Fluperamide
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| This article, Fluperamide, has recently been created via the Articles for creation process. Please check to see if the reviewer has accidentally left this template after accepting the draft and take appropriate action as necessary.
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| Chemical and physical data | |
| Formula | C30H32ClF3N2O2 |
| Molar mass | 545.04 g·mol−1 |
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Fluperamide is an antiperistaltic (antidiarrhoeal) drug similar to loperamide in molecular structure but differs in the choice of the functionalized piperidine. Loperamide is based on 4-(p-chlorophenyl)-4-piperidinol [39512-49-7], which is the same as for haloperidol. Fluperamide on the other hand is based on 4-(4-chloro-3-(trifluoromethyl)phenyl)piperidin-4-ol [21928-50-7], which is the same as for clofluperol and penfluridol. The addition of a meta-trifluoromethyl moiety (to the resultant structure) markedly alters the pharmacology.
Fluperamide has the potential for addiction due to its ability to cross the blood-brain barrier more effectively than loperamide. This property allows it to interact with opioid receptors in the central nervous system, which can lead to effects similar to other opioids, such as euphoria and sedation. These characteristics increase the risk of misuse and dependence.
Synthesis:[1] Patent:[2] ~78%:[3]
See also
References
- ^ Stokbroekx, R. A., Vandenberk, J., Van Heertum, A. H. M. T., Van Laar, G. M. L. W., Van der Aa, M. J. M. C., Van Bever, W. F. M., Janssen, P. A. J. (July 1973). "Synthetic antidiarrheal agents. 2,2-Diphenyl-4-(4'-aryl-4'-hydroxypiperidino)butyramides". Journal of Medicinal Chemistry. 16 (7): 782–786. doi:10.1021/jm00265a009.
- ^ Paul A J Janssen, et al. GB1319040 (1973 to Janssen Pharmaceutica NV).
- ^ Chen, Z., Davies, E., Miller, W. S., Shan, S., Valenzano, K. J., Kyle, D. J. (November 2004). "Design and synthesis of 4-phenyl piperidine compounds targeting the mu receptor". Bioorganic & Medicinal Chemistry Letters. 14 (21): 5275–5279. doi:10.1016/j.bmcl.2004.08.032.