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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
Structure of SELFOTEL

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

HIDE SMILES / InChI

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

(+)-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.

CNS Activity

Approval Year

Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
20676 ng/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
31622 ng × h/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
2 h
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

Doses

DosePopulationAdverse 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%)
Confusion (50%)
Delirium (33.3%)
Paranoid reaction (50%)
Coordination abnormal (16.7%)
Aphasia (16.7%)
Hallucination (50%)
Sources:
AEs

AEs

AESignificanceDosePopulation
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:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
CGS 19755, a selective and competitive N-methyl-D-aspartate-type excitatory amino acid receptor antagonist.
1988 Jul
Glutamatergic antagonism: effects on lidocaine-induced seizures in the rat.
1994 Oct
Anticonvulsant efficacy of N-methyl-D-aspartate antagonists against convulsions induced by cocaine.
1999 May
The 26th Congress of the Scandinavian Society of Anaesthesiology and Intensive Care Medicine, Tromso, Norway, 13-17 June 2001.
2001 Aug
A comparative assessment of the efficacy and side-effect liability of neuroprotective compounds in experimental stroke.
2001 Feb 23
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
Cannabinoid CB1 receptor activation does not prevent the toxicity of glutamate towards embryonic chick telencephalon primary cultures.
2003 Nov
The rise and fall of NMDA antagonists for ischemic stroke.
2004 Mar
Cerebral perfusion pressure and risk of brain hypoxia in severe head injury: a prospective observational study.
2005
The NMDA receptor complex: a long and winding road to therapeutics.
2005 Mar
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
Glutamate receptors in neuroinflammatory demyelinating disease.
2006
The NMDA receptor antagonist CGS 19755 disrupts recovery following cerebellar lesions.
2006
Neuroprotection associated with alternative splicing of NMDA receptors in rat cortical neurons.
2006 Mar
Increased cerebral oxygen consumption in Eker rats and effects of N-methyl-D-aspartate blockade: Implications for autism.
2007 Aug 15
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
Cerebral vasospasm following traumatic subarachnoid hemorrhage.
2009 Nov
Patents

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
In Vitro Use Guide
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 Sat Dec 16 15:51:19 UTC 2023
Edited
by admin
on Sat Dec 16 15:51:19 UTC 2023
Record UNII
4VGJ4A41L2
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SELFOTEL
INN   MART.   USAN   WHO-DD  
USAN   INN  
Official Name English
SELFOTEL [USAN]
Common Name English
CPDD-0027
Code English
Selfotel [WHO-DD]
Common Name English
CGS-19755
Code English
SELFOTEL [MART.]
Common Name English
CIS-4-(PHOSPHONOMETHYL)-2-PIPERIDINE CARBOXYLIC ACID
Systematic Name English
2-PIPERIDINECARBOXYLIC ACID, 4-(PHOSPHONOMETHYL)-, CIS-
Common Name English
CGS 19755
Code English
selfotel [INN]
Common Name English
GNF-PF-157
Code English
2-PIPERIDINECARBOXYLIC ACID, 4-(PHOSPHONOMETHYL)-, (2R,4S)-REL-
Systematic Name English
Classification Tree Code System Code
WIKIPEDIA NMDA receptor antagonist
Created by admin on Sat Dec 16 15:51:20 UTC 2023 , Edited by admin on Sat Dec 16 15:51:20 UTC 2023
NCI_THESAURUS C1509
Created by admin on Sat Dec 16 15:51:20 UTC 2023 , Edited by admin on Sat Dec 16 15:51:20 UTC 2023
Code System Code Type Description
CAS
110347-85-8
Created by admin on Sat Dec 16 15:51:20 UTC 2023 , Edited by admin on Sat Dec 16 15:51:20 UTC 2023
PRIMARY
FDA UNII
4VGJ4A41L2
Created by admin on Sat Dec 16 15:51:20 UTC 2023 , Edited by admin on Sat Dec 16 15:51:20 UTC 2023
PRIMARY
INN
6843
Created by admin on Sat Dec 16 15:51:20 UTC 2023 , Edited by admin on Sat Dec 16 15:51:20 UTC 2023
PRIMARY
USAN
CC-92
Created by admin on Sat Dec 16 15:51:20 UTC 2023 , Edited by admin on Sat Dec 16 15:51:20 UTC 2023
PRIMARY
NCI_THESAURUS
C152322
Created by admin on Sat Dec 16 15:51:20 UTC 2023 , Edited by admin on Sat Dec 16 15:51:20 UTC 2023
PRIMARY
WIKIPEDIA
SELFOTEL
Created by admin on Sat Dec 16 15:51:20 UTC 2023 , Edited by admin on Sat Dec 16 15:51:20 UTC 2023
PRIMARY
ChEMBL
CHEMBL39664
Created by admin on Sat Dec 16 15:51:20 UTC 2023 , Edited by admin on Sat Dec 16 15:51:20 UTC 2023
PRIMARY
EPA CompTox
DTXSID5045675
Created by admin on Sat Dec 16 15:51:20 UTC 2023 , Edited by admin on Sat Dec 16 15:51:20 UTC 2023
PRIMARY
EVMPD
SUB10476MIG
Created by admin on Sat Dec 16 15:51:20 UTC 2023 , Edited by admin on Sat Dec 16 15:51:20 UTC 2023
PRIMARY
MESH
C053672
Created by admin on Sat Dec 16 15:51:20 UTC 2023 , Edited by admin on Sat Dec 16 15:51:20 UTC 2023
PRIMARY
PUBCHEM
68736
Created by admin on Sat Dec 16 15:51:20 UTC 2023 , Edited by admin on Sat Dec 16 15:51:20 UTC 2023
PRIMARY
SMS_ID
100000084108
Created by admin on Sat Dec 16 15:51:20 UTC 2023 , Edited by admin on Sat Dec 16 15:51:20 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
BINDING
IC50
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
TARGET -> INHIBITOR
COMPETITIVE INHIBITOR
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ACTIVE MOIETY