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CGP-39551

From Wikipedia, the free encyclopedia
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 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).

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

Mechanism of action

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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

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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

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  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.