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Identification
NameInosine
Accession NumberDB04335  (EXPT02378)
TypeSmall Molecule
GroupsInvestigational
DescriptionA purine nucleoside that has hypoxanthine linked by the N9 nitrogen to the C1 carbon of ribose. It is an intermediate in the degradation of purines and purine nucleosides to uric acid and in pathways of purine salvage. It also occurs in the anticodon of certain transfer RNA molecules. (Dorland, 28th ed)
Structure
Thumb
Synonyms
beta-Inosine
Hypoxanthosine
INO
Inosina
Inosinum
Oxiamin
Ribonosine
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
CatacolAlcon
LumiclarValeant
Brand mixtures
NameLabellerIngredients
RejuvesolCitra Labs Llc
SaltsNot Available
Categories
UNII5A614L51CT
CAS number58-63-9
WeightAverage: 268.2261
Monoisotopic: 268.080769514
Chemical FormulaC10H12N4O5
InChI KeyUGQMRVRMYYASKQ-KQYNXXCUSA-N
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
IUPAC Name
9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-3H-purin-6-one
SMILES
OC[[email protected]]1O[[email protected]]([[email protected]](O)[C@@H]1O)N1C=NC2=C1NC=NC2=O
Pharmacology
IndicationThe primary popular claim made for inosine, that it enhances exercise and athletic performance, is refuted by the available research data. There is some preliminary evidence that inosine may have some neurorestorative, anti-inflammatory, immunomodulatory and cardioprotective effects.
Structured Indications Not Available
PharmacodynamicsInosine may have neuroprotective, cardioprotective, anti-inflammatory and immunomodulatory activities.
Mechanism of actionInosine has been found to have potent axon-promoting effects in vivo following unilateral transection of the corticospinal tract of rats. The mechanism of this action is unclear. Possibilities include serving as an agonist of a nerve growth factor-activated protein kinase (N-Kinase), conversion to cyclic nucleotides that enable advancing nerve endings to overcome the inhibitory effects of myelin, stimulation of differentiation in rat sympathetic neurons, augmentation of nerve growth factor-induced neuritogenesis and promotion of the survival of astrocytes, among others. The mechanism of inosine's possible cardioprotective effect is similarly unclear. Inosine has been reported to have a positive inotropic effect and also to have mild coronary vasodilation activity. Exogenous inosine may contribute to the high-energy phosphate pool of cardiac muscle cells and favorably affect bioenergetics generally. Inosine has also been reported to enhance the myocardial uptake of carbohydrates relative to free fatty acids as well as glycolysis. In cell culture studies, inosine has been found to inhibit the production, in immunostimulated macrophages and spleen cells, of the proinflammatory cytokines, tumor necrosis factor (TNF)-alpha, interleukin (IL)-1, interleukin (IL)-12, macrophage-inflammatory protein-1 alpha and interferon (IFN)-gamma. It also suppressed proinflammatory cytokine production and mortality in a mouse endotoxemic model. These actions might account for the possible immunomodulatory, anti-inflammatory and anti-ischemic actions of inosine.
TargetKindPharmacological actionActionsOrganismUniProt ID
Purine nucleoside phosphorylaseProteinunknownNot AvailableHumanP00491 details
IAG-nucleoside hydrolaseProteinunknownNot AvailableTrypanosoma vivaxQ9GPQ4 details
Purine nucleoside phosphorylase DeoD-typeProteinunknownNot AvailableEscherichia coli (strain K12)P0ABP8 details
Related Articles
AbsorptionIngested inosine is absorbed from the small intestine.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

In the liver, inosine may be catabolized by a series of reactions culminating in the production of uric acid and also may be metabolized to adenine- and guanine-containing nucleotides. Inosine not metabolized in the liver is transported via the systemic circulation and distributed to various tissues of the body, where it is metabolized in similar fashion as in the liver. Uric acid, the purine end-product of inosine catabolism, is excreted in the urine.

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Lesch-Nyhan Syndrome (LNS)DiseaseSMP00364
Myoadenylate deaminase deficiencyDiseaseSMP00537
Gout or Kelley-Seegmiller SyndromeDiseaseSMP00365
Azathioprine Action PathwayDrug actionSMP00427
Xanthinuria type IIDiseaseSMP00513
Purine MetabolismMetabolicSMP00050
Adenosine Deaminase DeficiencyDiseaseSMP00144
Xanthine Dehydrogenase Deficiency (Xanthinuria)DiseaseSMP00220
Adenylosuccinate Lyase DeficiencyDiseaseSMP00167
Molybdenum Cofactor DeficiencyDiseaseSMP00203
Purine Nucleoside Phosphorylase DeficiencyDiseaseSMP00210
Adenine phosphoribosyltransferase deficiency (APRT)DiseaseSMP00535
Mitochondrial DNA depletion syndromeDiseaseSMP00536
AICA-RibosiduriaDiseaseSMP00168
Mercaptopurine Action PathwayDrug actionSMP00428
Thioguanine Action PathwayDrug actionSMP00430
Xanthinuria type IDiseaseSMP00512
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
References
Synthesis Reference

U.S. Patent 3,049,536
U.S. Patent 3,111,459

General ReferencesNot Available
External Links
ATC CodesG01AX02D06BB05S01XA10
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9523
Blood Brain Barrier+0.7979
Caco-2 permeable-0.907
P-glycoprotein substrateNon-substrate0.6601
P-glycoprotein inhibitor INon-inhibitor0.9717
P-glycoprotein inhibitor IINon-inhibitor0.8979
Renal organic cation transporterNon-inhibitor0.9422
CYP450 2C9 substrateNon-substrate0.8063
CYP450 2D6 substrateNon-substrate0.8396
CYP450 3A4 substrateNon-substrate0.558
CYP450 1A2 substrateNon-inhibitor0.8425
CYP450 2C9 inhibitorNon-inhibitor0.9637
CYP450 2D6 inhibitorNon-inhibitor0.9629
CYP450 2C19 inhibitorNon-inhibitor0.9607
CYP450 3A4 inhibitorNon-inhibitor0.9825
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.954
Ames testNon AMES toxic0.9354
CarcinogenicityNon-carcinogens0.922
BiodegradationNot ready biodegradable0.7774
Rat acute toxicity2.0115 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9855
hERG inhibition (predictor II)Non-inhibitor0.908
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
SolutionExtracorporeal
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point218 dec °CPhysProp
water solubility1.58E+004 mg/L (at 20 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-2.10HANSCH,C ET AL. (1995)
logS-1.23ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility14.3 mg/mLALOGPS
logP-1.7ALOGPS
logP-2ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)6.94ChemAxon
pKa (Strongest Basic)2.74ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area129.2 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity60.9 m3·mol-1ChemAxon
Polarizability24.6 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0frt-0890000000-c0c5ebc2bbf12c1a7edfView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-00di-9440000000-566aadb777ee03fb22fbView in MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0fsi-1690000000-364bf8794afeeff6ba51View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0900000000-012b2024bf3b3837c54cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-0900000000-08a2204bd9dd4d300b73View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-2900000000-8da9aa27b202f672fb83View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0930000000-ee37a7516ef378cd665dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-0900000000-e0575da4ae91163a2a90View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-379f5383e1bd290db9b6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0900000000-cd539725f09d01a39e25View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0uxr-0930000000-b69310182305cd88dbc5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00l2-9300000000-65a24aadb3a2b262cacfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-9c77149cd916c0340573View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-e8f9aac2c9bfc820dc7dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-014r-0490020000-6eeacbf0ca8726ed8542View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0006-9100000000-cdcc2e477ba37ca8f07aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0900000000-f96733a8f63a90d3644dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0002-0900000000-b9b05cbee9a42ce87c0fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-015i-0696011000-c836d8cd13395c898ae1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0006-9100000000-d8c6fdb9231ac2c6e939View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0900000000-632ba91cd477e5aaf9e5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0910000000-fc11279b73334e4ea0a8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-0090000000-00981efb4a9571473866View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-014i-0390000000-989ff580a7b60b151996View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-000i-0920000000-b78cba83cbf8f1ae48f3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-000i-0910000000-505a6507fcb525fe9a14View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-052r-2900000000-33d1372d34f6b06e3a2fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-000i-0900000000-a0601a44cbbc12888cc2View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as purine nucleosides. These are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleosides
Sub ClassNot Available
Direct ParentPurine nucleosides
Alternative Parents
Substituents
  • Purine ribonucleoside
  • N-glycosyl compound
  • Glycosyl compound
  • Purinone
  • Hypoxanthine
  • 6-oxopurine
  • Purine
  • Imidazopyrimidine
  • Pyrimidone
  • Pyrimidine
  • N-substituted imidazole
  • Monosaccharide
  • Saccharide
  • Heteroaromatic compound
  • Vinylogous amide
  • Oxolane
  • Imidazole
  • Azole
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Purine-nucleoside phosphorylase activity
Specific Function:
The purine nucleoside phosphorylases catalyze the phosphorolytic breakdown of the N-glycosidic bond in the beta-(deoxy)ribonucleoside molecules, with the formation of the corresponding free purine bases and pentose-1-phosphate.
Gene Name:
PNP
Uniprot ID:
P00491
Molecular Weight:
32117.69 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Trypanosoma vivax
Pharmacological action
unknown
General Function:
Metal ion binding
Specific Function:
Not Available
Gene Name:
Not Available
Uniprot ID:
Q9GPQ4
Molecular Weight:
36330.44 Da
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
unknown
General Function:
Purine-nucleoside phosphorylase activity
Specific Function:
Cleavage of guanosine or inosine to respective bases and sugar-1-phosphate molecules.
Gene Name:
deoD
Uniprot ID:
P0ABP8
Molecular Weight:
25949.68 Da

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinducer
General Function:
Xanthine oxidase activity
Specific Function:
Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species. Has also low oxidase activity towards aldehydes (in vitro).
Gene Name:
XDH
Uniprot ID:
P47989
Molecular Weight:
146422.99 Da
References
  1. STIRPE F, DELLACORTE E: REGULATION OF XANTHINE DEHYDROGENASE IN CHICK LIVER. EFFECT OF STARVATION AND OF ADMINISTRATION OF PURINES AND PURINE NUCLEOSIDES. Biochem J. 1965 Feb;94:309-13. [PubMed:14348191 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Pyrimidine- and adenine-specific:sodium symporter activity
Specific Function:
Sodium-dependent, pyrimidine- and purine-selective. Involved in the homeostasis of endogenous nucleosides. Exhibits the transport characteristics of the nucleoside transport system cib or N3 subtype (N3/cib) (with marked transport of both thymidine and inosine). Employs a 2:1 sodium/nucleoside ratio. Also able to transport gemcitabine, 3'-azido-3'-deoxythymidine (AZT), ribavirin and 3-deazaurid...
Gene Name:
SLC28A3
Uniprot ID:
Q9HAS3
Molecular Weight:
76929.61 Da
References
  1. Badagnani I, Chan W, Castro RA, Brett CM, Huang CC, Stryke D, Kawamoto M, Johns SJ, Ferrin TE, Carlson EJ, Burchard EG, Giacomini KM: Functional analysis of genetic variants in the human concentrative nucleoside transporter 3 (CNT3; SLC28A3). Pharmacogenomics J. 2005;5(3):157-65. [PubMed:15738947 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:24