Selfotel: Difference between revisions
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{{Short description|Chemical compound}} |
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{{Drugbox |
{{Drugbox |
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| Verifiedfields = changed |
| Verifiedfields = changed |
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| verifiedrevid = |
| verifiedrevid = 450847044 |
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| IUPAC_name = (2''S'',4''R'')-4-(phosphonomethyl)piperidine-2-carboxylic acid |
| IUPAC_name = (2''S'',4''R'')-4-(phosphonomethyl)piperidine-2-carboxylic acid |
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| image = Selfotel.png |
| image = Selfotel.png |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 39664 |
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| width = 280 |
| width = 280 |
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| protein_bound = |
| protein_bound = |
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| metabolism = |
| metabolism = |
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| excretion = |
| excretion = |
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<!--Identifiers--> |
<!--Identifiers--> |
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| IUPHAR_ligand = 4155 |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 110347-85-8 |
| CAS_number = 110347-85-8 |
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| ATC_prefix = |
| ATC_prefix = |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = |
| DrugBank = |
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| UNII_Ref = {{fdacite| |
| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 4VGJ4A41L2 |
| UNII = 4VGJ4A41L2 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D02410 |
| KEGG = D02410 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 61982 |
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<!--Chemical data--> |
<!--Chemical data--> |
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| C=7 | H=14 | N=1 | O=5 | P=1 |
| C=7 | H=14 | N=1 | O=5 | P=1 |
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| molecular_weight = 223.164 g/mol |
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| smiles = C1CN[C@@H](C[C@@H]1CP(=O)(O)O)C(=O)O |
| smiles = C1CN[C@@H](C[C@@H]1CP(=O)(O)O)C(=O)O |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C7H14NO5P/c9-7(10)6-3-5(1-2-8-6)4-14(11,12)13/h5-6,8H,1-4H2,(H,9,10)(H2,11,12,13)/t5-,6+/m1/s1 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = LPMRCCNDNGONCD-RITPCOANSA-N |
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| synonyms = Selfotel |
| synonyms = Selfotel |
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⚫ | '''Selfotel''' ('''CGS-19755''') is a drug which acts as a competitive [[NMDA antagonist]], directly competing with [[glutamate]] for binding to the receptor.<ref>{{cite journal | vauthors = Lehmann J, Hutchison AJ, McPherson SE, Mondadori C, Schmutz M, Sinton CM, Tsai C, Murphy DE, Steel DJ, Williams M | display-authors = 6 | title = CGS 19755, a selective and competitive N-methyl-D-aspartate-type excitatory amino acid receptor antagonist | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 246 | issue = 1 | pages = 65–75 | date = July 1988 | pmid = 2899170 }}</ref> Initial studies showed it to have [[anticonvulsant]], [[anxiolytic]], [[analgesic]] and [[neuroprotective]] effects,<ref>{{cite journal | vauthors = Bennett DA, Lehmann J, Bernard PS, Liebman JM, Williams M, Wood PL, Boast CA, Hutchison AJ | display-authors = 6 | title = CGS 19755: a novel competitive N-methyl-D-aspartate (NMDA) receptor antagonist with anticonvulsant, anxiolytic and anti-ischemic properties | journal = Progress in Clinical and Biological Research | volume = 361 | pages = 519–24 | pmid = 1981269 | year = 1990 }}</ref><ref>{{cite journal | vauthors = France CP, Winger GD, Woods JH | title = Analgesic, anesthetic, and respiratory effects of the competitive N-methyl-D-aspartate (NMDA) antagonist CGS 19755 in rhesus monkeys | journal = Brain Research | volume = 526 | issue = 2 | pages = 355–8 | date = September 1990 | pmid = 2257491 | doi = 10.1016/0006-8993(90)91247-e | hdl = 2027.42/28393 | hdl-access = free }}</ref> and it was originally researched for the treatment of [[stroke]],<ref>{{cite journal | vauthors = Grotta J, Clark W, Coull B, Pettigrew LC, Mackay B, Goldstein LB, Meissner I, Murphy D, LaRue L | display-authors = 6 | title = Safety and tolerability of the glutamate antagonist CGS 19755 (Selfotel) in patients with acute ischemic stroke. Results of a phase IIa randomized trial | journal = Stroke | volume = 26 | issue = 4 | pages = 602–5 | date = April 1995 | pmid = 7709405 | doi = 10.1161/01.str.26.4.602 }}</ref> but subsequent animal and human studies showed [[phencyclidine]]-like effects,<ref>{{cite journal | vauthors = Bennett DA, Bernard PS, Amrick CL, Wilson DE, Liebman JM, Hutchison AJ | title = Behavioral pharmacological profile of CGS 19755, a competitive antagonist at N-methyl-D-aspartate receptors | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 250 | issue = 2 | pages = 454–60 | date = August 1989 | pmid = 2547931 }}</ref><ref>{{cite journal | vauthors = Koek W, Woods JH, Colpaert FC | title = N-methyl-D-aspartate antagonism and phencyclidine-like activity: a drug discrimination analysis | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 253 | issue = 3 | pages = 1017–25 | date = June 1990 | pmid = 2193142 }}</ref><ref>{{cite journal | vauthors = Lu Y, France CP, Woods JH | title = Tolerance to the cataleptic effect of the N-methyl-D-aspartate (NMDA) receptor antagonists in pigeons: cross-tolerance between PCP-like compounds and competitive NMDA antagonists | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 263 | issue = 2 | pages = 499–504 | date = November 1992 | pmid = 1432686 }}</ref><ref>{{cite journal | vauthors = Baron SP, Woods JH | title = Competitive and uncompetitive N-methyl-D-aspartate antagonist discriminations in pigeons: CGS 19755 and phencyclidine | journal = Psychopharmacology | volume = 118 | issue = 1 | pages = 42–51 | date = March 1995 | pmid = 7597121 | doi = 10.1007/bf02245248 | hdl = 2027.42/46346 | hdl-access = free }}</ref> as well as limited efficacy and evidence for possible [[neurotoxicity]] under some conditions,<ref>{{cite journal | vauthors = Morris GF, Bullock R, Marshall SB, Marmarou A, Maas A, Marshall LF | title = Failure of the competitive N-methyl-D-aspartate antagonist Selfotel (CGS 19755) in the treatment of severe head injury: results of two phase III clinical trials. The Selfotel Investigators | journal = Journal of Neurosurgery | volume = 91 | issue = 5 | pages = 737–43 | date = November 1999 | pmid = 10541229 | doi = 10.3171/jns.1999.91.5.0737 }}</ref><ref>{{cite journal | vauthors = Davis SM, Lees KR, Albers GW, Diener HC, Markabi S, Karlsson G, Norris J | title = Selfotel in acute ischemic stroke : possible neurotoxic effects of an NMDA antagonist | journal = Stroke | volume = 31 | issue = 2 | pages = 347–54 | date = February 2000 | pmid = 10657404 | doi = 10.1161/01.str.31.2.347 | doi-access = free }}</ref><ref>{{cite journal | vauthors = Dawson DA, Wadsworth G, Palmer AM | title = A comparative assessment of the efficacy and side-effect liability of neuroprotective compounds in experimental stroke | journal = Brain Research | volume = 892 | issue = 2 | pages = 344–50 | date = February 2001 | pmid = 11172782 | doi = 10.1016/s0006-8993(00)03269-8 | s2cid = 8793348 }}</ref> and so clinical development was ultimately discontinued.<ref>{{cite journal | vauthors = Ikonomidou C, Turski L | title = Why did NMDA receptor antagonists fail clinical trials for stroke and traumatic brain injury? | journal = The Lancet. Neurology | volume = 1 | issue = 6 | pages = 383–6 | date = October 2002 | pmid = 12849400 | doi = 10.1016/s1474-4422(02)00164-3 | s2cid = 31477519 }}</ref><ref>{{cite book | vauthors = Farin A, Marshall LF | chapter = Lessons from epidemiologic studies in clinical trials of traumatic brain injury | title = Mechanisms of Secondary Brain Damage from Trauma and Ischemia | journal = Acta Neurochirurgica. Supplement | volume = 89 | pages = 101–7 | pmid = 15335108 | doi = 10.1007/978-3-7091-0603-7_14 | year = 2004 | isbn = 978-3-7091-7206-3 }}</ref> |
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⚫ | '''Selfotel''' ('''CGS-19755''') is a drug which acts as a competitive [[NMDA antagonist]], directly competing with [[glutamate]] for binding to the receptor.<ref>Lehmann J, Hutchison AJ, McPherson SE, Mondadori C, Schmutz M, Sinton CM, Tsai C, Murphy DE, Steel DJ, Williams M |
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{{reflist}} |
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{{Hallucinogens}} |
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{{Ionotropic glutamate receptor modulators}} |
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[[Category:Dissociative drugs]] |
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{{Glutamate_receptor_ligands}} |
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[[Category:NMDA receptor antagonists]] |
[[Category:NMDA receptor antagonists]] |
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[[Category:Phosphonic acids]] |
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[[Category:Piperidines]] |
[[Category:Piperidines]] |
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[[Category: |
[[Category:Abandoned drugs]] |
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