Adenosine amine congener

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MedKoo CAT#: 555703

CAS#: 96760-69-9

Description: Adenosine amine congener, also known as ADAC, is a selective A1 adenosine receptor agonist, can ameliorate noise- and cisplatin-induced cochlear injury. ADAC mitigates noise-induced hearing loss in a dose- and time-dependent manner, but further studies are required to establish its translation as a clinical otological treatment. Adenosine amine congener exerts a neuroprotective effect against the development of striatal lesions and motor impairments in the 3-nitropropionic acid model of neurotoxicity.

Chemical Structure

Adenosine amine congener
CAS# 96760-69-9

Theoretical Analysis

MedKoo Cat#: 555703
Name: Adenosine amine congener
CAS#: 96760-69-9
Chemical Formula: C28H32N8O6
Exact Mass: 576.2445
Molecular Weight: 576.614
Elemental Analysis: C, 58.32; H, 5.59; N, 19.43; O, 16.65

Price and Availability

Size Price Availability Quantity
100.0mg USD 1250.0 2 Weeks
200.0mg USD 1850.0 2 Weeks
500.0mg USD 2850.0 2 Weeks
1.0g USD 3650.0 2 Weeks
2.0g USD 6450.0 2 Weeks
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Synonym: Adenosine amine congener; 6-Adac; ADAC.

IUPAC/Chemical Name: N-(2-aminoethyl)-2-(4-(2-(4-((9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)amino)phenyl)acetamido)phenyl)acetamide


InChi Code: InChI=1S/C28H32N8O6/c29-9-10-30-21(38)11-16-1-5-18(6-2-16)34-22(39)12-17-3-7-19(8-4-17)35-26-23-27(32-14-31-26)36(15-33-23)28-25(41)24(40)20(13-37)42-28/h1-8,14-15,20,24-25,28,37,40-41H,9-13,29H2,(H,30,38)(H,34,39)(H,31,32,35)/t20-,24-,25-,28-/m1/s1

SMILES Code: OC[C@@H]1[C@H]([C@H]([C@H](N2C=NC3=C(N=CN=C32)NC4=CC=C(CC(NC5=CC=C(CC(NCCN)=O)C=C5)=O)C=C4)O1)O)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: Soluble in DMSO

Shelf Life: >3 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 576.614 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

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1: Lin SCY, Thorne PR, Housley GD, Vlajkovic SM. Purinergic Signaling and Aminoglycoside Ototoxicity: The Opposing Roles of P1 (Adenosine) and P2 (ATP) Receptors on Cochlear Hair Cell Survival. Front Cell Neurosci. 2019 May 15;13:207. doi: 10.3389/fncel.2019.00207. eCollection 2019. PubMed PMID: 31156393; PubMed Central PMCID: PMC6529511.

2: Chang H, Telang RS, Sreebhavan S, Tingle M, Thorne PR, Vlajkovic SM. Pharmacokinetic Properties of Adenosine Amine Congener in Cochlear Perilymph after Systemic Administration. Biomed Res Int. 2017;2017:8091462. doi: 10.1155/2017/8091462. Epub 2017 Jan 18. PubMed PMID: 28194422; PubMed Central PMCID: PMC5286489.

3: Vlajkovic SM, Chang H, Paek SY, Chi HH, Sreebhavan S, Telang RS, Tingle M, Housley GD, Thorne PR. Adenosine amine congener as a cochlear rescue agent. Biomed Res Int. 2014;2014:841489. doi: 10.1155/2014/841489. Epub 2014 Aug 26. PubMed PMID: 25243188; PubMed Central PMCID: PMC4160640.

4: Vlajkovic SM, Lee KH, Wong AC, Guo CX, Gupta R, Housley GD, Thorne PR. Adenosine amine congener mitigates noise-induced cochlear injury. Purinergic Signal. 2010 Jun;6(2):273-81. doi: 10.1007/s11302-010-9188-5. Epub 2010 Jun 30. PubMed PMID: 20806018; PubMed Central PMCID: PMC2912992.

5: McLaughlin CW, Karl MO, Zellhuber-McMillan S, Wang Z, Do CW, Leung CT, Li A, Stone RA, Macknight AD, Civan MM. Electron probe X-ray microanalysis of intact pathway for human aqueous humor outflow. Am J Physiol Cell Physiol. 2008 Nov;295(5):C1083-91. doi: 10.1152/ajpcell.340.2008. Epub 2008 Aug 27. PubMed PMID: 18753314; PubMed Central PMCID: PMC2584983.

6: Booth LC, Tummers L, Jensen EC, Barrett CJ, Malpas SC, Gunn AJ, Bennet L. Differential effects of the adenosine A1 receptor agonist adenosine amine congener on renal, femoral and carotid vascular conductance in preterm fetal sheep. Clin Exp Pharmacol Physiol. 2008 Nov;35(11):1316-20. doi: 10.1111/j.1440-1681.2008.05013.x. Epub 2008 Jul 29. PubMed PMID: 18671718.

7: Roscoe WA, Messersmith E, Meyer-Franke A, Wipke B, Karlik SJ. Connexin 43 gap junction proteins are up-regulated in remyelinating spinal cord. J Neurosci Res. 2007 Apr;85(5):945-53. PubMed PMID: 17279545.

8: Kuwahata T. Effects of adenosine and ATP on the membrane potential and synaptic transmission in neurons of the rat locus coeruleus. Kurume Med J. 2004;51(2):109-23. PubMed PMID: 15373228.

9: Tsutsui S, Schnermann J, Noorbakhsh F, Henry S, Yong VW, Winston BW, Warren K, Power C. A1 adenosine receptor upregulation and activation attenuates neuroinflammation and demyelination in a model of multiple sclerosis. J Neurosci. 2004 Feb 11;24(6):1521-9. PubMed PMID: 14960625; PubMed Central PMCID: PMC6730323.

10: Blum D, Gall D, Galas MC, d'Alcantara P, Bantubungi K, Schiffmann SN. The adenosine A1 receptor agonist adenosine amine congener exerts a neuroprotective effect against the development of striatal lesions and motor impairments in the 3-nitropropionic acid model of neurotoxicity. J Neurosci. 2002 Oct 15;22(20):9122-33. PubMed PMID: 12388620; PubMed Central PMCID: PMC6757706.

11: Rubio R, Ceballos G. Sole activation of three luminal adenosine receptor subtypes in different parts of coronary vasculature. Am J Physiol Heart Circ Physiol. 2003 Jan;284(1):H204-14. Epub 2002 Sep 19. PubMed PMID: 12388293.

12: Gervitz LM, Lutherer LO, Hamilton ME, Fowler JC. Lack of central effects of peripherally administered adenosine A(1) agonists on synaptic transmission in the rat hippocampus. Brain Res. 2002 Sep 27;951(1):141-5. PubMed PMID: 12231468.

13: Bivalacqua TJ, Champion HC, Lambert DG, Kadowitz PJ. Vasodilator responses to adenosine and hyperemia are mediated by A(1) and A(2) receptors in the cat vascular bed. Am J Physiol Regul Integr Comp Physiol. 2002 Jun;282(6):R1696-709. PubMed PMID: 12010752.

14: Adén U, Leverin AL, Hagberg H, Fredholm BB. Adenosine A(1) receptor agonism in the immature rat brain and heart. Eur J Pharmacol. 2001 Aug 31;426(3):185-92. PubMed PMID: 11527543.

15: Li B, Roth S. Retinal ischemic preconditioning in the rat: requirement for adenosine and repetitive induction. Invest Ophthalmol Vis Sci. 1999 May;40(6):1200-16. PubMed PMID: 10235554.

16: Von Lubitz DK, Lin RC, Bischofberger N, Beenhakker M, Boyd M, Lipartowska R, Jacobson KA. Protection against ischemic damage by adenosine amine congener, a potent and selective adenosine A1 receptor agonist. Eur J Pharmacol. 1999 Mar 26;369(3):313-7. PubMed PMID: 10225368; PubMed Central PMCID: PMC3438899.

17: Richard LF, Dahms TE, Webster RO. Adenosine prevents permeability increase in oxidant-injured endothelial monolayers. Am J Physiol. 1998 Jan;274(1):H35-42. doi: 10.1152/ajpheart.1998.274.1.H35. PubMed PMID: 9458849.

18: Bischofberger N, Jacobson KA, von Lubitz DK. Adenosine A1 receptor agonists as clinically viable agents for treatment of ischemic brain disorders. Ann N Y Acad Sci. 1997 Oct 15;825:23-9. Review. PubMed PMID: 9369972; PubMed Central PMCID: PMC3445622.

19: Suh HW, Song DK, Kim YH. Differential effects of adenosine receptor antagonists injected intrathecally on antinociception induced by morphine and beta-endorphin administered intracerebroventricularly in the mouse. Neuropeptides. 1997 Aug;31(4):339-44. PubMed PMID: 9308021.

20: Stambaugh K, Jacobson KA, Jiang JL, Liang BT. A novel cardioprotective function of adenosine A1 and A3 receptors during prolonged simulated ischemia. Am J Physiol. 1997 Jul;273(1 Pt 2):H501-5. PubMed PMID: 9249524; PubMed Central PMCID: PMC5470722.