Details
Stereochemistry | RACEMIC |
Molecular Formula | C7H14NO5P |
Molecular Weight | 223.1635 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)[C@@H]1C[C@H](CP(O)(O)=O)CCN1
InChI
InChIKey=LPMRCCNDNGONCD-RITPCOANSA-N
InChI=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
Molecular Formula | C7H14NO5P |
Molecular Weight | 223.1635 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/2899170 | https://www.ncbi.nlm.nih.gov/pubmed/23766625 | https://www.ncbi.nlm.nih.gov/pubmed/2850065 | https://www.ncbi.nlm.nih.gov/pubmed/2547931 | https://www.ncbi.nlm.nih.gov/pubmed/10657404 | https://www.ncbi.nlm.nih.gov/pubmed/10541229https://www.ncbi.nlm.nih.gov/pubmed/2899170
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2899170 | https://www.ncbi.nlm.nih.gov/pubmed/23766625 | https://www.ncbi.nlm.nih.gov/pubmed/2850065 | https://www.ncbi.nlm.nih.gov/pubmed/2547931 | https://www.ncbi.nlm.nih.gov/pubmed/10657404 | https://www.ncbi.nlm.nih.gov/pubmed/10541229https://www.ncbi.nlm.nih.gov/pubmed/2899170
(+)-selfotel ((+)-CGS-19755) is an enantiomer of selfotel, a competitive antagonist at N-methyl-D-aspartate (NMDA)-preferring receptors. The inhibition of NMDA-evoked ACh release from rat striatal slices is stereospecific, with the (+)-enantiomer less potent than the (-)-enantiomer.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1907608 |
50.0 nM [IC50] | ||
Target ID: CHEMBL1907608 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2899170 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
20676 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7709405 |
2 mg/kg single, intravenous dose: 2 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
SELFOTEL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
31622 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7709405 |
2 mg/kg single, intravenous dose: 2 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
SELFOTEL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7709405 |
2 mg/kg single, intravenous dose: 2 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
SELFOTEL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
2 mg/kg single, intravenous Highest studied dose Dose: 2 mg/kg Route: intravenous Route: single Dose: 2 mg/kg Sources: |
unhealthy, ADULT n = 6 Health Status: unhealthy Condition: stroke Age Group: ADULT Sex: M Food Status: UNKNOWN Population Size: 6 Sources: |
Other AEs: Agitation, Confusion... Other AEs: Agitation (66.7%) Sources: Confusion (50%) Delirium (33.3%) Paranoid reaction (50%) Coordination abnormal (16.7%) Aphasia (16.7%) Hallucination (50%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Aphasia | 16.7% | 2 mg/kg single, intravenous Highest studied dose Dose: 2 mg/kg Route: intravenous Route: single Dose: 2 mg/kg Sources: |
unhealthy, ADULT n = 6 Health Status: unhealthy Condition: stroke Age Group: ADULT Sex: M Food Status: UNKNOWN Population Size: 6 Sources: |
Coordination abnormal | 16.7% | 2 mg/kg single, intravenous Highest studied dose Dose: 2 mg/kg Route: intravenous Route: single Dose: 2 mg/kg Sources: |
unhealthy, ADULT n = 6 Health Status: unhealthy Condition: stroke Age Group: ADULT Sex: M Food Status: UNKNOWN Population Size: 6 Sources: |
Delirium | 33.3% | 2 mg/kg single, intravenous Highest studied dose Dose: 2 mg/kg Route: intravenous Route: single Dose: 2 mg/kg Sources: |
unhealthy, ADULT n = 6 Health Status: unhealthy Condition: stroke Age Group: ADULT Sex: M Food Status: UNKNOWN Population Size: 6 Sources: |
Confusion | 50% | 2 mg/kg single, intravenous Highest studied dose Dose: 2 mg/kg Route: intravenous Route: single Dose: 2 mg/kg Sources: |
unhealthy, ADULT n = 6 Health Status: unhealthy Condition: stroke Age Group: ADULT Sex: M Food Status: UNKNOWN Population Size: 6 Sources: |
Hallucination | 50% | 2 mg/kg single, intravenous Highest studied dose Dose: 2 mg/kg Route: intravenous Route: single Dose: 2 mg/kg Sources: |
unhealthy, ADULT n = 6 Health Status: unhealthy Condition: stroke Age Group: ADULT Sex: M Food Status: UNKNOWN Population Size: 6 Sources: |
Paranoid reaction | 50% | 2 mg/kg single, intravenous Highest studied dose Dose: 2 mg/kg Route: intravenous Route: single Dose: 2 mg/kg Sources: |
unhealthy, ADULT n = 6 Health Status: unhealthy Condition: stroke Age Group: ADULT Sex: M Food Status: UNKNOWN Population Size: 6 Sources: |
Agitation | 66.7% | 2 mg/kg single, intravenous Highest studied dose Dose: 2 mg/kg Route: intravenous Route: single Dose: 2 mg/kg Sources: |
unhealthy, ADULT n = 6 Health Status: unhealthy Condition: stroke Age Group: ADULT Sex: M Food Status: UNKNOWN Population Size: 6 Sources: |
PubMed
Title | Date | PubMed |
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CGS 19755, a selective and competitive N-methyl-D-aspartate-type excitatory amino acid receptor antagonist. | 1988 Jul |
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Yohimbine-induced seizures involve NMDA and GABAergic transmission. | 1992 Apr |
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Glutamatergic antagonism: effects on lidocaine-induced seizures in the rat. | 1994 Oct |
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Anticonvulsant efficacy of N-methyl-D-aspartate antagonists against convulsions induced by cocaine. | 1999 May |
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The 26th Congress of the Scandinavian Society of Anaesthesiology and Intensive Care Medicine, Tromso, Norway, 13-17 June 2001. | 2001 Aug |
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A comparative assessment of the efficacy and side-effect liability of neuroprotective compounds in experimental stroke. | 2001 Feb 23 |
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Regional distribution and pharmacological characteristics of [3H]N-acetyl-aspartyl-glutamate (NAAG) binding sites in rat brain. | 2001 Jan |
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Effects of antagonism of NMDA receptors on transient lower esophageal sphincter relaxations in the dog. | 2001 Nov 16 |
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Glutamate AMPA receptor antagonist treatment for ischaemic stroke. | 2002 |
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Antiepileptic drugs and agents that inhibit voltage-gated sodium channels prevent NMDA antagonist neurotoxicity. | 2002 |
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Why did NMDA receptor antagonists fail clinical trials for stroke and traumatic brain injury? | 2002 Oct |
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Excitatory amino acid antagonists for acute stroke. | 2003 |
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Stroke: trial by jury. | 2003 |
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NMDA-evoked consumption and recovery of mitochondrially targeted aequorin suggests increased Ca2+ uptake by a subset of mitochondria in hippocampal neurons. | 2003 Dec 12 |
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Glutamate receptor antagonists modulate heat shock protein response in focal brain ischemia. | 2003 Mar |
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Cannabinoid CB1 receptor activation does not prevent the toxicity of glutamate towards embryonic chick telencephalon primary cultures. | 2003 Nov |
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Neuroprotective effects of N-methyl-D-aspartate receptor antagonist on aspartate induced neurotoxicity in the spinal cord in vivo. | 2003 Oct |
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Lessons from epidemiologic studies in clinical trials of traumatic brain injury. | 2004 |
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Nicotine exerts a permissive role on NMDA receptor function in hippocampal noradrenergic terminals. | 2004 Jul |
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The rise and fall of NMDA antagonists for ischemic stroke. | 2004 Mar |
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Neuroprotection against ischemic/hypoxic brain damage: blockers of ionotropic glutamate receptor and voltage sensitive calcium channels. | 2004 Oct |
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Acute nociceptive somatic stimulus sensitizes neurones in the spinal cord to colonic distension in the rat. | 2004 Oct 1 |
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Cerebral perfusion pressure and risk of brain hypoxia in severe head injury: a prospective observational study. | 2005 |
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Cognitive effects of dopaminergic and glutamatergic blockade in nucleus accumbens in pigeons. | 2005 Aug |
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Homocysteine, a risk factor for atherosclerosis, biphasically changes the endothelial production of kynurenic acid. | 2005 Jul 11 |
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Effects of the N-methyl-D-aspartate receptor antagonist perzinfotel [EAA-090; [2-(8,9-dioxo-2,6-diazabicyclo[5.2.0]non-1(7)-en-2-yl)-ethyl]phosphonic acid] on chemically induced thermal hypersensitivity. | 2005 Jun |
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The NMDA receptor complex: a long and winding road to therapeutics. | 2005 Mar |
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Methodological quality of animal studies on neuroprotection in focal cerebral ischaemia. | 2005 Sep |
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Severe brain injury ICU outcomes are associated with Cranial-Arterial Pressure Index and noninvasive Bispectral Index and transcranial oxygen saturation: a prospective, preliminary study. | 2006 |
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Glutamate receptors in neuroinflammatory demyelinating disease. | 2006 |
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The NMDA receptor antagonist CGS 19755 disrupts recovery following cerebellar lesions. | 2006 |
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Some prognostic models for traumatic brain injury were not valid. | 2006 Feb |
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Neuroprotection associated with alternative splicing of NMDA receptors in rat cortical neurons. | 2006 Mar |
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NMDA receptor activity in learning spatial procedural strategies II. The influence of cerebellar lesions. | 2006 Oct 16 |
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NMDA receptor activity in learning spatial procedural strategies I. The influence of hippocampal lesions. | 2006 Oct 16 |
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Acute D2/D3 dopaminergic agonism but chronic D2/D3 antagonism prevents NMDA antagonist neurotoxicity. | 2006 Sep 15 |
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Intracranial pressure monitoring in intensive care: clinical advantages of a computerized system over manual recording. | 2007 |
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Increased cerebral oxygen consumption in Eker rats and effects of N-methyl-D-aspartate blockade: Implications for autism. | 2007 Aug 15 |
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Repeated treatment with N-methyl-d-aspartate antagonists in neonatal, but not adult, rats causes long-term deficits of radial-arm maze learning. | 2007 Sep 12 |
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Risks associated with magnetic resonance imaging and cervical collar in comatose, blunt trauma patients with negative comprehensive cervical spine computed tomography and no apparent spinal deficit. | 2008 |
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Pharmacology of traumatic brain injury: where is the "golden bullet"? | 2008 Nov-Dec |
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Molecular mechanisms of traumatic brain injury: the missing link in management. | 2009 Feb 2 |
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NMDA-mediated modulation of dopamine release is modified in rat prefrontal cortex and nucleus accumbens after chronic nicotine treatment. | 2009 Jan |
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Cerebral vasospasm following traumatic subarachnoid hemorrhage. | 2009 Nov |
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Resistin is associated with mortality in patients with traumatic brain injury. | 2010 |
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Integrative emphases on intimate, intrinsic propensity/pathological processes--causes of self recovery limits and also, subtle related targets for neuroprotectionl pleiotropicity/multimodal actions, by accessible therapeutic approaches--in spinal cord injuries. | 2010 Jul-Sep |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10657404
Two pivotal phase 3 ischemic stroke trials tested the hypothesis, by double-blind, randomized, placebo-controlled parallel design, that a single intravenous 1.5 mg/kg dose of Selfotel, administered within 6 hours of stroke onset, would improve functional outcome at 90 days, defined as the proportion of patients achieving a Barthel Index score of >/=60. The trials were performed in patients aged 40 to 85 years with acute ischemic hemispheric stroke and a motor deficit.
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2899170
Selfotel (CGS 19755 [cis-4-phosphonomethyl-2-piperidine carboxylic acid]) was found to be a potent, stereospecific inhibitor of N-methyl-D-aspartate (NMDA)-evoked, but not KCl-evoked, [3H] acetylcholine release from slices of the rat striatum. The concentration-response curve to NMDA was shifted to the right by CGS 19755 (pA2 = 5.94), suggesting a competitive interaction with NMDA-type receptors.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 15:51:19 GMT 2023
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on
Sat Dec 16 15:51:19 GMT 2023
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Record UNII |
4VGJ4A41L2
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Record Status |
Validated (UNII)
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Record Version |
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WIKIPEDIA |
NMDA receptor antagonist
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NCI_THESAURUS |
C1509
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110347-85-8
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4VGJ4A41L2
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6843
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CC-92
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C152322
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SELFOTEL
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CHEMBL39664
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DTXSID5045675
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C053672
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68736
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100000084108
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Related Record | Type | Details | ||
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TARGET -> INHIBITOR |
BINDING
IC50
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ENANTIOMER -> RACEMATE |
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ENANTIOMER -> RACEMATE |
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TARGET -> INHIBITOR |
COMPETITIVE INHIBITOR
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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