S-NITROSOGLUTATHIONE

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C10H16N4O7S
Molecular Weight	336.322
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

N[C@@H](CCC(=O)N[C@@H](CSN=O)C(=O)NCC(O)=O)C(O)=O

InChI

InChIKey=HYHSBSXUHZOYLX-WDSKDSINSA-N

InChI=1S/C10H16N4O7S/c11-5(10(19)20)1-2-7(15)13-6(4-22-14-21)9(18)12-3-8(16)17/h5-6H,1-4,11H2,(H,12,18)(H,13,15)(H,16,17)(H,19,20)/t5-,6-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C10H16N4O7S
Molecular Weight	336.322
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://clinicaltrials.gov/ct2/show/NCT03926741 | https://www.ncbi.nlm.nih.gov/pubmed/27780722 | https://www.ncbi.nlm.nih.gov/pubmed/28271419 | https://adisinsight.springer.com/drugs/800027742

S-nitrosoglutathione (GSNO) is an endogenous S-nitrosothiol that acts as a NO pool. The level of GSNO is tightly regulated by S-nitrosoglutathione reductase (GSNOR), an enzyme that degrades GSNO. GSNOR inhibitors offer a potentially promising option for the management of pre-eclampsia, a cause of maternal death and of perinatal morbidity. The GSNO treatment of traumatic brain injury improved neurobehavioral functions. GSNO can increase the expression of certain proteins at concentrations present in the normal human airway. GSNO has an important role in regulating respiratory function (breathing) and preventing inflammation in the respiratory tract, that is why this compound participated in phase I clinical trials for patients with asthma. In addition, GSNO was studied in the cystic fibrosis airway. The obtained results have shown that GSNO replacement therapy could be an effective treatment. In addition, GSNO was investigated for patients with chronic obstructive pulmonary disease.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Alcohol dehydrogenase class-3 1 Target ID: P11766 Gene ID: 128.0 Gene Symbol: ADH5 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/12631283	Substrate 661

PubMed

Title	Date	PubMed
Dysfunctional nitric oxide signalling increases risk of myocardial infarction.	2013-12-19	24213632
S-Nitrosylation of parkin as a novel regulator of p53-mediated neuronal cell death in sporadic Parkinson's disease.	2013-08-28	23985028
S-nitrosoglutathione covalently modifies cysteine residues of human carbonyl reductase 1 and affects its activity.	2013-02-25	23295225
Studies on reduction of S-nitrosoglutathione by human carbonyl reductases 1 and 3.	2011-05-30	21256830
Heterologous down-regulation of angiotensin type 1 receptors by purinergic P2Y2 receptor stimulation through S-nitrosylation of NF-kappaB.	2011-04-19	21464294
Biliary secretion of S-nitrosoglutathione is involved in the hypercholeresis induced by ursodeoxycholic acid in the normal rat.	2010-08	20683964
The induction of reactive oxygen species and loss of mitochondrial Omi/HtrA2 is associated with S-nitrosoglutathione-induced apoptosis in human endothelial cells.	2010-05-01	20153346
Resveratrol activation of nitric oxide synthase in rabbit brain synaptosomes: singlet oxygen (1O2) formation as a causative factor of neurotoxicity.	2010-02-06	20133975
Comprehensive identification and modified-site mapping of S-nitrosylated targets in prostate epithelial cells.	2010-02-05	20140087
Structural analysis of cysteine S-nitrosylation: a modified acid-based motif and the emerging role of trans-nitrosylation.	2010-01-29	19854201
[Effects of dinitrosyl iron complex with glutathione and its components on ischemic rat heart during reperfusion].	2010-01-14	20067190
Atherosclerosis: pathogenesis and increased occurrence in individuals with HIV and Mycobacterium tuberculosis infection.	2010	22096400
Increased nitrosoglutathione reductase activity in hypoxic pulmonary hypertension in mice.	2010	20431245
Lipids modulate H(2)S/HS(-) induced NO release from S-nitrosoglutathione.	2009-12-25	19879245
What is the real physiological NO concentration in vivo?	2009-09	19602444
Medium-chain fatty acids and glutathione derivatives as inhibitors of S-nitrosoglutathione reduction mediated by alcohol dehydrogenase 3.	2009-06-15	19428350
Sequential effects of GSNO and H2O2 on the Ca2+ sensitivity of the contractile apparatus of fast- and slow-twitch skeletal muscle fibers from the rat.	2009-05	19225165
The Janus face of alcohol dehydrogenase 3.	2009-03-16	19038239
Plant cells oxidize hydroxylamines to NO.	2009	19357430
Atrial glutathione content, calcium current, and contractility.	2007-09-21	17656369
Platelet aggregation is affected by nitrosothiols in patients with chronic hepatitis: in vivo and in vitro studies.	2007-07-21	17659726
Glutathione S-transferase omega in the lung and sputum supernatants of COPD patients.	2007-07-06	17617905
Glutathione synthesis is regulated by nitric oxide in Medicago truncatula roots.	2007-05	17195940
Mitochondrial aconitase reaction with nitric oxide, S-nitrosoglutathione, and peroxynitrite: mechanisms and relative contributions to aconitase inactivation.	2007-04-01	17349934
S-nitrosothiol detection via amperometric nitric oxide sensor with surface modified hydrogel layer containing immobilized organoselenium catalyst.	2006-12-05	17129067
Further evidence that rat liver microsomal glutathione transferase 1 is not a cellular protein target for S-nitrosylation.	2006-09-25	16899233
NMDA receptor-nitric oxide transmission mediates neuronal iron homeostasis via the GTPase Dexras1.	2006-08-17	16908409
Reactive nitrogen species derived activation of rat liver microsomal glutathione S-transferase.	2006-05-22	16386761
Glutathione and growth inhibition of Mycobacterium tuberculosis in healthy and HIV infected subjects.	2006-02-20	16504020
Yeast flavohemoglobin protects against nitrosative stress and controls ferric reductase activity.	2006	17132272
Effect of the molecular adsorbent recirculating system and Prometheus devices on systemic haemodynamics and vasoactive agents in patients with acute-on-chronic alcoholic liver failure.	2006	16859530
Fundamental roles of reactive oxygen species and protective mechanisms in the female reproductive system.	2005-09-02	16137335
Nitrosoglutathione triggers collagen deposition in cutaneous wound repair.	2005-07-13	16008727
Direct detection of S-nitrosothiols using planar amperometric nitric oxide sensor modified with polymeric films containing catalytic copper species.	2005-06-01	15924383
[Nitric oxide in malignant astrocytes].	2005-04-26	15849679
Detection of S-glutathionylated proteins by glutathione S-transferase overlay.	2005-03-01	15680905
Reversible silencing of CFTR chloride channels by glutathionylation.	2005-02	15657297
Nitrosoglutathione promotes flap survival via suppression of reperfusion injury-induced superoxide and inducible nitric oxide synthase induction.	2004-11	15580027
Beneficial effects of quinaprilat on coronary vasomotor function, endothelial oxidative stress, and endothelin activation after human heart transplantation.	2004-06-27	15223904
Nitrosoglutathione modulation of platelet activation and nitric oxide synthase expression in promotion of flap survival after ischemia/reperfusion injury.	2004-06-01	15126088
Nitric oxide and BCNU chemoresistance in C6 glioma cells: role of S-nitrosoglutathione.	2004-05-15	15110396
Concentration-dependent effects of endogenous S-nitrosoglutathione on gene regulation by specificity proteins Sp3 and Sp1.	2004-05-15	14766015
Nitrosoglutathione improves blood perfusion and flap survival by suppressing iNOS but protecting eNOS expression in the flap vessels after ischemia/reperfusion injury.	2004-04	15041968
Contrasting effects of metal ions on S-nitrosoglutathione, related to coordination equilibria: GSNO decomposition assisted by Ni(II) vs stability Increase in the presence of Zn(II) and Cd(II).	2004-03	15025510
[Mechanisms of acetylcholine-dependent production of H2O2 and NO2- by stromal cells of endometrium].	2003-12-20	14681996
[Role of extra- and intracellular Ca2+ in changes of NO2- and H2O2 production by endometrium].	2003-10-28	14577156
Regulatory role of nitric oxide on monocyte-derived dendritic cell functions.	2003-08	13678430
Hypersensitivity of ataxia-telangiectasia fibroblasts to a nitric oxide donor.	1997	8958160
Nitric oxide donors induce apoptosis in glomerular mesangial cells, epithelial cells and endothelial cells.	1996-12-12	8982730
Expression of heme oxygenase isozyme mRNAs in the human brain and induction of heme oxygenase-1 by nitric oxide donors.	1996-08	8764571

Patents

Sample Use Guides

In Vivo Use Guide

patient will use a nebulizer to inhale (breathe in) a solution of GSNO followed by repeated measurements of airway function (breathing tests)

Route of Administration: Other

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:27:17 GMT 2025` Edited by `admin` on `Mon Mar 31 18:27:17 GMT 2025`
Record UNII	78RRI89ZTO
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

N-30-201

Preferred Name

English

S-NITROSOGLUTATHIONE

Systematic Name

English

N30-201

Common Name

English

GLYCINE, N-(N-L-.GAMMA.-GLUTAMYL-S-NITROSO-L-CYSTEINYL)-

Systematic Name

English

RVC 588 (PEPTIDE)

Common Name

English

SNO-G

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

358511