Diphenylpyraline

Diphenylpyraline
Systematic (IUPAC) name
4-benzhydryloxy-1-methyl-piperidine
Clinical data
AHFS/Drugs.com International Drug Names
Legal status
  • ℞ (Prescription only)
Routes of
administration		 Oral, Topical
Pharmacokinetic data
Biological half-life 24–40 hours[1]
Identifiers
CAS Number 147-20-6 YesY
ATC code R06AA07
PubChem CID 3103
IUPHAR/BPS 7165
DrugBank DB01146 YesY
ChemSpider 2992 YesY
UNII 33361OE3AV YesY
KEGG D07862 YesY
ChEBI CHEBI:59788 YesY
ChEMBL CHEMBL1492 YesY
Synonyms 4-(diphenylmethoxy)-1-methyl-piperidine
Chemical data
Formula C19H23NO
Molar mass 281.392 g/mol
  (verify)

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]

Synthesis

Diphenylpyraline synthesis:[8][9]

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

Trade names

Arbid, Dafen, Dayfen, Histyn, Hispril, etc.

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. 1 2 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. 1 2 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.
  8. ↑ H.K. Lawrence, R. Kapp, U.S. Patent 2,479,843 (1949).
  9. ↑ W.A. Schuler, DE 934890 (1951).

This article is issued from Wikipedia - version of the Sunday, January 03, 2016. The text is available under the Creative Commons Attribution/Share Alike but additional terms may apply for the media files.