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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
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
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

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2678
 9.0 null [pEC50]
Antagonist
2778
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase I
428
Unknown

Approved Use

Unknown
Primary
Phase I
428
Unknown

Approved Use

Unknown
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
1587
inhibitor
1767
inhibitor
1852

OverviewOther

Other InhibitorOther SubstrateOther Inducer
P-gp
1537
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP2C9
1819
 yes [IC50 10.684 uM]
CYP3A4
1925
 yes [IC50 4.7724 uM]
CYP2D6
1891
 yes [IC50 9.5221 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
P-gp
1537
 no
Sourcing

Sourcing

Vendor/AggregatorIDURL
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

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

20070049576
12

Sample Use Guides

In Vivo Use Guide
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
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:10:36 UTC 2023
Edited
by admin
on Fri Dec 15 16:10:36 UTC 2023
Record UNII
7SNB18Q89D
Record Status Validated (UNII)
Record Version
  • Download
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 UTC 2023 , Edited by admin on Fri Dec 15 16:10:36 UTC 2023
Code System Code Type Description
FDA UNII
7SNB18Q89D
Created by admin on Fri Dec 15 16:10:36 UTC 2023 , Edited by admin on Fri Dec 15 16:10:36 UTC 2023
PRIMARY
SMS_ID
300000037041
Created by admin on Fri Dec 15 16:10:36 UTC 2023 , Edited by admin on Fri Dec 15 16:10:36 UTC 2023
PRIMARY
INN
8980
Created by admin on Fri Dec 15 16:10:36 UTC 2023 , Edited by admin on Fri Dec 15 16:10:36 UTC 2023
PRIMARY
PUBCHEM
9887537
Created by admin on Fri Dec 15 16:10:36 UTC 2023 , Edited by admin on Fri Dec 15 16:10:36 UTC 2023
PRIMARY
CAS
222551-17-9
Created by admin on Fri Dec 15 16:10:36 UTC 2023 , Edited by admin on Fri Dec 15 16:10:36 UTC 2023
PRIMARY
EPA CompTox
DTXSID40944914
Created by admin on Fri Dec 15 16:10:36 UTC 2023 , Edited by admin on Fri Dec 15 16:10:36 UTC 2023
PRIMARY
NCI_THESAURUS
C81482
Created by admin on Fri Dec 15 16:10:36 UTC 2023 , Edited by admin on Fri Dec 15 16:10:36 UTC 2023
PRIMARY
Related Record Type Details
D(3) DOPAMINE RECEPTOR
TARGET -> INHIBITOR
D(2) DOPAMINE RECEPTOR
TARGET -> INHIBITOR
5-HYDROXYTRYPTAMINE RECEPTOR 1A
TARGET -> AGONIST
Structure of ADOPRAZINE HYDROCHLORIDE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of ADOPRAZINE
ACTIVE MOIETY
NIH
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