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
Expression of heme oxygenase isozyme mRNAs in the human brain and induction of heme oxygenase-1 by nitric oxide donors.	1996 Aug	8764571
Nitric oxide donors induce apoptosis in glomerular mesangial cells, epithelial cells and endothelial cells.	1996 Dec 12	8982730
Hypersensitivity of ataxia-telangiectasia fibroblasts to a nitric oxide donor.	1997	8958160
Induction of heme oxygenase-1 as a response in sensing the signals evoked by distinct nitric oxide donors.	1999 Jul 15	10423162
S-nitrosothiols as novel, reversible inhibitors of human rhinovirus 3C protease.	2000 Sep 18	10999479
Combined effect of propofol and GSNO on oxidative phosphorylation of isolated rat liver mitochondria.	2001 Apr	11292365
Nitric oxide suppresses the expression of Bcl-2 binding protein BNIP3 in hepatocytes.	2001 Dec 14	11592958
Induction of vascular endothelial growth factor by nitric oxide in cultured human articular chondrocytes.	2001 Jun	11506896
Resolution, detection, and characterization of redox conformers of human HSF1.	2001 Jun 29	11320084
The modulation of oxygen radical production by nitric oxide in mitochondria.	2001 Mar 9	11106647
Regulation of the hypoxia-inducible factor 1alpha by the inflammatory mediators nitric oxide and tumor necrosis factor-alpha in contrast to desferroxamine and phenylarsine oxide.	2001 Oct 26	11514583
Effects of nitrosopropofol on mitochondrial energy-converting system.	2002 Oct 1	12234616
Nitric oxide exposure of CC531 rat colon carcinoma cells induces gamma-glutamyltransferase which may counteract glutathione depletion and cell death.	2003 Jan	12653223
Redox modulation of NO-dependent induction of interleukin 8 gene in monocytic U937 cells.	2003 Jul	12901850
[Mechanisms of acetylcholine-dependent production of H2O2 and NO2- by stromal cells of endometrium].	2003 Sep-Oct	14681996
Nitrosoglutathione modulation of platelet activation and nitric oxide synthase expression in promotion of flap survival after ischemia/reperfusion injury.	2004 Jun 1	15126088
Beneficial effects of quinaprilat on coronary vasomotor function, endothelial oxidative stress, and endothelin activation after human heart transplantation.	2004 Jun 27	15223904
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 Mar	15025510
Nitric oxide and BCNU chemoresistance in C6 glioma cells: role of S-nitrosoglutathione.	2004 May 15	15110396
Nitrosoglutathione promotes flap survival via suppression of reperfusion injury-induced superoxide and inducible nitric oxide synthase induction.	2004 Nov	15580027
[Nitric oxide in malignant astrocytes].	2005 Apr 1-15	15849679
Reversible silencing of CFTR chloride channels by glutathionylation.	2005 Feb	15657297
Direct detection of S-nitrosothiols using planar amperometric nitric oxide sensor modified with polymeric films containing catalytic copper species.	2005 Jun 1	15924383
Fundamental roles of reactive oxygen species and protective mechanisms in the female reproductive system.	2005 Sep 2	16137335
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
Glutathione and growth inhibition of Mycobacterium tuberculosis in healthy and HIV infected subjects.	2006 Feb 20	16504020
Mitochondrial aconitase reaction with nitric oxide, S-nitrosoglutathione, and peroxynitrite: mechanisms and relative contributions to aconitase inactivation.	2007 Apr 1	17349934
Platelet aggregation is affected by nitrosothiols in patients with chronic hepatitis: in vivo and in vitro studies.	2007 Jul 21	17659726
Atrial glutathione content, calcium current, and contractility.	2007 Sep 21	17656369
The Janus face of alcohol dehydrogenase 3.	2009 Mar 16	19038239
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 May	19225165
[Effects of dinitrosyl iron complex with glutathione and its components on ischemic rat heart during reperfusion].	2009 Nov-Dec	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
The induction of reactive oxygen species and loss of mitochondrial Omi/HtrA2 is associated with S-nitrosoglutathione-induced apoptosis in human endothelial cells.	2010 May 1	20153346
Heterologous down-regulation of angiotensin type 1 receptors by purinergic P2Y2 receptor stimulation through S-nitrosylation of NF-kappaB.	2011 Apr 19	21464294
S-Nitrosylation of parkin as a novel regulator of p53-mediated neuronal cell death in sporadic Parkinson's disease.	2013 Aug 28	23985028
Dysfunctional nitric oxide signalling increases risk of myocardial infarction.	2013 Dec 19	24213632
S-nitrosoglutathione covalently modifies cysteine residues of human carbonyl reductase 1 and affects its activity.	2013 Feb 25	23295225

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 `Fri Dec 15 16:24:57 GMT 2023` Edited by `admin` on `Fri Dec 15 16:24:57 GMT 2023`
Record UNII	78RRI89ZTO
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

S-NITROSOGLUTATHIONE

Systematic Name

English

N30-201

Common Name

English

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

Systematic Name

English

N-30-201

Common Name

English

RVC 588 (PEPTIDE)

Common Name

English

SNO-G

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

358511