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{{Short description|Chemical compound}}
{{drugbox |
{{Drugbox
⚫ | IUPAC_name = (E,2R)-2-amino-4-methyl-5-phosphonopent-3-enoic acid
| Verifiedfields = changed
⚫ | image = CGP-37849.png
| Watchedfields = changed
⚫ | width = 240
| verifiedrevid = 402321381
⚫ | CAS_number = 137424-81-8
⚫ | IUPAC_name = (E,2R)-2-amino-4-methyl-5-phosphonopent-3-enoic acid
⚫ | synonyms = CGP-37849, CGP-40116
⚫ | image = CGP-37849.svg
⚫ | ATC_prefix =
⚫ | width = 240
⚫ | ATC_suffix =
| PubChem = 5950212
⚫ | DrugBank =
⚫ | C = 6 | H = 12 | N = 1 | O = 5 | P = 1
| molecular_weight = 209.137 g/mol
⚫ | smiles = C/C(=C\(C(=O)O)N)/CP(=O)(O)O
⚫ | bioavailability =
⚫ | protein_bound =
⚫ | metabolism =
⚫ | elimination_half-life =
⚫ | excretion =
⚫ | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
⚫ | pregnancy_US = <!-- A / B / C / D / X -->
⚫ | pregnancy_category=
⚫ | legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
⚫ | legal_CA =
⚫ | legal_UK =
⚫ | legal_US =
⚫ | legal_status =
⚫ | routes_of_administration =
⚫ }}


<!--Clinical data-->
⚫ '''CGP-37849''' is a competitive ] at the ].<ref>Fagg GE, Olpe HR, Pozza MF, Baud J, Steinmann M, Schmutz M, Portet C, Baumann P, Thedinga K, Bittiger H, et al. CGP 37849 and CGP 39551: novel and potent competitive N-methyl-D-aspartate receptor antagonists with oral activity. ''British Journal of Pharmacology''. 1990 Apr;99(4):791-7. PMID 1972895</ref> It is a potent, orally active ] in animal models,<ref>Schmutz M, Portet C, Jeker A, Klebs K, Vassout A, Allgeier H, Heckendorn R, Fagg GE, Olpe HR, van Riezen H. The competitive NMDA receptor antagonists CGP 37849 and CGP 39551 are potent, orally-active anticonvulsants in rodents. ''Naunyn-Schmiedebergs Archives of Pharmacology''. 1990 Jul;342(1):61-6. PMID 1976233</ref> and was researched for the treatment of ].<ref>Fujikawa DG, Daniels AH, Kim JS. The competitive NMDA receptor antagonist CGP 40116 protects against status epilepticus-induced neuronal damage. ''Epilepsy Research''. 1994 Mar;17(3):207-19. PMID 7912191</ref> It also has ] activity<ref>Gutnikov SA, Gaffan D. Systemic NMDA receptor antagonist CGP-40116 does not impair memory acquisition but protects against NMDA neurotoxicity in rhesus monkeys. ''Journal of Neuroscience''. 1996 Jun 15;16(12):4041-5. PMID 8656297</ref> and shows ]<ref>Maj J, Klimek V, Gołembiowska K, Rogóz Z, Skuza G. Central effects of repeated treatment with CGP 37849, a competitive NMDA receptor antagonist with potential antidepressant activity. ''Polish Journal of Pharmacology''. 1993 Sep-Dec;45(5-6):455-66. PMID 7912134</ref><ref>Papp M, Moryl E. Antidepressant activity of non-competitive and competitive NMDA receptor antagonists in a chronic mild stress model of depression. ''European Journal of Pharmacology''. 1994 Sep 22;263(1-2):1-7. PMID 7821340</ref> and ] effects.<ref>Jessa M, Nazar M, Bidzinski A, Plaznik A. The effects of repeated administration of diazepam, MK-801 and CGP 37849 on rat behavior in two models of anxiety. ''European Neuropsychopharmacology''. 1996 Mar;6(1):55-61. PMID 8866939</ref><ref>Przegaliński E, Tatarczyńska E, Chojnacka-Wójcik E. The influence of the benzodiazepine receptor antagonist flumazenil on the anxiolytic-like effects of CGP 37849 and ACPC in rats. ''Neuropharmacology''. 2000 Jul 24;39(10):1858-64. PMID 10884566</ref>
| tradename =
⚫ | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
⚫ | pregnancy_US = <!-- A / B / C / D / X -->
⚫ | pregnancy_category =
⚫ | legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
⚫ | legal_CA =
⚫ | legal_UK =
⚫ | legal_US =
⚫ | legal_status =
⚫ | routes_of_administration =


<!--Pharmacokinetic data-->
⚫ | bioavailability =
⚫ | protein_bound =
⚫ | metabolism =
⚫ | elimination_half-life =
⚫ | excretion =

<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|CAS}}
⚫ | CAS_number = 137424-81-8
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 76IND1BS43
⚫ | ATC_prefix =
⚫ | ATC_suffix =
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
⚫ | DrugBank =
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 29811
| PubChem = 6604869
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 5037128
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C6H12NO5P/c1-4(3-13(10,11)12)2-5(7)6(8)9/h2,5H,3,7H2,1H3,(H,8,9)(H2,10,11,12)/b4-2+/t5-/m1/s1
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = BDYHNCZIGYIOGJ-XWCPEMDWSA-N

<!--Chemical data-->
⚫ | C=6 | H=12 | N=1 | O=5 | P=1
⚫ | smiles = C/C(=C\(C(=O)O)N)/CP(=O)(O)O
⚫ | synonyms = CGP-37849, CGP-40116
⚫ }}


⚫ '''CGP-37849''' is a competitive ] at the ].<ref>{{cite journal | vauthors = Fagg GE, Olpe HR, Pozza MF, Baud J, Steinmann M, Schmutz M, Portet C, Baumann P, Thedinga K, Bittiger H | display-authors = 6 | title = CGP 37849 and CGP 39551: novel and potent competitive N-methyl-D-aspartate receptor antagonists with oral activity | journal = British Journal of Pharmacology | volume = 99 | issue = 4 | pages = 791–7 | date = April 1990 | pmid = 1972895 | pmc = 1917531 | doi = 10.1111/j.1476-5381.1990.tb13008.x }}</ref> It is a potent, orally active ] in animal models,<ref>{{cite journal | vauthors = Schmutz M, Portet C, Jeker A, Klebs K, Vassout A, Allgeier H, Heckendorn R, Fagg GE, Olpe HR, van Riezen H | display-authors = 6 | title = The competitive NMDA receptor antagonists CGP 37849 and CGP 39551 are potent, orally-active anticonvulsants in rodents | journal = Naunyn-Schmiedeberg's Archives of Pharmacology | volume = 342 | issue = 1 | pages = 61–6 | date = July 1990 | pmid = 1976233 | doi = 10.1007/bf00178973 | s2cid = 25531153 }}</ref> and was researched for the treatment of ].<ref>{{cite journal | vauthors = Fujikawa DG, Daniels AH, Kim JS | title = The competitive NMDA receptor antagonist CGP 40116 protects against status epilepticus-induced neuronal damage | journal = Epilepsy Research | volume = 17 | issue = 3 | pages = 207–19 | date = March 1994 | pmid = 7912191 | doi = 10.1016/0920-1211(94)90051-5 | s2cid = 13656613 }}</ref> It also has ] activity<ref>{{cite journal | vauthors = Gutnikov SA, Gaffan D | title = Systemic NMDA receptor antagonist CGP-40116 does not impair memory acquisition but protects against NMDA neurotoxicity in rhesus monkeys | journal = The Journal of Neuroscience | volume = 16 | issue = 12 | pages = 4041–5 | date = June 1996 | pmid = 8656297 | pmc = 6578604 | doi = 10.1523/JNEUROSCI.16-12-04041.1996 }}</ref> and shows ]<ref>{{cite journal | vauthors = Maj J, Klimek V, Gołembiowska K, Rogóz Z, Skuza G | title = Central effects of repeated treatment with CGP 37849, a competitive NMDA receptor antagonist with potential antidepressant activity | journal = Polish Journal of Pharmacology | volume = 45 | issue = 5–6 | pages = 455–66 | pmid = 7912134 | year = 1993 }}</ref><ref>{{cite journal | vauthors = Papp M, Moryl E | title = Antidepressant activity of non-competitive and competitive NMDA receptor antagonists in a chronic mild stress model of depression | journal = European Journal of Pharmacology | volume = 263 | issue = 1–2 | pages = 1–7 | date = September 1994 | pmid = 7821340 | doi = 10.1016/0014-2999(94)90516-9 }}</ref> and ] effects.<ref>{{cite journal | vauthors = Jessa M, Nazar M, Bidzinski A, Plaznik A | title = The effects of repeated administration of diazepam, MK-801 and CGP 37849 on rat behavior in two models of anxiety | journal = European Neuropsychopharmacology | volume = 6 | issue = 1 | pages = 55–61 | date = March 1996 | pmid = 8866939 | doi = 10.1016/0924-977x(95)00068-z | s2cid = 45953054 }}</ref><ref>{{cite journal | vauthors = Przegaliński E, Tatarczyńska E, Chojnacka-Wójcik E | title = The influence of the benzodiazepine receptor antagonist flumazenil on the anxiolytic-like effects of CGP 37849 and ACPC in rats | journal = Neuropharmacology | volume = 39 | issue = 10 | pages = 1858–64 | date = July 2000 | pmid = 10884566 | doi = 10.1016/s0028-3908(00)00023-x | s2cid = 33660694 }}</ref>
⚫ ==References==
<references/>


⚫ == References ==
{{Glutamate_receptor_ligands}}
{{reflist}}


{{Ionotropic glutamate receptor modulators}}


] ]
] ]
] ]
]

Latest revision as of 16:28, 17 September 2023

Chemical compound Pharmaceutical compound
CGP-37849
Clinical data
Other namesCGP-37849, CGP-40116
Identifiers
IUPAC name
  • (E,2R)-2-amino-4-methyl-5-phosphonopent-3-enoic acid
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC6H12NO5P
Molar mass209.138 g·mol
3D model (JSmol)
SMILES
  • C/C(=C\(C(=O)O)N)/CP(=O)(O)O
InChI
  • InChI=1S/C6H12NO5P/c1-4(3-13(10,11)12)2-5(7)6(8)9/h2,5H,3,7H2,1H3,(H,8,9)(H2,10,11,12)/b4-2+/t5-/m1/s1
  • Key:BDYHNCZIGYIOGJ-XWCPEMDWSA-N
  (what is this?)  (verify)

CGP-37849 is a competitive antagonist at the NMDA receptor. It is a potent, orally active anticonvulsant in animal models, and was researched for the treatment of epilepsy. It also has neuroprotective activity and shows antidepressant and anxiolytic effects.

References

  1. Fagg GE, Olpe HR, Pozza MF, Baud J, Steinmann M, Schmutz M, et al. (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): 791–7. doi:10.1111/j.1476-5381.1990.tb13008.x. PMC 1917531. PMID 1972895.
  2. Schmutz M, Portet C, Jeker A, Klebs K, Vassout A, Allgeier H, et al. (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): 61–6. doi:10.1007/bf00178973. PMID 1976233. S2CID 25531153.
  3. Fujikawa DG, Daniels AH, Kim JS (March 1994). "The competitive NMDA receptor antagonist CGP 40116 protects against status epilepticus-induced neuronal damage". Epilepsy Research. 17 (3): 207–19. doi:10.1016/0920-1211(94)90051-5. PMID 7912191. S2CID 13656613.
  4. Gutnikov SA, Gaffan D (June 1996). "Systemic NMDA receptor antagonist CGP-40116 does not impair memory acquisition but protects against NMDA neurotoxicity in rhesus monkeys". The Journal of Neuroscience. 16 (12): 4041–5. doi:10.1523/JNEUROSCI.16-12-04041.1996. PMC 6578604. PMID 8656297.
  5. Maj J, Klimek V, Gołembiowska K, Rogóz Z, Skuza G (1993). "Central effects of repeated treatment with CGP 37849, a competitive NMDA receptor antagonist with potential antidepressant activity". Polish Journal of Pharmacology. 45 (5–6): 455–66. PMID 7912134.
  6. Papp M, Moryl E (September 1994). "Antidepressant activity of non-competitive and competitive NMDA receptor antagonists in a chronic mild stress model of depression". European Journal of Pharmacology. 263 (1–2): 1–7. doi:10.1016/0014-2999(94)90516-9. PMID 7821340.
  7. Jessa M, Nazar M, Bidzinski A, Plaznik A (March 1996). "The effects of repeated administration of diazepam, MK-801 and CGP 37849 on rat behavior in two models of anxiety". European Neuropsychopharmacology. 6 (1): 55–61. doi:10.1016/0924-977x(95)00068-z. PMID 8866939. S2CID 45953054.
  8. Przegaliński E, Tatarczyńska E, Chojnacka-Wójcik E (July 2000). "The influence of the benzodiazepine receptor antagonist flumazenil on the anxiolytic-like effects of CGP 37849 and ACPC in rats". Neuropharmacology. 39 (10): 1858–64. doi:10.1016/s0028-3908(00)00023-x. PMID 10884566. S2CID 33660694.
Ionotropic glutamate receptor modulators
AMPARTooltip α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor
KARTooltip Kainate receptor
NMDARTooltip N-Methyl-D-aspartate receptor
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