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
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
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
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 |
|
| Nitric oxide donors induce apoptosis in glomerular mesangial cells, epithelial cells and endothelial cells. | 1996 Dec 12 |
|
| Hypersensitivity of ataxia-telangiectasia fibroblasts to a nitric oxide donor. | 1997 |
|
| Nitric oxide inhibits apoptosis via AP-1-dependent CD95L transactivation. | 2000 May 1 |
|
| Resolution, detection, and characterization of redox conformers of human HSF1. | 2001 Jun 29 |
|
| The modulation of oxygen radical production by nitric oxide in mitochondria. | 2001 Mar 9 |
|
| Nitric oxide and blood pressure in mice lacking extracellular-superoxide dismutase. | 2002 Jul |
|
| Effects of nitrosopropofol on mitochondrial energy-converting system. | 2002 Oct 1 |
|
| [Identification of genes induced to chondrocytes by nitric oxide]. | 2002 Sep-Oct |
|
| The metabolism of S-nitrosothiols in the trypanosomatids: the role of ovothiol A and trypanothione. | 2003 Apr 1 |
|
| Regulatory role of nitric oxide on monocyte-derived dendritic cell functions. | 2003 Aug |
|
| [Role of extra- and intracellular Ca2+ in changes of NO2- and H2O2 production by endometrium]. | 2003 May-Jun |
|
| [Mechanisms of acetylcholine-dependent production of H2O2 and NO2- by stromal cells of endometrium]. | 2003 Sep-Oct |
|
| Nitrosoglutathione modulation of platelet activation and nitric oxide synthase expression in promotion of flap survival after ischemia/reperfusion injury. | 2004 Jun 1 |
|
| Beneficial effects of quinaprilat on coronary vasomotor function, endothelial oxidative stress, and endothelin activation after human heart transplantation. | 2004 Jun 27 |
|
| Concentration-dependent effects of endogenous S-nitrosoglutathione on gene regulation by specificity proteins Sp3 and Sp1. | 2004 May 15 |
|
| [Nitric oxide in malignant astrocytes]. | 2005 Apr 1-15 |
|
| Nitrosoglutathione triggers collagen deposition in cutaneous wound repair. | 2005 Jul-Aug |
|
| Direct detection of S-nitrosothiols using planar amperometric nitric oxide sensor modified with polymeric films containing catalytic copper species. | 2005 Jun 1 |
|
| Fundamental roles of reactive oxygen species and protective mechanisms in the female reproductive system. | 2005 Sep 2 |
|
| Yeast flavohemoglobin protects against nitrosative stress and controls ferric reductase activity. | 2006 |
|
| 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 |
|
| NMDA receptor-nitric oxide transmission mediates neuronal iron homeostasis via the GTPase Dexras1. | 2006 Aug 17 |
|
| S-nitrosothiol detection via amperometric nitric oxide sensor with surface modified hydrogel layer containing immobilized organoselenium catalyst. | 2006 Dec 5 |
|
| Glutathione and growth inhibition of Mycobacterium tuberculosis in healthy and HIV infected subjects. | 2006 Feb 20 |
|
| Reactive nitrogen species derived activation of rat liver microsomal glutathione S-transferase. | 2006 May 22 |
|
| Further evidence that rat liver microsomal glutathione transferase 1 is not a cellular protein target for S-nitrosylation. | 2006 Sep 25 |
|
| Mitochondrial aconitase reaction with nitric oxide, S-nitrosoglutathione, and peroxynitrite: mechanisms and relative contributions to aconitase inactivation. | 2007 Apr 1 |
|
| Platelet aggregation is affected by nitrosothiols in patients with chronic hepatitis: in vivo and in vitro studies. | 2007 Jul 21 |
|
| Glutathione S-transferase omega in the lung and sputum supernatants of COPD patients. | 2007 Jul 6 |
|
| Glutathione synthesis is regulated by nitric oxide in Medicago truncatula roots. | 2007 May |
|
| Atrial glutathione content, calcium current, and contractility. | 2007 Sep 21 |
|
| Plant cells oxidize hydroxylamines to NO. | 2009 |
|
| Lipids modulate H(2)S/HS(-) induced NO release from S-nitrosoglutathione. | 2009 Dec 25 |
|
| Medium-chain fatty acids and glutathione derivatives as inhibitors of S-nitrosoglutathione reduction mediated by alcohol dehydrogenase 3. | 2009 Jun 15 |
|
| The Janus face of alcohol dehydrogenase 3. | 2009 Mar 16 |
|
| 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 |
|
| [Effects of dinitrosyl iron complex with glutathione and its components on ischemic rat heart during reperfusion]. | 2009 Nov-Dec |
|
| Atherosclerosis: pathogenesis and increased occurrence in individuals with HIV and Mycobacterium tuberculosis infection. | 2010 |
|
| Increased nitrosoglutathione reductase activity in hypoxic pulmonary hypertension in mice. | 2010 |
|
| Biliary secretion of S-nitrosoglutathione is involved in the hypercholeresis induced by ursodeoxycholic acid in the normal rat. | 2010 Aug |
|
| Comprehensive identification and modified-site mapping of S-nitrosylated targets in prostate epithelial cells. | 2010 Feb 5 |
|
| Resveratrol activation of nitric oxide synthase in rabbit brain synaptosomes: singlet oxygen (1O2) formation as a causative factor of neurotoxicity. | 2010 Jan-Feb |
|
| 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 |
|
| Heterologous down-regulation of angiotensin type 1 receptors by purinergic P2Y2 receptor stimulation through S-nitrosylation of NF-kappaB. | 2011 Apr 19 |
|
| Studies on reduction of S-nitrosoglutathione by human carbonyl reductases 1 and 3. | 2011 May 30 |
|
| S-Nitrosylation of parkin as a novel regulator of p53-mediated neuronal cell death in sporadic Parkinson's disease. | 2013 Aug 28 |
|
| Dysfunctional nitric oxide signalling increases risk of myocardial infarction. | 2013 Dec 19 |
|
| S-nitrosoglutathione covalently modifies cysteine residues of human carbonyl reductase 1 and affects its activity. | 2013 Feb 25 |
| Name | Type | Language | ||
|---|---|---|---|---|
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
FDA ORPHAN DRUG |
358511
Created by
admin on Fri Dec 15 16:24:57 GMT 2023 , Edited by admin on Fri Dec 15 16:24:57 GMT 2023
|
||
|
FDA ORPHAN DRUG |
281609
Created by
admin on Fri Dec 15 16:24:57 GMT 2023 , Edited by admin on Fri Dec 15 16:24:57 GMT 2023
|
||
|
EU-Orphan Drug |
EU/3/11/870
Created by
admin on Fri Dec 15 16:24:57 GMT 2023 , Edited by admin on Fri Dec 15 16:24:57 GMT 2023
|
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
DTXSID1040613
Created by
admin on Fri Dec 15 16:24:57 GMT 2023 , Edited by admin on Fri Dec 15 16:24:57 GMT 2023
|
PRIMARY | |||
|
104858
Created by
admin on Fri Dec 15 16:24:57 GMT 2023 , Edited by admin on Fri Dec 15 16:24:57 GMT 2023
|
PRIMARY | |||
|
50091
Created by
admin on Fri Dec 15 16:24:57 GMT 2023 , Edited by admin on Fri Dec 15 16:24:57 GMT 2023
|
PRIMARY | |||
|
78RRI89ZTO
Created by
admin on Fri Dec 15 16:24:57 GMT 2023 , Edited by admin on Fri Dec 15 16:24:57 GMT 2023
|
PRIMARY | |||
|
D026422
Created by
admin on Fri Dec 15 16:24:57 GMT 2023 , Edited by admin on Fri Dec 15 16:24:57 GMT 2023
|
PRIMARY | |||
|
S-NITROSOGLUTATHIONE
Created by
admin on Fri Dec 15 16:24:57 GMT 2023 , Edited by admin on Fri Dec 15 16:24:57 GMT 2023
|
PRIMARY | |||
|
57564-91-7
Created by
admin on Fri Dec 15 16:24:57 GMT 2023 , Edited by admin on Fri Dec 15 16:24:57 GMT 2023
|
PRIMARY | |||
|
100000177251
Created by
admin on Fri Dec 15 16:24:57 GMT 2023 , Edited by admin on Fri Dec 15 16:24:57 GMT 2023
|
PRIMARY |
ACTIVE MOIETY
