APLINDORE FUMARATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H18N2O3.C4H4O4
Molecular Weight	426.4193
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)\C=C\C(O)=O.O=C1CC2=C(N1)C=CC3=C2O[C@@H](CNCC4=CC=CC=C4)CO3

InChI

InChIKey=GELJVTSEGKGLDF-QDSMGTAFSA-N

InChI=1S/C18H18N2O3.C4H4O4/c21-17-8-14-15(20-17)6-7-16-18(14)23-13(11-22-16)10-19-9-12-4-2-1-3-5-12;5-3(6)1-2-4(7)8/h1-7,13,19H,8-11H2,(H,20,21);1-2H,(H,5,6)(H,7,8)/b;2-1+/t13-;/m0./s1

HIDE SMILES / InChI

Molecular Formula	C4H4O4
Molecular Weight	116.0722
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Molecular Formula	C18H18N2O3
Molecular Weight	310.3471
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17056032
Curator's Comment: description was created based on several sources, including: http://www.businesswire.com/news/home/20081014005485/en/Neurogen-Announces-Positive-Results-Aplindore-Restless-Legs | http://adisinsight.springer.com/drugs/800016255

Aplindore (DAB-452) is a small molecule that displays potent dopamine D2 receptor partial agonist activity in in vitro and in vivo assays and is predicted to have antipsychotic efficacy without motor side effects. Aplindore had been in phase II clinical trials for the treatment of Parkinson's disease and restless legs syndrome. Aplindore was generally well tolerated and there were no withdrawals due to adverse events and no serious adverse events.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Dopamine D2 receptor 290 Target ID: CHEMBL217 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17056032	Partial Agonist 283	9.1 null [pKi]
Dopamine D3 receptor 89 Target ID: CHEMBL234 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17056032	Binding Agent 1037	8.54 null [pKi]
Dopamine D4 receptor 69 Target ID: CHEMBL219 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17056032	Binding Agent 1037	7.21 null [pKi]
Serotonin 1a (5-HT1a) receptor 171 Target ID: CHEMBL273 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17056032	Binding Agent 1037	7.64 null [pKi]
Serotonin 2a (5-HT2a) receptor 229 Target ID: CHEMBL322 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17056032	Binding Agent 1037	4.87 null [pKi]
Adrenergic receptor alpha-1 167 Target ID: CHEMBL1907610 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17056032	Binding Agent 1037	6.83 null [pKi]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Restless legs syndrome 16 Sources: https://clinicaltrials.gov/ct2/show/NCT00834327 http://adisinsight.springer.com/drugs/800016255	Palliative		Phase II 1133	Unknown Approved Use Unknown
Early Parkinson's disease 2 Sources: https://clinicaltrials.gov/ct2/show/NCT00809302 https://www.ncbi.nlm.nih.gov/pubmed/19834698	Primary		Phase II 1133	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
Chemspace	CSC011146959	https://chem-space.com/CSC011146959
Chemspace	CSC030516506	https://chem-space.com/CSC030516506
Compound Cloud	158784
Compound Cloud	6440763
Enamine	BBV-78187139	http://www.enaminestore.com/catalog/BBV-78187139
Enamine	BBV-78214655	http://www.enaminestore.com/catalog/BBV-78214655
MuseChem	I002596	https://www.musechem.com/product/I002596.html
eMolecules	76745247	https://orderbb.emolecules.com/search/#?query=76745247

PubMed

Title	Date	PubMed

Patents

Sample Use Guides

In Vivo Use Guide

1, 3, and 6 mg twice daily

Route of Administration: Oral

In Vitro Use Guide

CHO-D2S-Gαq/o cells were challenged with various doses (up to 10 uM) of aplindore, aripiprazole and quinpirole in the absence and presence of quinpirole (10 nM). Aplindore (at 10 uM, Emax= 56 ± 1%, in the absence and 58 ± 2% in the presence of quinpirole) showed less antagonist activity than aripiprazole (at 10 uM, Emax= 33 ± 6% and 50 ± 2%, respectively) on quinpirole-mediated [Ca2+]i response.

Substance Class	Chemical Created by `admin` on `Fri Dec 16 18:39:28 UTC 2022` Edited by `admin` on `Fri Dec 16 18:39:28 UTC 2022`
Record UNII	P13TV5A758
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

APLINDORE FUMARATE

Official Name

English

DAB-452

Code

English

8H-1,4-DIOXINO(2,3-E)INDOL-8-ONE, 2,3,7,9-TETRAHYDRO-2-(((PHENYLMETHYL)AMINO)METHYL)-, (2S)-, (2E)-2-BUTENEDIOTATE (1:1)

Common Name

English

(2S)-2-((BENZYLAMINO)METHYL)-2,3,7,9-TETRAHYDRO-8H-1,4-DIOXINO(2,3-E)INDOL-8-ONE (E)-BUTENEDIOATE (1:1)

Systematic Name

English

APLINDORE FUMARATE [USAN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C66884