{{Short description|Chemical compound}} {{Drugbox | Watchedfields = changed | verifiedrevid = 446899189 | IUPAC_name = 5-imino-3-morpholin-4-yl-5''H''-1,2,3-oxadiazol-3-ium-2-ide | image = Linsidomine structure.svg | image_class = skin-invert-image

<!--Clinical data--> | tradename = | Drugs.com = {{drugs.com|international|linsidomine}} | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_US = <!-- A / B / C / D / X --> | pregnancy_category = | legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> | legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> | legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> | legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> | legal_status = | routes_of_administration =

<!--Pharmacokinetic data--> | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =

<!--Identifiers--> | CAS_number_Ref = {{cascite|correct|CAS}} | CAS_number = 33876-97-0 | CAS_supplemental = <br />{{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

<!--Chemical data--> | 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'''<ref name="Wen-2005">{{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 }}</ref>) 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&nbsp;mg produces usable erection<ref>{{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 }}</ref> 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.<ref name="Wallace-2006">{{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 }}</ref> Linsidomine is a peroxynitrite-generating compound involved in the pathogenesis of neurodegenerative diseases.<ref name="Jang-2004">{{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 }}</ref>

== References == {{Reflist}}

{{Vasodilators used in cardiac diseases}} {{Nitric oxide signaling}}

Category:4-Morpholinyl compounds Category:Vasodilators Category:Oxadiazoles