SELFOTEL

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 Search

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

Description
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Glutamate NMDA receptor 47 Target ID: CHEMBL1907608 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2899170 \| https://www.ncbi.nlm.nih.gov/pubmed/2850065	Antagonist 2849		50.0 nM [IC50]
Glutamate NMDA receptor 47 Target ID: CHEMBL1907608 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2899170	Antagonist 2849

Conditions

Condition	Modality	Highest Phase	Product
Head injury 5 Sources: http://adisinsight.springer.com/drugs/800001276 https://www.ncbi.nlm.nih.gov/pubmed/10541229 https://www.ncbi.nlm.nih.gov/pubmed/23766625	Primary	Phase III 665	Unknown Approved Use Unknown
Stroke 144 Sources: http://adisinsight.springer.com/drugs/800001276 https://www.ncbi.nlm.nih.gov/pubmed/10657404 https://www.ncbi.nlm.nih.gov/pubmed/23766625	Primary	Phase III 665	Unknown Approved Use Unknown
Unknown 2596

C_max

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

T_1/2

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: https://pubmed.ncbi.nlm.nih.gov/7709405	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7709405	Other AEs: Hallucination, Agitation... Other AEs: Hallucination (50%) Agitation (66.7%) Confusion (50%) Delirium (33.3%) Paranoid reaction (50%) Coordination abnormal (16.7%) Aphasia (16.7%) Sources: https://pubmed.ncbi.nlm.nih.gov/7709405

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: https://pubmed.ncbi.nlm.nih.gov/7709405	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7709405
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: https://pubmed.ncbi.nlm.nih.gov/7709405	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7709405
Delirium	33.3%	2 mg/kg single, intravenous Highest studied dose Dose: 2 mg/kg Route: intravenous Route: single Dose: 2 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/7709405	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7709405
Confusion	50%	2 mg/kg single, intravenous Highest studied dose Dose: 2 mg/kg Route: intravenous Route: single Dose: 2 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/7709405	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7709405
Hallucination	50%	2 mg/kg single, intravenous Highest studied dose Dose: 2 mg/kg Route: intravenous Route: single Dose: 2 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/7709405	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7709405
Paranoid reaction	50%	2 mg/kg single, intravenous Highest studied dose Dose: 2 mg/kg Route: intravenous Route: single Dose: 2 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/7709405	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7709405
Agitation	66.7%	2 mg/kg single, intravenous Highest studied dose Dose: 2 mg/kg Route: intravenous Route: single Dose: 2 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/7709405	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7709405

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inducer 1087			inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP19A1 429	P-gp 2052

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/743139#sid=144204496	no
CYP3A4 2633	inducer 1966 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1346984#sid=144204496	no

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 2052	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1346987#sid=144204496	no

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/588834#sid=144204496

PubMed

Title	Date	PubMed
Glutamatergic antagonism: effects on lidocaine-induced seizures in the rat.	1994 Oct	7943778
Antiepileptic drugs and agents that inhibit voltage-gated sodium channels prevent NMDA antagonist neurotoxicity.	2002	12192617
NMDA-evoked consumption and recovery of mitochondrially targeted aequorin suggests increased Ca2+ uptake by a subset of mitochondria in hippocampal neurons.	2003 Dec 12	14642837
Cerebral perfusion pressure and risk of brain hypoxia in severe head injury: a prospective observational study.	2005	16356218
Cognitive effects of dopaminergic and glutamatergic blockade in nucleus accumbens in pigeons.	2005 Aug	15979133
Homocysteine, a risk factor for atherosclerosis, biphasically changes the endothelial production of kynurenic acid.	2005 Jul 11	15961072
Methodological quality of animal studies on neuroprotection in focal cerebral ischaemia.	2005 Sep	16170651
Neuroprotection associated with alternative splicing of NMDA receptors in rat cortical neurons.	2006 Mar	16314856
Molecular mechanisms of traumatic brain injury: the missing link in management.	2009 Feb 2	19187555
NMDA-mediated modulation of dopamine release is modified in rat prefrontal cortex and nucleus accumbens after chronic nicotine treatment.	2009 Jan	19046354
Cerebral vasospasm following traumatic subarachnoid hemorrhage.	2009 Nov	21772907
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	20945817

Patents

Sample Use Guides

In Vivo Use Guide

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 `Wed Apr 02 06:52:48 GMT 2025` Edited by `admin` on `Wed Apr 02 06:52:48 GMT 2025`
Record UNII	4VGJ4A41L2
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SELFOTEL

Official Name

English

CGS 19755

Preferred 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

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