 494–503. doi:10.1002/pds.1258. PMID 16700077. S2CID 24273650.
  11. ^ Duchene-Marullaz P, Rispat G, Perriere JP, Hache J, Labrid C (1971). "[Some pharmacodynamical properties of niaprazine, a new antihistaminic agent]". Thérapie (in French). 26 (6): 1203–9. PMID 4401719.
  12. ^ a b c Scherman D, Hamon M, Gozlan H, et al. (1988). "Molecular pharmacology of niaprazine". Progress in Neuro-psychopharmacology & Biological Psychiatry. 12 (6): 989–1001. doi:10.1016/0278-5846(88)90093-0. PMID 2853885. S2CID 40566589.
  13. ^ a b Keane PE, Strolin Benedetti M, Dow J (February 1982). "The effect of niaprazine on the turnover of 5-hydroxytryptamine in the rat brain". Neuropharmacology. 21 (2): 163–9. doi:10.1016/0028-3908(82)90157-5. PMID 6460945. S2CID 22310059.
  14. ^ Garattini S, Mennini T (1988). "Critical notes on the specificity of drugs in the study of metabolism and functions of brain monoamines". International Review of Neurobiology. 29: 259–80. doi:10.1016/s0074-7742(08)60089-6. ISBN 9780123668295. PMID 3042665.

January 20, 2023
niaprazine, brand, name, nopron, sedative, hypnotic, drug, phenylpiperazine, group, been, used, treatment, sleep, disturbances, since, early, 1970s, several, european, countries, including, france, italy, luxembourg, commonly, used, with, children, adolescents. 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 NiaprazineClinical dataTrade namesNopronOther namesCERM 1709AHFS Drugs comInternational Drug NamesRoutes ofadministrationOralATC codeN05CM16 WHO Legal statusLegal statusIn general Prescription only Pharmacokinetic dataElimination half life 4 5 hoursIdentifiersIUPAC name N 4 4 4 fluorophenyl piperazin 1 yl butan 2 yl pyridine 3 carboxamideCAS Number27367 90 4PubChem CID71919ChemSpider64930UNIIR2H3YN6E3LKEGGD07333ECHA InfoCard100 044 014Chemical and physical dataFormulaC 20H 25F N 4OMolar mass356 445 g mol 13D model JSmol Interactive imageSMILES Fc3ccc N2CCN CCC NC O c1cccnc1 C CC2 cc3InChI InChI 1S C20H25FN4O c1 16 23 20 26 17 3 2 9 22 15 17 8 10 24 11 13 25 14 12 24 19 6 4 18 21 5 7 19 h2 7 9 15 16H 8 10 14H2 1H3 H 23 26 Key RSKQGBFMNPDPLR UHFFFAOYSA NOriginally 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 gt 1 mM and was instead found to act as a potent and selective 5 HT2A and a1 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 b adrenergic as well as at SERT and VMAT Ki all gt 1 mM but it does have some affinity for the a2 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 Edit Elks J 14 November 2014 The Dictionary of Drugs Chemical Data Chemical Data Structures and Bibliographies Springer pp 862 ISBN 978 1 4757 2085 3 Kent A Billiard M 2003 Sleep physiology investigations and medicine New York Kluwer Academic Plenum ISBN 978 0 306 47406 4 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 Triggle DJ 1996 Dictionary of Pharmacological Agents Boca Raton Chapman amp Hall CRC ISBN 978 0 412 46630 4 Franzoni E Masoni P Mambelli M Marzano P Donati C 1987 Niaprazine in behavior disorders in children Double blind comparison with placebo La Pediatria Medica e Chirurgica Medical and Surgical Pediatrics in Italian 9 2 185 7 PMID 2958783 Bodiou C Bavoux F 1988 Niaprazine and side effects in pediatrics Cooperative evaluation of French centers of pharmacovigilance Therapie in French 43 4 307 11 PMID 2903572 Ottaviano S Giannotti F Cortesi F 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 7 6 332 5 doi 10 1007 bf00304832 PMID 1837245 S2CID 35908448 Montanari G Schiaulini P Covre A Steffan A Furlanut M 1992 Niaprazine vs chlordesmethyldiazepam in sleep disturbances in pediatric outpatients Pharmacological Research 25 Suppl 1 83 4 doi 10 1016 1043 6618 92 90551 l PMID 1354861 Younus M Labellarte MJ 2002 Insomnia in children when are hypnotics indicated Paediatric Drugs 4 6 391 403 doi 10 2165 00128072 200204060 00006 PMID 12038875 S2CID 33340367 Mancini J Thirion X Masut A et al July 2006 Anxiolytics hypnotics and antidepressants dispensed to adolescents in a French region in 2002 Pharmacoepidemiology and Drug Safety 15 7 494 503 doi 10 1002 pds 1258 PMID 16700077 S2CID 24273650 Duchene Marullaz P Rispat G Perriere JP Hache J Labrid C 1971 Some pharmacodynamical properties of niaprazine a new antihistaminic agent Therapie in French 26 6 1203 9 PMID 4401719 a b c Scherman D Hamon M Gozlan H et al 1988 Molecular pharmacology of niaprazine Progress in Neuro psychopharmacology amp Biological Psychiatry 12 6 989 1001 doi 10 1016 0278 5846 88 90093 0 PMID 2853885 S2CID 40566589 a b Keane PE Strolin Benedetti M Dow J February 1982 The effect of niaprazine on the turnover of 5 hydroxytryptamine in the rat brain Neuropharmacology 21 2 163 9 doi 10 1016 0028 3908 82 90157 5 PMID 6460945 S2CID 22310059 Garattini S Mennini T 1988 Critical notes on the specificity of drugs in the study of metabolism and functions of brain monoamines International Review of Neurobiology 29 259 80 doi 10 1016 s0074 7742 08 60089 6 ISBN 9780123668295 PMID 3042665 Retrieved from https en wikipedia org w index php title Niaprazine amp oldid 1105337410, wikipedia, wiki, book, 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