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

Molecular Formula	C24H24FN3O2
Molecular Weight	405.4647
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
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
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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:10:36 GMT 2023` Edited by `admin` on `Fri Dec 15 16:10:36 GMT 2023`
Record UNII	7SNB18Q89D
Record Status	`Validated (UNII)`
Record Version

Download

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