CGP-39551

CGP-39551

Names
IUPAC name [(E)-4-amino-5-ethoxy-2-methyl-5-oxopent-2-enyl]phosphonic acid
Identifiers
CAS Number	127910-32-1^N
3D model (JSmol)	Interactive image
ChemSpider	4899607
EC Number	694-678-0
PubChem CID	6372334
InChI 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
SMILES CCOC(=O)C(/C=C(\C)/CP(=O)(O)O)N
Properties
Chemical formula	C8H16NO5P
Molar mass	237.192 g·mol^−1
Hazards
GHS labelling:[1]
Pictograms
Signal word	Danger
Hazard statements	H301
Precautionary statements	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). Infobox references

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

Mechanism of action

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

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

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.