Preladenant
Preladenant, also known as SCH 420814, is a potent and selective antagonist at the adenosine A2A receptor, which 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.
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Chemical Information
| Name | Preladenant |
|---|---|
| Iupac Chemical Name | 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 |
| Synonyms | SCH420814; SCH-420814; SCH 420814; MK-3814; MK 3814; MK3814; Preladenant |
| Molecular Formula | C25H29N9O3 |
| Molecular Weight | 503.567 |
| Smile | NC1=NC(N(CCN2CCN(C3=CC=C(OCCOC)C=C3)CC2)N=C4)=C4C5=NC(C6=CC=CO6)=NN15 |
| InChiKey | DTYWJKSSUANMHD-UHFFFAOYSA-N |
| InChi | 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) |
| CAS Number | 377727-87-2 |
| Related CAS |
Ordering Information
| Packaging | Price | Availability | Purity | Shipping Time |
|---|---|---|---|---|
| Bulk | Enquiry | Enquiry | Enquiry |
| Formulation | Solid powder |
|---|---|
| Purity | 98% Min. |
| Storage | Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years). |
| Solubility | Soluble in DMSO |
| Handling | |
| Shipping Condition | Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs. |
| HS Code |
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| Mechanism | |
| Cell study | |
| Animal study | |
| Clinical study |
1: Hauser RA, Stocchi F, Rascol O, Huyck SB, Capece R, Ho TW, Sklar P, Lines C, Michelson D, Hewitt D. Preladenant as an Adjunctive Therapy With Levodopa in Parkinson Disease: Two Randomized Clinical Trials and Lessons Learned. JAMA Neurol. 2015 Dec 1;72(12):1491-500. doi: 10.1001/jamaneurol.2015.2268. PubMed PMID: 26523919.
2: Zhou X, Khanapur S, Huizing AP, Zijlma R, Schepers M, Dierckx RA, van Waarde A, de Vries EF, Elsinga PH. Synthesis and preclinical evaluation of 2-(2-furanyl)-7-[2-[4-[4-(2-[11C]methoxyethoxy)phenyl]-1-piperazinyl]ethyl]7H-pyr azolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine-5-amine ([11C]Preladenant) as a PET tracer for the imaging of cerebral adenosine A2A receptors. J Med Chem. 2014 Nov 13;57(21):9204-10. doi: 10.1021/jm501065t. Epub 2014 Oct 15. PubMed PMID: 25279444.
3: Barret O, Hannestad J, Alagille D, Vala C, Tavares A, Papin C, Morley T, Fowles K, Lee H, Seibyl J, Tytgat D, Laruelle M, Tamagnan G. Adenosine 2A receptor occupancy by tozadenant and preladenant in rhesus monkeys. J Nucl Med. 2014 Oct;55(10):1712-8. doi: 10.2967/jnumed.114.142067. Epub 2014 Jul 31. PubMed PMID: 25082853.
4: Wang Z, Xuan F, Lin WH, Troyer MD, Tendolkar A, Cutler DL. Preladenant, a selective adenosine A₂A receptor antagonist, is not associated with QT/QTc prolongation. Eur J Clin Pharmacol. 2013 Oct;69(10):1761-7. doi: 10.1007/s00228-013-1541-5. Epub 2013 Jul 16. PubMed PMID: 23857248.
5: Factor SA, Wolski K, Togasaki DM, Huyck S, Cantillon M, Ho TW, Hauser RA, Pourcher E. Long-term safety and efficacy of preladenant in subjects with fluctuating Parkinson's disease. Mov Disord. 2013 Jun;28(6):817-20. doi: 10.1002/mds.25395. Epub 2013 Apr 15. PubMed PMID: 23589371.
6: Rosse G. Metabolites of the pyrimidine amine preladenant as adenosine a2a receptor antagonists. ACS Med Chem Lett. 2012 Nov 30;4(1):5-6. doi: 10.1021/ml300397j. eCollection 2013 Jan 10. PubMed PMID: 24900549; PubMed Central PMCID: PMC4027435.
7: Cutler DL, Tendolkar A, Grachev ID. Safety, tolerability and pharmacokinetics after single and multiple doses of preladenant (SCH420814) administered in healthy subjects. J Clin Pharm Ther. 2012 Oct;37(5):578-87. doi: 10.1111/j.1365-2710.2012.01349.x. Epub 2012 Jun 7. PubMed PMID: 22676397.
8: Cutler DL, Tendolkar A, Grachev ID. Evaluation of the effects of a high-fat meal on the oral bioavailability of a single dose of preladenant in healthy subjects. J Clin Pharmacol. 2012 Nov;52(11):1698-703. doi: 10.1177/0091270011428321. Epub 2011 Dec 13. PubMed PMID: 22167566.
9: Hauser RA, Cantillon M, Pourcher E, Micheli F, Mok V, Onofrj M, Huyck S, Wolski K. Preladenant in patients with Parkinson's disease and motor fluctuations: a phase 2, double-blind, randomised trial. Lancet Neurol. 2011 Mar;10(3):221-9. doi: 10.1016/S1474-4422(11)70012-6. PubMed PMID: 21315654.
10: Salamone JD. Preladenant, a novel adenosine A(2A) receptor antagonist for the potential treatment of parkinsonism and other disorders. IDrugs. 2010 Oct;13(10):723-31. Review. PubMed PMID: 20878595.
11: Hodgson RA, Bedard PJ, Varty GB, Kazdoba TM, Di Paolo T, Grzelak ME, Pond AJ, Hadjtahar A, Belanger N, Gregoire L, Dare A, Neustadt BR, Stamford AW, Hunter JC. Preladenant, a selective A(2A) receptor antagonist, is active in primate models of movement disorders. Exp Neurol. 2010 Oct;225(2):384-90. doi: 10.1016/j.expneurol.2010.07.011. Epub 2010 Jul 23. PubMed PMID: 20655910.
12: Hodgson RA, Bertorelli R, Varty GB, Lachowicz JE, Forlani A, Fredduzzi S, Cohen-Williams ME, Higgins GA, Impagnatiello F, Nicolussi E, Parra LE, Foster C, Zhai Y, Neustadt BR, Stamford AW, Parker EM, Reggiani A, Hunter JC. 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. J Pharmacol Exp Ther. 2009 Jul;330(1):294-303. doi: 10.1124/jpet.108.149617. Epub 2009 Mar 30. PubMed PMID: 19332567.
Chemical Structure
