INOSINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C10H12N4O5
Molecular Weight	268.2261
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N2C=NC3=C2N=CNC3=O

InChI

InChIKey=UGQMRVRMYYASKQ-KQYNXXCUSA-N

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

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24880154 | https://www.ncbi.nlm.nih.gov/pubmed/20945982 | https://www.ncbi.nlm.nih.gov/pubmed/24366103

Inosine is a naturally occurring nucleoside which serves as an intermediate in purine metabolism. The metabolism of purines in humans generates a potent antioxidant compound, uric acid, which is known to be a natural scavenger of both oxygen and nitrogen reactive species as well as having chelator properties. Inosine, as a precursor of uric acid, was shown to have neuroprotective effect in vitro and is being tested in phase III of clinical trials for the treatment of Parkinson disease. The treatment with inosine is belived to prevent or slow the disease.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
reactive oxygen species biosynthetic process 37 Target ID: GO:1903409 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20945982	Inhibitor 8297
reactive nitrogen species metabolic process 3 Target ID: GO:2001057 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20945982	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Parkinson's disease 226 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24366103	Primary		Phase III 656	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Use of DNA molecules substituted with unnatural nucleotides to probe specific drug-DNA interactions.	2001	11494865
Intracellular Ca(2+)-mobilizing adenine nucleotides. Synthesis and biological activity of cyclic ADP-carbocyclic-ribose and C-glycosidic analog of adenophostin A.	2001 Apr-Jul	11563061
Acyclic/carbocyclic guanosine analogues as anti-herpesvirus agents.	2001 Apr-Jul	11563039
Inosine attenuates tourniquet-induced skeletal muscle reperfusion injury.	2001 Aug	11469903
High adenosine and deoxyadenosine concentrations in mononuclear cells of hemodialyzed patients.	2001 Aug	11461945
Induction of Tmolt4 leukemia cell death by 3,3-disubstituted-6,6-pentamethylene-1,5-diazabicyclo[3.1.0]hexane-2-4-diones: specificity for type II inosine 5'-monophasphate dehydrogenase.	2001 Aug	11454943
Pyruvate improves cerebral metabolism during hemorrhagic shock.	2001 Aug	11454591
In vitro effects of mycophenolic acid on the nucleotide pool and on the expression of adhesion molecules of human umbilical vein endothelial cells.	2001 Aug 1	11485760
Determination of the effects of mycophenolic acid on the nucleotide pool of human peripheral blood mononuclear cells in vitro by high-performance liquid chromatography.	2001 Aug 1	11485759
Specific cleavage of hyper-edited dsRNAs.	2001 Aug 1	11483527
The fate of dsRNA in the nucleus: a p54(nrb)-containing complex mediates the nuclear retention of promiscuously A-to-I edited RNAs.	2001 Aug 24	11525732
International Union of Pharmacology. XXV. Nomenclature and classification of adenosine receptors.	2001 Dec	11734617
Anti-inflammatory effects of inosine in human monocytes, neutrophils and epithelial cells in vitro.	2001 Dec	11712075
Identification and determination of nucleosides in rat brain microdialysates by liquid chromatography/electrospray tandem mass spectrometry.	2001 Dec	11600309
Wobble base-pairing in codon-anticodon interactions: a theoretical modelling study.	2001 Feb-Apr	11563322
Chronic ethanol enhances adenosine antiadrenergic actions in the isolated rat heart.	2001 Jul	11505020
Separation of inosine, hypoxanthine, and guanosine by high-performance liquid chromatography on silica.	2001 Jul	11471987
Mollusk-derived growth factor: cloning and developmental expression in the central nervous system and reproductive tract of Aplysia.	2001 Jul 13	11457505
Stereocontrolled syntheses of carbocyclic C-nucleosides and related compounds.	2001 Jul 13	11442416
Multiple cleavage activities of endonuclease V from Thermotoga maritima: recognition and strand nicking mechanism.	2001 Jul 31	11467933
F13459, a new derivative of mycophenolic acid. I. Taxonomy, isolation, and biological properties.	2001 Jun	11513037
Inosine monophosphate dehydrogenase (IMPDH) inhibition in vitro suppresses lymphocyte proliferation and the production of immunoglobulins, autoantibodies and cytokines in splenocytes from MRLlpr/lpr mice.	2001 Jun	11472413
The salivary adenosine deaminase activity of the mosquitoes Culex quinquefasciatus and Aedes aegypti.	2001 Jun	11441041
Factors that modify penicillamine-induced autoimmunity in Brown Norway rats: failure of the Th1/Th2 paradigm.	2001 Jun 21	11516529
Direct observation of radical intermediates in protein-dependent DNA charge transport.	2001 May 16	11457224
Long-range cooperativity in molecular recognition of RNA by oligodeoxynucleotides with multiple C5-(1-propynyl) pyrimidines.	2001 May 9	11457173
5'-Adenosine monophosphate and adenosine metabolism, and adenosine responses in mouse, rat and guinea pig heart.	2001 Nov	11691599
Formation of 2-chloroinosine from guanosine by treatment of HNO(2) in the presence of NaCl.	2001 Nov	11597475
Synthesis of 9-(2,3-dideoxy-2-fluoro-beta-D-threo-pentofuranosyl)adenine (FddA) via a purine 3'-deoxynucleoside.	2001 Nov 2	11681963
Inactivation of peroxynitrite in multiple sclerosis patients after oral administration of inosine may suggest possible approaches to therapy of the disease.	2001 Oct	11724447
Hamao Umezawa Memorial Award Lecture: "An Odyssey in the Viral Chemotherapy Field".	2001 Oct	11691563
Pre-conditioning activates adenosine utilization in a cost-effective way during myocardial ischaemia.	2001 Oct	11683676
Cardioprotection with adenosine metabolism inhibitors in ischemic-reperfused mouse heart.	2001 Oct	11557240
Inosine reduces systemic inflammation and improves survival in septic shock induced by cecal ligation and puncture.	2001 Oct 1	11673212
Mechanism of action of the antitumor agents 6-benzoyl-3,3-disubstituted-1,5-diazabicyclo[3.1.0]hexane-2,4-diones: potent inhibitors of human type II inosine 5'-monophosphate dehydrogenase.	2001 Oct 15	11668509
Vaccinia virus E3L interferon resistance protein inhibits the interferon-induced adenosine deaminase A-to-I editing activity.	2001 Oct 25	11689059
Catabolism of exogenous deoxyinosine in cultured epithelial amniotic cells.	2001 Oct 3	11687292
Receptor-mediated interaction between the sympathetic nervous system and immune system in inflammation.	2001 Sep	11699931
Effect of transketolase modifications on carbon flow to the purine-nucleotide pathway in Corynebacterium ammoniagenes.	2001 Sep	11601619
Effect of glycerol-induced hyperhydration on thermoregulation and metabolism during exercise in heat.	2001 Sep	11591882
Concentrations of nucleotides, nucleosides, purine bases, oxypurines, uric acid, and neuron-specific enolase in the cerebrospinal fluid of children with sepsis.	2001 Sep	11575617
Profiles of purine and pyrimidine nucleotides in fresh and manufactured tea leaves.	2001 Sep	11559141
Taste perception with age: generic or specific losses in threshold sensitivity to the five basic tastes?	2001 Sep	11555480
In vitro effects of isoprinosine and a dipeptide methyl ester on Echinococcus multilocularis protoscoleces.	2001 Sep	11551315
Early onset of lipid peroxidation after human traumatic brain injury: a fatal limitation for the free radical scavenger pharmacological therapy?	2001 Sep	11523701
Cytosolic O-GlcNAc accumulation is not involved in beta-cell death in HIT-T15 or Min6.	2001 Sep 21	11554736
Stabilities and isomeric equilibria in solutions of monomeric metal-ion complexes of guanosine 5'-triphosphate (GTP4-) and inosine 5'-triphosphate (ITP4-) in comparison with those of adenosine 5'-triphosphate (ATP4-).	2001 Sep 3	11575773
Ophidian envenomation strategies and the role of purines.	2002 Apr	11738231
Transition state analogue inhibitors of purine nucleoside phosphorylase from Plasmodium falciparum.	2002 Feb 1	11707439
Purine-less death in Plasmodium falciparum induced by immucillin-H, a transition state analogue of purine nucleoside phosphorylase.	2002 Feb 1	11706018

Patents

Sample Use Guides

In Vivo Use Guide

Capsules containing 500 mg of inosine should be taken orally up to two capsules three times per day (i.e., up to 3 g/day) for 24 months.

Route of Administration: Oral

In Vitro Use Guide

Rodent MES 23.5 dopaminergic cell were pretreated with inosine (0.1–100 uM) for 24 hours before addition of the oxidative stress inducer H2O2 (200 uM). Inosine decreased toxicant-induced oxidative stress at 3 hours.

Name

Type

Language

INOSINE

Official Name

English

HYPOXANTHINE RIBOSIDE

Common Name

English

INOSINE [MART.]

Common Name

English

9-.BETA.-D-RIBOFURANOSYL-1,9-DIHYDRO-6H-PURIN-6-ONE

Systematic Name

English

inosine [INN]

Common Name

English

9-.BETA.-D-RIBOFURANOSYLHYPOXANTHINE

Common Name

English

INOSINE [MI]

Common Name

English

DIDANOSINE IMPURITY B [EP IMPURITY]

Common Name

English

INOSINE [WHO-IP]

Common Name

English

INOSINE [JAN]

Common Name

English

INOSINE [INCI]

Common Name

English

NSC-20262

Code

English

INOTIN

Brand Name

English

9-.BETA.-D-RIBOFURANOSYL-1,9-DIHYDRO-6H-PURIN-6-ONE [WHO-IP]

Common Name

English

HYPOXANTHOSINE

Common Name

English

INOSINE [USP IMPURITY]

Common Name

English

ADENOSINE IMPURITY G [EP IMPURITY]

Common Name

English

DIDANOSINE IMPURITY B [WHO-IP]

Common Name

English

Inosine [WHO-DD]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QG01AX02