Linsidomine

Linsidomine
Clinical data
Other names	SIN-1
AHFS/Drugs.com	International Drug Names
ATC code	C01DX18 (WHO) ;
Identifiers
	IUPAC name 5-imino-3-morpholin-4-yl-5H-1,2,3-oxadiazol-3-ium-2-ide;
CAS Number	33876-97-0 ; 16142-27-1 (hydrochloride);
PubChem CID	5219;
ChemSpider	10561427;
UNII	5O5U71P6VQ;
KEGG	D07161 ;
CompTox Dashboard (EPA)	DTXSID501026026 ;
Chemical and physical data
Formula	C6H10N4O2
Molar mass	170.172 g·mol−1
3D model (JSmol)	Interactive image;
	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;
	(verify)

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.^{[citation needed]}

Linsidomine is neurotoxic and promotes oxidative stress on neurons.^[3] Linsidomine is a peroxynitrite-generating compound involved in the pathogenesis of neurodegenerative diseases.^[4]

^ Wen TC, Rogido MR, Moore JE, Genetta T, Peng H, Sola A (October 2005). "Cardiotrophin-1 protects cortical neuronal cells against free radical-induced injuries in vitro". Neuroscience Letters. 387 (1): 38–42. doi:10.1016/j.neulet.2005.07.018. PMID 16084018.
^ Lemaire A, Buvat J (June 1998). "[Erectile response to intracavernous injection of linsidomine in 38 impotent patients. Comparison with prostaglandin E1]". Progres en Urologie. 8 (3): 388–91. PMID 9689672.
^ Wallace DR, Dodson S, Nath A, Booze RM (January 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.
^ Jang JH, Aruoma OI, Jen LS, Chung HY, Surh YJ (February 2004). "Ergothioneine rescues PC12 cells from beta-amyloid-induced apoptotic death". Free Radical Biology & Medicine. 36 (3): 288–99. doi:10.1016/j.freeradbiomed.2003.11.005. PMID 15036348.

[Wen-2005-1] Wen TC, Rogido MR, Moore JE, Genetta T, Peng H, Sola A (October 2005). "Cardiotrophin-1 protects cortical neuronal cells against free radical-induced injuries in vitro". Neuroscience Letters. 387 (1): 38–42. doi:10.1016/j.neulet.2005.07.018. PMID 16084018.

[2] Lemaire A, Buvat J (June 1998). "[Erectile response to intracavernous injection of linsidomine in 38 impotent patients. Comparison with prostaglandin E1]". Progres en Urologie. 8 (3): 388–91. PMID 9689672.

[Wallace-2006-3] Wallace DR, Dodson S, Nath A, Booze RM (January 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.

[Jang-2004-4] Jang JH, Aruoma OI, Jen LS, Chung HY, Surh YJ (February 2004). "Ergothioneine rescues PC12 cells from beta-amyloid-induced apoptotic death". Free Radical Biology & Medicine. 36 (3): 288–99. doi:10.1016/j.freeradbiomed.2003.11.005. PMID 15036348.

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