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MedKoo Cat#: 465902 | Name: MRS5980

Description:

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

MRS5980 a A3AR agonist containing multiple receptor affinity- and selectivity-enhancing modifications and a therapeutic candidate drug for many inflammatory diseases. MRS5980 inhibit neuronal (N-type) voltage-dependent Ca2+ currents in dorsal root ganglia, a known pain-related mechanism. Male mice treated with intraperitoneal injections of MRS5980 (1 mg/kg) had reduced secondary tissue injury and brain infarction than vehicle-treated mice with TBI. MRS5980 also attenuated TBI-induced CD4+ and CD8+ T cell influx.

Chemical Structure

MRS5980
MRS5980
CAS#1639420-13-5

Theoretical Analysis

MedKoo Cat#: 465902

Name: MRS5980

CAS#: 1639420-13-5

Chemical Formula: C20H19ClN6O3S

Exact Mass: 458.0928

Molecular Weight: 458.92

Elemental Analysis: C, 52.34; H, 4.17; Cl, 7.72; N, 18.31; O, 10.46; S, 6.99

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
MRS5980; MRS 5980; MRS-5980;
IUPAC/Chemical Name
(1S,2R,3S,4R,5S)-4-(2-((5-chlorothiophen-2-yl)ethynyl)-6-(methylamino)-9H-purin-9-yl)-2,3-dihydroxy-N-methylbicyclo[3.1.0]hexane-1-carboxamide
InChi Key
RVLAHZAHALVQKF-AQPYCOETSA-N
InChi Code
InChI=1S/C20H19ClN6O3S/c1-22-17-13-18(26-12(25-17)6-4-9-3-5-11(21)31-9)27(8-24-13)14-10-7-20(10,19(30)23-2)16(29)15(14)28/h3,5,8,10,14-16,28-29H,7H2,1-2H3,(H,23,30)(H,22,25,26)/t10-,14-,15+,16+,20+/m1/s1
SMILES Code
CNC([C@]12[C@@H](O)[C@@H](O)[C@H](N3C=NC4=C3N=C(C#CC5=CC=C(Cl)S5)N=C4NC)[C@H]1C2)=O
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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
Agonists of the Gi protein-coupled A3 adenosine receptor (A3AR) have shown important pain-relieving properties in preclinical settings of several pain models. Active as a monotherapy against chronic pain, A3AR agonists can also be used in combination with classic opioid analgesics. Their safe pharmacological profile, as shown by clinical trials for other pathologies, i.e., rheumatoid arthritis, psoriasis and fatty liver diseases, confers a realistic translational potential, thus encouraging research studies on the molecular mechanisms underpinning their antinociceptive actions. A number of pathways, involving central and peripheral mechanisms, have been proposed.

Preparing Stock Solutions

The following data is based on the product molecular weight 458.92 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.

Recalculate based on batch purity %
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: Singh AK, Mahalingam R, Squillace S, Jacobson KA, Tosh DK, Dharmaraj S, Farr SA, Kavelaars A, Salvemini D, Heijnen CJ. Targeting the A3 adenosine receptor to prevent and reverse chemotherapy-induced neurotoxicities in mice. Acta Neuropathol Commun. 2022 Jan 29;10(1):11. doi: 10.1186/s40478-022-01315-w. PMID: 35093182; PMCID: PMC8800287. 2: Coppi E, Cherchi F, Lucarini E, Ghelardini C, Pedata F, Jacobson KA, Di Cesare Mannelli L, Pugliese AM, Salvemini D. Uncovering the Mechanisms of Adenosine Receptor-Mediated Pain Control: Focus on the A3 Receptor Subtype. Int J Mol Sci. 2021 Jul 26;22(15):7952. doi: 10.3390/ijms22157952. PMID: 34360719; PMCID: PMC8347395. 3: Farr SA, Cuzzocrea S, Esposito E, Campolo M, Niehoff ML, Doyle TM, Salvemini D. Adenosine A3 receptor as a novel therapeutic target to reduce secondary events and improve neurocognitive functions following traumatic brain injury. J Neuroinflammation. 2020 Nov 12;17(1):339. doi: 10.1186/s12974-020-02009-7. PMID: 33183330; PMCID: PMC7659122. 4: Lucarini E, Coppi E, Micheli L, Parisio C, Vona A, Cherchi F, Pugliese AM, Pedata F, Failli P, Palomino S, Wahl J, Largent-Milnes TM, Vanderah TW, Tosh DK, Jacobson KA, Salvemini D, Ghelardini C, Di Cesare Mannelli L. Acute visceral pain relief mediated by A3AR agonists in rats: involvement of N-type voltage- gated calcium channels. Pain. 2020 Sep 1;161(9):2179-2190. doi: 10.1097/j.pain.0000000000001905. PMID: 32379223; PMCID: PMC8272921. 5: Coppi E, Cherchi F, Fusco I, Failli P, Vona A, Dettori I, Gaviano L, Lucarini E, Jacobson KA, Tosh DK, Salvemini D, Ghelardini C, Pedata F, Di Cesare Mannelli L, Pugliese AM. Adenosine A3 receptor activation inhibits pronociceptive N-type Ca2+ currents and cell excitability in dorsal root ganglion neurons. Pain. 2019 May;160(5):1103-1118. doi: 10.1097/j.pain.0000000000001488. PMID: 31008816; PMCID: PMC6669900. 6: Carlin JL, Tosh DK, Xiao C, Piñol RA, Chen Z, Salvemini D, Gavrilova O, Jacobson KA, Reitman ML. Peripheral Adenosine A3 Receptor Activation Causes Regulated Hypothermia in Mice That Is Dependent on Central Histamine H1 Receptors. J Pharmacol Exp Ther. 2016 Feb;356(2):474-82. doi: 10.1124/jpet.115.229872. Epub 2015 Nov 25. PMID: 26606937; PMCID: PMC4746492. 7: Fang ZZ, Tosh DK, Tanaka N, Wang H, Krausz KW, O'Connor R, Jacobson KA, Gonzalez FJ. Metabolic mapping of A3 adenosine receptor agonist MRS5980. Biochem Pharmacol. 2015 Sep 15;97(2):215-23. doi: 10.1016/j.bcp.2015.07.007. Epub 2015 Jul 23. PMID: 26212548; PMCID: PMC4581425. 8: Tosh DK, Finley A, Paoletta S, Moss SM, Gao ZG, Gizewski ET, Auchampach JA, Salvemini D, Jacobson KA. In vivo phenotypic screening for treating chronic neuropathic pain: modification of C2-arylethynyl group of conformationally constrained A3 adenosine receptor agonists. J Med Chem. 2014 Dec 11;57(23):9901-14. doi: 10.1021/jm501021n. Epub 2014 Nov 25. PMID: 25422861; PMCID: PMC4266358.

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