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
| 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 |
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| 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
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
5.08 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7509893/ |
0.8 mg/h single, intravenous dose: 0.8 mg/h route of administration: Intravenous experiment type: SINGLE co-administered: |
LINSIDOMINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
21.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7509893/ |
0.8 mg/h single, intravenous dose: 0.8 mg/h route of administration: Intravenous experiment type: SINGLE co-administered: |
LINSIDOMINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
29.5 h |
1 mg single, intravenous dose: 1 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
LINSIDOMINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
2 mg single, intravenous Highest studied dose Dose: 2 mg Route: intravenous Route: single Dose: 2 mg Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: |
Other AEs: Discomfort... |
2 mg single, intravenous Highest studied dose Dose: 2 mg Route: intravenous Route: single Dose: 2 mg Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Other AEs: Headache... |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Discomfort | grade 1, 5% | 2 mg single, intravenous Highest studied dose Dose: 2 mg Route: intravenous Route: single Dose: 2 mg Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: |
| Headache | grade 1, 20% | 2 mg single, intravenous Highest studied dose Dose: 2 mg Route: intravenous Route: single Dose: 2 mg Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Antioxidants and NOS inhibitors selectively targets manganese-induced cell volume via Na-K-Cl cotransporter-1 in astrocytes. | 2015-06-12 |
|
| Neuroprotective effects of Cyperus rotundus on SIN-1 induced nitric oxide generation and protein nitration: ameliorative effect against apoptosis mediated neuronal cell damage. | 2013-01 |
|
| Attenuated vasodilatation in lambs with endogenous and exogenous activation of cGMP signaling: role of protein kinase G nitration. | 2011-12 |
|
| Induction of CCAAT/enhancer-binding protein-homologous protein by cigarette smoke through the superoxide anion-triggered PERK-eIF2α pathway. | 2011-09-05 |
|
| Effects of modulating in vivo nitric oxide production on the incidence and severity of PDE4 inhibitor-induced vascular injury in Sprague-Dawley rats. | 2011-07 |
|
| Peroxynitrite mediates muscle insulin resistance in mice via nitration of IRbeta/IRS-1 and Akt. | 2009-11-15 |
|
| Cisplatin upregulates mitochondrial nitric oxide synthase and peroxynitrite formation to promote renal injury. | 2009-01-15 |
|
| Antioxidants and phase 2 enzymes in macrophages: regulation by Nrf2 signaling and protection against oxidative and electrophilic stress. | 2008-04 |
|
| Involvement of selective reactive oxygen species upstream of proapoptotic branches of unfolded protein response. | 2008-02-15 |
|
| Nitrotyrosylation of Ca2+ channels prevents c-Src kinase regulation of colonic smooth muscle contractility in experimental colitis. | 2007-09 |
|
| Alcohol-induced blood-brain barrier dysfunction is mediated via inositol 1,4,5-triphosphate receptor (IP3R)-gated intracellular calcium release. | 2007-01 |
|
| Nitric oxide regulates prolidase activity by serine/threonine phosphorylation. | 2005-12-01 |
|
| Increased nuclear factor-erythroid 2 p45-related factor 2 activity protects SH-SY5Y cells against oxidative damage. | 2005-10 |
|
| Peroxynitrite in the pathogenesis of Parkinson's disease and the neuroprotective role of metallothioneins. | 2005 |
|
| PKC downstream of Pl3-kinase regulates peroxynitrite formation for Nrf2-mediated GSTA2 induction. | 2004-07 |
|
| Peroxynitrite irreversibly inactivates the human xenobiotic-metabolizing enzyme arylamine N-acetyltransferase 1 (NAT1) in human breast cancer cells: a cellular and mechanistic study. | 2004-02-27 |
|
| Metallothionein attenuates 3-morpholinosydnonimine (SIN-1)-induced oxidative stress in dopaminergic neurons. | 2003-06 |
|
| Reactive nitrogen species block cell cycle re-entry through sustained production of hydrogen peroxide. | 2003-06 |
|
| 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. | 2002-12 |
|
| Dynamic and biphasic modulation of nitrosation reaction by superoxide dismutases. | 2002-08-02 |
|
| Protection of myocytes from hypoxia-reoxygenation injury by nitric oxide is mediated by modulation of transforming growth factor-beta1. | 2002-05-07 |
|
| The effect of the nitric oxide synthesis inhibitor L-NAME on amitriptyline-induced hypotension in rats. | 2002 |
|
| Nitric oxide inhibits apoptosis via AP-1-dependent CD95L transactivation. | 2000-05-01 |
|
| Protective effect of bilobalide against nitric oxide-induced neurotoxicity in PC12 cells. | 2000-05 |
|
| 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. | 1999-09-01 |
|
| Nitric oxide enhances the manganese superoxide dismutase-dependent suppression of proliferation in HT-1080 fibrosarcoma cells. | 1999-09 |
|
| Induction of heme oxygenase-1 as a response in sensing the signals evoked by distinct nitric oxide donors. | 1999-07-15 |
|
| Growth factors prevent changes in Bcl-2 and Bax expression and neuronal apoptosis induced by nitric oxide. | 1998-10 |
|
| Peroxynitrite modulates MnSOD gene expression in lung epithelial cells. | 1998-09 |
|
| Expression of heme oxygenase isozyme mRNAs in the human brain and induction of heme oxygenase-1 by nitric oxide donors. | 1996-08 |
|
| Mediation by prostaglandins of the nitric oxide-induced neurogenic vasodilatation in rat skin. | 1995-11 |
|
| Splenic B lymphocyte programmed cell death is prevented by nitric oxide release through mechanisms involving sustained Bcl-2 levels. | 1995-04 |
|
| Metabolism of glyceryl trinitrate to nitric oxide by endothelial cells and smooth muscle cells and its induction by Escherichia coli lipopolysaccharide. | 1992-02-01 |
|
| Nitroglycerin-resistant coronary spasm treated with intracoronary linsidomine chlorhydrate (SIN-1). | 1990-05 |
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
Mon Mar 31 18:46:47 GMT 2025
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on
Mon Mar 31 18:46:47 GMT 2025
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| Record UNII |
Y0054U597M
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| Record Status |
Validated (UNII)
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| Record Version |
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