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MedKoo Cat#: 531860 | Name: GR79236
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Description:

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

GR79236 is a highly potent and selective adenosine A1 receptor agonist (Ki = 3.1 nM) that has analgesic and anti-inflammatory actions in humans and animals.

Chemical Structure

GR79236
GR79236
CAS#124555-18-6

Theoretical Analysis

MedKoo Cat#: 531860

Name: GR79236

CAS#: 124555-18-6

Chemical Formula: C15H21N5O5

Exact Mass: 351.1543

Molecular Weight: 351.36

Elemental Analysis: C, 51.28; H, 6.02; N, 19.93; O, 22.77

Price and Availability

Size Price Availability Quantity
10mg USD 350.00 2 Weeks
50mg USD 1,050.00 2 Weeks
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Related CAS #
No Data
Synonym
GR79236; GR-79236; GR 79236
IUPAC/Chemical Name
(2R,3R,4S,5R)-2-(6-{[(1S,2S)-2-hydroxycyclopentyl]amino}-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
InChi Key
GYWXTRVEUURNEW-TVDBPQCTSA-N
InChi Code
InChI=1S/C15H21N5O5/c21-4-9-11(23)12(24)15(25-9)20-6-18-10-13(16-5-17-14(10)20)19-7-2-1-3-8(7)22/h5-9,11-12,15,21-24H,1-4H2,(H,16,17,19)/t7-,8-,9+,11+,12+,15+/m0/s1
SMILES Code
O[C@H]1[C@H](N2C=NC3=C(N[C@@H]4[C@@H](O)CCC4)N=CN=C23)O[C@H](CO)[C@H]1O
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
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:
GR79236 is a highly potent, selective and orally active adenosine A1 receptor agonist with a Kis of 3.1 nM and 1300 nM for A1 and A2 receptors, respectively.
In vitro activity:
GR79236 inhibited the NHE-stimulatory effect of phenylephrine in a concentration-dependent manner, such that the α1-AR agonist no longer produced a significant increase in NHE activity when given in combination with 1 or 10 μm GR79236. Reference: Br J Pharmacol. 2000 Oct;131(4):659-62. https://pubmed.ncbi.nlm.nih.gov/11030712/
In vivo activity:
Intravenous administration of the vehicle for DPCPX, or the vehicle (saline) for GR79236, had little effect on MAP or HR. In rabbits pre-treated with the vehicle for DPCPX, GR79236 reduced MAP and HR by approximately 15%. The effect on MAP was transient and had returned to basal values just prior to occlusion. However, HR remained significantly (P<0.01) lower, just prior to occlusion, than in all other groups (Table 1). Reference: Br J Pharmacol. 1999 Sep;128(2):385-95. https://pubmed.ncbi.nlm.nih.gov/10510449/
Solvent mg/mL mM
Solubility
DMSO 100.0 284.61
Water 100.0 284.61
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 351.36 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
Formulation protocol:
1. Avkiran M, Yokoyama H. Adenosine A(1) receptor stimulation inhibits alpha(1)-adrenergic activation of the cardiac sarcolemmal Na(+)/H(+) exchanger. Br J Pharmacol. 2000 Oct;131(4):659-62. doi: 10.1038/sj.bjp.0703647. PMID: 11030712; PMCID: PMC1572400. 2. Sheldrick A, Gray KM, Drew GM, Louttit JB. The effect of body temperature on myocardial protection conferred by ischaemic preconditioning or the selective adenosine A1 receptor agonist GR79236, in an anaesthetized rabbit model of myocardial ischaemia and reperfusion. Br J Pharmacol. 1999 Sep;128(2):385-95. doi: 10.1038/sj.bjp.0702799. PMID: 10510449; PMCID: PMC1571642. 3. Knutsen LJ, Lau J, Petersen H, Thomsen C, Weis JU, Shalmi M, Judge ME, Hansen AJ, Sheardown MJ. N-substituted adenosines as novel neuroprotective A(1) agonists with diminished hypotensive effects. J Med Chem. 1999 Sep 9;42(18):3463-77. doi: 10.1021/jm960682u. PMID: 10479279.
In vitro protocol:
1. Avkiran M, Yokoyama H. Adenosine A(1) receptor stimulation inhibits alpha(1)-adrenergic activation of the cardiac sarcolemmal Na(+)/H(+) exchanger. Br J Pharmacol. 2000 Oct;131(4):659-62. doi: 10.1038/sj.bjp.0703647. PMID: 11030712; PMCID: PMC1572400.
In vivo protocol:
1. Sheldrick A, Gray KM, Drew GM, Louttit JB. The effect of body temperature on myocardial protection conferred by ischaemic preconditioning or the selective adenosine A1 receptor agonist GR79236, in an anaesthetized rabbit model of myocardial ischaemia and reperfusion. Br J Pharmacol. 1999 Sep;128(2):385-95. doi: 10.1038/sj.bjp.0702799. PMID: 10510449; PMCID: PMC1571642. 2. Knutsen LJ, Lau J, Petersen H, Thomsen C, Weis JU, Shalmi M, Judge ME, Hansen AJ, Sheardown MJ. N-substituted adenosines as novel neuroprotective A(1) agonists with diminished hypotensive effects. J Med Chem. 1999 Sep 9;42(18):3463-77. doi: 10.1021/jm960682u. PMID: 10479279.
1: Arulmani U, Heiligers JP, Centurión D, Garrelds IM, Villalón CM, Saxena PR. Lack of effect of the adenosine A1 receptor agonist, GR79236, on capsaicin-induced CGRP release in anaesthetized pigs. Cephalalgia. 2005 Nov;25(11):1082-90. PubMed PMID: 16232161. 2: Giffin NJ, Kowacs F, Libri V, Williams P, Goadsby PJ, Kaube H. Effect of the adenosine A1 receptor agonist GR79236 on trigeminal nociception with blink reflex recordings in healthy human subjects. Cephalalgia. 2003 May;23(4):287-92. PubMed PMID: 12716347. 3: Sheldrick A, Gray KM, Drew GM, Louttit JB. The effect of body temperature on myocardial protection conferred by ischaemic preconditioning or the selective adenosine A1 receptor agonist GR79236, in an anaesthetized rabbit model of myocardial ischaemia and reperfusion. Br J Pharmacol. 1999 Sep;128(2):385-95. PubMed PMID: 10510449; PubMed Central PMCID: PMC1571642. 4: Louttit JB, Hunt AA, Maxwell MP, Drew GM. The time course of cardioprotection induced by GR79236, a selective adenosine A1-receptor agonist, in myocardial ischaemia-reperfusion injury in the pig. J Cardiovasc Pharmacol. 1999 Feb;33(2):285-91. PubMed PMID: 10028938. 5: Carley DW, Hagan RM, Sheehan M, Trbovic S, Thai T, Radulovacki M. Adenosine A1 receptor agonist GR79236 suppresses apnea during all sleep stages in the rat. Sleep. 1997 Dec;20(12):1093-8. PubMed PMID: 9493917. 6: Qu X, Cooney G, Donnelly R. Short-term metabolic and haemodynamic effects of GR79236 in normal and fructose-fed rats. Eur J Pharmacol. 1997 Nov 12;338(3):269-76. PubMed PMID: 9424021. 7: Webster JM, Heseltine L, Taylor R. In vitro effect of adenosine agonist GR79236 on the insulin sensitivity of glucose utilisation in rat soleus and human rectus abdominus muscle. Biochim Biophys Acta. 1996 Jun 7;1316(2):109-13. PubMed PMID: 8672547. 8: Merkel LA, Hawkins ED, Colussi DJ, Greenland BD, Smits GJ, Perrone MH, Cox BF. Cardiovascular and antilipolytic effects of the adenosine agonist GR79236. Pharmacology. 1995 Oct;51(4):224-36. PubMed PMID: 8577816. 9: Gardner CJ, Twissell DJ, Coates J, Strong P. The effects of GR79236 on plasma fatty acid concentrations, heart rate and blood pressure in the conscious rat. Eur J Pharmacol. 1994 May 12;257(1-2):117-21. PubMed PMID: 8082691. 10: Strong P, Anderson R, Coates J, Ellis F, Evans B, Gurden MF, Johnstone J, Kennedy I, Martin DP. Suppression of non-esterified fatty acids and triacylglycerol in experimental animals by the adenosine analogue GR79236. Clin Sci (Lond). 1993 Jun;84(6):663-9. PubMed PMID: 8334813.