SCH-58261 | CAS#160098-96-4 | adenosine A(2A) receptor antagonist

MedKoo Cat#: 526655 | Name: SCH-58261

Description:

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

SCH-58261 is a potent and selective adenosine A(2A) receptor antagonist. SCH-58261 is a useful ligand in autoradiographic studies. Blockade of adenosine A2A receptors by SCH-58261 results in neuroprotective effects in cerebral ischaemia in rats. SCH-58261 counteracts parkinsonian-like muscle rigidity in rats. SCH-58261 reduces striatal transmitter outflow, turning behavior and ischemic brain damage induced by permanent focal ischemia in the rat. SCH-58261 protects from neurological deficit, brain damage and activation of p38 MAPK in rat focal cerebral ischemia.

Chemical Structure

SCH-58261

CAS#160098-96-4

Theoretical Analysis

MedKoo Cat#: 526655

Name: SCH-58261

CAS#: 160098-96-4

Chemical Formula: C18H15N7O

Exact Mass: 345.1338

Molecular Weight: 345.37

Elemental Analysis: C, 62.60; H, 4.38; N, 28.39; O, 4.63

Price and Availability

Size	Price	Availability
25mg	USD 250.00	2 Weeks
50mg	USD 450.00	2 Weeks
100mg	USD 750.00	2 weeks
200mg	USD 1,250.00	2 Weeks
500mg	USD 2,650.00	2 Weeks
1g	USD 3,950.00	2 Weeks
2g	USD 6,250.00	2 Weeks

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Related CAS #

No Data

Synonym

SCH-58261; SCH 58261; SCH58261.

IUPAC/Chemical Name

2-(furan-2-yl)-7-phenethyl-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine

InChi Key

UTLPKQYUXOEJIL-UHFFFAOYSA-N

InChi Code

InChI=1S/C18H15N7O/c19-18-22-16-13(11-20-24(16)9-8-12-5-2-1-3-6-12)17-21-15(23-25(17)18)14-7-4-10-26-14/h1-7,10-11H,8-9H2,(H2,19,22)

SMILES Code

NC1=NC(N(CCC2=CC=CC=C2)N=C3)=C3C4=NC(C5=CC=CO5)=NN14

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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

SCH-58261 is a A2A adenosine receptor competitive antagonist (Ki = 1.3 nM) that displays 323-, 53- and 100-fold selectivity over A1, A2B, and A3 receptors, respectively. SCH-58261 reduces melanoma tumor growth and TGF-β levels in WT and P2X7R-null mice.

In vitro activity:

In an intermittent hypoxia model in PC12 cells, the inhibition of A2a receptor by SCH-58261 increased cellular viability and suppressed PKC and SUR1 expression levels, ultimately showing a protective role in PC12 cells. Reference: Brain Res Bull. 2019 Aug;150:118-126. https://pubmed.ncbi.nlm.nih.gov/31129168/

In vivo activity:

SCH-58261 diminishes oxidative stress, thereby alleviating 3-NP-induced striatal toxicity. SCH-58261 partially countered 3-NP-induced body weight loss and mitigated impairments in motor coordination and locomotor activity in rats. SCH-58261 did not restore succinate dehydrogenase activity but effectively reduced oxidative stress. Higher doses additionally attenuated protein carbonyl levels and prevented the inhibition of glutathione peroxidase activity. Reference: Metab Brain Dis. 2017 Dec;32(6):1919-1927. https://pubmed.ncbi.nlm.nih.gov/28795281/

	Solvent	mg/mL	mM	comments
Solubility
	DMSO	34.5	100.00

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 345.37 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

Formulation protocol:

1. Singh BL, Chen L, Cai H, Shi H, Wang Y, Yu C, Chen X, Han X, Cai X. Activation of adenosine A2a receptor accelerates and A2a receptor antagonist reduces intermittent hypoxia induced PC12 cell injury via PKC-KATP pathway. Brain Res Bull. 2019 Aug;150:118-126. doi: 10.1016/j.brainresbull.2019.05.015. Epub 2019 May 23. PMID: 31129168. 2. Shah U, Lankin CM, Boyle CD, Chackalamannil S, Greenlee WJ, Neustadt BR, Cohen-Williams ME, Higgins GA, Ng K, Varty GB, Zhang H, Lachowicz JE. Design, synthesis, and evaluation of fused heterocyclic analogs of SCH 58261 as adenosine A2A receptor antagonists. Bioorg Med Chem Lett. 2008 Jul 15;18(14):4204-9. doi: 10.1016/j.bmcl.2008.05.069. Epub 2008 May 22. PMID: 18558486. 3. Bortolatto CF, Reis AS, Pinz MP, Voss GT, Oliveira RL, Vogt AG, Roman S, Jesse CR, Luchese C, Wilhelm EA. Selective A2A receptor antagonist SCH 58261 modulates striatal oxidative stress and alleviates toxicity induced by 3-Nitropropionic acid in male Wistar rats. Metab Brain Dis. 2017 Dec;32(6):1919-1927. doi: 10.1007/s11011-017-0086-1. Epub 2017 Aug 9. PMID: 28795281. 4. Melani A, Gianfriddo M, Vannucchi MG, Cipriani S, Baraldi PG, Giovannini MG, Pedata F. The selective A2A receptor antagonist SCH 58261 protects from neurological deficit, brain damage and activation of p38 MAPK in rat focal cerebral ischemia. Brain Res. 2006 Feb 16;1073-1074:470-80. doi: 10.1016/j.brainres.2005.12.010. Epub 2006 Jan 26. PMID: 16443200.

In vitro protocol:

In vivo protocol:

1. Bortolatto CF, Reis AS, Pinz MP, Voss GT, Oliveira RL, Vogt AG, Roman S, Jesse CR, Luchese C, Wilhelm EA. Selective A2A receptor antagonist SCH 58261 modulates striatal oxidative stress and alleviates toxicity induced by 3-Nitropropionic acid in male Wistar rats. Metab Brain Dis. 2017 Dec;32(6):1919-1927. doi: 10.1007/s11011-017-0086-1. Epub 2017 Aug 9. PMID: 28795281. 2. Melani A, Gianfriddo M, Vannucchi MG, Cipriani S, Baraldi PG, Giovannini MG, Pedata F. The selective A2A receptor antagonist SCH 58261 protects from neurological deficit, brain damage and activation of p38 MAPK in rat focal cerebral ischemia. Brain Res. 2006 Feb 16;1073-1074:470-80. doi: 10.1016/j.brainres.2005.12.010. Epub 2006 Jan 26. PMID: 16443200.

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