PRELADENANT

Details

Stereochemistry	ACHIRAL
Molecular Formula	C25H29N9O3
Molecular Weight	503.5563
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COCCOC1=CC=C(C=C1)N2CCN(CCN3N=CC4=C3N=C(N)N5N=C(N=C45)C6=CC=CO6)CC2

InChI

InChIKey=DTYWJKSSUANMHD-UHFFFAOYSA-N

InChI=1S/C25H29N9O3/c1-35-15-16-36-19-6-4-18(5-7-19)32-11-8-31(9-12-32)10-13-33-23-20(17-27-33)24-28-22(21-3-2-14-37-21)30-34(24)25(26)29-23/h2-7,14,17H,8-13,15-16H2,1H3,(H2,26,29)

HIDE SMILES / InChI

Molecular Formula	C25H29N9O3
Molecular Weight	503.5563
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/20878595
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/19332567

Preladenant (SCH-420814) is an adenosine A(2A) receptor antagonist with a high affinity and very high selectivity for adenosine A(2A) receptors, which is being developed by Merck & Co Inc (following its acquisition of Schering-Plough Corp) for the potential treatment of Parkinson's disease. Preladenant is a potent competitive antagonist of the human A2Areceptor (Ki = 1.1 nM) and has >1000-fold selectivity over all other adenosine receptors, making this compound the most selective A2A receptor antagonist reported to date. Preladenant was being researched as a potential treatment for Parkinson's disease. Positive results were reported in Phase II clinical trials in humans, but it did not prove itself to be more effective than a placebo during Phase III trials, and so was discontinued in May 2013.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Adenosine A2a receptor 30 Target ID: CHEMBL251 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19332567	Antagonist 2778		1.1 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Parkinson's disease 226 Sources: http://adisinsight.springer.com/drugs/800006597	Primary		Phase III 656	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
478 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22676397	50 mg 1 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered:	PRELADENANT plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
90.8 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22676397	10 mg 1 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered:	PRELADENANT plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
857 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22676397	200 mg 1 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered:	PRELADENANT plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
846 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22676397	100 mg 1 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered:	PRELADENANT plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
254 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22676397	25 mg 1 times / day multiple, oral dose: 25 mg route of administration: Oral experiment type: MULTIPLE co-administered:	PRELADENANT plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Analyte	Population
2266 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22676397	50 mg 1 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered:	PRELADENANT plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
260 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22676397	10 mg 1 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered:	PRELADENANT plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
3312 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22676397	200 mg 1 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered:	PRELADENANT plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
3339 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22676397	100 mg 1 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered:	PRELADENANT plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
696 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22676397	25 mg 1 times / day multiple, oral dose: 25 mg route of administration: Oral experiment type: MULTIPLE co-administered:	PRELADENANT plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Analyte	Population
12.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22676397	50 mg 1 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered:	PRELADENANT plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
2.64 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22676397	10 mg 1 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered:	PRELADENANT plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
16.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22676397	200 mg 1 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered:	PRELADENANT plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
15.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22676397	100 mg 1 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered:	PRELADENANT plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
3.66 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22676397	25 mg 1 times / day multiple, oral dose: 25 mg route of administration: Oral experiment type: MULTIPLE co-administered:	PRELADENANT plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

Doses

Dose	Population	Adverse events
10 mg 2 times / day multiple, oral (unknown) Highest studied dose Dose: 10 mg, 2 times / day Route: oral Route: multiple Dose: 10 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/28490648	unhealthy n = 200 Health Status: unhealthy Condition: Parkinson disease Sex: M+F Food Status: UNKNOWN Population Size: 200 Sources: https://pubmed.ncbi.nlm.nih.gov/28490648	Disc. AE: Adverse event... AEs leading to discontinuation/dose reduction: Adverse event (5%) Sources: https://pubmed.ncbi.nlm.nih.gov/28490648

AEs

AE	Significance	Dose	Population
Adverse event	5% Disc. AE	10 mg 2 times / day multiple, oral (unknown) Highest studied dose Dose: 10 mg, 2 times / day Route: oral Route: multiple Dose: 10 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/28490648	unhealthy n = 200 Health Status: unhealthy Condition: Parkinson disease Sex: M+F Food Status: UNKNOWN Population Size: 200 Sources: https://pubmed.ncbi.nlm.nih.gov/28490648

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY100653	https://www.001chemical.com/chem/search?q=DY100653
1PlusChem LLC	1P0078E6	https://www.1pchem.com/search?query=1P0078E6
A2B Chem	AD36670	http://a2bchem.com/prod/AD36670
AChemBlock	R16063	http://www.achemblock.com/catalogsearch/result/?q=R16063
AK Scientific	4830AB	https://aksci.com/item_detail.php?cat=4830AB
AbovChem LLC	AC050943	http://www.abovchem.com/pc/en/product_list.aspx?wd=AC050943
Accela ChemBio Inc	SY031359	http://accelachem.com/cn/search.html?keyword=SY031359&attname=0
Ambeed	A120930	http://www.ambeed.com/search/Search.html?keyword=A120930
ApexBio Technology	A3735	https://www.apexbt.com/catalogsearch/result/?q=A3735
AstaTech	83199	http://astatechinc.com/CPSResult.php?CRNO=83199
BOC Sciences	377727-87-2	http://www.bocsci.com/description.asp?cas=377727-87-2
Chem Scene	CS-0999	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0999
ChemDiv	BB95-8044	http://chemistryondemand.com:8080/eShop/search_results.jsp?idnumber=BB95-8044
ChemShuttle	113976	https://www.chemshuttle.com/catalogsearch/result/?q=113976
Combi-Blocks	QK-7623	http://www.combi-blocks.com/cgi-bin/find.cgi?QK-7623
Debye Scientific	DA-42600	https://www.debyesci.com/index.php?id=product&ext[cno]=DA-42600
Excenen	EX-A1325	http://www.excenen.com/searchresultlist.php?id=EX-A1325
KeyOrganics	DS-14327	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=DS-14327
Lab Seeker	SC-86949	http://www.labseeker.com/search.php?keywords=SC-86949&category=0
LabSeeker	SC-86949	http://www.labseeker.com/search.php?keywords=SC-86949&category=0
Matrix Scientific	96394	http://www.matrixscientific.com/096394.html
MedChem Express	HY-10889	https://www.medchemexpress.com/search.html?q=HY-10889&ft=&fa=&fp=
MolPort	MolPort-023-333-316	https://www.molport.com/shop/molecule-link/MolPort-023-333-316
Molcore	MC100653	http://www.molcore.com/CatMC100653.html
Molnova	M14304	https://www.molnova.com/en/serch-list.html?keywords=M14304
MuseChem	I003387	https://www.musechem.com/product/I003387.html
ShangHai Biochempartner	BCP000605	http://www.biochempartner.com/search_BCP000605
ShangHai Biochempartner	BCP05239	http://www.biochempartner.com/search_BCP05239
TargetMol	T4290	https://www.targetmol.com/search?keyword=T4290
Toronto Research Chemicals	P712600	https://www.trc-canada.com/product-detail/?CatNum=P712600
Wonderchem	WD060OQ	http://www.wonder-chem.com/search.html?text=WD060OQ
eMolecules	42854702	https://orderbb.emolecules.com/search/#?query=42854702
eNovation Chemicals	D374793	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D374793&searchbtn.x=0&searchbtn.y=0
mcule	MCULE-7590424843	https://mcule.com/MCULE-7590424843/

PubMed

Title	Date	PubMed
Blocking striatal adenosine A2A receptors: a new strategy for basal ganglia disorders.	2007 Jan	18221214
Potent, selective, and orally active adenosine A2A receptor antagonists: arylpiperazine derivatives of pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidines.	2007 Mar 1	17236762

Patents

Sample Use Guides

In Vivo Use Guide

2, 5, or 10 mg tablets taken orally twice daily (BID)

Route of Administration: Oral

In Vitro Use Guide

Preladenant [1 uM] prevented the adenosine-induced process retraction in activated murine microglia

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:52:59 GMT 2023` Edited by `admin` on `Fri Dec 15 15:52:59 GMT 2023`
Record UNII	950O97NUPO
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PRELADENANT

Official Name

English

2-(Furan-2-yl)-7-[2-[4-[4-(2-methoxyethoxy)phenyl]piperazin-1-yl]ethyl]-7H-pyrazolo[4,3-E][1,2,4]triazolo[1,5-c]pyrimidin-5-amine

Systematic Name

English

SCH-420814

Code

English

SCH 420814

Code

English

Preladenant [WHO-DD]

Common Name

English

PRELADENANT [USAN]

Common Name

English

MK-3814

Code

English

preladenant [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C38149