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A0230200

Adenosine

European Pharmacopoeia (EP) Reference Standard

Synonym(s):

9-β-D-Ribofuranosyladenine, Adenine riboside, Adenine-9-β-D-ribofuranoside

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About This Item

Empirical Formula (Hill Notation):
C10H13N5O4
CAS Number:
58-61-7
Molecular Weight:
267.24
Beilstein/REAXYS Number:
93029
MDL number:
MFCD00005752
UNSPSC Code:
41116107
PubChem Substance ID:
329770589
NACRES:
NA.24

grade

pharmaceutical primary standard

description

API family: adenosine

API family

adenosine

manufacturer/tradename

EDQM

mp

234-236 °C (lit.)

application(s)

pharmaceutical (small molecule)

format

neat

storage temp.

2-8°C

SMILES string

Nc1ncnc2n(cnc12)[C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O

InChI

1S/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6-,7-,10-/m1/s1

InChI key

OIRDTQYFTABQOQ-KQYNXXCUSA-N

Gene Information

human ... ADORA1(134) , ADORA2A(135) , ADORA2B(136) , ADORA3(140)

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General description

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the issuing Pharmacopoeia.
For further information and support please go to the website of the issuing Pharmacopoeia.

Application

Adenosine EP Reference standard, intended for use in laboratory tests only as specifically prescribed in the European Pharmacopoeia.

Biochem/physiol Actions

Endogenous neurotransmitter at adenosine receptors. Cardioprotective effects may relate to activation of A1 adenosine receptors. The antiplatelet and anti−inflammatory actions of adenosine appear to be mediated via the A2 adenosine receptor. In contrast, adenosine appears to be a pro-inflammatory mediator in asthma and chronic obstructive pulmonary disease (COPD).

Packaging

The product is delivered as supplied by the issuing Pharmacopoeia. For the current unit quantity, please visit the EDQM reference substance catalogue.

Other Notes

Sales restrictions may apply.

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

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Antonella Fioravanti et al.
PLoS genetics, 9(5), e1003541-e1003541 (2013-06-06)
Several regulators are involved in the control of cell cycle progression in the bacterial model system Caulobacter crescentus, which divides asymmetrically into a vegetative G1-phase (swarmer) cell and a replicative S-phase (stalked) cell. Here we report a novel functional interaction
R W Jansen et al.
Hepatology (Baltimore, Md.), 18(1), 146-152 (1993-07-01)
We covalently coupled 9-beta-D-arabinofuranosyladenine 5'-monophosphate (ara-AMP) to the carrier molecule lactosaminated human serum albumin using a water-soluble carbodiimide with a two-step conjugation method (pH 4.5 and pH 7.5) instead of the commonly used single-step conjugation at pH 7.5. This resulted
Deepak Mittal et al.
Cancer research, 74(14), 3652-3658 (2014-07-06)
Adenosine targeting is an attractive new approach to cancer treatment, but no clinical study has yet examined adenosine inhibition in oncology despite the safe clinical profile of adenosine A2A receptor inhibitors (A2ARi) in Parkinson disease. Metastasis is the main cause
Luca Antonioli et al.
Nature reviews. Cancer, 13(12), 842-857 (2013-11-15)
Cancer is a complex disease that is dictated by both cancer cell-intrinsic and cell-extrinsic processes. Adenosine is an ancient extracellular signalling molecule that can regulate almost all aspects of tissue function. As such, several studies have recently highlighted a crucial
Dennis T L Wong et al.
Journal of the American College of Cardiology, 63(18), 1904-1912 (2014-03-25)
The goal of this study was to compare the diagnostic accuracy of combined computed tomography perfusion (CTP) + computed tomography angiography (CTA), transluminal attenuation gradient by 320-detector row computed tomography (TAG320) + CTA, and CTP + TAG320 + CTA (multidetector computed tomography-integrated protocol [MDCT-IP])
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