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
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)
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/20878595Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/19332567
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 |
---|---|---|---|
Target ID: CHEMBL251 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19332567 |
1.1 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | 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 | Co-administered | 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 |
T1/2
Value | Dose | Co-administered | 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: |
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
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: |
unhealthy n = 200 Health Status: unhealthy Condition: Parkinson disease Sex: M+F Food Status: UNKNOWN Population Size: 200 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Potent and selective adenosine A2A receptor antagonists: 1,2,4-Triazolo[1,5-c]pyrimidines. | 2009 Feb 1 |
|
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
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT01294800
2, 5, or 10 mg tablets taken orally twice daily (BID)
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24807189
Preladenant [1 uM] prevented the adenosine-induced process retraction in activated murine microglia
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Systematic Name | English | ||
|
Code | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
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 | ||
---|---|---|---|---|---|
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 |
ACTIVE MOIETY