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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 of PRELADENANT

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
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
1.1 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
478 ng/mL
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
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
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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
2266 ng × h/mL
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
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
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
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
12.3 h
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
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
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
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
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

Doses

DosePopulationAdverse 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:
unhealthy
n = 200
Health Status: unhealthy
Condition: Parkinson disease
Sex: M+F
Food Status: UNKNOWN
Population Size: 200
Sources:
Disc. AE: Adverse event...
AEs leading to
discontinuation/dose reduction:
Adverse event (5%)
Sources:
AEs

AEs

AESignificanceDosePopulation
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:
unhealthy
n = 200
Health Status: unhealthy
Condition: Parkinson disease
Sex: M+F
Food Status: UNKNOWN
Population Size: 200
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Potent and selective adenosine A2A receptor antagonists: 1,2,4-Triazolo[1,5-c]pyrimidines.
2009 Feb 1
Characterization of the potent and highly selective A2A receptor antagonists preladenant and SCH 412348 [7-[2-[4-2,4-difluorophenyl]-1-piperazinyl]ethyl]-2-(2-furanyl)-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine] in rodent models of movement disorders and depression.
2009 Jul
Novel investigational adenosine A2A receptor antagonists for Parkinson's disease.
2009 Nov
Preladenant, a novel adenosine A(2A) receptor antagonist for the potential treatment of parkinsonism and other disorders.
2010 Oct
Preladenant, a selective A(2A) receptor antagonist, is active in primate models of movement disorders.
2010 Oct
Discovery of phosphoric acid mono-{2-[(E/Z)-4-(3,3-dimethyl-butyrylamino)-3,5-difluoro-benzoylimino]-thiazol-3-ylmethyl} ester (Lu AA47070): a phosphonooxymethylene prodrug of a potent and selective hA(2A) receptor antagonist.
2011 Feb 10
The metabotropic glutamate receptor 4-positive allosteric modulator VU0364770 produces efficacy alone and in combination with L-DOPA or an adenosine 2A antagonist in preclinical rodent models of Parkinson's disease.
2012 Feb
Patents

Patents

Sample Use Guides

2, 5, or 10 mg tablets taken orally twice daily (BID)
Route of Administration: Oral
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
  • Download
Name Type Language
PRELADENANT
INN   USAN   WHO-DD  
INN   USAN  
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
Created by admin on Fri Dec 15 15:52:59 GMT 2023 , Edited by admin on Fri Dec 15 15:52:59 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C76394
Created by admin on Fri Dec 15 15:52:59 GMT 2023 , Edited by admin on Fri Dec 15 15:52:59 GMT 2023
PRIMARY
DRUG BANK
DB11864
Created by admin on Fri Dec 15 15:52:59 GMT 2023 , Edited by admin on Fri Dec 15 15:52:59 GMT 2023
PRIMARY
WIKIPEDIA
PRELADENANT
Created by admin on Fri Dec 15 15:52:59 GMT 2023 , Edited by admin on Fri Dec 15 15:52:59 GMT 2023
PRIMARY
CAS
377727-87-2
Created by admin on Fri Dec 15 15:52:59 GMT 2023 , Edited by admin on Fri Dec 15 15:52:59 GMT 2023
PRIMARY
FDA UNII
950O97NUPO
Created by admin on Fri Dec 15 15:52:59 GMT 2023 , Edited by admin on Fri Dec 15 15:52:59 GMT 2023
PRIMARY
PUBCHEM
10117987
Created by admin on Fri Dec 15 15:52:59 GMT 2023 , Edited by admin on Fri Dec 15 15:52:59 GMT 2023
PRIMARY
USAN
SS-73
Created by admin on Fri Dec 15 15:52:59 GMT 2023 , Edited by admin on Fri Dec 15 15:52:59 GMT 2023
PRIMARY
EVMPD
SUB126822
Created by admin on Fri Dec 15 15:52:59 GMT 2023 , Edited by admin on Fri Dec 15 15:52:59 GMT 2023
PRIMARY
INN
8880
Created by admin on Fri Dec 15 15:52:59 GMT 2023 , Edited by admin on Fri Dec 15 15:52:59 GMT 2023
PRIMARY
SMS_ID
100000153027
Created by admin on Fri Dec 15 15:52:59 GMT 2023 , Edited by admin on Fri Dec 15 15:52:59 GMT 2023
PRIMARY
EPA CompTox
DTXSID90191219
Created by admin on Fri Dec 15 15:52:59 GMT 2023 , Edited by admin on Fri Dec 15 15:52:59 GMT 2023
PRIMARY
ChEMBL
CHEMBL240624
Created by admin on Fri Dec 15 15:52:59 GMT 2023 , Edited by admin on Fri Dec 15 15:52:59 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
Approximately 1000-fold more selective over other ARs.
Ki
Related Record Type Details
ACTIVE MOIETY