Identification
- Summary
Inosine is a nutritional supplement touted to improve athletic performance and a drug used in vitro as a red blood cell rejuvenator for a unit of red blood cells that will be used in a clinical setting.
- Brand Names
- Rejuvesol
- Generic Name
- Inosine
- DrugBank Accession Number
- DB04335
- Background
A 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)
- Type
- Small Molecule
- Groups
- Experimental, Investigational
- Structure
Structure for Inosine (DB04335)
- Weight
- Average: 268.2261
Monoisotopic: 268.080769514 - Chemical Formula
- C10H12N4O5
- Synonyms
- 9-β-D-ribofuranosyl-9H-purin-6-ol
- 9-β-D-ribofuranosylhypoxanthine
- beta-Inosine
- hypoxanthine D-riboside
- Hypoxanthosine
- INO
- Inosin
- Inosina
- Inosine
- Inosinum
Pharmacology
- Indication
The 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.
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- Contraindications & Blackbox Warnings
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Inosine may have neuroprotective, cardioprotective, anti-inflammatory and immunomodulatory activities.
- Mechanism of action
Inosine 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.
Target Actions Organism UPurine nucleoside phosphorylase Not Available Humans UIAG-nucleoside hydrolase Not Available Trypanosoma vivax UPurine nucleoside phosphorylase DeoD-type Not Available Escherichia coli (strain K12) - Absorption
Ingested inosine is absorbed from the small intestine.
- Volume of distribution
Not Available
- Protein binding
Not 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 elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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Not Available
- Pathways
Pathway Category Adenylosuccinate Lyase Deficiency Disease Xanthine Dehydrogenase Deficiency (Xanthinuria) Disease Xanthinuria Type I Disease Mitochondrial DNA Depletion Syndrome Disease Myoadenylate Deaminase Deficiency Disease Purine Metabolism Metabolic Purine Nucleoside Phosphorylase Deficiency Disease Lesch-Nyhan Syndrome (LNS) Disease Gout or Kelley-Seegmiller Syndrome Disease Mercaptopurine Action Pathway Drug action Adenine Phosphoribosyltransferase Deficiency (APRT) Disease Adenosine Deaminase Deficiency Disease AICA-Ribosiduria Disease Molybdenum Cofactor Deficiency Disease Azathioprine Action Pathway Drug action Thioguanine Action Pathway Drug action Xanthinuria Type II Disease - Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Catacol (Alcon) / Inotin / Lumiclar (Valeant)
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Rejuvesol Inosine (1.34 g/50mL) + Adenine (0.034 g/50mL) + Sodium pyruvate (0.55 g/50mL) + Sodium phosphate, dibasic, unspecified form (0.73 g/50mL) + Sodium phosphate, monobasic, monohydrate (0.311 g/50mL) Solution Extracorporeal Citra Labs, LLC 1997-02-26 Not applicable US 
Categories
- ATC Codes
- G01AX02 — Inosine
- G01AX — Other antiinfectives and antiseptics
- G01A — ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS
- G01 — GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
- G — GENITO URINARY SYSTEM AND SEX HORMONES
- S01XA — Other ophthalmologicals
- S01X — OTHER OPHTHALMOLOGICALS
- S01 — OPHTHALMOLOGICALS
- S — SENSORY ORGANS
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This 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.
- Kingdom
- Organic compounds
- Super Class
- Nucleosides, nucleotides, and analogues
- Class
- Purine nucleosides
- Sub Class
- Not Available
- Direct Parent
- Purine nucleosides
- Alternative Parents
- Glycosylamines / 6-oxopurines / Pentoses / Hypoxanthines / Pyrimidones / N-substituted imidazoles / Vinylogous amides / Tetrahydrofurans / Heteroaromatic compounds / Secondary alcohols show 7 more
- Substituents
- 6-oxopurine / Alcohol / Aromatic heteropolycyclic compound / Azacycle / Azole / Glycosyl compound / Heteroaromatic compound / Hydrocarbon derivative / Hypoxanthine / Imidazole show 22 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- inosines (CHEBI:17596)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 5A614L51CT
- CAS number
- 58-63-9
- InChI Key
- UGQMRVRMYYASKQ-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[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1NC=NC2=O
References
- Synthesis Reference
U.S. Patent 3,049,536 U.S. Patent 3,111,459
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0000195
- KEGG Drug
- D00054
- KEGG Compound
- C00294
- PubChem Compound
- 6021
- PubChem Substance
- 175426857
- ChemSpider
- 5799
- BindingDB
- 22104
- 1483575
- ChEBI
- 17596
- ChEMBL
- CHEMBL1556
- ZINC
- ZINC000008855117
- PharmGKB
- PA130230922
- PDBe Ligand
- NOS
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Inosine
- PDB Entries
- 1a9s / 1kic / 1pr0 / 1rct / 1z38 / 2bsx / 2fqw / 3b1p / 3b1q / 3b9x … show 12 more
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Other Sickle Cell Disease (SCD) 1 4 Withdrawn Basic Science Heart Defects,Congenital 1 3 Completed Other Parkinson's Disease (PD) 1 3 Completed Treatment Cognitive Dysfunctions 1 3 Completed Treatment Diabetic Neuropathies 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Solution Extracorporeal - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 218 dec °C PhysProp water solubility 1.58E+004 mg/L (at 20 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) logP -2.10 HANSCH,C ET AL. (1995) logS -1.23 ADME Research, USCD - Predicted Properties
Property Value Source Water Solubility 14.3 mg/mL ALOGPS logP -1.7 ALOGPS logP -2 Chemaxon logS -1.3 ALOGPS pKa (Strongest Acidic) 10.93 Chemaxon pKa (Strongest Basic) 2.74 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 8 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 129.2 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 60.9 m3·mol-1 Chemaxon Polarizability 24.6 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9523 Blood Brain Barrier + 0.7979 Caco-2 permeable - 0.907 P-glycoprotein substrate Non-substrate 0.6601 P-glycoprotein inhibitor I Non-inhibitor 0.9717 P-glycoprotein inhibitor II Non-inhibitor 0.8979 Renal organic cation transporter Non-inhibitor 0.9422 CYP450 2C9 substrate Non-substrate 0.8063 CYP450 2D6 substrate Non-substrate 0.8396 CYP450 3A4 substrate Non-substrate 0.558 CYP450 1A2 substrate Non-inhibitor 0.8425 CYP450 2C9 inhibitor Non-inhibitor 0.9637 CYP450 2D6 inhibitor Non-inhibitor 0.9629 CYP450 2C19 inhibitor Non-inhibitor 0.9607 CYP450 3A4 inhibitor Non-inhibitor 0.9825 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.954 Ames test Non AMES toxic 0.9354 Carcinogenicity Non-carcinogens 0.922 Biodegradation Not ready biodegradable 0.7774 Rat acute toxicity 2.0115 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9855 hERG inhibition (predictor II) Non-inhibitor 0.908
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 169.0414332 predictedDarkChem Lite v0.1.0 [M-H]- 167.9155332 predictedDarkChem Lite v0.1.0 [M-H]- 168.9635332 predictedDarkChem Lite v0.1.0 [M-H]- 149.04985 predictedDeepCCS 1.0 (2019) [M-H]- 169.0414332 predictedDarkChem Lite v0.1.0 [M-H]- 167.9155332 predictedDarkChem Lite v0.1.0 [M-H]- 168.9635332 predictedDarkChem Lite v0.1.0 [M-H]- 149.04985 predictedDeepCCS 1.0 (2019) [M+H]+ 169.7581332 predictedDarkChem Lite v0.1.0 [M+H]+ 168.6665332 predictedDarkChem Lite v0.1.0 [M+H]+ 169.7317332 predictedDarkChem Lite v0.1.0 [M+H]+ 151.44542 predictedDeepCCS 1.0 (2019) [M+H]+ 169.7581332 predictedDarkChem Lite v0.1.0 [M+H]+ 168.6665332 predictedDarkChem Lite v0.1.0 [M+H]+ 169.7317332 predictedDarkChem Lite v0.1.0 [M+H]+ 151.44542 predictedDeepCCS 1.0 (2019) [M+Na]+ 169.1629332 predictedDarkChem Lite v0.1.0 [M+Na]+ 168.3755332 predictedDarkChem Lite v0.1.0 [M+Na]+ 169.6233332 predictedDarkChem Lite v0.1.0 [M+Na]+ 158.05357 predictedDeepCCS 1.0 (2019) [M+Na]+ 169.1629332 predictedDarkChem Lite v0.1.0 [M+Na]+ 168.3755332 predictedDarkChem Lite v0.1.0 [M+Na]+ 169.6233332 predictedDarkChem Lite v0.1.0 [M+Na]+ 158.05357 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- 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 ...
- Gene Name
- PNP
- Uniprot ID
- P00491
- Uniprot Name
- Purine nucleoside phosphorylase
- Molecular Weight
- 32117.69 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Trypanosoma vivax
- Pharmacological action
- Unknown
- General Function
- Metal ion binding
- Specific Function
- Not Available
- Gene Name
- Not Available
- Uniprot ID
- Q9GPQ4
- Uniprot Name
- IAG-nucleoside hydrolase
- 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
- Uniprot Name
- Purine nucleoside phosphorylase DeoD-type
- Molecular Weight
- 25949.68 Da
Enzymes
- Kind
- Protein
- Organism
- Humans
- 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. Ha...
- Gene Name
- XDH
- Uniprot ID
- P47989
- Uniprot Name
- Xanthine dehydrogenase/oxidase
- Molecular Weight
- 146422.99 Da
References
- 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. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- 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 subtyp...
- Gene Name
- SLC28A3
- Uniprot ID
- Q9HAS3
- Uniprot Name
- Solute carrier family 28 member 3
- Molecular Weight
- 76929.61 Da
References
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at September 28, 2021 21:54