ADOPRAZINE

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 Search

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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24164194
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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Serotonin 1a (5-HT1a) receptor 172 Target ID: CHEMBL214 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16710314	Agonist 2678		9.0 null [pEC50]
Dopamine receptors; D2 & D3 3 Target ID: CHEMBL2095169 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16710314	Antagonist 2778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Schizophrenia 298 Sources: https://clinicaltrials.gov/ct2/show/NCT00620568	Primary		Phase I 428	Unknown Approved Use Unknown
Bipolar disorder 34 Sources: http://www.solvay.com/en/binaries/20080930_Pharma-135290.pdf	Primary		Phase I 428	Unknown Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587	inhibitor 1767	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	P-gp 1537

Drug as perpetrator

Target	Modality	Activity
CYP2C9 1819	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645842#sid=363678304	yes [IC50 10.684 uM]
CYP3A4 1925	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645841#sid=363678304	yes [IC50 4.7724 uM]
CYP2D6 1891	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645840#sid=363678304	yes [IC50 9.5221 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 1537	substrate 3367 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1346987#sid=363678304	no

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00BFIN	https://www.1pchem.com/search?query=1P00BFIN
AK Scientific	3422AH	https://aksci.com/item_detail.php?cat=3422AH
BLD Pharm	BD630557	http://www.bldpharm.com/search/Search.html?keyword=BD630557
BOC Sciences	222551-17-9	http://www.bocsci.com/description.asp?cas=222551-17-9
Chem Scene	CS-0673	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0673
MedChem Express	HY-14782	https://www.medchemexpress.com/search.html?q=HY-14782&ft=&fa=&fp=
MolPort	MolPort-039-139-539	https://www.molport.com/shop/molecule-link/MolPort-039-139-539
MuseChem	I001228	https://www.musechem.com/product/I001228.html
eMolecules	44811502	https://orderbb.emolecules.com/search/#?query=44811502
mcule	MCULE-3822913051	https://mcule.com/MCULE-3822913051/

PubMed

Title	Date	PubMed
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	15996562
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	16946546
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	16710314
Principal component analysis differentiates the receptor binding profiles of three antipsychotic drug candidates from current antipsychotic drugs.	2007 Oct 18	17880057
Differences among conventional, atypical and novel putative D(2)/5-HT(1A) antipsychotics on catalepsy-associated behaviour in cynomolgus monkeys.	2009 Nov 5	19464324

Patents

Sample Use Guides

In Vivo Use Guide

ablets taken once daily for 14 days

Route of Administration: Oral

In Vitro Use Guide

Unknown

Name

Type

Language

ADOPRAZINE

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