Diphenylpyraline
From Wikipedia, the free encyclopedia
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| Systematic (IUPAC) name | |
| 4-benzhydryloxy-1-methyl-piperidine | |
| Clinical data | |
| AHFS/Drugs.com | International Drug Names |
| Pregnancy cat. | ? |
| Legal status | ℞ Prescription only |
| Routes | Oral, Topical |
| Pharmacokinetic data | |
| Half-life | 24-40 hours[1] |
| Identifiers | |
| CAS number | 147-20-6  |
| ATC code | R06AA07 |
| PubChem | CID 3103 |
| DrugBank | APRD00719 |
| ChemSpider | 2992 |
| UNII | 33361OE3AV |
| KEGG | D07862 |
| ChEBI | CHEBI:59788 |
| ChEMBL | CHEMBL1492 |
| Synonyms | 4-(diphenylmethoxy)-1-methyl-piperidine |
| Chemical data | |
| Formula | C19H23NO |
| Mol. mass | 281.392 g/mol |
| SMILES | eMolecules & PubChem |
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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]
[edit] Chemistry
Diphenylpyraline, 4-diphenylmethoxy-1-methylpiperidine, is synthesized by alkylating 4-hydroxy-1-methylpiperidine with benzhydrylbromide. 
- H.K. Lawrence, R. Kapp, U.S. Patent 2,479,843 (1949).
- W.A. Schuler, DE 934890 (1951).
[edit] See also
[edit] References
- ^ 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.
- ^ a b Swiss Pharmaceutical Society (2000). Index Nominum 2000: International Drug Directory (Book with CD-ROM). Boca Raton: Medpharm Scientific Publishers. ISBN 3-88763-075-0. http://books.google.com/?id=5GpcTQD_L2oC&lpg=PA358&dq=Diphenylpyraline&pg=PA358#v=onepage&q.
- ^ a b 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.
- ^ 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.
- ^ Hruby, Victor J.; Ruben Vardanyan; Vardanyan, ۊRuben (2006). Synthesis of essential drugs. Amsterdam: Elsevier. ISBN 0-444-52166-6. http://books.google.com/?id=Jjc7KYWZdOYC&lpg=PA230&dq=Diphenylpyraline&pg=PA230#v=onepage&q.
- ^ 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.
- ^ 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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