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Adenosine
"Descrizione"
by Al222 (19786 pt)
2022-Jan-23 19:47

Review Consensus: 10 Rating: 10 Number of users: 1
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Adenosine is a purine nucleoside that occurs naturally in all living cells and is a homeostatic bioenergetic regulator of cardiac, nervous system and skeletal muscle function. Its half-life in human blood is approximately 10 seconds, but it is a powerful vasodilator.

Industrially it appears in the form of a fine white powder. 

What it is used for and where

Medical

Caffeine is an adenosine A and can therefore be considered a co-factor in the treatment of certain neurological disorders. Conversely, adenosine is also known to counteract insomnia and reduce convulsions.

Adenosine can mitigate intoxication, sedation, motor coordination disorders due to the effects of alcohol and help limit many of the different effects of alcohol on the brain and other organ systems in the body (1). Furthermore, in view of the protective properties of adenosine, this nucleoside may play the role of a cardioprotector (2).

Scientific research has gone even further and investigated the possibilities of adenosine and its analogues as anti-cancer drugs (3).

Used in the treatment of angina, coronary dysfunction, cerebrovascular disorders, atherosclerosis, hypertension, progressive muscular atrophy, etc.,

Cosmetics

Adenosine applied in cream or patch form has demonstrated a skin-improving effect and is considered a new, safe and effective cosmetic to improve wrinkles, dermal density, elasticity and skin hydration (4) confirming, in 2018, the results of this 2007 study on the anti-wrinkle effect induced by the application of a soluble film containing adenosine (5).

Other applications

It is an important intermediate component for synthesising adenine, adenosine triphosphate, adenylate and adenosine arabinase.

Adenosina studies

Caratteristiche tipiche ottimali del prodotto commerciale  Adenosine

AppearanceFine white powder
Boiling Point
676.3±65.0 °C at 760 mmHg
Melting Point
234-236ºC
Density2.1±0.1 g/cm3
Flash Point
362.8±34.3°C
Loss on Drying
<1.0%
Heavy Metals
≤10ppm
Arsenic≤3ppm
Lead≤3ppm
Plate Count
≤1000cfu/g
Yeast & Mold
≤100cfu/g
PSA139.54000
Vapour Pressure
0.0±2.2 mmHg at 25°C
LogP-1.02
Index of Refraction
1.907



  • Molecular Formula  C10H13N5O4
  • Molecular Weight     267.24
  • Exact Mass   267.096741
  • CAS  58-61-7
  • UNII    K72T3FS567
  • EC Number   200-389-9
  • DSSTox Substance ID  DTXSID1022558
  • IUPAC  (2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
  • 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  
  • InChl Key      OIRDTQYFTABQOQ-KQYNXXCUSA-N
  • SMILES   C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)CO)O)O)N
  • MDL number   MFCD00005752
  • PubChem Substance ID    24277685
  • ChEBI  16335
  • Beilstein    93029
  • NSC   755857
  • eCl@ss     32160413
  • NACRES  NA.77   
  • NCI   C207

Synonyms:

  • (2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
  • Adenocard
  • Adenoscan
  • 9-beta-D-Ribofuranosyladenine

References_______________________________________________________________________

(1) Dohrman DP, Diamond I, Gordon AS. The role of the neuromodulator adenosine in alcohol's actions. Alcohol Health Res World. 1997;21(2):136-43.

(2) Riksen NP, Rongen GA, Yellon D, Smits P. Human in vivo research on the vascular effects of adenosine. Eur J Pharmacol. 2008 May 13;585(2-3):220-7. doi: 10.1016/j.ejphar.2008.01.053. 

(3) Man S, Lu Y, Yin L, Cheng X, Ma L. Potential and promising anticancer drugs from adenosine and its analogs. Drug Discov Today. 2021 Jun;26(6):1490-1500. doi: 10.1016/j.drudis.2021.02.020. 

(4) Kang G, Tu TNT, Kim S, Yang H, Jang M, Jo D, Ryu J, Baek J, Jung H. Adenosine-loaded dissolving microneedle patches to improve skin wrinkles, dermal density, elasticity and hydration. Int J Cosmet Sci. 2018 Apr;40(2):199-206. doi: 10.1111/ics.12453.

(5) Legendre JY, Schnitzler I, Li QY, Hausen C, Huart M, Luengo GS, Abella ML, Roreger M. Formulation, characterization, and efficacy of an adenosine-containing dissolvable film for a localized anti-wrinkle effect. J Cosmet Sci. 2007 Mar-Apr;58(2):147-55. 

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