Feprosidnine

Feprosidnine

Systematic (IUPAC) name
5-Imino-3-(1-phenylpropan-2-yl)-5H-1,2,3-oxadiazol-3-ium-2-ide
Identifiers
CAS Number	3441-64-3
ATC code	none
PubChem	CID 72088
ChemSpider	65073
UNII	1G4W8NR1PT
ChEMBL	CHEMBL2104320
Chemical data
Formula	C11H13N3O
Molar mass	203.24 g/mol
SMILES n1oc([NH-])c[n+]1C(Cc2ccccc2)C
InChI InChI=1S/C11H13N3O/c1-9(14-8-11(12)15-13-14)7-10-5-3-2-4-6-10/h2-6,8-9,12H,7H2,1H3 Key:HFLCEELTJROKMJ-UHFFFAOYSA-N
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Feprosidnine (Sydnophen) is a stimulant drug which was developed in the USSR in the 1970s.^[1][2] It is structurally related to another Russian drug mesocarb but unlike mesocarb it has not been developed for medical use in humans.

Sydnophen has multiple mechanisms of action, the relative importance of which has not been clearly established. Effects on the body include cholinergic,^[3] adrenergic,^[4] opioid^[5] and nitric oxide donating^[6] actions, all of which may contribute to its pharmacological effects to some extent.

Chemistry

Feprosidnine is a mesoionic sydnone imine.

References

1. Veksler IG, Riabukha VN, Balitskiĭ KP, Al'tshuler RA, Mashkovskiĭ MD. Immunostimulating and antitumor action of psychotropic preparations of the sydnonimine series. (Russian) Farmakologiia i Toksikologiia. 1980 May-Jun;43(3):349-52.
2. Koniaeva EI, Beketov AI. Effect of caffeine and sidnofen on the blood supply of the brain, kidneys and hindlimbs during antiorthostatism. (Russian) Farmakologiia i Toksikologiia 1987 May-Jun;50(3):39-42.
3. Samonina GE, Mandriko EV. Peripheral cholinolytic action--one of the effects of sidnofen. (Russian) Biulleten Eksperimental'noi Biologii i Meditsiny. 1989 Apr;107(4):449-51.
4. Babskaia NE. Sidnofen-dependent pre- and postsynaptic activation of peripheral adrenergic transmission. (Russian) Eksperimental'naia i Klinicheskaia Farmakologiia. 1992 Sep-Oct;55(5):21-5.
5. D'iakonova TL, Samonina GE. The naloxone-dependent effects of the psychostimulant sidnofen: a study on identified neurons of the snail. (Russian) Zhurnal Vysshei Nervnoi Deiatelnosti Imeni I P Pavlova. 1994 Jul-Oct;44(4-5):786-95.
6. Arzamastsev AP, Severina IS, Grigor'ev NB, Granik VG. Exogenous donors of nitric oxide and inhibitors of NO-synthase (chemical aspects). (Russian). Vestnik Rossiiskoi Akademii Meditsinskikh Nauk. 2003;(12):88-95.