U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C24H24FN3O2
Molecular Weight 405.4647
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ADOPRAZINE

SMILES

FC1=CC=C(C=C1)C2=CN=CC(CN3CCN(CC3)C4=CC=CC5=C4OCCO5)=C2

InChI

InChIKey=IUVSEUFHPNITEQ-UHFFFAOYSA-N
InChI=1S/C24H24FN3O2/c25-21-6-4-19(5-7-21)20-14-18(15-26-16-20)17-27-8-10-28(11-9-27)22-2-1-3-23-24(22)30-13-12-29-23/h1-7,14-16H,8-13,17H2

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including http://www.solvay.com/en/binaries/20080930_Pharma-135290.pdf

Adoprazine (SVL-313) is a full 5-HT1A receptor agonist and full D2/3 receptor antagonist possessing characteristics of an atypical antipsychotic, representing a potential novel treatment for schizophrenia and bipolar disorder. This drug together with some others, e.g. Mazapertine succinate, PF-217830 was discontinued from clinical trials due to either non-optimal pharmacokinetic properties or insufficient therapeutical efficacy.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
9.0 null [pEC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Drug as perpetrator​

Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
PubMed

PubMed

TitleDatePubMed
Novel antipsychotic agents with 5-HT(1A) agonist properties: role of 5-HT(1A) receptor activation in attenuation of catalepsy induction in rats.
2005 Aug
SAR study of 1-aryl-4-(phenylarylmethyl)piperazines as ligands for both dopamine D2 and serotonin 5-HT1A receptors showing varying degrees of (Ant)agonism. Selection of a potential atypical antipsychotic.
2006 Sep
SLV313 (1-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-4- [5-(4-fluoro-phenyl)-pyridin-3-ylmethyl]-piperazine monohydrochloride): a novel dopamine D2 receptor antagonist and 5-HT1A receptor agonist potential antipsychotic drug.
2007 Jan
Principal component analysis differentiates the receptor binding profiles of three antipsychotic drug candidates from current antipsychotic drugs.
2007 Oct 18
Differences among conventional, atypical and novel putative D(2)/5-HT(1A) antipsychotics on catalepsy-associated behaviour in cynomolgus monkeys.
2009 Nov 5
Patents

Patents

Sample Use Guides

ablets taken once daily for 14 days
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment: SLV313 (ADOPRAZINE) possessed high affinity at human recombinant D(2), D(3), D(4), 5-HT(2B), and 5-HT(1A) receptors, moderate affinity at 5-HT(7) and weak affinity at 5-HT(2A) receptors, with little-no affinity at 5-HT(4), 5-HT(6), alpha(1), and alpha(2) (rat), H(1) (guinea pig), M(1), M(4), 5-HT(3) receptors, and the 5-HT transporter. SLV313 had full agonist activity at cloned h5-HT(1A) receptors (pEC(50)=9.0) and full antagonist activity at hD(2) (pA(2)=9.3) and hD(3) (pA(2)=8.9) receptors.
Unknown
Name Type Language
ADOPRAZINE
INN   WHO-DD  
INN  
Official Name English
1-(2,3-DIHYDRO-1,4-BENZODIOXIN-5-YL)-4-((5-(4-FLUOROPHENYL)PYRIDIN-3-YL)METHYL)PIPERAZINE
Systematic Name English
Adoprazine [WHO-DD]
Common Name English
adoprazine [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C265
Created by admin on Fri Dec 15 16:10:36 GMT 2023 , Edited by admin on Fri Dec 15 16:10:36 GMT 2023
Code System Code Type Description
FDA UNII
7SNB18Q89D
Created by admin on Fri Dec 15 16:10:36 GMT 2023 , Edited by admin on Fri Dec 15 16:10:36 GMT 2023
PRIMARY
SMS_ID
300000037041
Created by admin on Fri Dec 15 16:10:36 GMT 2023 , Edited by admin on Fri Dec 15 16:10:36 GMT 2023
PRIMARY
INN
8980
Created by admin on Fri Dec 15 16:10:36 GMT 2023 , Edited by admin on Fri Dec 15 16:10:36 GMT 2023
PRIMARY
PUBCHEM
9887537
Created by admin on Fri Dec 15 16:10:36 GMT 2023 , Edited by admin on Fri Dec 15 16:10:36 GMT 2023
PRIMARY
CAS
222551-17-9
Created by admin on Fri Dec 15 16:10:36 GMT 2023 , Edited by admin on Fri Dec 15 16:10:36 GMT 2023
PRIMARY
EPA CompTox
DTXSID40944914
Created by admin on Fri Dec 15 16:10:36 GMT 2023 , Edited by admin on Fri Dec 15 16:10:36 GMT 2023
PRIMARY
NCI_THESAURUS
C81482
Created by admin on Fri Dec 15 16:10:36 GMT 2023 , Edited by admin on Fri Dec 15 16:10:36 GMT 2023
PRIMARY