GUANOSINE

Possibly Marketed Outside US

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C10H13N5O5
Molecular Weight	283.2407
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC1=NC2=C(N=CN2[C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)C(=O)N1

InChI

InChIKey=NYHBQMYGNKIUIF-UUOKFMHZSA-N

InChI=1S/C10H13N5O5/c11-10-13-7-4(8(19)14-10)12-2-15(7)9-6(18)5(17)3(1-16)20-9/h2-3,5-6,9,16-18H,1H2,(H3,11,13,14,19)/t3-,5-,6-,9-/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11200257 | https://www.ncbi.nlm.nih.gov/pubmed/26695181 | https://www.ncbi.nlm.nih.gov/pubmed/27699087

Guanosine is an endogenous guanine nucleoside. Guanosine was shown to be protective in several in vitro and/or in vivo experimental models of central nervous system (CNS) diseases including ischemic stroke, Alzheimer's disease, Parkinson's disease, spinal cord injury, nociception, and depression. The mechanisms underlying the neurobiological properties of guanosine seem to involve the activation of several intracellular signaling pathways and a close interaction with the adenosinergic system, with a consequent stimulation of neuroprotective and regenerative processes in the CNS. Several guanosine analogues, i.e. acyclovir (and its oral prodrug valaciclovir), penciclovir (in its oral prodrug form, famciclovir) and ganciclovir, are widely used for the treatment of herpesvirus (i.e. HSV-1, HSV-2, VZV and HCMV) infections.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
apoptotic process 51 Target ID: GO:0006915 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18600524	Inhibitor 8504
Oxidative Stress 162 Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20846477	Inhibitor 8504
cell proliferation 28 Target ID: GO:0008283 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24152836	Activator 1447

Conditions

Condition	Modality	Targets	Highest Phase	Product
Stroke 144 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18191898 https://www.ncbi.nlm.nih.gov/pubmed/26695181	Primary		Preclinical	Unknown Approved Use Unknown
Hepatic encephalopathy 5 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24788896	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Ca2+-induced contraction of cat esophageal circular smooth muscle cells.	2001-04	11245615
G protein coupling to M1 and M3 muscarinic receptors in sublingual glands.	2001-04	11245606
[Identification and isolation of GTP-binding regulator protein from plasma membranes of oocytes from the starfish Asterias amurensis].	2001-03-10	11236575
Structural origins of aminoglycoside specificity for prokaryotic ribosomes.	2001-03-09	11237617
Structure of a eukaryotic decoding region A-site RNA.	2001-03-09	11237616
Tetraplex formation by the progressive myoclonus epilepsy type-1 repeat: implications for instability in the repeat expansion diseases.	2001-03-02	11240124
Inhibitory effects of SR141716A on G-protein activation in rat brain.	2001-03-02	11239913
Radioligand binding properties of VV-hemorphin 7, an atypical opioid peptide.	2001-03-02	11237710
Modulation of the neuronal glutamate transporter EAAT4 by two interacting proteins.	2001-03-01	11242047
Selective inactivation of guanine-nucleotide-binding regulatory protein (G-protein) alpha and betagamma subunits by urea.	2001-03-01	11171112
Characterization of [3H]CGP 12177 binding to beta-adrenergic receptors in intact eel hepatocytes.	2001-03	11254364
Biochemical detection of monovalent metal ion binding sites within RNA.	2001-03	11243839
Heparin modulates integrin function in human platelets.	2001-03	11241131
Effect of mycophenolate mofetil therapy on inosine monophosphate dehydrogenase induction in red blood cells of heart transplant recipients.	2001-03	11240978
Differential expression of functional guanylyl cyclases in melanocytes: absence of nitric-oxide-sensitive isoform in metastatic cells.	2001-03	11231315
Insertional mutagenesis of the arginine cage domain of the gonadotropin-releasing hormone receptor.	2001-03	11222740
Na+ reabsorption in cultured rat epididymal epithelium via the Na+/nucleoside cotransporter.	2001-03	11207189
Maturation depresses cGMP-mediated decreases in [Ca2+]i and Ca2+ sensitivity in ovine cranial arteries.	2001-03	11179043
Ontogenic and longitudinal activity of Na(+)-nucleoside transporters in the human intestine.	2001-03	11171631
Effects of cellular ATP depletion on glucose transport and insulin signaling in 3T3-L1 adipocytes.	2001-03	11171597
cAMP-independent phosphorylation activation of CFTR by G proteins in native human sweat duct.	2001-03	11171580
RGS2 regulates signal transduction in olfactory neurons by attenuating activation of adenylyl cyclase III.	2001-02-22	11234015
Neuropeptide Y receptors differentially modulate G-protein-activated inwardly rectifying K+ channels and high-voltage-activated Ca2+ channels in rat thalamic neurons.	2001-02-15	11179392
Nitric oxide, peroxynitrite and cGMP in atherosclerosis-induced hypertension in rabbits: beneficial effects of cicletanine.	2001-02-15	11173993
Synthesis and photodynamic activity of a cationic zinc monoazaporphyrin bearing a nitrogen atom at the peripheral position.	2001-02-12	11212111
Effects of wortmannin upon the late stages of the secretory pathway of AtT-20 cells.	2001-02-09	11173063
Phosphorylation and desensitization of alpha1d-adrenergic receptors.	2001-02-01	11171057
The stringent response, sigmaH-dependent gene expression and sporulation in Bacillus subtilis.	2001-02	11254139
The anti-herpesvirus activity of (1'S,2'R)-9-[[1',2'-bis(hydroxymethyl)-cycloprop-1'-yl]methyl]guanine is markedly potentiated by the immunosuppressive agent mycophenolate mofetil.	2001-02	11248364
Methylene blue reduces lung fluid filtration during the early phase of endotoxemia in awake sheep.	2001-02	11246319
TRAPP I implicated in the specificity of tethering in ER-to-Golgi transport.	2001-02	11239471
Electron transfer vs. proton transfer within radical-cation clusters of guanosine and deoxyguanosine with substituted naphthalenes and sinapinic acid.	2001-02	11212002
Diurnal rhythmicity in intestinal SGLT-1 function, V(max), and mRNA expression topography.	2001-02	11208542
G(q/11) and G(i/o) activation profiles in CHO cells expressing human muscarinic acetylcholine receptors: dependence on agonist as well as receptor-subtype.	2001-02	11181437
LPS induction of I kappa B-alpha degradation and iNOS expression in a skin dendritic cell line is prevented by the janus kinase 2 inhibitor, Tyrphostin b42.	2001-02	11178937
Probing structure and dynamics of DNA with 2-aminopurine: effects of local environment on fluorescence.	2001-01-30	11170416
New 3-[4-(aryl)piperazin-1-yl]-1-(benzo[b]thiophen-3-yl)propane derivatives with dual action at 5-HT1A serotonin receptors and serotonin transporter as a new class of antidepressants.	2001-01	11231049
A ribozyme selected from variants of U6 snRNA promotes 2',5'-branch formation.	2001-01	11214178
Nitric oxide-mediated inhibition of DNA repair potentiates oxidative DNA damage in cholangiocytes.	2001-01	11208728
Reconstitution of clathrin-independent endocytosis at the apical domain of permeabilized MDCK II cells: requirement for a Rho-family GTPase.	2001-01	11208166
Metabotropic glutamate receptors modify ionotropic glutamate responses in neocortical pyramidal cells and interneurons.	2001-01	11204411
Determination of nucleosides in natural Cordyceps sinensis and cultured Cordyceps mycelia by capillary electrophoresis.	2001-01	11197164
Angiotensin type 2 receptors: potential importance in the regulation of blood pressure.	2001-01	11195059
Saccharin activates cation conductance via inositol 1,4,5-trisphosphate production in a subset of isolated rod taste cells in the frog.	2001-01	11168535
Purification and properties of a GTPase-activating protein for yeast Rab GTPases.	2001	11210577
Preparation and assay of recombinant ADP-ribosylation factor-like protein-1 (ARL1).	2001	11210562
Purification, properties, and analysis of yARL3.	2001	11210561
Biological properties and measurement of phospholipase D activation by ADP-ribosylation factor (ARF).	2001	11210555
Functional analysis of ADP-ribosylation factor (ARF) guanine nucleotide exchange factors Gea1p and Gea2p in yeast.	2001	11210546
Effectiveness of specific RNA-mediated interference through ingested double-stranded RNA in Caenorhabditis elegans.	2001	11178279

Patents

Sample Use Guides

In Vivo Use Guide

rat model of chronic hepatic encephalopathy: i.p. injection of guanosine 7.5 mg/kg once a day for 1-week.

Route of Administration: Other

In Vitro Use Guide

Guanosine incubated concomitantly with Rot/oligo abolished Rot/oligo-induced cell death and ROS production in a human neuroblastoma cell line, SH-SY5Y, in a concentration dependent manner; maximum protection was achieved at the concentration of 1 mM.

Name

Type

Language

GUANOSINE

Official Name

English

NSC-19994

Preferred Name

English

GUANOSINE [MI]

Common Name

English

GUANOSINE [MART.]

Common Name

English

DL-GUANOSINE

Common Name

English

2-AMINO-9-.BETA.-D-RIBOFURANOSYL-9H-PURINE-6(1H)-ONE

Common Name

English

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

Systematic Name

English

Guanosine [WHO-DD]

Common Name

English

ADENOSINE IMPURITY H [EP IMPURITY]

Common Name

English

VERNINE

Common Name

English

GUANOSINE [USP IMPURITY]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C707