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

Molecular Formula	C10H12N4O5
Molecular Weight	268.2261
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

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 41 Target ID: GO:1903409 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20945982	Inhibitor 8504
reactive nitrogen species metabolic process 3 Target ID: GO:2001057 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20945982	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Parkinson's disease 232 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24366103	Primary		Phase III 665	Unknown Approved Use Unknown

T_1/2

Value	Dose	Co-administered	Analyte	Population
50 min REVIEW https://pubmed.ncbi.nlm.nih.gov/2431857/	single, oral		INOSINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
100% OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/790005_3999007F1031_1_M01_1F.pdf#page=21			INOSINE plasma	Homo sapiens

Doses

Dose	Population	Adverse events
10 g 2 times / day multiple, oral Highest studied dose Dose: 10 g, 2 times / day Route: oral Route: multiple Dose: 10 g, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10660865/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: FED Sources: https://pubmed.ncbi.nlm.nih.gov/10660865/	Sources: https://pubmed.ncbi.nlm.nih.gov/10660865/

PubMed

Title	Date	PubMed
Ophidian envenomation strategies and the role of purines.	2002-04	11738231
Transition state analogue inhibitors of purine nucleoside phosphorylase from Plasmodium falciparum.	2002-02-01	11707439
Purine-less death in Plasmodium falciparum induced by immucillin-H, a transition state analogue of purine nucleoside phosphorylase.	2002-02-01	11706018
International Union of Pharmacology. XXV. Nomenclature and classification of adenosine receptors.	2001-12	11734617
Anti-inflammatory effects of inosine in human monocytes, neutrophils and epithelial cells in vitro.	2001-12	11712075
Identification and determination of nucleosides in rat brain microdialysates by liquid chromatography/electrospray tandem mass spectrometry.	2001-12	11600309
Synthesis of 9-(2,3-dideoxy-2-fluoro-beta-D-threo-pentofuranosyl)adenine (FddA) via a purine 3'-deoxynucleoside.	2001-11-02	11681963
5'-Adenosine monophosphate and adenosine metabolism, and adenosine responses in mouse, rat and guinea pig heart.	2001-11	11691599
Formation of 2-chloroinosine from guanosine by treatment of HNO(2) in the presence of NaCl.	2001-11	11597475
Vaccinia virus E3L interferon resistance protein inhibits the interferon-induced adenosine deaminase A-to-I editing activity.	2001-10-25	11689059
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.	2001-10-15	11668509
Catabolism of exogenous deoxyinosine in cultured epithelial amniotic cells.	2001-10-03	11687292
Inosine reduces systemic inflammation and improves survival in septic shock induced by cecal ligation and puncture.	2001-10-01	11673212
Inactivation of peroxynitrite in multiple sclerosis patients after oral administration of inosine may suggest possible approaches to therapy of the disease.	2001-10	11724447
Hamao Umezawa Memorial Award Lecture: "An Odyssey in the Viral Chemotherapy Field".	2001-10	11691563
Pre-conditioning activates adenosine utilization in a cost-effective way during myocardial ischaemia.	2001-10	11683676
Cardioprotection with adenosine metabolism inhibitors in ischemic-reperfused mouse heart.	2001-10	11557240
Wobble base-pairing in codon-anticodon interactions: a theoretical modelling study.	2001-09-21	11563322
Intracellular Ca(2+)-mobilizing adenine nucleotides. Synthesis and biological activity of cyclic ADP-carbocyclic-ribose and C-glycosidic analog of adenophostin A.	2001-09-21	11563061
Acyclic/carbocyclic guanosine analogues as anti-herpesvirus agents.	2001-09-21	11563039
Cytosolic O-GlcNAc accumulation is not involved in beta-cell death in HIT-T15 or Min6.	2001-09-21	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-).	2001-09-03	11575773
Receptor-mediated interaction between the sympathetic nervous system and immune system in inflammation.	2001-09	11699931
Effect of transketolase modifications on carbon flow to the purine-nucleotide pathway in Corynebacterium ammoniagenes.	2001-09	11601619
Effect of glycerol-induced hyperhydration on thermoregulation and metabolism during exercise in heat.	2001-09	11591882
Concentrations of nucleotides, nucleosides, purine bases, oxypurines, uric acid, and neuron-specific enolase in the cerebrospinal fluid of children with sepsis.	2001-09	11575617
Profiles of purine and pyrimidine nucleotides in fresh and manufactured tea leaves.	2001-09	11559141
Taste perception with age: generic or specific losses in threshold sensitivity to the five basic tastes?	2001-09	11555480
In vitro effects of isoprinosine and a dipeptide methyl ester on Echinococcus multilocularis protoscoleces.	2001-09	11551315
Early onset of lipid peroxidation after human traumatic brain injury: a fatal limitation for the free radical scavenger pharmacological therapy?	2001-09	11523701
The fate of dsRNA in the nucleus: a p54(nrb)-containing complex mediates the nuclear retention of promiscuously A-to-I edited RNAs.	2001-08-24	11525732
In vitro effects of mycophenolic acid on the nucleotide pool and on the expression of adhesion molecules of human umbilical vein endothelial cells.	2001-08-01	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.	2001-08-01	11485759
Specific cleavage of hyper-edited dsRNAs.	2001-08-01	11483527
Inosine attenuates tourniquet-induced skeletal muscle reperfusion injury.	2001-08	11469903
High adenosine and deoxyadenosine concentrations in mononuclear cells of hemodialyzed patients.	2001-08	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.	2001-08	11454943
Pyruvate improves cerebral metabolism during hemorrhagic shock.	2001-08	11454591
Multiple cleavage activities of endonuclease V from Thermotoga maritima: recognition and strand nicking mechanism.	2001-07-31	11467933
Mollusk-derived growth factor: cloning and developmental expression in the central nervous system and reproductive tract of Aplysia.	2001-07-13	11457505
Stereocontrolled syntheses of carbocyclic C-nucleosides and related compounds.	2001-07-13	11442416
Chronic ethanol enhances adenosine antiadrenergic actions in the isolated rat heart.	2001-07	11505020
Separation of inosine, hypoxanthine, and guanosine by high-performance liquid chromatography on silica.	2001-07	11471987
Factors that modify penicillamine-induced autoimmunity in Brown Norway rats: failure of the Th1/Th2 paradigm.	2001-06-21	11516529
F13459, a new derivative of mycophenolic acid. I. Taxonomy, isolation, and biological properties.	2001-06	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.	2001-06	11472413
The salivary adenosine deaminase activity of the mosquitoes Culex quinquefasciatus and Aedes aegypti.	2001-06	11441041
Direct observation of radical intermediates in protein-dependent DNA charge transport.	2001-05-16	11457224
Long-range cooperativity in molecular recognition of RNA by oligodeoxynucleotides with multiple C5-(1-propynyl) pyrimidines.	2001-05-09	11457173
Use of DNA molecules substituted with unnatural nucleotides to probe specific drug-DNA interactions.	2001	11494865

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.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 09:16:50 GMT 2025` Edited by `admin` on `Wed Apr 02 09:16:50 GMT 2025`
Record UNII	5A614L51CT
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

INOSINE

Official Name

English

INOTIN

Preferred 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

NSC-20262

Code

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