Diphenylpyraline: Difference between revisions

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__NOTOC__
__NOTOC__
{{SI}}
{{SI}}
{{CMG}}
{{CMG}}
==Overview==
==Overview==
'''Diphenylpyraline''' ('''DPP'''; sold as '''Allergen''', '''Arbid''', '''Belfene''', '''Diafen''', '''Hispril''', '''Histyn''', '''Lergobine''', '''Lyssipol''', '''Mepiben''', '''Neargal''') is a [[first-generation antihistamine]] with [[anticholinergic]] effects of the [[benzhydryl|diphenyl]][[piperidine]] class.<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=PA358&dq=Diphenylpyraline&pg=PA358#v=onepage&q}}</ref><ref name="pmid14039">{{cite journal | author = Puhakka H, Rantanen T, Virolainen E | title = Diphenylpyraline (Lergobine) in the treatment of patients suffering from allergic and vasomotor rhinitis | journal = J Int Med Res | volume = 5 | issue = 1 | pages = 37–41 | year = 1977 | pmid = 14039}}</ref><ref name="pmid2884340">{{cite journal | author = Kubo N, Shirakawa O, Kuno T, Tanaka C | title = Antimuscarinic effects of antihistamines: quantitative evaluation by receptor-binding assay | journal = Japanese Journal of Pharmacology | volume = 43 | issue = 3 | pages = 277–82 |date=March 1987 | pmid = 2884340 | doi = 10.1254/jjp.43.277| url = }}</ref> It is marketed in [[Europe]] for the treatment of [[allergy|allergies]].<ref name="isbn3-88763-075-0" /><ref name="pmid14039" /><ref name="isbn0-444-52166-6">{{cite book | author = Hruby, Victor J.; Ruben Vardanyan; Vardanyan, ۊRuben | title = Synthesis of essential drugs | publisher = Elsevier | location = Amsterdam | year = 2006 | pages = | isbn = 0-444-52166-6 | oclc = | doi = | url = http://books.google.com/?id=Jjc7KYWZdOYC&lpg=PA230&dq=Diphenylpyraline&pg=PA230#v=onepage&q}}</ref> DPP has also been found to act as a [[dopamine reuptake inhibitor]] and produces [[hyperactivity]] in rodents.<ref name="pmid15627433">{{cite journal | author = Lapa G, Mathews T, Harp J, Budygin E, Jones S | title = Diphenylpyraline, a histamine H1 receptor antagonist, has psychostimulant properties | journal = Eur J Pharmacol | volume = 506 | issue = 3 | pages = 237–40 | year = 2005 | pmid = 15627433 | doi = 10.1016/j.ejphar.2004.11.017}}</ref> It has been shown to be useful in the treatment of [[Parkinsonism]].<ref name="pmid11137513">{{cite journal | author = Ohno T, Kobayashi S, Hayashi M, Sakurai M, Kanazawa I | title = Diphenylpyraline-responsive parkinsonism in cerebrotendinous xanthomatosis: long-term follow up of three patients | journal = J Neurol Sci | volume = 182 | issue = 2 | pages = 95–7 | year = 2001 | pmid = 11137513 | doi = 10.1016/S0022-510X(00)00441-X}}</ref>
'''Diphenylpyraline''' ('''DPP'''; sold as '''Allergen''', '''Arbid''', '''Belfene''', '''Diafen''', '''Hispril''', '''Histyn''', '''Lergobine''', '''Lyssipol''', '''Mepiben''', '''Neargal''') is a [[first-generation antihistamine]] with [[anticholinergic]] effects of the [[benzhydryl|diphenyl]][[piperidine]] class.<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=PA358&dq=Diphenylpyraline&pg=PA358#v=onepage&q}}</ref><ref name="pmid14039">{{cite journal | author = Puhakka H, Rantanen T, Virolainen E | title = Diphenylpyraline (Lergobine) in the treatment of patients suffering from allergic and vasomotor rhinitis | journal = J Int Med Res | volume = 5 | issue = 1 | pages = 37–41 | year = 1977 | pmid = 14039}}</ref><ref name="pmid2884340">{{cite journal | author = Kubo N, Shirakawa O, Kuno T, Tanaka C | title = Antimuscarinic effects of antihistamines: quantitative evaluation by receptor-binding assay | journal = Japanese Journal of Pharmacology | volume = 43 | issue = 3 | pages = 277–82 |date=March 1987 | pmid = 2884340 | doi = 10.1254/jjp.43.277| url = }}</ref> It is marketed in [[Europe]] for the treatment of [[allergy|allergies]].<ref name="isbn3-88763-075-0" /><ref name="pmid14039" /><ref name="isbn0-444-52166-6">{{cite book | author = Hruby, Victor J.; Ruben Vardanyan; Vardanyan, ۊRuben | title = Synthesis of essential drugs | publisher = Elsevier | location = Amsterdam | year = 2006 | pages = | isbn = 0-444-52166-6 | oclc = | doi = | url = http://books.google.com/?id=Jjc7KYWZdOYC&lpg=PA230&dq=Diphenylpyraline&pg=PA230#v=onepage&q}}</ref> DPP has also been found to act as a [[dopamine reuptake inhibitor]] and produces [[hyperactivity]] in rodents.<ref name="pmid15627433">{{cite journal | author = Lapa G, Mathews T, Harp J, Budygin E, Jones S | title = Diphenylpyraline, a histamine H1 receptor antagonist, has psychostimulant properties | journal = Eur J Pharmacol | volume = 506 | issue = 3 | pages = 237–40 | year = 2005 | pmid = 15627433 | doi = 10.1016/j.ejphar.2004.11.017}}</ref> It has been shown to be useful in the treatment of [[Parkinsonism]].<ref name="pmid11137513">{{cite journal | author = Ohno T, Kobayashi S, Hayashi M, Sakurai M, Kanazawa I | title = Diphenylpyraline-responsive parkinsonism in cerebrotendinous xanthomatosis: long-term follow up of three patients | journal = J Neurol Sci | volume = 182 | issue = 2 | pages = 95–7 | year = 2001 | pmid = 11137513 | doi = 10.1016/S0022-510X(00)00441-X}}</ref>
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==Chemistry==
==Chemistry==
Diphenylpyraline, 4-diphenylmethoxy-1-methylpiperidine, is synthesized by alkylating 4-hydroxy-1-methylpiperidine with benzhydrylbromide.
Diphenylpyraline, 4-diphenylmethoxy-1-methylpiperidine, is synthesized by alkylating 4-hydroxy-1-methylpiperidine with benzhydrylbromide.
[[File:Diphenylpyraline synthesis.png|500px]]
[[File:Diphenylpyraline synthesis.png|none|left|500px]]


== See also ==
== See also ==
* [[Benzatropine]]
* [[Benzatropine]]
* [[2-Diphenylmethylpyrrolidine]]
* [[Difemetorex]]
* [[Diphenylprolinol]]
* [[Desoxypipradrol]]
* [[Desoxypipradrol]]
* [[Pipradrol]]
* [[Pipradrol]]
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{{Antihistamines}}
{{Antihistamines}}
{{Antiparkinsonian}}
{{Stimulants}}
{{Stimulants}}
{{Cholinergics}}
[[Category:H1 receptor antagonists]]
{{Dopaminergics}}
{{Histaminergics}}
{{Respiratory-system-drug-stub}}[[Category:H1 receptor antagonists]]
[[Category:Piperidines]]
[[Category:Piperidines]]
[[Category:Ethers]]
[[Category:Ethers]]
[[Category:Stimulants]]
[[Category:Stimulants]]
[[Category:Drug]]
[[Category:Drug]]

Latest revision as of 17:26, 10 April 2015

Diphenylpyraline
Clinical data
Synonyms4-(diphenylmethoxy)-1-methyl-piperidine
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Oral, Topical
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Elimination half-life24-40 hours[1]
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC19H23NO
Molar mass281.392 g/mol
3D model (JSmol)
  (verify)

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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Diphenylpyraline (DPP; sold as Allergen, Arbid, Belfene, Diafen, Hispril, Histyn, Lergobine, Lyssipol, Mepiben, Neargal) is a first-generation antihistamine with anticholinergic effects of the diphenylpiperidine class.[2][3][4] It is marketed in Europe for the treatment of allergies.[2][3][5] DPP has also been found to act as a dopamine reuptake inhibitor and produces hyperactivity in rodents.[6] It has been shown to be useful in the treatment of Parkinsonism.[7]

Chemistry

Diphenylpyraline, 4-diphenylmethoxy-1-methylpiperidine, is synthesized by alkylating 4-hydroxy-1-methylpiperidine with benzhydrylbromide.

See also

References

  1. ↑ Graham G, Bolt AG (June 1974). "Half-life of diphenylpyraline in man". Journal of Pharmacokinetics and Biopharmaceutics. 2 (3): 191–5. doi:10.1007/BF01059761. PMID 4156058.
  2. ↑ 2.0 2.1 Swiss Pharmaceutical Society (2000). Index Nominum 2000: International Drug Directory (Book with CD-ROM). Boca Raton: Medpharm Scientific Publishers. ISBN 3-88763-075-0.
  3. ↑ 3.0 3.1 Puhakka H, Rantanen T, Virolainen E (1977). "Diphenylpyraline (Lergobine) in the treatment of patients suffering from allergic and vasomotor rhinitis". J Int Med Res. 5 (1): 37–41. PMID 14039.
  4. ↑ Kubo N, Shirakawa O, Kuno T, Tanaka C (March 1987). "Antimuscarinic effects of antihistamines: quantitative evaluation by receptor-binding assay". Japanese Journal of Pharmacology. 43 (3): 277–82. doi:10.1254/jjp.43.277. PMID 2884340.
  5. ↑ Hruby, Victor J.; Ruben Vardanyan; Vardanyan, ۊRuben (2006). Synthesis of essential drugs. Amsterdam: Elsevier. ISBN 0-444-52166-6.
  6. ↑ Lapa G, Mathews T, Harp J, Budygin E, Jones S (2005). "Diphenylpyraline, a histamine H1 receptor antagonist, has psychostimulant properties". Eur J Pharmacol. 506 (3): 237–40. doi:10.1016/j.ejphar.2004.11.017. PMID 15627433.
  7. ↑ Ohno T, Kobayashi S, Hayashi M, Sakurai M, Kanazawa I (2001). "Diphenylpyraline-responsive parkinsonism in cerebrotendinous xanthomatosis: long-term follow up of three patients". J Neurol Sci. 182 (2): 95–7. doi:10.1016/S0022-510X(00)00441-X. PMID 11137513.

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