CGP-39551
| Names | |
|---|---|
| IUPAC name
[(E)-4-amino-5-ethoxy-2-methyl-5-oxopent-2-enyl]phosphonic acid
| |
| Identifiers | |
| |
3D model (JSmol)
|
|
| ChemSpider | |
| EC Number |
|
PubChem CID
|
|
| |
| |
| Properties | |
| C8H16NO5P | |
| Molar mass | 237.192 g·mol−1 |
| Hazards | |
| GHS labelling:[1] | |
| GHS06: Toxic | |
| Danger | |
| H301 | |
| P264, P270, P301+P316, P321, P330, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
-(4-Amino-5-ethoxy-2-methyl-5-oxopent-2-en-1-yl)phosphonic_acid.png){kind=link}
CGP-39551 is a drug used in scientific research, it is investigated as an anti-convulsant.[2]
Mechanism of action
[edit ]CGP-39551 and some related molecules are competitive antagonists of the N-methyl D-aspartate receptor, an excitatory receptor activated by glutamate.[3] [4]
Potential
[edit ]As other glutamate antagonists, CGP-39551 possesses anti-convulsant properties. It is able to suppress seizures caused by electroshock, with a duration of action superior to 24 hours.[5]
It has also been shown to be able to block convulsions caused by vestibular stimulation.[6]
Additionally, CGP-39551 appears to be better than some other NMDA blockers in terms of side effects, since the dose required for its anti-convulsant action does not have significant impact on memory and learning, unlike certain drugs with a similar mechanism of action such as Dizocilpine.[7]
References
[edit ]- ^ "(E)-(4-Amino-5-ethoxy-2-methyl-5-oxopent-2-en-1-yl)phosphonic acid". pubchem.ncbi.nlm.nih.gov.
- ^ "CGP 39551 | NMDA Receptor Antagonist".
- ^ Fagg, G. E.; Olpe, H. R.; Pozza, M. F.; Baud, J.; Steinmann, M.; Schmutz, M.; Portet, C.; Baumann, P.; Thedinga, K.; Bittiger, H. (April 1990). "CGP 37849 and CGP 39551: novel and potent competitive N-methyl-D-aspartate receptor antagonists with oral activity". British Journal of Pharmacology. 99 (4): 791–797. doi:10.1111/j.1476-5381.1990.tb13008.x. ISSN 0007-1188. PMC 1917531 . PMID 1972895.
- ^ Pozza, M. F.; Olpe, H. R.; Brugger, F.; Fagg, G. E. (1990年06月21日). "Electrophysiological characterization of a novel potent and orally active NMDA receptor antagonist: CGP 37849 and its ethylester CGP 39551". European Journal of Pharmacology. 182 (1): 91–100. doi:10.1016/0014-2999(90)90496-s. ISSN 0014-2999. PMID 1976098.
- ^ Schmutz, M.; Portet, C.; Jeker, A.; Klebs, K.; Vassout, A.; Allgeier, H.; Heckendorn, R.; Fagg, G. E.; Olpe, H. R.; van Riezen, H. (July 1990). "The competitive NMDA receptor antagonists CGP 37849 and CGP 39551 are potent, orally-active anticonvulsants in rodents". Naunyn-Schmiedeberg's Archives of Pharmacology. 342 (1): 61–66. doi:10.1007/BF00178973. ISSN 0028-1298. PMID 1976233.
- ^ D'Hooge, R.; Raes, A.; Hiramatsu, M.; Mori, A.; Van Bogaert, P. P.; De Deyn, P. P. (December 1998). "Effects of the competitive N-methyl-D-aspartate antagonist CGP 37849 and its ethylester CGP 39551 on N-methyl-D-aspartate-evoked whole-cell currents in cultured spinal neurones and on vestibular stimulation-induced seizures in EL mice". Arzneimittel-Forschung. 48 (12): 1121–1125. ISSN 0004-4172. PMID 9893924.
- ^ Bischoff, C.; Tiedtke, P. I. (1992年03月24日). "Competitive and non-competitive NMDA receptor antagonists in spatial learning tasks". European Journal of Pharmacology. 213 (2): 269–273. doi:10.1016/0014-2999(92)90691-v. ISSN 0014-2999. PMID 1355738.