Synonym
MRS5698; MRS 5698; MRS-5698.
IUPAC/Chemical Name
(1S,2R,3S,4R,5S)-4-(6-{[(3-chlorophenyl)methyl]amino}-2-[2-(3,4-difluorophenyl)ethynyl]-9H-purin-9-yl)-2,3-dihydroxy-N-methylbicyclo[3.1.0]hexane-1-carboxamide
InChi Key
LYLLLJJYBWLGHW-CIZVZKTGSA-N
InChi Code
InChI=1S/C28H23ClF2N6O3/c1-32-27(40)28-11-17(28)22(23(38)24(28)39)37-13-34-21-25(33-12-15-3-2-4-16(29)9-15)35-20(36-26(21)37)8-6-14-5-7-18(30)19(31)10-14/h2-5,7,9-10,13,17,22-24,38-39H,11-12H2,1H3,(H,32,40)(H,33,35,36)/t17-,22-,23+,24+,28+/m1/s1
SMILES Code
O=C([C@]12[C@@H](O)[C@@H](O)[C@H](N3C=NC4=C(NCC5=CC=CC(Cl)=C5)N=C(C#CC6=CC=C(F)C(F)=C6)N=C34)[C@@]1([H])C2)NC
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
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
564.98
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: 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. PubMed PMID: 26606937; PubMed Central PMCID: PMC4746492.
2: Tosh DK, Padia J, Salvemini D, Jacobson KA. Efficient, large-scale synthesis and preclinical studies of MRS5698, a highly selective A3 adenosine receptor agonist that protects against chronic neuropathic pain. Purinergic Signal. 2015 Sep;11(3):371-87. doi: 10.1007/s11302-015-9459-2. Epub 2015 Jun 27. PubMed PMID: 26111639; PubMed Central PMCID: PMC4529848.
3: Ford A, Castonguay A, Cottet M, Little JW, Chen Z, Symons-Liguori AM, Doyle T, Egan TM, Vanderah TW, De Konnick Y, Tosh DK, Jacobson KA, Salvemini D. Engagement of the GABA to KCC2 signaling pathway contributes to the analgesic effects of A3AR agonists in neuropathic pain. J Neurosci. 2015 Apr 15;35(15):6057-67. doi: 10.1523/JNEUROSCI.4495-14.2015. Erratum in: J Neurosci. 2015 Jun 10;35(23):8971. PubMed PMID: 25878279; PubMed Central PMCID: PMC4397603.
4: 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. PubMed PMID: 25422861; PubMed Central PMCID: PMC4266358.
5: Tosh DK, Deflorian F, Phan K, Gao ZG, Wan TC, Gizewski E, Auchampach JA, Jacobson KA. Structure-guided design of A(3) adenosine receptor-selective nucleosides: combination of 2-arylethynyl and bicyclo[3.1.0]hexane substitutions. J Med Chem. 2012 May 24;55(10):4847-60. doi: 10.1021/jm300396n. Epub 2012 May 16. PubMed PMID: 22559880; PubMed Central PMCID: PMC3371665.
