Tozadenant | CAS#870070-55-6 | adenosine A2A receptor antagonist

MedKoo Cat#: 319738 | Name: Tozadenant

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Tozadenant, also known as RO-4494351 and SYN115, is an oral, selective adenosine A2A receptor antagonist that improves motor function in animal models of Parkinson's disease. Adenosine A(2a) receptor antagonists reduce symptom severity in Parkinson disease (PD) and animal models. Rodent studies support the hypothesis that A(2a) antagonists produce this benefit by reducing the inhibitory output of the basal ganglia indirect pathway.

Chemical Structure

Tozadenant

CAS#870070-55-6

Theoretical Analysis

MedKoo Cat#: 319738

Name: Tozadenant

CAS#: 870070-55-6

Chemical Formula: C19H26N4O4S

Exact Mass: 406.1675

Molecular Weight: 406.50

Elemental Analysis: C, 56.14; H, 6.45; N, 13.78; O, 15.74; S, 7.89

Price and Availability

Size	Price	Availability	Quantity
25mg	USD 350.00
50mg	USD 550.00
100mg	USD 800.00

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Related CAS #

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Synonym

RO-4494351; RO4494351; RO 4494351; SYN115; SYN-115; SYN 115; RO4494351-002; RO4494351-000; Tozadenant

IUPAC/Chemical Name

4-hydroxy-N-(4-methoxy-7-morpholinobenzo[d]thiazol-2-yl)-4-methylpiperidine-1-carboxamide

InChi Key

XNBRWUQWSKXMPW-UHFFFAOYSA-N

InChi Code

InChI=1S/C19H26N4O4S/c1-19(25)5-7-23(8-6-19)18(24)21-17-20-15-14(26-2)4-3-13(16(15)28-17)22-9-11-27-12-10-22/h3-4,25H,5-12H2,1-2H3,(H,20,21,24)

SMILES Code

O=C(N1CCC(C)(O)CC1)NC2=NC3=C(OC)C=CC(N4CCOCC4)=C3S2

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

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.

Storage Condition

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, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 406.50 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Humpert S, Schneider D, Lang M, Schulze A, Neumaier F, Holschbach M, Bier D, Neumaier B. Radiosynthesis and In Vitro Evaluation of [11C]tozadenant as Adenosine A2A Receptor Radioligand. Molecules. 2024 Feb 29;29(5):1089. doi: 10.3390/molecules29051089. PMID: 38474602; PMCID: PMC10935082. 2: Gündel D, Toussaint M, Lai TH, Deuther-Conrad W, Cumming P, Schröder S, Teodoro R, Moldovan RP, Pan-Montojo F, Sattler B, Kopka K, Sabri O, Brust P. Quantitation of the A2A Adenosine Receptor Density in the Striatum of Mice and Pigs with [18F]FLUDA by Positron Emission Tomography. Pharmaceuticals (Basel). 2022 Apr 22;15(5):516. doi: 10.3390/ph15050516. PMID: 35631343; PMCID: PMC9146919. 3: Saini A, Patel R, Gaba S, Singh G, Gupta GD, Monga V. Adenosine receptor antagonists: Recent advances and therapeutic perspective. Eur J Med Chem. 2022 Jan 5;227:113907. doi: 10.1016/j.ejmech.2021.113907. Epub 2021 Oct 13. PMID: 34695776. 4: Renk DR, Skraban M, Bier D, Schulze A, Wabbals E, Wedekind F, Neumaier F, Neumaier B, Holschbach M. Design, synthesis and biological evaluation of Tozadenant analogues as adenosine A2A receptor ligands. Eur J Med Chem. 2021 Mar 15;214:113214. doi: 10.1016/j.ejmech.2021.113214. Epub 2021 Jan 30. PMID: 33548636. 5: Lai TH, Toussaint M, Teodoro R, Dukić-Stefanović S, Kranz M, Deuther-Conrad W, Moldovan RP, Brust P. Synthesis and Biological Evaluation of a Novel 18F-Labeled Radiotracer for PET Imaging of the Adenosine A2A Receptor. Int J Mol Sci. 2021 Jan 25;22(3):1182. doi: 10.3390/ijms22031182. PMID: 33504051; PMCID: PMC7865263. 6: LeWitt PA, Aradi SD, Hauser RA, Rascol O. The challenge of developing adenosine A2A antagonists for Parkinson disease: Istradefylline, preladenant, and tozadenant. Parkinsonism Relat Disord. 2020 Nov;80 Suppl 1:S54-S63. doi: 10.1016/j.parkreldis.2020.10.027. Epub 2020 Dec 19. PMID: 33349581. 7: Schneider A, Sari AT, Alhaddad H, Sari Y. Overview of Therapeutic Drugs and Methods for the Treatment of Parkinson's Disease. CNS Neurol Disord Drug Targets. 2020;19(3):195-206. doi: 10.2174/1871527319666200525011110. PMID: 32448109. 8: Lee BI, Park MH, Shin SH, Byeon JJ, Park Y, Kim N, Choi J, Shin YG. Quantitative Analysis of Tozadenant Using Liquid Chromatography-Mass Spectrometric Method in Rat Plasma and Its Human Pharmacokinetics Prediction Using Physiologically Based Pharmacokinetic Modeling. Molecules. 2019 Apr 2;24(7):1295. doi: 10.3390/molecules24071295. PMID: 30987056; PMCID: PMC6479388. 9: Cacciari B, Spalluto G, Federico S. A2A Adenosine Receptor Antagonists as Therapeutic Candidates: Are They Still an Interesting Challenge? Mini Rev Med Chem. 2018;18(14):1168-1174. doi: 10.2174/1389557518666180423113051. PMID: 29692248. 10: Yuan G, Jankins TC, Patrick CG Jr, Philbrook P, Sears O, Hatfield S, Sitkovsky M, Vasdev N, Liang SH, Ondrechen MJ, Pollastri MP, Jones GB. Fluorinated Adenosine A2A Receptor Antagonists Inspired by Preladenant as Potential Cancer Immunotherapeutics. Int J Med Chem. 2017;2017:4852537. doi: 10.1155/2017/4852537. Epub 2017 Oct 19. PMID: 29201461; PMCID: PMC5671725. 11: Michel A, Nicolas JM, Rose S, Jackson M, Colman P, Briône W, Sciberras D, Muglia P, Scheller DK, Citron M, Downey P. Antiparkinsonian effects of the "Radiprodil and Tozadenant" combination in MPTP-treated marmosets. PLoS One. 2017 Aug 30;12(8):e0182887. doi: 10.1371/journal.pone.0182887. PMID: 28854243; PMCID: PMC5576667. 12: Kim JW, Lee MN, Jeong BC, Oh SH, Kook MS, Koh JT. Chemical inhibitors of c-Met receptor tyrosine kinase stimulate osteoblast differentiation and bone regeneration. Eur J Pharmacol. 2017 Jul 5;806:10-17. doi: 10.1016/j.ejphar.2017.03.032. Epub 2017 Mar 16. PMID: 28322831. 13: Oertel W, Schulz JB. Current and experimental treatments of Parkinson disease: A guide for neuroscientists. J Neurochem. 2016 Oct;139 Suppl 1:325-337. doi: 10.1111/jnc.13750. Epub 2016 Aug 30. PMID: 27577098. 14: Mancel V, Mathy FX, Boulanger P, English S, Croft M, Kenney C, Knott T, Stockis A, Bani M. Pharmacokinetics and metabolism of [14C]-tozadenant (SYN-115), a novel A2a receptor antagonist ligand, in healthy volunteers. Xenobiotica. 2017 Aug;47(8):705-718. doi: 10.1080/00498254.2016.1221164. Epub 2016 Sep 2. PMID: 27489076. 15: Michel A, Downey P, Van Damme X, De Wolf C, Schwarting R, Scheller D. Behavioural Assessment of the A2a/NR2B Combination in the Unilateral 6-OHDA- Lesioned Rat Model: A New Method to Examine the Therapeutic Potential of Non- Dopaminergic Drugs. PLoS One. 2015 Aug 31;10(8):e0135949. doi: 10.1371/journal.pone.0135949. PMID: 26322641; PMCID: PMC4555651. 16: Rascol O, Perez-Lloret S, Ferreira JJ. New treatments for levodopa-induced motor complications. Mov Disord. 2015 Sep 15;30(11):1451-60. doi: 10.1002/mds.26362. Epub 2015 Aug 21. PMID: 26293004. 17: Pourcher E, Huot P. Adenosine 2A Receptor Antagonists for the Treatment of Motor Symptoms in Parkinson's Disease. Mov Disord Clin Pract. 2015 Jul 25;2(4):331-340. doi: 10.1002/mdc3.12187. Erratum in: Mov Disord Clin Pract. 2016 Jun 01;3(3):320. doi: 10.1002/mdc3.12357. PMID: 30363540; PMCID: PMC6178748. 18: Stewart SB, Koller JM, Campbell MC, Black KJ. Arterial spin labeling versus BOLD in direct challenge and drug-task interaction pharmacological fMRI. PeerJ. 2014 Dec 11;2:e687. doi: 10.7717/peerj.687. PMID: 25538867; PMCID: PMC4266850. 19: Michel A, Downey P, Nicolas JM, Scheller D. Unprecedented therapeutic potential with a combination of A2A/NR2B receptor antagonists as observed in the 6-OHDA lesioned rat model of Parkinson's disease. PLoS One. 2014 Dec 16;9(12):e114086. doi: 10.1371/journal.pone.0114086. PMID: 25513815; PMCID: PMC4267740. 20: 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. PMID: 25082853.