Adenosine

Structural formula
General
Non-proprietary name	Adenosine
other names	A (short code); 9-β- D- ribofuranosyladenine; 9 - [(2 R , 3 R , 4 S , 5 R ) -3,4-dihydroxy-5- (hydroxymethyl) oxolan-2-yl] -6-aminopurine; Ado; ADENOSINE ( INCI ) ;
Molecular formula	C 10 H 13 N 5 O 4
Brief description	white and odorless solid
External identifiers / databases
EC number	200-389-9
ECHA InfoCard	100,000,354
PubChem	60961
ChemSpider	54923
DrugBank	DB00640
Wikidata	Q190012
Drug information
ATC code	C01 EB10
Drug class	Antiarrhythmic
properties
Molar mass	267.24 g mol −1
Physical state	firmly
density	0.31 g cm −3
Melting point	234-237 ° C
solubility	practically insoluble in ethanol ; soluble in hot water;
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
Toxicological data	> 20 g kg −1 ( LD 50 , mouse , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Adenosine (A, Ado) is a nucleoside and consists of the nucleic base adenine and the sugar β- D- ribose . The analogue with deoxyribose is deoxyadenosine . It is part of the energy-rich compounds ATP , ADP , AMP , ribonucleic acid (RNA), various cofactors (e.g. coenzyme A , NADPH , NADH ) and also in a neuromodulator .

properties

Adenosine is a white and odorless solid that practically does not dissolve in ethanol, but is soluble in hot water.

Biological importance

Adenosine is part of ribonucleic acid (RNA) and forms a base pair there with uridine , dihydrouridine or pseudouridine .


AU base pair	AD base pair	A Ψ base pair

Pharmaceutical importance

effect

Adenosine blocks the release of all invigorating and activating neurotransmitters such as dopamine , acetylcholine or norepinephrine . This causes dilation (widening of the blood vessels), which lowers blood pressure. Adenosine also lowers the heart rate and increases the conduction time in the AV node . This is done by activating a G _i -modulated potassium channel via A ₁ adenosine receptors.

Adenosine also triggers the nucleus praeopticus ventrolateralis in the hypothalamus , which inhibits the waking and waking centers of the brain through the neurotransmitter GABA , and thus has a sleep-inducing effect . The xanthines caffeine , theobromine and theophylline as well as the artificial drug istradefylline act as antagonists of various adenosine receptors . Partial inhibition of the receptors in the nucleus praeopticus ventrolateralis also contributes to their sleep-suppressing effect.

indication

Adenosine is indicated for the termination of AV nodal reentry tachycardia . It blocks the conduction of excitation from the atrium to the ventricle , causing a cardiac arrest lasting a few seconds. The physiological half-life ( half-life ) of adenosine is in the range of seconds. With theophylline one exists antidote .

Adenosine is predominantly used for the pharmacological exposure of myocardial scintigraphy .

Commercial preparations

Monopreparations

Adenoscan (D), Adrekar (D), Krenosin (CH), Generics (D, A)

Combination preparations

ViaSpan organ preservation solution (A), Vita-Gerin "Geistlich" (A)

Web links

Commons : Adenosine - Collection of pictures, videos and audio files

Commons : Adenosine derivatives - collection of pictures, videos and audio files

Entry for adenosine in the Human Metabolome Database (HMDB) , accessed October 21, 2013.
Modification Summary of Adenosine in the Modomics database, accessed January 13, 2014.

Individual evidence

↑ Entry on ADENOSINE in the CosIng database of the EU Commission, accessed on March 26, 2020.
↑ ^a ^b ^c ^d ^e data sheet adenosine (PDF) from Carl Roth , accessed on November 28, 2013.
↑ ^a ^b Wissenschaft-Online-Lexika: Entry on adenosine in the Lexikon der Chemie ; Retrieved November 28, 2013.
↑ C. Cajochen: Sleep Regulation . In: Somnologie - Schlafforschung und Schlafmedizin, Volume 13, Number 2, June 2009, pp. 64–71 ( doi : 10.1007 / s11818-009-0423-7 ).
↑ Wolfgang Hauber: Adenosine: a purine nucleoside with neuromodulatory effects. Neuroforum 3/02, pp. 228-234 ( PDF , 212 kB).

[CosIng-1] Entry on ADENOSINE in the CosIng database of the EU Commission, accessed on March 26, 2020.

[Roth-2] ↑ ^a ^b ^c ^d ^e data sheet adenosine (PDF) from Carl Roth , accessed on November 28, 2013.

[woc-3] Wissenschaft-Online-Lexika: Entry on adenosine in the Lexikon der Chemie ; Retrieved November 28, 2013.

[4] C. Cajochen: Sleep Regulation . In: Somnologie - Schlafforschung und Schlafmedizin, Volume 13, Number 2, June 2009, pp. 64–71 ( doi : 10.1007 / s11818-009-0423-7 ).

[5] Wolfgang Hauber: Adenosine: a purine nucleoside with neuromodulatory effects. Neuroforum 3/02, pp. 228-234 ( PDF , 212 kB).