Inosine

Short description: Chemical compound

Inosine

Clinical data
AHFS/Drugs.com| International Drug Names
ATC code|

* D06BB05 (WHO) G01AX02 (WHO) S01XA10 (WHO)

Legal status
Legal status|

* In general: Over-the-counter (OTC)

Pharmacokinetic data
Metabolism| Hepatic
Identifiers

IUPAC name

* 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-3H-purin-6-one

CAS Number|

* 58-63-9 Y

PubChem CID|

* 6021

IUPHAR/BPS|

* 4554

DrugBank|

* DB04335 N

ChemSpider|

* 5799 Y

UNII|

* 5A614L51CT

KEGG|

* C00294 Y

ChEBI|

* CHEBI:17596 Y

ChEMBL|

* ChEMBL1556 N

Chemical and physical data
Formula| C10H12N4O5
Molar mass| 268.229 g·mol−1
3D model (JSmol)|

* Interactive image

SMILES

* c1[nH]c2c(c(=O)n1)ncn2[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O

InChI

* InChI=1S/C10H12N4O5/c15-1-4-6(16)7(17)10(19-4)14-3-13-5-8(14)11-2-12-9(5)18/h2-4,6-7,10,15-17H,1H2,(H,11,12,18)/t4-,6-,7-,10-/m1/s1 Y

* Key:UGQMRVRMYYASKQ-KQYNXXCUSA-N Y

NY (what is this?) (verify)

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. It was discovered in 1965 in analysis of RNA transferase.[1] Inosine is commonly found in tRNAs and is essential for proper translation of the genetic code in wobble base pairs.

Wobble base pairs for inosine and guanine

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 granulomatosis with polyangiitis 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 inosine monophosphate dehydrogenase (IMD) inhibition.

## Contents

* 1 Reactions
* 2 Clinical significance
* 3 Binding
* 4 Biotechnology
* 5 Fitness
* 6 Feeding stimulant
* 7 See also
* 8 References
* 9 External links

## 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).[citation needed]

Purine nucleoside phosphorylase intraconverts inosine and hypoxanthine.

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

## Clinical significance

In the 1970s, inosine was used by athletes in Eastern countries in an attempt to improve performance.[citation needed] Subsequent studies in humans suggest that inosine supplementation has no effect on athletic performance.[2] Animal studies have suggested that inosine has neuroprotective properties. It has been proposed for spinal cord injury[3] and for administration after stroke, because observation suggests that inosine induces axonal rewiring.[4]

After ingestion, inosine is metabolized into uric acid, which has been suggested to be a natural antioxidant and peroxynitrite scavenger with potential benefits to patients with multiple sclerosis (MS).[5] Peroxynitrite has been correlated with axon degeneration [6] In 2003, a study was initiated at the University of Pennsylvania MS Center to determine whether raising the levels of uric acid by the administration of inosine would slow the progression of MS.[7] The study was completed in 2006 but the results were not reported to NIH. A subsequent publication hinted at potential benefits but the sample size (16 patients) was too small for a definitive conclusion.[8] In addition, the side effect of the treatment was the development of kidney stones in four of 16 patients.[citation needed]

With phase II trials for Parkinson's disease completed, inosine will continue to phase III trials. Earlier trials suggested that patients with the highest serum urate levels had slower progression of Parkinson's symptoms. The trial uses inosine to raise urate levels in those with levels lower than the population mean (6 mg/dL).[9][10][11]

Alseres Pharmaceuticals (named Boston Life Sciences when patent was granted) patented the use of inosine to treat stroke[12] and was investigating the drug in the MS setting.[13]

In the Anatomical Therapeutic Chemical Classification System, it is classified as an antiviral.[14]

## Binding

Inosine is a natural ligand for the benzodiazepine binding site on the GABA A receptor.[15]

## Biotechnology

When designing primers for polymerase chain reaction, inosine is useful in that it can pair with any natural base.[16] This allows for design of primers that span a single-nucleotide polymorphism, without the polymorphism disrupting the primer's annealing efficiency.

However, inosine pairs preferentially with cytosine (C) and its introduction to RNA, e.g. by the action of ADARs, thereby destabilizes double-stranded RNA by changing AU base-pairs to IU mismatches.[17]

## Fitness

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

## Feeding stimulant

Inosine has also been found to be an important feed stimulant by itself or in combination with certain amino acids in some species of farmed fish. For example, inosine and inosine-5-monophosphate have been reported as specific feeding stimulants for turbot fry, (Scophthalmus maximus) [18] and Japanese amberjack, (Seriola quinqueradiata).[19] The main problem of using inosine and/or inosine-5-monophosphate as feeding attractants is their high cost. However, their use may be economically justified within larval feeds for marine fish larvae during the early weaning period, since the total quantity of feed consumed is relatively small.

## See also

* Inosine monophosphate dehydrogenase
* Inosine pranobex
* Nucleobase

## References

1. ↑ "Inosine in Biology and Disease". Genes 12 (4): 600. April 2021. doi:10.3390/genes12040600. PMID 33921764.
2. ↑ "ISSN exercise & sports nutrition review update: research & recommendations". Journal of the International Society of Sports Nutrition 15 (1): 38. August 2018. doi:10.1186/s12970-018-0242-y. PMID 30068354.
3. ↑ "Secondary degeneration reduced by inosine after spinal cord injury in rats". Spinal Cord 44 (7): 421–426. July 2006. doi:10.1038/sj.sc.3101878. PMID 16317421.
4. ↑ "Inosine induces axonal rewiring and improves behavioral outcome after stroke". Proceedings of the National Academy of Sciences of the United States of America 99 (13): 9031–9036. June 2002. doi:10.1073/pnas.132076299. PMID 12084941. Bibcode: 2002PNAS...99.9031C.
5. ↑ "Uric Acid In Multiple Sclerosis". WebCite. 2018. http://www.geocities.com/hotsprings/3468/uric_acid-peroxynitrite2-98.html.
6. ↑ "Immune mediated injury, oxidative toxicity and excitotoxicity in multiple sclerosis. Possibilities for immune modulation and neuroprotection". http://www.fedem.org/revista/n17/neuhausing.htm.
7. ↑ Clinical trial number NCT00067327 for "Treatment of Multiple Sclerosis Using Over the Counter Inosine" at ClinicalTrials.gov
8. ↑ "The treatment of multiple sclerosis with inosine". Journal of Alternative and Complementary Medicine 15 (6): 619–625. June 2009. doi:10.1089/acm.2008.0513. PMID 19425822.
9. ↑ "Safety of Urate Elevation in Parkinson's Disease". Fox Trial Finder. 2018. https://foxtrialfinder.michaeljfox.org/trial/468/.
10. ↑ Clinical trial number NCT00833690 for "Safety of Urate Elevation in Parkinson's Disease" at ClinicalTrials.gov
11. ↑ "Inosine Trial Secures Phase III Funding to Study Effect on Slowing Parkinson's". Michael J. Fox Foundation. September 1, 2015. https://www.michaeljfox.org/foundation/news-detail.php?inosine-trial-secures-phase-iii-funding-to-study-effect-on-slowing-parkinson.
12. ↑ "Boston Life Sciences Announces Issuance of Inosine Patent for Treatment of Spinal Cord Injury". November 17, 2003. http://www.bostonlifesciences.com/news111.htm.
13. ↑ "The inosine conundrum.". Science-Business EXchange 2 (29): 1132. 2009. doi:10.1038/scibx.2009.1132.
14. ↑ "ATC/DDD Index". World Health Organization Collaborating Centre. http://www.whocc.no/atc_ddd_index/?code=D06BB05.
15. ↑ "Identification of inosine as an endogenous modulator for the benzodiazepine binding site of the GABAA receptors". Journal of Biomedical Science 5 (4): 274–280. July 1998. doi:10.1007/bf02255859. PMID 9691220.
16. ↑ "Advantage of using inosine at the 3' termini of 16S rRNA gene universal primers for the study of microbial diversity". Applied and Environmental Microbiology 72 (11): 6902–6906. November 2006. doi:10.1128/AEM.00849-06. PMID 16950904.
17. ↑ "An unwinding activity that covalently modifies its double-stranded RNA substrate". Cell 55 (6): 1089–1098. December 1988. doi:10.1016/0092-8674(88)90253-x. PMID 3203381.
18. ↑ "Identification of the gustatory feeding stimulants.". Chemoreception in Fishes. Amsterdam: Elsevier Scientific Publishing Co.. 1987. pp. 275–291.
19. ↑ "Identification of feeding stimulants for juvenile eel.". Bulletin of the Japanese Society of Scientific Fisheries 50 (4): 645–651. 1984. doi:10.2331/suisan.50.645.

## External links

* PDR health study

* v
* t
* e

Nucleic acid constituents

Nucleobase|

* Purine
* Adenine
* Guanine
* Hypoxanthine
* Xanthine
* Purine analogue
* Pyrimidine
* Uracil
* Thymine
* Cytosine
* Pyrimidine analogue
* Unnatural base pair (UBP)

Nucleoside|

| Ribonucleoside|

* Adenosine
* Guanosine
* 5-Methyluridine
* Uridine
* 5-Methylcytidine
* Cytidine
* Pseudouridine
* Inosine
* N6-Methyladenosine
* Xanthosine
* Wybutosine

|

Deoxyribonucleoside|

* Deoxyadenosine
* Deoxyguanosine
* Thymidine
* Deoxyuridine
* Deoxycytidine
* Deoxyinosine
* Deoxyxanthosine

Nucleotide
(Nucleoside monophosphate)|

| Ribonucleotide|

* AMP
* GMP
* m5UMP
* UMP
* CMP
* IMP
* XMP

|

Deoxyribonucleotide|

* dAMP
* dGMP
* dTMP
* dUMP
* dCMP
* dIMP
* dXMP

Cyclic nucleotide|

* cAMP
* cGMP
* c-di-GMP
* c-di-AMP
* cADPR

Nucleoside diphosphate|

* ADP
* GDP
* m5UDP
* UDP
* CDP

* dADP
* dGDP
* dTDP
* dUDP
* dCDP

Nucleoside triphosphate|

* ATP
* GTP
* m5UTP
* UTP
* CTP
* ITP
* XTP

* dATP
* dGTP
* dTTP
* dUTP
* dCTP
* dITP
* dXTP

* v
* t
* e

Antibiotics and chemotherapeutics for dermatological use (D06)

Antibiotics|

| Tetracycline and derivatives|

* Demeclocycline
* Chlortetracycline
* Oxytetracycline
* Tetracycline

|

Others|

* Amphenicol: Chloramphenicol

* Aminoglycosides: Neomycin
* Gentamicin
* Amikacin

* Quinolones: Nadifloxacin

* Streptogramin: Virginiamycin

* Rifamycin: Rifaximin

* other: Fusidic acid
* Bacitracin
* Tyrothricin
* Mupirocin

Chemotherapeutics|

| Sulfonamides|

* Silver sulfadiazine
* Sulfathiazole
* Mafenide
* Sulfamethizole
* Sulfanilamide
* Sulfamerazine

|

Antivirals|

* Aciclovir
* Penciclovir
* Idoxuridine
* Edoxudine
* Imiquimod
* Resiquimod
* Podophyllotoxin
* Docosanol
* Tromantadine
* Inosine
* Lysozyme
* Ibacitabine
* Lysine

Other|

* Ingenol mebutate
* Metronidazole

* v
* t
* e

Gynecological anti-infectives and antiseptics (G01)

Antibiotics|

* Candicidin
* Chloramphenicol
* Hachimycin
* Oxytetracycline
* Carfecillin
* Mepartricin
* Clindamycin
* Pentamycin

Arsenic compounds|

* Acetarsol

Quinoline derivatives|

* Diiodohydroxyquinoline
* Clioquinol
* Chlorquinaldol
* Dequalinium
* Broxyquinoline
* Oxyquinoline

Organic acids|

* Lactic acid
* Acetic acid
* Ascorbic acid

Sulfonamides|

* Sulfatolamide

Antifungals|

| Imidazoles|

* Metronidazole
* Clotrimazole
* Miconazole
* Econazole
* Ornidazole
* Isoconazole
* Tioconazole
* Ketoconazole
* Fenticonazole
* Azanidazole
* Propenidazole
* Butoconazole
* Omoconazole
* Oxiconazole
* Flutrimazole

|

Triazoles|

* Terconazole

Polyenes|

* Nystatin
* Natamycin
* Amphotericin B

Other|

* Ciclopirox
* Methylrosaniline

Other|

* Clodantoin
* Inosine
* Policresulen
* Nifuratel
* Furazolidone
* Povidone-iodine
* Protiofate
* Lactobacillus fermentum
* Copper usnate

* v
* t
* e

DNA virus antivirals (primarily J05, also S01AD and D06BB)

Baltimore I|

| Herpesvirus|

| DNA-synthesis
inhibitor|

| TK activated|

| Purine analogue|

* guanine (Aciclovir#/Valaciclovir
* Ganciclovir/Valganciclovir#
* Penciclovir/Famciclovir)

* adenine (Vidarabine)

|

Pyrimidine analogue|

* uridine (Idoxuridine
* Trifluridine (+tipiracil)
* Edoxudine)

* thymine
* Brivudine
* Sorivudine

* [[Chemistry:Cytocytosine (Cytarabine|Cytarabine]])

Not TK activated|

* Foscarnet

Other|

* Docosanol
* early protein (Fomivirsen)
* Tromantadine

HPV/MC|

* Imiquimod/Resiquimod
* Podophyllotoxin

Vaccinia|

* assembly: Rifampicin

Poxviridae|

* Methisazone

Hepatitis B (VII)|

* Nucleoside analogues/NARTIs: Entecavir#
* Lamivudine
* Telbivudine
* Clevudine

* Nucleotide analogues/NtRTIs: Adefovir
* Tenofovir disoproxil
* Tenofovir alafenamide

Multiple/general|

| Nucleic acid inhibitors|

* Cidofovir

|

Interferon|

* Interferon alfa 2b
* Peginterferon alfa-2a

Multiple/unknown|

* Ribavirin#/Taribavirin†
* Moroxydine

* #WHO-EM
* ‡Withdrawn from market
* Clinical trials:
* †Phase III
* §Never to phase III

* v
* t
* e

Purine receptor modulators

Receptor
(ligands)|

| P0 (adenine)|

* Agonists: 8-Aminoadenine
* Adenine

|

(adenosine)|

* Agonists: 2-(1-Hexynyl)-N-methyladenosine
* 2-Cl-IB-MECA
* 2'-MeCCPA
* 4'-O-β-D-Glucosyl-9-O-(6''-deoxysaccharosyl)olivil
* 5'-N-ethylcarboxamidoadenosine
* Adenosine
* ADP
* AMP
* Apadenoson
* ATL-146e
* ATP
* BAY 60–6583
* Binodenoson
* Capadenoson
* CCPA
* CGS-21680
* CP-532,903
* Evodenoson
* GR 79236
* LUF-5835
* LUF-5845
* N6-Cyclopentyladenosine
* Namodenoson
* Neladenoson dalanate
* Piclidenoson
* Regadenoson
* SDZ WAG 994
* Selodenoson
* Sonedenoson
* Tecadenoson
* UK-432,097

* Antagonists: 8-Chlorotheophylline
* 8-Phenyl-1,3-dipropylxanthine
* 8-Phenyltheophylline
* Acefylline
* Aminophylline
* ATL-444
* Bamifylline
* Cafedrine
* Caffeine
* Caffeine citrate
* Cartazolate
* CGH-2466
* CGS-15943
* Choline theophyllinate
* Ciforadenant
* CPX
* CVT-6883
* Dimethazan
* DMPX
* DPCPX
* Dyphylline
* Enprofylline
* Etazolate
* Fenethylline
* IBMX
* Isovaleric acid
* Istradefylline
* KF-26777
* MRE3008F20
* MRS-1220
* MRS-1334
* MRS-1706
* MRS-1754
* MRS-3777
* Paraxanthine
* Pentoxifylline
* Preladenant
* Propentofylline
* Proxyphylline
* PSB-10
* PSB-11
* PSB-36
* PSB-603
* PSB-788
* PSB-1115
* Reversine
* Rolofylline
* SCH-442,416
* SCH-58261
* Theacrine
* Theobromine
* Theodrenaline
* Theophylline
* Tozadenant
* Tracazolate
* VUF-5574
* ZM-241,385

(nucleotide)|

| P2X
(ATP)|

* Agonists: 2-Me-SATP
* α,β-Me-ATP
* Adenosine
* ADP
* AMP
* Ap4A
* Ap5A
* ATP
* ATPγS
* BzATP
* Cibacron blue
* CTP
* D-β,γ-Me-ATP
* GTP
* HT-AMP
* Ivermectin
* L-β,γ-Me-ATP
* MRS-2219
* PAPET-ATP
* UTP
* Zinc

* Antagonists: 5-BDBD
* A-317491
* A-438079
* A-740003
* A-804598
* A-839977
* AF-353
* AZ-10606120
* AZ-11645373
* BBG
* Calcium
* Calmidazolium
* Chelerythrine
* Copper
* Emodin (Rheum officinale)
* Evans Blue
* Gefapixant
* GW-791343
* HMA
* Ip5I
* isoPPADS
* JNJ-47965567
* KN-04
* KN-62
* Magnesium
* MRS-2159
* NF-023
* NF-110
* NF-157
* NF-279
* NF-449
* Opiranserin (VVZ-149)
* Oxidized-ATP
* Phenol Red
* Phenolphthalein
* PPADS
* PPNDS
* PSB-12062
* Puerarin (Radix puerariae)
* Purotoxin 1
* RB-2
* Ro 0437626
* Ro 51
* RO-3
* Sodium ferulate (Angelica sinensis, Ligusticum wallichii)
* Suramin
* TC-P 262
* Tetramethylpyrazine (ligustrazine) (Ligusticum wallichii)
* TNP-ATP
* Zinc

|

P2Y|

* Agonists: 2-Me-SADP
* 2-Me-SATP
* 2-Thio-UTP
* 5-Br-UDP
* 5-OMe-UDP
* α,β-Me-ATP
* Adenosine
* ADP
* ADPβS
* Ap3A
* AR-C 67085MX
* ATP
* ATPγS
* CTP
* dATP
* Denufosol
* Diquafosol
* IDP
* ITP
* INS-365
* INS-37217
* MRS-2365
* MRS-2690
* MRS-2693
* MRS-2768
* MRS-2957
* MRS-4062
* NF-546
* PAPET-ATP
* PSB-0474
* PSB-1114
* UDP
* UDPβS
* UDP-galactose
* UDP-glucose
* UDP-N-acetylglucosamine
* Up3U
* UTP
* UTPγS

* Antagonists: 2-Me-SAMP
* A3P5PS
* AMPαS
* Ap4A
* AR-C 66096
* AR-C 67085MX
* AR-C 69931MX
* AR-C 118925XX
* ATP
* BzATP
* C1330-7
* Cangrelor
* Clopidogrel
* Elinogrel
* Ip5I
* MRS-2179
* MRS-2211
* MRS-2279
* MRS-2395
* MRS-2500
* MRS-2578
* NF-157
* NF-340
* PIT
* PPADS
* Prasugrel
* PSB-0739
* RB-2
* Regrelor
* Suramin
* Ticagrelor
* Ticlopidine
* UDP

Transporter
(blockers)|

| CNTs|

* 6-Hydroxy-7-methoxyflavone
* Adenosine
* dMeThPmR
* Estradiol
* KGO-2142
* KGO-2173
* MeThPmR
* Phloridzin
* Progesterone

|

ENTs|

* Barbiturates
* Benzodiazepines
* Cilostazol
* Dilazep
* Dipyridamole
* Estradiol
* Ethanol
* Hexobendine
* NBMPR
* Pentoxifylline
* Progesterone
* Propentofylline

PMAT|

* Decynium-22

Enzyme
(inhibitors)|

| XO|

* Allopurinol
* Amflutizole
* Benzbromarone
* Caffeic acid
* Cinnamaldehyde
* Cinnamomum osmophloeum
* Febuxostat
* Myo-inositol
* Kaempferol
* Myricetin
* Niraxostat
* Oxipurinol
* Phytic acid
* Pistacia integerrima
* Propolis
* Quercetin
* Tisopurine
* Topiroxostat

|

Others|

* Aminopterin
* Azathioprine
* Methotrexate
* Mycophenolic acid
* Pemetrexed
* Pralatrexate
* Many others

Others|

* Precursors: Adenine
* Adenosine
* AMP
* ADP
* ATP
* Cytosine
* Cytidine
* CMP
* CDP
* CTP
* Guanine
* Guanosine
* GMP
* GDP
* GTP
* Hypoxanthine
* Inosine
* IMP
* IDP
* ITP
* Ribose
* Uracil
* Uridine
* UMP
* UDP
* UTP

* Others: Chrysophanol (rhubarb)

See also: Receptor/signaling modulators

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Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Inosine&oldid=32529"
*[CID]: Compound ID
*[v]: View this template
*[t]: Discuss this template
*[e]: Edit this template
*[ATP]: Adenosine triphosphate
*[CNTs]: Concentrative nucleoside transporters
*[ENTs]: Equilibrative nucleoside transporters
*[PMAT]: Plasma membrane monoamine transporter
*[XO]: Xanthine oxidase