Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C6H10N4O2 |
| Molecular Weight | 170.1692 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[NH-]C1=C[N+](=NO1)N2CCOCC2
InChI
InChIKey=FKDHHVKWGRFRTG-UHFFFAOYSA-N
InChI=1S/C6H10N4O2/c7-6-5-10(8-12-6)9-1-3-11-4-2-9/h5,7H,1-4H2
| Molecular Formula | C6H11N4O2 |
| Molecular Weight | 171.1771 |
| Charge | 1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.drugs.com/international/linsidomine.html | https://www.ncbi.nlm.nih.gov/pubmed/1953615 | https://www.ncbi.nlm.nih.gov/pubmed/9458423 | https://www.ncbi.nlm.nih.gov/pubmed/26381495
Curator's Comment: description was created based on several sources, including
https://www.drugs.com/international/linsidomine.html | https://www.ncbi.nlm.nih.gov/pubmed/1953615 | https://www.ncbi.nlm.nih.gov/pubmed/9458423 | https://www.ncbi.nlm.nih.gov/pubmed/26381495
Linsidomine (SIN-1, chemically 3-morpholinosydnonimin), is a vasodilator and antianginal drug. It is the direct hepatic metabolite of molsidomine. The dosage recommended by its manufacturer for its initial purpose, coronary angiography, is 0.4-1 mg. Contrary to molsidomine, which is widely used as an antianginal drug, linsidomine is used only for coronary angiography. The plasma half-life of Linsidomine is about 1 hour. Linsidomine is nonenzymatically metabolized to SIN-1A which spontaneously releases NO. NO, probably released directly from nonadrenergic, noncholinergic (NANC) nerves in the penis, is believed to cause smooth muscle relaxation by stimulating the soluble form of guanylate cyclase leading to an increase of intracellular cyclic guanosine 3',5' monophosphate (cGMP) with subsequent smooth muscle relaxation. Linsidomine also hyperpolarizes the cell membrane, making the smooth muscle less susceptible to adrenergic stimulation. NO further interacts with platelets when released intraluminally causing an increase in cGMP that decreases platelet aggregation and adhesion
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Nitroglycerin-resistant coronary spasm treated with intracoronary linsidomine chlorhydrate (SIN-1). | 1990 May |
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| Metabolism of glyceryl trinitrate to nitric oxide by endothelial cells and smooth muscle cells and its induction by Escherichia coli lipopolysaccharide. | 1992 Feb 1 |
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| Splenic B lymphocyte programmed cell death is prevented by nitric oxide release through mechanisms involving sustained Bcl-2 levels. | 1995 Apr |
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| Mediation by prostaglandins of the nitric oxide-induced neurogenic vasodilatation in rat skin. | 1995 Nov |
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| Expression of heme oxygenase isozyme mRNAs in the human brain and induction of heme oxygenase-1 by nitric oxide donors. | 1996 Aug |
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| Growth factors prevent changes in Bcl-2 and Bax expression and neuronal apoptosis induced by nitric oxide. | 1998 Oct |
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| Peroxynitrite modulates MnSOD gene expression in lung epithelial cells. | 1998 Sep |
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| Protective effect of bilobalide against nitric oxide-induced neurotoxicity in PC12 cells. | 2000 May |
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| Nitric oxide inhibits apoptosis via AP-1-dependent CD95L transactivation. | 2000 May 1 |
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| The effect of the nitric oxide synthesis inhibitor L-NAME on amitriptyline-induced hypotension in rats. | 2002 |
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| Dynamic and biphasic modulation of nitrosation reaction by superoxide dismutases. | 2002 Aug 2 |
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| Peroxynitrite activates NF-E2-related factor 2/antioxidant response element through the pathway of phosphatidylinositol 3-kinase: the role of nitric oxide synthase in rat glutathione S-transferase A2 induction. | 2002 Dec |
|
| Protection of myocytes from hypoxia-reoxygenation injury by nitric oxide is mediated by modulation of transforming growth factor-beta1. | 2002 May 7 |
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| Metallothionein attenuates 3-morpholinosydnonimine (SIN-1)-induced oxidative stress in dopaminergic neurons. | 2003 Jun |
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| Reactive nitrogen species block cell cycle re-entry through sustained production of hydrogen peroxide. | 2003 Jun |
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| Peroxynitrite irreversibly inactivates the human xenobiotic-metabolizing enzyme arylamine N-acetyltransferase 1 (NAT1) in human breast cancer cells: a cellular and mechanistic study. | 2004 Feb 27 |
|
| PKC downstream of Pl3-kinase regulates peroxynitrite formation for Nrf2-mediated GSTA2 induction. | 2004 Jul |
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| Peroxynitrite in the pathogenesis of Parkinson's disease and the neuroprotective role of metallothioneins. | 2005 |
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| Nitric oxide regulates prolidase activity by serine/threonine phosphorylation. | 2005 Dec 1 |
|
| Increased nuclear factor-erythroid 2 p45-related factor 2 activity protects SH-SY5Y cells against oxidative damage. | 2005 Oct |
|
| Alcohol-induced blood-brain barrier dysfunction is mediated via inositol 1,4,5-triphosphate receptor (IP3R)-gated intracellular calcium release. | 2007 Jan |
|
| Nitrotyrosylation of Ca2+ channels prevents c-Src kinase regulation of colonic smooth muscle contractility in experimental colitis. | 2007 Sep |
|
| Antioxidants and phase 2 enzymes in macrophages: regulation by Nrf2 signaling and protection against oxidative and electrophilic stress. | 2008 Apr |
|
| Involvement of selective reactive oxygen species upstream of proapoptotic branches of unfolded protein response. | 2008 Feb 15 |
|
| Cisplatin upregulates mitochondrial nitric oxide synthase and peroxynitrite formation to promote renal injury. | 2009 Jan 15 |
|
| Peroxynitrite mediates muscle insulin resistance in mice via nitration of IRbeta/IRS-1 and Akt. | 2009 Nov 15 |
|
| Attenuated vasodilatation in lambs with endogenous and exogenous activation of cGMP signaling: role of protein kinase G nitration. | 2011 Dec |
|
| Effects of modulating in vivo nitric oxide production on the incidence and severity of PDE4 inhibitor-induced vascular injury in Sprague-Dawley rats. | 2011 Jul |
|
| Induction of CCAAT/enhancer-binding protein-homologous protein by cigarette smoke through the superoxide anion-triggered PERK-eIF2α pathway. | 2011 Sep 5 |
|
| Neuroprotective effects of Cyperus rotundus on SIN-1 induced nitric oxide generation and protein nitration: ameliorative effect against apoptosis mediated neuronal cell damage. | 2013 Jan |
|
| Antioxidants and NOS inhibitors selectively targets manganese-induced cell volume via Na-K-Cl cotransporter-1 in astrocytes. | 2015 Jun 12 |
Patents
Sample Use Guides
Recommended dose range is 0.4-1 mg per diagnostic procedure.
Route of Administration:
Intracoronary
HUVECs were pre-treated with 100 mkM SIN-1 (Linsidomine) or 100 mkM tempol (Sigma-Aldrich) for 1 h and then stimulated with 5 U/ml thrombin (Sigma-Aldrich) for 30 min. The amount of vWF released into the media was measured using a commercial enzyme-linked immunosorbent assay kit (Corgenix, Westminster, CO, USA).
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:23:21 GMT 2023
by
admin
on
Fri Dec 15 16:23:21 GMT 2023
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| Record UNII |
5O5U71P6VQ
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| Record Status |
Validated (UNII)
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NCI_THESAURUS |
C45845
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WHO-ATC |
C01DX18
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WHO-VATC |
QC01DX18
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NCI_THESAURUS |
C29707
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SUB08524MIG
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LINSIDOMINE
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5219
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5O5U71P6VQ
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DB13400
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DTXSID501026026
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C002385
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100000082338
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33876-97-0
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4589
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6201
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CHEMBL1189150
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C72628
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PARENT -> METABOLITE |
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METABOLITE -> PARENT |
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METABOLITE INACTIVE -> PARENT |
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