linsidomine

{{Short description|Chemical compound}}

{{Drugbox

| Watchedfields = changed

| verifiedrevid = 446899189

| IUPAC_name = 5-imino-3-morpholin-4-yl-5H-1,2,3-oxadiazol-3-ium-2-ide

| image = Linsidomine structure.svg

| tradename =

| Drugs.com = {{drugs.com|international|linsidomine}}

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| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 33876-97-0

| CAS_supplemental =
{{CAS|16142-27-1}} (hydrochloride)

| ATC_prefix = C01

| ATC_suffix = DX18

| PubChem = 5219

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank =

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 5O5U71P6VQ

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D07161

| synonyms = SIN-1

| ChemSpiderID = 10561427

| C=6 | H=10 | N=4 | O=2

| smiles = C1COCCN1[N+]2=NOC(=C2)[NH-]

| StdInChI = 1S/C6H10N4O2/c7-6-5-10(8-12-6)9-1-3-11-4-2-9/h5,7H,1-4H2

| StdInChIKey = FKDHHVKWGRFRTG-UHFFFAOYSA-N

}}

Linsidomine (3-morpholinosydnonimine or SIN-1{{cite journal | vauthors = Wen TC, Rogido MR, Moore JE, Genetta T, Peng H, Sola A | title = Cardiotrophin-1 protects cortical neuronal cells against free radical-induced injuries in vitro | journal = Neuroscience Letters | volume = 387 | issue = 1 | pages = 38–42 | date = October 2005 | pmid = 16084018 | doi = 10.1016/j.neulet.2005.07.018 }}) is a vasodilator. It is a metabolite of the antianginal drug molsidomine and acts by releasing NO from the endothelial cells nonenzymatically. It also hyperpolarizes the cell membrane through influencing the sodium-potassium pump and thereby rendering it less responsive to adrenergic stimulation. Linsidomine injection at a dose of 1 mg produces usable erection{{cite journal | vauthors = Lemaire A, Buvat J | title = [Erectile response to intracavernous injection of linsidomine in 38 impotent patients. Comparison with prostaglandin E1] | journal = Progres en Urologie | volume = 8 | issue = 3 | pages = 388–91 | date = June 1998 | pmid = 9689672 }} in about 70% of patients and full erection in up to 50% of patients. Linsidomine does not appear to be associated with priapism.{{fact|date=January 2012}}

Linsidomine is neurotoxic and promotes oxidative stress on neurons.{{cite journal | vauthors = Wallace DR, Dodson S, Nath A, Booze RM | title = Estrogen attenuates gp120- and tat1-72-induced oxidative stress and prevents loss of dopamine transporter function | journal = Synapse | volume = 59 | issue = 1 | pages = 51–60 | date = January 2006 | pmid = 16237680 | doi = 10.1002/syn.20214 }} Linsidomine is a peroxynitrite-generating compound involved in the pathogenesis of neurodegenerative diseases.{{cite journal | vauthors = Jang JH, Aruoma OI, Jen LS, Chung HY, Surh YJ | title = Ergothioneine rescues PC12 cells from beta-amyloid-induced apoptotic death | journal = Free Radical Biology & Medicine | volume = 36 | issue = 3 | pages = 288–99 | date = February 2004 | pmid = 15036348 | doi = 10.1016/j.freeradbiomed.2003.11.005 }}