Diphenylpyraline
Chemical compound
- R06AA07 (WHO)
- In general: ℞ (Prescription only)
- 4-benzhydryloxy-1-methyl-piperidine
- 147-20-6 Y
- 3103
- 7165
- DB01146 Y
- 2992 Y
- 33361OE3AV
- D07862 Y
- CHEBI:59788 Y
- ChEMBL1492 Y
- DTXSID3022952
- Interactive image
- O(C(c1ccccc1)c2ccccc2)C3CCN(C)CC3
InChI
- InChI=1S/C19H23NO/c1-20-14-12-18(13-15-20)21-19(16-8-4-2-5-9-16)17-10-6-3-7-11-17/h2-11,18-19H,12-15H2,1H3 Y
- Key:OWQUZNMMYNAXSL-UHFFFAOYSA-N Y
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
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. S2CID 38955052.
- ^ 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.
- ^ 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. doi:10.1177/030006057700500106. PMID 14039. S2CID 19330175.
- ^ 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 VJ, Vardanyan R, Vardanyan R (2006). "Antihistamine Drugs". Synthesis of Essential Drugs. Amsterdam: Elsevier. ISBN 0-444-52166-6.
- ^ 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.
- ^ 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. S2CID 35946097.
- ^ US 2479843, Knox LH, Kapp R, "1-Alkylpiperidyl-4-benzhydryl ethers, acid salts thereof and their preparation", issued 23 August 1949, assigned to Nopco Chemical Company.
- ^ DE 934890, Schuler WA, "Verfahren zur Herstellung von basischen Benzhydryläthern [Process for the production of basic benzhydrylethers]", issued 10 November 1955, assigned to Chemische Fabrik Promonta LLC.
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- Diarylmethoxyalkylamines: Bromazine (bromodiphenhydramine)
- Carbinoxamine
- Chlorphenoxamine
- Clemastine
- Diphenhydramine (+naproxen)
- Diphenylpyraline
- Doxylamine
- Ebastine
- Orphenadrine
- Diphenylmethylpiperazines: Buclizine
- Cetirizine
- Chlorcyclizine
- Cinnarizine
- Cyclizine
- Etodroxizine
- Hydroxyzine
- Meclizine
- Oxatomide
- Phenylpyridinylpropanamines: Brompheniramine
- Chlorphenamine
- Dexbrompheniramine (+pseudoephedrine)
- Dexchlorpheniramine (+betamethasone)
- Pheniramine
- Phenylpiperazines: Antidepressants (e.g., trazodone)
- Phenbenzamine
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