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Details

Stereochemistry ABSOLUTE
Molecular Formula C10H13N5O5.2H2O
Molecular Weight 319.2713
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GUANOSINE DIHYDRATE

SMILES

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

InChI

InChIKey=HNZAKYGFPANILR-LGVAUZIVSA-N
InChI=1S/C10H13N5O5.2H2O/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);2*1H2/t3-,5-,6-,9-;;/m1../s1

HIDE SMILES / InChI
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.

Originator

Sources: Schulze E. and Bosshard E., Z. physiol. Chem., 9, 420 (1885); 10, 80 (1886)
Curator's Comment: reference was retrieved from https://books.google.ru/books?id=DcxcpI79b40C&hl=ru&source=gbs_navlinks_s

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
1H-NMR spectroscopy of body fluids: inborn errors of purine and pyrimidine metabolism.
1999 Apr
Molecular cloning and functional characterization of inhibitor-sensitive (mENT1) and inhibitor-resistant (mENT2) equilibrative nucleoside transporters from mouse brain.
2000 Dec 1
Biological properties and measurement of phospholipase D activation by ADP-ribosylation factor (ARF).
2001
Constitutive activity at serotonin 5-HT(1D) receptors: detection by homologous GTPgammaS versus [(35)S]-GTPgammaS binding isotherms.
2001
Electron transfer vs. proton transfer within radical-cation clusters of guanosine and deoxyguanosine with substituted naphthalenes and sinapinic acid.
2001 Feb
CB1 receptor-G protein association. Subtype selectivity is determined by distinct intracellular domains.
2001 Feb
A novel proton-dependent nucleoside transporter, CeCNT3, from Caenorhabditis elegans.
2001 Feb
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 Jan
Nitric oxide-mediated inhibition of DNA repair potentiates oxidative DNA damage in cholangiocytes.
2001 Jan
Reconstitution of clathrin-independent endocytosis at the apical domain of permeabilized MDCK II cells: requirement for a Rho-family GTPase.
2001 Jan
Metabotropic glutamate receptors modify ionotropic glutamate responses in neocortical pyramidal cells and interneurons.
2001 Jan
The critical role of adenosine and guanosine in the affinity of dinucleoside polyphosphates to P(2X)-receptors in the isolated perfused rat kidney.
2001 Jan
Identified serotonergic neurons in the Tritonia swim CPG activate both ionotropic and metabotropic receptors.
2001 Jan
Extracellular adenosine modulates a volume-sensitive-like chloride conductance in immortalized rabbit DC1 cells.
2001 Jan
Lymphocytes from spontaneously hypertensive rats exhibit enhanced adenylyl cyclase-Gi protein signaling.
2001 Jan
The coenzyme b12 analog 5'-deoxyadenosylcobinamide-gdp supports catalysis by methylmalonyl-coa mutase in the absence of trans-ligand coordination.
2001 Jan 12
tRNA recognition of tRNA-guanine transglycosylase from a hyperthermophilic archaeon, Pyrococcus horikoshii.
2001 Jan 26
Probing structure and dynamics of DNA with 2-aminopurine: effects of local environment on fluorescence.
2001 Jan 30
Nitric oxide, peroxynitrite and cGMP in atherosclerosis-induced hypertension in rabbits: beneficial effects of cicletanine.
2001 Jan-Feb
Characterization of [3H]CGP 12177 binding to beta-adrenergic receptors in intact eel hepatocytes.
2001 Mar
Ontogenic and longitudinal activity of Na(+)-nucleoside transporters in the human intestine.
2001 Mar
Effects of cellular ATP depletion on glucose transport and insulin signaling in 3T3-L1 adipocytes.
2001 Mar
Modulation of the neuronal glutamate transporter EAAT4 by two interacting proteins.
2001 Mar 1
Tetraplex formation by the progressive myoclonus epilepsy type-1 repeat: implications for instability in the repeat expansion diseases.
2001 Mar 2
Patents

Sample Use Guides

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
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 DIHYDRATE
MI  
Systematic Name English
GUANOSINE, HYDRATE (1:2)
Systematic Name English
GUANOSINE DIHYDRATE [MI]
Common Name English
Code System Code Type Description
CAS
6010-14-6
Created by admin on Sat Dec 16 08:25:30 GMT 2023 , Edited by admin on Sat Dec 16 08:25:30 GMT 2023
PRIMARY
FDA UNII
E62RXW39EW
Created by admin on Sat Dec 16 08:25:30 GMT 2023 , Edited by admin on Sat Dec 16 08:25:30 GMT 2023
PRIMARY
PUBCHEM
135565581
Created by admin on Sat Dec 16 08:25:30 GMT 2023 , Edited by admin on Sat Dec 16 08:25:30 GMT 2023
PRIMARY
EPA CompTox
DTXSID90737611
Created by admin on Sat Dec 16 08:25:30 GMT 2023 , Edited by admin on Sat Dec 16 08:25:30 GMT 2023
PRIMARY
MERCK INDEX
m5871
Created by admin on Sat Dec 16 08:25:30 GMT 2023 , Edited by admin on Sat Dec 16 08:25:30 GMT 2023
PRIMARY Merck Index