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Inosine
Systematic (IUPAC) name
9-[(2R,3R,4S,5 R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-3 H-purin-6-one
Identifiers
CAS number 58-63-9
ATC code D06BB05 G01AX02
PubChem 6021
DrugBank EXPT02378
Chemical data
Formula C 10H12N4O5  
Mol. mass 268.23 g/mol
Pharmacokinetic data
Bioavailability  ?
Metabolism Hepatic
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status OTC
Routes  ?
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Inosine is a nucleoside that is formed when hypoxanthine is attached to a ribose ring (also known as a ribofuranose) via a β-N9-glycosidic bond.

Inosine is commonly found in tRNAs and is essential for proper translation of the genetic code in wobble base pairs.

Knowledge of inosine metabolism has led to advances in immunotherapy in recent decades. Inosine monophosphate is oxidised by the enzyme inosine monophosphate dehydrogenase yielding xanthosine monophosphate, a key precursor in purine metabolism. Mycophenolate mofetil is an anti-metabolite, anti-proliferative drug that acts as an inhibitor of inosine monophosphate dehydrogenase. It is used in the treatment of a variety of autoimmune diseases including Wegener's granulomatosis because the uptake of purine by actively dividing B cells can exceed 8 times that of normal body cells and therefore this set of white cells (which cannot operate purine salvage pathways) is selectively targeted by the purine deficiency resulting from IMD inhibition.

Contents

Reactions

Adenine is converted to adenosine or inosine monophosphate (IMP), either of which in turn is converted into inosine (I), which pairs with Adenine (A), cytosine (C) and uracil (U).

Purine nucleoside phosphorylase intraconverts inosine and hypoxanthine.

Inosine is also an intermediate in a chain of purine nucleotides reactions required for muscle movements.

Clinical significance

It was tried in the seventies in eastern countries for improving athletic performance. Nevertheless the clinical trials for this purpose showed no improvement.[1] It has been shown that inosine has neuroprotective properties. It has been proposed for spinal cord injury;[2] because it improves axonal rewiring, and for administration after stroke, because observation has shown that axonal re-wiring is encouraged.[3]

It is currently in phase II trials for multiple sclerosis (MS).[4] It produces uric acid after ingestion, which is a natural antioxidant and a peroxynitrite scavenger, which can suggest possible benefit in multiple sclerosis[5] (peroxynitrite has been correlated with the axons degeneration[1]).

Alseres Pharmaceuticals (named Boston Life Sciences when patent was granted) patented the treatment for stroke[2] and is currently investigating the drug in the MS setting.[6]

In the Anatomical Therapeutic Chemical Classification System, it is classified as an antiviral.[7]

Biotechnology

When designing primers for polymerase chain reaction, inosine is useful in that it will indiscriminately pair with adenine, thymine, or cytosine. This allows for design of primers that span a single nucleotide polymorphism, without the polymorphism disrupting the primer's annealing efficiency.

Fitness

Despite a lack of clinical evidence that it improves muscle development, inosine remains an ingredient in some fitness supplements.

Experimental

NOV-205 manufactured by Novelos Therapeutics is A new class of Antiviral medication that is approved for use in Russia under the tradename of "Molixan" and currently being tested in the USA under FDA clinical studies.
This medication follows the Glutathione pathway via GSSG and therefore acts as an immunomodulator, hepatoprotective, and has anti inflammatory properties.
Under oxidative stress (attack by virus at the cellular level) Oxidized Gluatathione (spent side) appears to modulate inosine causing knock-out of "viral load."

See also

References

  1. ^ McNaughton L, Dalton B, Tarr J (1999). "Inosine supplementation has no effect on aerobic or anaerobic cycling performance". International journal of sport nutrition 9 (4): 333–44. PMID 10660865.  
  2. ^ Liu F, You SW, Yao LP et al. (2006). "Secondary degeneration reduced by inosine after spinal cord injury in rats". Spinal Cord 44 (7): 421–6. doi:10.1038/sj.sc.3101878. PMID 16317421.  
  3. ^ Chen P, Goldberg DE, Kolb B, Lanser M, Benowitz LI (2002). "Inosine induces axonal rewiring and improves behavioral outcome after stroke". Proc. Natl. Acad. Sci. U.S.A. 99 (13): 9031–6. doi:10.1073/pnas.132076299. PMID 12084941. http://www.pnas.org/cgi/content/full/99/13/9031.  
  4. ^ Treatment of Multiple Sclerosis Using Over the Counter Inosine - Full Text View - ClinicalTrials.gov
  5. ^ Uric Acid: Natural Scavenger Of Peroxynitrite
  6. ^ Alseres pharma drug description
  7. ^ "ATC/DDD Index". http://www.whocc.no/atcddd/indexdatabase/index.php?query=D06BB05.  

External links

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