Linsidomine

Linsidomine

Systematic (IUPAC) name
5-imino-3-morpholin-4-yl-5H-1,2,3-oxadiazol-3-ium-2-ide
Clinical data
AHFS/Drugs.com	International Drug Names
Identifiers
ATC code	C01DX18 (WHO)
PubChem	CID 5219
ChemSpider	10561427
UNII	5O5U71P6VQ
KEGG	D07161
Synonyms	SIN-1
Chemical data
Formula	C6H10N4O2
Molar mass	170.17 g/mol
SMILES C1COCCN1[N+]2=NOC(=C2)[NH-]
InChI InChI=1S/C6H10N4O2/c7-6-5-10(8-12-6)9-1-3-11-4-2-9/h5,7H,1-4H2 Key:FKDHHVKWGRFRTG-UHFFFAOYSA-N
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Linsidomine (3-morpholinosydnonimine or SIN-1^[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^[2] 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.^[3] Linsidomine is a peroxynitrite-generating compound involved in the pathogenesis of neurodegenerative diseases.^[4]

References

1. Wen, TC.; Rogido, MR.; Moore, JE.; Genetta, T.; Peng, H.; Sola, A. (Oct 2005). "Cardiotrophin-1 protects cortical neuronal cells against free radical-induced injuries in vitro.". Neurosci Lett 387 (1): 38–42. doi:10.1016/j.neulet.2005.07.018. PMID 16084018.
2. Lemaire, A.; Buvat, J. (1998). "Erectile response to intracavernous injection of linsidomine in 38 impotent patients. Comparison with prostaglandin E1". Progres en urologie : journal de l'Association francaise d'urologie et de la Societe francaise d'urologie 8 (3): 388–391. PMID 9689672.
3. Wallace, DR.; Dodson, S.; Nath, A.; Booze, RM. (Jan 2006). "Estrogen attenuates gp120- and tat1-72-induced oxidative stress and prevents loss of dopamine transporter function.". Synapse 59 (1): 51–60. doi:10.1002/syn.20214. PMID 16237680.
4. Jang, JH.; Aruoma, OI.; Jen, LS.; Chung, HY.; Surh, YJ. (Feb 2004). "Ergothioneine rescues PC12 cells from beta-amyloid-induced apoptotic death.". Free Radic Biol Med 36 (3): 288–99. doi:10.1016/j.freeradbiomed.2003.11.005. PMID 15036348.