Molsidomine

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Molsidomine
Molsidomine.svg
Names
IUPAC name
1-Ethoxy-N-(3-morpholino-5-oxadiazol-3-iumyl)methanimidate
Identifiers
25717-80-0 YesY
ChEMBL ChEMBL1256353 N
ChemSpider 4090 YesY
Jmol 3D model Interactive image
KEGG D01320 YesY
PubChem 5353788
UNII D46583G77X YesY
Properties
C9H14N4O4
Molar mass 242.23 g/mol
Pharmacology
C01DX12 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
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][edit]

Activation of molsidomine.svg

Chemistry[edit]

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

Synthesis[edit]

A mesoionic sydnone is active as an antianginal agent.

Molsidomine synthesis:[3]

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.

See also[edit]

References[edit]

  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.