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CGP-39551

From Wikipedia, the free encyclopedia
Competitive NMDA receptor antagonist
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
  • 694-678-0
  • InChI=1S/C8H16NO5P/c1-3-14-8(10)7(9)4-6(2)5-15(11,12)13/h4,7H,3,5,9H2,1-2H3,(H2,11,12,13)/b6-4+
    Key: OKDOWCKDTWNRCB-GQCTYLIASA-N
  • CCOC(=O)C(/C=C(\C)/CP(=O)(O)O)N
Properties
C8H16NO5P
Molar mass237.192 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 theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

CGP-39551 is a drug used in scientific research, it is investigated as ananti-convulsant.[2]

Mechanism of action

[edit]

CGP-39551 and some related molecules are competitive antagonists of theN-methyl D-aspartate receptor, an excitatory receptor activated byglutamate.[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 byvestibular 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 asDizocilpine.[7]

References

[edit]
  1. ^"(E)-(4-Amino-5-ethoxy-2-methyl-5-oxopent-2-en-1-yl)phosphonic acid".pubchem.ncbi.nlm.nih.gov.
  2. ^"CGP 39551 | NMDA Receptor Antagonist".
  3. ^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.
  4. ^Pozza, M. F.; Olpe, H. R.; Brugger, F.; Fagg, G. E. (1990-06-21). "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.
  5. ^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.
  6. ^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.
  7. ^Bischoff, C.; Tiedtke, P. I. (1992-03-24). "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.
AMPARTooltip α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor
KARTooltip Kainate receptor
NMDARTooltip N-Methyl-D-aspartate receptor
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