ELTOPRAZINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C12H16N2O2
Molecular Weight	220.2676
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C1CN(CCN1)C2=CC=CC3=C2OCCO3

InChI

InChIKey=WVLHGCRWEHCIOT-UHFFFAOYSA-N

InChI=1S/C12H16N2O2/c1-2-10(14-6-4-13-5-7-14)12-11(3-1)15-8-9-16-12/h1-3,13H,4-9H2

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Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1982626 | https://clinicaltrials.gov/ct2/show/NCT02439125 | https://clinicaltrials.gov/ct2/show/NCT01266174

Eltoprazine, a 5-HT1A/B receptor partial agonist, was created by Duphar in the 1980s (as DU-28853) and was subsequently developed by Solvay to treat pathological aggression. This drug is in clinical development for the treatment of Parkinson's disease levodopa-induced dyskinesia (PD-LID), Alzheimer's aggression and adult attention deficit hyperactivity disorder (adult ADHD). In addition, was shown, that the drug could be useful for normalizing prefrontal cognitive abilities, reducing aggression and impulsivity, and improving cognitive function in schizophrenia.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
5-hydroxytryptamine receptor 1A 54 Target ID: P08908 Gene ID: 3350.0 Gene Symbol: HTR1A Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/1982626	Partial Agonist 290		40.0 nM [Ki]
5-hydroxytryptamine receptor 1B 21 Target ID: P28222 Gene ID: 3351.0 Gene Symbol: HTR1B Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/1982626	Partial Agonist 290		52.0 nM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Drug-induced dyskinesia 4 Sources: https://clinicaltrials.gov/ct2/show/NCT02439125	Primary	Phase II 1132	Unknown Approved Use Unknown
Schizophrenia 298 Sources: https://clinicaltrials.gov/ct2/show/NCT01266174	Primary	Phase II 1132	Unknown Approved Use Unknown
Attention deficit hyperactivity disorder 68 Sources: https://www.amarantus.com/news/press-releases/detail/1644/amarantus-provides-program-update-on-phase-2b-eltoprazine	Primary	Phase II 1132	Unknown Approved Use Unknown
Alzheimer's aggression 2 Sources: https://www.amarantus.com/news/press-releases/detail/2033/amarantus-announces-positive-phase-2-data-for-eltoprazine	Primary	Phase II 1132	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
62.9 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1761079	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:		ELTOPRAZINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

AUC

Value	Dose	Co-administered	Analyte	Population
746 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1761079	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:		ELTOPRAZINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

T_1/2

Value	Dose	Co-administered	Analyte	Population
5.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1761079	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:		ELTOPRAZINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
9.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2288834	8 mg single, intravenous dose: 8 mg route of administration: Intravenous experiment type: SINGLE co-administered:		ELTOPRAZINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

PubMed

Title	Date	PubMed
		252159897
Comparison of hippocampal G protein activation by 5-HT(1A) receptor agonists and the atypical antipsychotics clozapine and S16924.	2003 Sep	12923612
New 3-[4-(2,3-dihydro-14-benzodioxin-5-yl)piperazin-1-yl]-1-(5-substituted benzo[b]thiophen-3-yl)propanol derivatives with dual action at 5-HT(1A) serotonin receptors and serotonin transporter as a new class of antidepressants.	2004 Jul	15296084
The roles of different types of serotonin receptors in activation of the hypophyseal-testicular complex induced in mice by the presence of a female.	2004 Oct	15587814
5-HT1A and 5-HT1B receptor agonists and aggression: a pharmacological challenge of the serotonin deficiency hypothesis.	2005 Dec 5	16310183
Efficient single nucleotide polymorphism discovery in laboratory rat strains using wild rat-derived SNP candidates.	2005 Nov 29	16316463
Delay aversion: effects of 7-OH-DPAT, 5-HT1A/1B-receptor stimulation and D-cycloserine.	2006 Dec	17208285
Anxiety in mice: a principal component analysis study.	2007	17502910

Patents

Sample Use Guides

In Vivo Use Guide

eltoprazine HCl 2.5; 5 or 7.5 mg capsules to be taken orally b.i.d. (ie, 5 mg/day) for 3 weeks

Route of Administration: Oral

In Vitro Use Guide

There was localized and characterized the binding sites of [3H]eltoprazine in the rat brain. The binding of [3H]eltoprazine to whole tissue sections was saturable and revealed an apparent dissociation constant (Kd) of 11 nM. Autoradiographic studies demonstrated a widespread distribution of [3H]eltoprazine binding sites throughout the brain. Specific [3H]eltoprazine binding was completely displaced by 5-HT; conversely, unlabeled eltoprazine reduced [3H]5-HT binding to the levels of non-specific binding. The pharmacological and anatomical data indicate that eltoprazine binds to 5-HT1A, 5-HT1B and to a lesser extent to 5-HT1C binding sites in the rat brain.

Name

Type

Language

ELTOPRAZINE

Official Name

English

eltoprazine [INN]

Common Name

English

ELTOPRAZINE [MART.]

Common Name

English

ELTOPRAZINE [MI]

Common Name

English

1-(1,4-BENZODIOXAN-5-YL)PIPERAZINE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C47794