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 48 Target ID: GO:0006915 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18600524	Inhibitor 8297
Oxidative Stress 160 Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20846477	Inhibitor 8297
cell proliferation 28 Target ID: GO:0008283 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24152836	Activator 1430

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
Molecular cloning and functional characterization of inhibitor-sensitive (mENT1) and inhibitor-resistant (mENT2) equilibrative nucleoside transporters from mouse brain.	2000 Dec 1	11085929
Biological properties and measurement of phospholipase D activation by ADP-ribosylation factor (ARF).	2001	11210555
Effectiveness of specific RNA-mediated interference through ingested double-stranded RNA in Caenorhabditis elegans.	2001	11178279
Constitutive activity at serotonin 5-HT(1D) receptors: detection by homologous GTPgammaS versus [(35)S]-GTPgammaS binding isotherms.	2001	11077071
Modulation of 5-HT(1A) receptor activation by its interaction with wild-type and mutant g(alphai3) proteins.	2001	11077069
Retrograde transport of transcription factor NF-kappa B in living neurons.	2001 Apr 13	11096106
Electron transfer vs. proton transfer within radical-cation clusters of guanosine and deoxyguanosine with substituted naphthalenes and sinapinic acid.	2001 Feb	11212002
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 Feb	11181437
CB1 receptor-G protein association. Subtype selectivity is determined by distinct intracellular domains.	2001 Feb	11168387
Effect of different 5-hydroxytryptamine receptor subtype antagonists on the micturition reflex in rats.	2001 Feb	11167653
Modulation of neuronal nitric oxide release by soluble guanylyl cyclase in guinea pig colon.	2001 Feb 2	11162644
A single nucleotide polymorphic mutation in the human mu-opioid receptor severely impairs receptor signaling.	2001 Feb 2	11067846
RGS2 regulates signal transduction in olfactory neurons by attenuating activation of adenylyl cyclase III.	2001 Feb 22	11234015
Phospholipase Cdelta1 is a guanine nucleotide exchanging factor for transglutaminase II (Galpha h) and promotes alpha 1B-adrenoreceptor-mediated GTP binding and intracellular calcium release.	2001 Feb 23	11087745
Nrg-1 belongs to the endothelial differentiation gene family of G protein-coupled sphingosine-1-phosphate receptors.	2001 Feb 23	11069896
The main products of the low molecular mass fraction in the venom of the spider Latrodectus menavodi.	2001 Feb-Mar	10978765
Saccharin activates cation conductance via inositol 1,4,5-trisphosphate production in a subset of isolated rod taste cells in the frog.	2001 Jan	11168535
Protein kinase C and meiotic regulation in isolated mouse oocytes.	2001 Jan	11144213
Induction of ppGpp synthesis in Streptomyces coelicolor A3(2) grown under conditions of nutritional sufficiency elicits actII-ORF4 transcription and actinorhodin biosynthesis.	2001 Jan	11123695
Lymphocytes from spontaneously hypertensive rats exhibit enhanced adenylyl cyclase-Gi protein signaling.	2001 Jan	11121816
Opioid peptide receptor studies. 14. Stereochemistry determines agonist efficacy and intrinsic efficacy in the [(35)S]GTP-gamma-S functional binding assay.	2001 Jan	11071711
Apical heterotrimeric g-proteins activate CFTR in the native sweat duct.	2001 Jan 1	11155209
[(3)H]ZM241385--an antagonist radioligand for adenosine A(2A) receptors in rat brain.	2001 Jan 12	11164377
The coenzyme b12 analog 5'-deoxyadenosylcobinamide-gdp supports catalysis by methylmalonyl-coa mutase in the absence of trans-ligand coordination.	2001 Jan 12	11031263
tRNA recognition of tRNA-guanine transglycosylase from a hyperthermophilic archaeon, Pyrococcus horikoshii.	2001 Jan 26	11060284
Structure-activity relationships in flexible protein domains: regulation of rho GTPases by RhoGDI and D4 GDI.	2001 Jan 5	11114252
[Identification and isolation of GTP-binding regulator protein from plasma membranes of oocytes from the starfish Asterias amurensis].	2001 Jan-Feb	11236575
Characterization of [3H]CGP 12177 binding to beta-adrenergic receptors in intact eel hepatocytes.	2001 Mar	11254364
Evaluating the signal transduction mechanism of the parathyroid hormone 1 receptor. Effect of receptor-G-protein interaction on the ligand binding mechanism and receptor conformation.	2001 Mar 16	11108715
Radioligand binding properties of VV-hemorphin 7, an atypical opioid peptide.	2001 Mar 2	11237710
Cytosolic high K(m) 5'-nucleotidase and 5'(3')-deoxyribonucleotidase in substrate cycles involved in nucleotide metabolism.	2001 Mar 2	11083867
Human mismatch repair and G*T mismatch binding by hMutSalpha in vitro is inhibited by adriamycin, actinomycin D, and nogalamycin.	2001 Mar 30	11134041
A direct inhibitory role for the Rab3-specific effector, Noc2, in Ca2+-regulated exocytosis in neuroendocrine cells.	2001 Mar 30	11134008

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

GUANOSINE [INCI]

Common 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

NSC-19994

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C707