Details
| Stereochemistry | ABSOLUTE |
| 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
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 |
|---|---|---|
| CGS 19755, a selective and competitive N-methyl-D-aspartate-type excitatory amino acid receptor antagonist. | 1988 Jul |
|
| Yohimbine-induced seizures involve NMDA and GABAergic transmission. | 1992 Apr |
|
| Glutamatergic antagonism: effects on lidocaine-induced seizures in the rat. | 1994 Oct |
|
| Regional distribution and pharmacological characteristics of [3H]N-acetyl-aspartyl-glutamate (NAAG) binding sites in rat brain. | 2001 Jan |
|
| Effects of antagonism of NMDA receptors on transient lower esophageal sphincter relaxations in the dog. | 2001 Nov 16 |
|
| Why did NMDA receptor antagonists fail clinical trials for stroke and traumatic brain injury? | 2002 Oct |
|
| Excitatory amino acid antagonists for acute stroke. | 2003 |
|
| Stroke: trial by jury. | 2003 |
|
| NMDA-evoked consumption and recovery of mitochondrially targeted aequorin suggests increased Ca2+ uptake by a subset of mitochondria in hippocampal neurons. | 2003 Dec 12 |
|
| Glutamate receptor antagonists modulate heat shock protein response in focal brain ischemia. | 2003 Mar |
|
| Neuroprotective effects of N-methyl-D-aspartate receptor antagonist on aspartate induced neurotoxicity in the spinal cord in vivo. | 2003 Oct |
|
| Lessons from epidemiologic studies in clinical trials of traumatic brain injury. | 2004 |
|
| Cerebral perfusion pressure and risk of brain hypoxia in severe head injury: a prospective observational study. | 2005 |
|
| Glutamate receptors in neuroinflammatory demyelinating disease. | 2006 |
|
| The NMDA receptor antagonist CGS 19755 disrupts recovery following cerebellar lesions. | 2006 |
|
| Acute D2/D3 dopaminergic agonism but chronic D2/D3 antagonism prevents NMDA antagonist neurotoxicity. | 2006 Sep 15 |
|
| 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 |
|
| Resistin is associated with mortality in patients with traumatic brain injury. | 2010 |
Patents
Sample Use Guides
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
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 08:22:50 UTC 2023
by
admin
on
Sat Dec 16 08:22:50 UTC 2023
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| Record UNII |
N0905W44Y3
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| Record Status |
Validated (UNII)
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| Record Version |
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-
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113229-62-2
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68736
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admin on Sat Dec 16 08:22:50 UTC 2023 , Edited by admin on Sat Dec 16 08:22:50 UTC 2023
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| Related Record | Type | Details | ||
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ENANTIOMER -> ENANTIOMER |
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RACEMATE -> ENANTIOMER |
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