Linsidomine

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Chemical compound

title: "Linsidomine" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["4-morpholinyl-compounds", "vasodilators", "oxadiazoles"] description: "Chemical compound" topic_path: "general/4-morpholinyl-compounds" source: "https://en.wikipedia.org/wiki/Linsidomine" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

| 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 | image_class = skin-invert-image

| tradename = | Drugs.com = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration =

| bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =

| CAS_number_Ref = | CAS_number = 33876-97-0 | CAS_supplemental = (hydrochloride) | ATC_prefix = C01 | ATC_suffix = DX18 | PubChem = 5219 | DrugBank_Ref = | DrugBank = | UNII_Ref = | UNII = 5O5U71P6VQ | KEGG_Ref = | 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) 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 in about 70% of patients and full erection in up to 50% of patients. Linsidomine does not appear to be associated with priapism.

Linsidomine is neurotoxic and promotes oxidative stress on neurons. Linsidomine is a peroxynitrite-generating compound involved in the pathogenesis of neurodegenerative diseases.

References

References

  1. (October 2005). "Cardiotrophin-1 protects cortical neuronal cells against free radical-induced injuries in vitro". Neuroscience Letters.
  2. (June 1998). "[Erectile response to intracavernous injection of linsidomine in 38 impotent patients. Comparison with prostaglandin E1]". Progres en Urologie.
  3. (January 2006). "Estrogen attenuates gp120- and tat1-72-induced oxidative stress and prevents loss of dopamine transporter function". Synapse.
  4. (February 2004). "Ergothioneine rescues PC12 cells from beta-amyloid-induced apoptotic death". Free Radical Biology & Medicine.

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4-morpholinyl-compoundsvasodilatorsoxadiazoles