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Details

Stereochemistry ACHIRAL
Molecular Formula C20H23N3O2.ClH
Molecular Weight 373.876
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of E-52862 HYDROCHLORIDE

SMILES

Cl.CC1=CC(OCCN2CCOCC2)=NN1C3=CC4=C(C=CC=C4)C=C3

InChI

InChIKey=SHRYQZBTQDMGLZ-UHFFFAOYSA-N
InChI=1S/C20H23N3O2.ClH/c1-16-14-20(25-13-10-22-8-11-24-12-9-22)21-23(16)19-7-6-17-4-2-3-5-18(17)15-19;/h2-7,14-15H,8-13H2,1H3;1H

HIDE SMILES / InChI
Molecular Formula C20H23N3O2
Molecular Weight 337.4155
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/22784008 | https://www.ncbi.nlm.nih.gov/pubmed/22404321

E-52862, also known as sigma-1 receptor antagonist (API-001, S1RA) successfully completed Phase I clinical trials for the treatment of pain, showing good safety and tolerability, and a pharmacokinetic profile compatible with once a day oral administration.

CNS Activity

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Sigma non-opioid intracellular receptor 1
26
Target ID: Q99720|||Q7Z653
Gene ID: 10280.0
Gene Symbol: SIGMAR1
Target Organism: Homo sapiens (Human)
Antagonist
2778
 17.0 nM [Ki]
Antagonist
2778
 17.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase I
428
Unknown

Approved Use

Unknown
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
5580.1 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/26291080
800 mg single, oral
dose: 800 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
E-52862 plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
155911 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/26291080
800 mg single, oral
dose: 800 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
E-52862 plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
41.5 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/26291080
800 mg single, oral
dose: 800 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
E-52862 plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
Doses

Doses

DosePopulationAdverse events​
400 mg 1 times / day multiple, oral
Highest studied dose
Dose: 400 mg, 1 times / day
Route: oral
Route: multiple
Dose: 400 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/22607269/
healthy
n = 8
Health Status: healthy
Sex: M+F
Food Status: FASTED
Population Size: 8
Sources:
https://pubmed.ncbi.nlm.nih.gov/22607269/
Sources:
https://pubmed.ncbi.nlm.nih.gov/22607269/
800 mg single, oral (unknown)
Highest studied dose
Dose: 800 mg
Route: oral
Route: single
Dose: 800 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/22607269/
healthy
n = 31
Health Status: healthy
Sex: M+F
Food Status: FASTED
Population Size: 31
Sources:
https://pubmed.ncbi.nlm.nih.gov/22607269/
Other AEs: Dissociation, Euphoric mood...
Other AEs:
Dissociation (6.5%)
Euphoric mood (6.5%)
Dizziness (19.4%)
headache (19.4%)
Nausea (12.9%)
Abnormal thinking (9.7%)
Euphoric mood (3.2%)
Palpitations (3.2%)
Sinus tachycardia (6.5%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/22607269/
AEs

AEs

AESignificanceDosePopulation
Nausea 12.9%
800 mg single, oral (unknown)
Highest studied dose
Dose: 800 mg
Route: oral
Route: single
Dose: 800 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/22607269/
healthy
n = 31
Health Status: healthy
Sex: M+F
Food Status: FASTED
Population Size: 31
Sources:
https://pubmed.ncbi.nlm.nih.gov/22607269/
Dizziness 19.4%
800 mg single, oral (unknown)
Highest studied dose
Dose: 800 mg
Route: oral
Route: single
Dose: 800 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/22607269/
healthy
n = 31
Health Status: healthy
Sex: M+F
Food Status: FASTED
Population Size: 31
Sources:
https://pubmed.ncbi.nlm.nih.gov/22607269/
headache 19.4%
800 mg single, oral (unknown)
Highest studied dose
Dose: 800 mg
Route: oral
Route: single
Dose: 800 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/22607269/
healthy
n = 31
Health Status: healthy
Sex: M+F
Food Status: FASTED
Population Size: 31
Sources:
https://pubmed.ncbi.nlm.nih.gov/22607269/
Euphoric mood 3.2%
800 mg single, oral (unknown)
Highest studied dose
Dose: 800 mg
Route: oral
Route: single
Dose: 800 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/22607269/
healthy
n = 31
Health Status: healthy
Sex: M+F
Food Status: FASTED
Population Size: 31
Sources:
https://pubmed.ncbi.nlm.nih.gov/22607269/
Palpitations 3.2%
800 mg single, oral (unknown)
Highest studied dose
Dose: 800 mg
Route: oral
Route: single
Dose: 800 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/22607269/
healthy
n = 31
Health Status: healthy
Sex: M+F
Food Status: FASTED
Population Size: 31
Sources:
https://pubmed.ncbi.nlm.nih.gov/22607269/
Dissociation 6.5%
800 mg single, oral (unknown)
Highest studied dose
Dose: 800 mg
Route: oral
Route: single
Dose: 800 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/22607269/
healthy
n = 31
Health Status: healthy
Sex: M+F
Food Status: FASTED
Population Size: 31
Sources:
https://pubmed.ncbi.nlm.nih.gov/22607269/
Euphoric mood 6.5%
800 mg single, oral (unknown)
Highest studied dose
Dose: 800 mg
Route: oral
Route: single
Dose: 800 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/22607269/
healthy
n = 31
Health Status: healthy
Sex: M+F
Food Status: FASTED
Population Size: 31
Sources:
https://pubmed.ncbi.nlm.nih.gov/22607269/
Sinus tachycardia 6.5%
800 mg single, oral (unknown)
Highest studied dose
Dose: 800 mg
Route: oral
Route: single
Dose: 800 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/22607269/
healthy
n = 31
Health Status: healthy
Sex: M+F
Food Status: FASTED
Population Size: 31
Sources:
https://pubmed.ncbi.nlm.nih.gov/22607269/
Abnormal thinking 9.7%
800 mg single, oral (unknown)
Highest studied dose
Dose: 800 mg
Route: oral
Route: single
Dose: 800 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/22607269/
healthy
n = 31
Health Status: healthy
Sex: M+F
Food Status: FASTED
Population Size: 31
Sources:
https://pubmed.ncbi.nlm.nih.gov/22607269/
PubMed

PubMed

TitleDatePubMed
Pharmacological properties of S1RA, a new sigma-1 receptor antagonist that inhibits neuropathic pain and activity-induced spinal sensitization.
2012 Aug
Synthesis and biological evaluation of the 1-arylpyrazole class of σ(1) receptor antagonists: identification of 4-{2-[5-methyl-1-(naphthalen-2-yl)-1H-pyrazol-3-yloxy]ethyl}morpholine (S1RA, E-52862).
2012 Oct 11
Safety, tolerability and pharmacokinetics of single and multiple doses of a novel sigma-1 receptor antagonist in three randomized phase I studies.
2013 Jan
Effects of the selective sigma-1 receptor antagonist S1RA on formalin-induced pain behavior and neurotransmitter release in the spinal cord in rats.
2014 May
The selective sigma-1 receptor antagonist E-52862 attenuates neuropathic pain of different aetiology in rats.
2016 Apr 18
Patents

Patents

WO2016138135A1
2

Sample Use Guides

In Vivo Use Guide
In a phase II study, treatment with single 400 mg dose of E 52862 before hysterectomy showed a clinically relevant reduction in pain intensity up to 24 hours post-surgery and a meaningful reduction for the need of concomitant anti-emetic medication in patients undergoing abdominal hysterectomy.
Route of Administration: Oral
In Vitro Use Guide
30 uM S1RA (E-52862) inhibited the spinal nociceptive C-fibre–dependent wind-up phenom-enon found when trains of stimuli were applied
Substance Class Chemical
Created
by admin
on Sat Dec 16 11:10:41 GMT 2023
Edited
by admin
on Sat Dec 16 11:10:41 GMT 2023
Record UNII
18XZ7850YN
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
E-52862 HYDROCHLORIDE
Code English
S1RA HYDROCHLORIDE
Common Name English
P-027
Code English
Code System Code Type Description
FDA UNII
18XZ7850YN
Created by admin on Sat Dec 16 11:10:41 GMT 2023 , Edited by admin on Sat Dec 16 11:10:41 GMT 2023
PRIMARY
PUBCHEM
50914801
Created by admin on Sat Dec 16 11:10:41 GMT 2023 , Edited by admin on Sat Dec 16 11:10:41 GMT 2023
PRIMARY
SMS_ID
300000038540
Created by admin on Sat Dec 16 11:10:41 GMT 2023 , Edited by admin on Sat Dec 16 11:10:41 GMT 2023
PRIMARY
CAS
1265917-14-3
Created by admin on Sat Dec 16 11:10:41 GMT 2023 , Edited by admin on Sat Dec 16 11:10:41 GMT 2023
PRIMARY
Related Record Type Details
Structure of E-52862
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of E-52862
ACTIVE MOIETY
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