Details
Stereochemistry | ACHIRAL |
Molecular Formula | C6H11N4O2.Cl |
Molecular Weight | 206.63 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Cl-].NC1=C[N+](=NO1)N2CCOCC2
InChI
InChIKey=ZRFWHHCXSSACAW-UHFFFAOYSA-M
InChI=1S/C6H11N4O2.ClH/c7-6-5-10(8-12-6)9-1-3-11-4-2-9;/h5H,1-4,7H2;1H/q+1;/p-1
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/8775048Curator'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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8775048
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
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1250411 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16998480 |
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Target ID: nitric oxide Sources: https://www.ncbi.nlm.nih.gov/pubmed/8775048 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8775048 |
Diagnostic | Corvasal intracoronaire Approved UseUnknown |
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Primary | Corvasal intracoronaire Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Induction of heme oxygenase-1 as a response in sensing the signals evoked by distinct nitric oxide donors. | 1999 Jul 15 |
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Nitric oxide enhances the manganese superoxide dismutase-dependent suppression of proliferation in HT-1080 fibrosarcoma cells. | 1999 Sep |
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Nitric oxide stimulates ACTH secretion and the transcription of the genes encoding for NGFI-B, corticotropin-releasing factor, corticotropin-releasing factor receptor type 1, and vasopressin in the hypothalamus of the intact rat. | 1999 Sep 1 |
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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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Reactive nitrogen species block cell cycle re-entry through sustained production of hydrogen peroxide. | 2003 Jun |
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PKC downstream of Pl3-kinase regulates peroxynitrite formation for Nrf2-mediated GSTA2 induction. | 2004 Jul |
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Nitrotyrosylation of Ca2+ channels prevents c-Src kinase regulation of colonic smooth muscle contractility in experimental colitis. | 2007 Sep |
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Involvement of selective reactive oxygen species upstream of proapoptotic branches of unfolded protein response. | 2008 Feb 15 |
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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 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1953615
Recommended dose range is 0.4-1 mg per diagnostic procedure.
Route of Administration:
Intracoronary
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26381495
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).
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SUB21667
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C002385
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DBSALT002925
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PARENT (SALT/SOLVATE)
SUBSTANCE RECORD