Molsidomine

Molsidomine
Names
	IUPAC name 1-Ethoxy-N-(3-morpholino-5-oxadiazol-3-iumyl)methanimidate
Identifiers
CAS Number	25717-80-0 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL1256353 ;
ChemSpider	4090 ;
ECHA InfoCard	100.042.902
KEGG	D01320 ;
PubChem CID	5353788;
UNII	D46583G77X ;
CompTox Dashboard (EPA)	DTXSID0045171 ;
	InChI InChI=1S/C9H14N4O4/c1-2-16-9(14)10-8-7-13(11-17-8)12-3-5-15-6-4-12/h7H,2-6H2,1H3 Key: XLFWDASMENKTKL-UHFFFAOYSA-N ; InChI=1/C9H14N4O4/c1-2-16-9(14)10-8-7-13(11-17-8)12-3-5-15-6-4-12/h7H,2-6H2,1H3 Key: XLFWDASMENKTKL-UHFFFAOYAC;
	SMILES [O-]C(OCC)=Nc2on[n+](N1CCOCC1)c2;
Properties
Chemical formula	C9H14N4O4
Molar mass	242.23 g/mol
Pharmacology
ATC code	C01DX12 (WHO)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Molsidomine is an orally active, long acting vasodilating drug. Molsidomine is metabolized in the liver to the active metabolite linsidomine. Linsidomine is an unstable compound that releases nitric oxide (NO) upon decay as the actual vasodilating compound.^[1]

Release of nitric oxide^[2]

Chemistry

Molsidomine as well as linsidomine are sydnone imines, a class of mesoionic heterocyclic aromatic chemical compounds.

Synthesis

A mesoionic sydnone is active as an antianginal agent.

Its synthesis starts by reacting 1-aminomorpholine with formaldehyde and hydrogen cyanide to give 2. Nitrosation gives the N-nitroso analog (3) which cyclizes to the sydnone (4) on treatment with anhydrous acid. Formation of the ethyl urethane is then made possible by reacting Linsidomine with Ethyl chloroformate.

References

^ Rosenkranz, B.; Winkelmann, B. R.; Parnham, M. J. (1996). "Clinical pharmacokinetics of molsidomine". Clinical pharmacokinetics. 30 (5): 372–384. doi:10.2165/00003088-199630050-00004. PMID 8743336.
^ Mutschler, Ernst; Schäfer-Korting, Monika (2001). Arzneimittelwirkungen (in German) (8 ed.). Stuttgart: Wissenschaftliche Verlagsgesellschaft. p. 558. ISBN 3-8047-1763-2.
^ Chemical & pharmaceutical bulletin 19(1), 72-79, 1971-01-25.

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[1] Rosenkranz, B.; Winkelmann, B. R.; Parnham, M. J. (1996). "Clinical pharmacokinetics of molsidomine". Clinical pharmacokinetics. 30 (5): 372–384. doi:10.2165/00003088-199630050-00004. PMID 8743336.

[2] Mutschler, Ernst; Schäfer-Korting, Monika (2001). Arzneimittelwirkungen (in German) (8 ed.). Stuttgart: Wissenschaftliche Verlagsgesellschaft. p. 558. ISBN 3-8047-1763-2.

[3] Chemical & pharmaceutical bulletin 19(1), 72-79, 1971-01-25.

[1]

[2]

[3]

v t e Vasodilators used in cardiac diseases (C01D)
Nitrovasodilators	Nitroglycerin # Isosorbide dinitrate # Isosorbide mononitrate Itramin tosilate Linsidomine Molsidomine Nicorandil Pentaerythritol tetranitrate Propatylnitrate Tenitramine Trolnitrate
Quinolone vasodilators	Flosequinan^‡
Others	Benziodarone Carbocromen Cinepazet Cloridarol Dilazep Efloxate Etafenone Gapicomine Heptaminol Hexobendine Imolamine Levosimendan Nesiritide Nicorandil Oxyfedrine Pimobendan Prenylamine Serelaxin Trapidil Vericiguat
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III

Release of nitric oxide[2]

Chemistry

Synthesis

See also

References

Release of nitric oxide^[2]