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{{ | {{Drugbox | ||
| IUPAC_name | | IUPAC_name = ''N''-{4-[4-(4-fluorophenyl)piperazin- 1-yl]butan- 2-yl}pyridine- 3-carboxamide | ||
| image | | image = Niaprazine.png | ||
<!--Clinical data--> | |||
| tradename = | |||
| Drugs.com = {{drugs.com|international|niaprazine}} | |||
| pregnancy_category = | |||
| legal_status = Rx-only | |||
| | |||
| | |||
| | |||
| | |||
| | |||
| | |||
| routes_of_administration = Oral | | routes_of_administration = Oral | ||
<!--Pharmacokinetic data--> | |||
| metabolism = | |||
| elimination_half-life = ~4.5 hours | |||
| excretion = | |||
<!--Identifiers--> | |||
| CAS_number = 27367-90-4 | |||
| ATC_prefix = N05 | |||
| ATC_suffix = CM16 | |||
| PubChem = 71919 | |||
| ChemSpiderID = 64930 | |||
| UNII_Ref = {{fdacite|correct|FDA}} | |||
| UNII = R2H3YN6E3L | |||
| KEGG = D07333 | |||
<!--Chemical data--> | |||
| C=20 | H=25 | F=1 | N=4 | O=1 | |||
| molecular_weight = 356.437 g/mol | |||
| smiles = Fc3ccc(N2CCN(CCC(NC(=O)c1cccnc1)C)CC2)cc3 | |||
}} | }} | ||
__NOTOC__ | |||
{{SI}} | |||
{{CMG}} | |||
==Overview== | |||
'''Niaprazine''' ('''Nopron''') is a [[sedative]]-[[hypnotic]] [[drug]] of the [[phenylpiperazine]] class.<ref name="isbn0-306-47406-9">{{cite book | author = Kent, Angela; M. Billiard | title = Sleep: physiology, investigations, and medicine | publisher = Kluwer Academic/Plenum | location = New York | year = 2003 | pages = | isbn = 0-306-47406-9 | oclc = | doi = | url = http://books.google.com/?id=IorPrIY6dOYC&lpg=PA291&vq=niaprazine&pg=PA291#v=onepage&q}}</ref> It has been used in the treatment of [[sleep disorder|sleep disturbance]]s since the early 1970s in several [[Europe]]an countries, including [[France]], [[Italy]], and [[Luxembourg]].<ref name="isbn3-88763-075-0">{{cite book | author = Swiss Pharmaceutical Society | title = Index Nominum 2000: International Drug Directory (Book with CD-ROM) | publisher = Medpharm Scientific Publishers | location = Boca Raton | year = 2000 | pages = | isbn = 3-88763-075-0 | oclc = | doi = | url = http://books.google.com/?id=5GpcTQD_L2oC&lpg=PA726&dq=niaprazine&pg=PA726#v=onepage&q}}</ref><ref name="isbn0-412-46630-9">{{cite book | author = David J. Triggle | title = Dictionary of Pharmacological Agents | publisher = Chapman & Hall/CRC | location = Boca Raton | year = 1996 | pages = | isbn = 0-412-46630-9 | oclc = | doi = | url = http://books.google.com/?id=A0THacd46ZsC&lpg=PA1418&dq=niaprazine&pg=PA1418#v=onepage&q}}</ref> It is commonly used with children and adolescents on account of its favorable [[safety]] and [[tolerability]] profile and lack of [[abuse potential]].<ref name="pmid2958783">{{cite journal | author = Franzoni E, Masoni P, Mambelli M, Marzano P, Donati C | title = [Niaprazine in behavior disorders in children. Double-blind comparison with placebo] | language = Italian | journal = La Pediatria Medica E Chirurgica : Medical and Surgical Pediatrics | volume = 9 | issue = 2 | pages = 185–7 | year = 1987 | pmid = 2958783 | doi = | url = }}</ref><ref name="pmid2903572">{{cite journal | author = Bodiou C, Bavoux F | title = [Niaprazine and side effects in pediatrics. Cooperative evaluation of French centers of pharmacovigilance] | language = French | journal = Thérapie | volume = 43 | issue = 4 | pages = 307–11 | year = 1988 | pmid = 2903572 | doi = | url = }}</ref><ref name="pmid1837245">{{cite journal | author = Ottaviano S, Giannotti F, Cortesi F | title = The effect of niaprazine on some common sleep disorders in children. A double-blind clinical trial by means of continuous home-videorecorded sleep | journal = Child's Nervous System : ChNS : Official Journal of the International Society for Pediatric Neurosurgery | volume = 7 | issue = 6 | pages = 332–5 |date=October 1991 | pmid = 1837245 | doi = 10.1007/bf00304832| url = }}</ref><ref name="pmid1354861">{{cite journal | author = Montanari G, Schiaulini P, Covre A, Steffan A, Furlanut M | title = Niaprazine vs chlordesmethyldiazepam in sleep disturbances in pediatric outpatients | journal = Pharmacological Research : the Official Journal of the Italian Pharmacological Society | volume = 25 Suppl 1 | issue = | pages = 83–4 | year = 1992 | pmid = 1354861 | doi = 10.1016/1043-6618(92)90551-l| url = }}</ref><ref name="pmid12038875">{{cite journal | author = Younus M, Labellarte MJ | title = Insomnia in children: when are hypnotics indicated? | journal = Paediatric Drugs | volume = 4 | issue = 6 | pages = 391–403 | year = 2002 | pmid = 12038875 | doi = 10.2165/00128072-200204060-00006| url = http://content.wkhealth.com/linkback/openurl?issn=1174-5878&volume=4&issue=6&spage=391}}</ref><ref name="pmid16700077">{{cite journal | author = Mancini J, Thirion X, Masut A, ''et al.'' | title = Anxiolytics, hypnotics, and antidepressants dispensed to adolescents in a French region in 2002 | journal = Pharmacoepidemiology and Drug Safety | volume = 15 | issue = 7 | pages = 494–503 |date=July 2006 | pmid = 16700077 | doi = 10.1002/pds.1258}}</ref> | |||
{{ | Originally believed to act as an [[antihistamine]] and [[anticholinergic]],<ref name="pmid4401719">{{cite journal | author = Duchene-Marullaz P, Rispat G, Perriere JP, Hache J, Labrid C | title = [Some pharmacodynamical properties of niaprazine, a new antihistaminic agent] | language = French | journal = Thérapie | volume = 26 | issue = 6 | pages = 1203–9 | year = 1971 | pmid = 4401719 | doi = | url = }}</ref> niaprazine was later discovered to have no significant [[binding (molecular)|binding]] [[affinity (pharmacology)|affinity]] for either the [[H1 receptor|H<sub>1</sub>]] or the [[muscarinic acetylcholine receptor|mACh receptor]]s (K<sub>i</sub> = > 1 μM), and was instead found to act as a [[potency (pharmacology)|potent]] and [[binding selectivity|selective]] [[5-HT2A receptor|5-HT<sub>2A</sub>]] and [[alpha-1 adrenergic receptor|α<sub>1</sub>-adrenergic receptor]] [[receptor antagonist|antagonist]] (K<sub>i</sub> = 75 nM and 86 nM, respectively).<ref name="pmid2853885">{{cite journal | author = Scherman D, Hamon M, Gozlan H, ''et al.'' | title = Molecular pharmacology of niaprazine | journal = Progress in Neuro-psychopharmacology & Biological Psychiatry | volume = 12 | issue = 6 | pages = 989–1001 | year = 1988 | pmid = 2853885 | doi = 10.1016/0278-5846(88)90093-0| url = }}</ref> It is virtually inactive at [[5-HT1A receptor|5-HT<sub>1A</sub>]], [[5-HT2B receptor|5-HT<sub>2B</sub>]], [[D2 receptor|D<sub>2</sub>]], and [[beta-adrenergic receptor|β-adrenergic]], as well as at [[serotonin transporter|SERT]] and [[vesicular monoamine transporter|VMAT]] (K<sub>i</sub> = all > 1 μM), but it does have some weak affinity for the [[alpha-2 adrenergic receptor|α<sub>2</sub>-adrenergic receptor]] (K<sub>i</sub> = 730 nM),<ref name="pmid2853885" /> likely acting as an antagonist there as well. | ||
Niaprazine has been shown to [[metabolize]] to the compound [[para-Fluorophenylpiperazine|''p''FPP]] in a similar manner to how [[trazodone]] and [[nefazodone]] metabolize to [[meta-Chlorophenylpiperazine|''m''CPP]].<ref name="pmid6460945">{{cite journal | author = Keane PE, Strolin Benedetti M, Dow J | title = The effect of niaprazine on the turnover of 5-hydroxytryptamine in the rat brain | journal = Neuropharmacology | volume = 21 | issue = 2 | pages = 163–9 |date=February 1982 | pmid = 6460945 | doi = 10.1016/0028-3908(82)90157-5| url = }}</ref><ref name="isbn0-12-366829-8">{{Cite book | title = International review of neurobiology | year = 1988 | publisher = Academic Press | location = New York | isbn = 0-12-366829-8 | pages = | url = http://books.google.com/?id=Uf_BWXKXW2cC&lpg=PA274&dq=niaprazine&pg=PA274#v=onepage&q}}</ref> It is unclear what role, if any, ''p''FPP plays in the clinical effects of niaprazine.<ref name="pmid2853885" /> However, from animal studies it is known that ''p''FPP, unlike niaprazine, does not produce sedative effects, and instead exerts a behavioral profile indicative of [[serotonergic]] activation.<ref name="pmid6460945" /> | |||
== References == | == References == | ||
{{ | {{Reflist|2}} | ||
[[Category:Carboxamides]] | |||
[[Category:Organofluorides]] | |||
[[Category:Piperazines]] | [[Category:Piperazines]] | ||
[[Category:Pyridines]] | |||
[[Category:Drug]] | |||
Latest revision as of 16:47, 20 August 2015
{{Drugbox | IUPAC_name = N-{4-[4-(4-fluorophenyl)piperazin- 1-yl]butan- 2-yl}pyridine- 3-carboxamide | image = Niaprazine.png
| tradename = | Drugs.com = International Drug Names | pregnancy_category = | legal_status = Rx-only | routes_of_administration = Oral
| metabolism = | elimination_half-life = ~4.5 hours | excretion =
| CAS_number = 27367-90-4
| ATC_prefix = N05
| ATC_suffix = CM16
| PubChem = 71919
| ChemSpiderID = 64930
| UNII_Ref = 
| UNII = R2H3YN6E3L
| KEGG = D07333
| C=20 | H=25 | F=1 | N=4 | O=1 | molecular_weight = 356.437 g/mol | smiles = Fc3ccc(N2CCN(CCC(NC(=O)c1cccnc1)C)CC2)cc3 }}
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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]
Overview
Niaprazine (Nopron) is a sedative-hypnotic drug of the phenylpiperazine class.[1] It has been used in the treatment of sleep disturbances since the early 1970s in several European countries, including France, Italy, and Luxembourg.[2][3] It is commonly used with children and adolescents on account of its favorable safety and tolerability profile and lack of abuse potential.[4][5][6][7][8][9]
Originally believed to act as an antihistamine and anticholinergic,[10] niaprazine was later discovered to have no significant binding affinity for either the H1 or the 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).[11] It is virtually inactive at 5-HT1A, 5-HT2B, D2, and β-adrenergic, as well as at SERT and VMAT (Ki = all > 1 μM), but it does have some weak affinity for the α2-adrenergic receptor (Ki = 730 nM),[11] likely acting as an antagonist there as well.
Niaprazine has been shown to metabolize to the compound pFPP in a similar manner to how trazodone and nefazodone metabolize to mCPP.[12][13] It is unclear what role, if any, pFPP plays in the clinical effects of niaprazine.[11] 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.[12]
References
- ↑ Kent, Angela; M. Billiard (2003). Sleep: physiology, investigations, and medicine. New York: Kluwer Academic/Plenum. ISBN 0-306-47406-9.
- ↑ Swiss Pharmaceutical Society (2000). Index Nominum 2000: International Drug Directory (Book with CD-ROM). Boca Raton: Medpharm Scientific Publishers. ISBN 3-88763-075-0.
- ↑ David J. Triggle (1996). Dictionary of Pharmacological Agents. Boca Raton: Chapman & Hall/CRC. ISBN 0-412-46630-9.
- ↑ 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]". Thérapie (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 : ChNS : Official Journal of the International Society for Pediatric Neurosurgery. 7 (6): 332–5. doi:10.1007/bf00304832. PMID 1837245.
- ↑ Montanari G, Schiaulini P, Covre A, Steffan A, Furlanut M (1992). "Niaprazine vs chlordesmethyldiazepam in sleep disturbances in pediatric outpatients". Pharmacological Research : the Official Journal of the Italian Pharmacological Society. 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.
- ↑ 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.
- ↑ 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.
- ↑ 11.0 11.1 11.2 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.
- ↑ 12.0 12.1 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.
- ↑ International review of neurobiology. New York: Academic Press. 1988. ISBN 0-12-366829-8.