Feprosidnine

Feprosidnine
Clinical data

ATC code	none
Identifiers
IUPAC name 5-Imino-3-(1-phenylpropan-2-yl)-5H-1,2,3-oxadiazol-3-ium-2-ide
CAS Number	3441-64-3^Y
PubChem (CID)	72088
ChemSpider	65073^Y
UNII	1G4W8NR1PT^Y
ChEMBL	CHEMBL2104320
Chemical and physical data
Formula	C₁₁H₁₃N₃O
Molar mass	203.24 g/mol
3D model (Jmol)	Interactive image
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^Y Key:HFLCEELTJROKMJ-UHFFFAOYSA-N^Y
(verify)

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

↑ 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.
↑ 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.
↑ 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.
↑ 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.
↑ 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.
↑ 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.

Stimulants (category)

Adamantanes	Adaphenoxate Adapromine Amantadine Bromantane Chlodantane Gludantane Memantine Rimantadine

Adenosine antagonists	8-Chlorotheophylline 8-Cyclopentyltheophylline 8-Phenyltheophylline Aminophylline Caffeine CGS-15943 Dimethazan Paraxanthine SCH-58261 Theobromine Theophylline

Alkylamines	Cyclopentamine Cypenamine Cyprodenate Heptaminol Isometheptene Levopropylhexedrine Methylhexaneamine Octodrine Propylhexedrine Tuaminoheptane

Ampakines	CX-516 CX-546 CX-614 CX-691 CX-717 IDRA-21 LY-404,187 LY-503,430 Nooglutyl Org 26576 PEPA S-18986 Sunifiram Unifiram

Arylcyclohexylamines	Benocyclidine Dieticyclidine Esketamine Eticyclidine Gacyclidine Ketamine Phencyclamine Phencyclidine Rolicyclidine Tenocyclidine Tiletamine

Benzazepines	6-Br-APB SKF-77434 SKF-81297 SKF-82958

Cholinergics	A-84,543 A-366,833 ABT-202 ABT-418 AR-R17779 Altinicline Anabasine Arecoline Bradanicline Cotinine Cytisine Dianicline Epibatidine Epiboxidine GTS-21 Ispronicline Nicotine PHA-543,613 PNU-120,596 PNU-282,987 Pozanicline Rivanicline Sazetidine A SIB-1553A SSR-180,711 TC-1698 TC-1827 TC-2216 Tebanicline UB-165 Varenicline WAY-317,538

Convulsants	Anatoxin-a Bicuculline DMCM Flurothyl Gabazine Pentetrazol Picrotoxin Strychnine Thujone

Eugeroics	Adrafinil Armodafinil CRL-40,940 CRL-40,941 Fluorenol JZ-IV-10 Modafinil

Oxazolines	4-Methylaminorex Aminorex Clominorex Cyclazodone Fenozolone Fluminorex Pemoline Thozalinone

Phenethylamines	1-(4-Methylphenyl)-2-aminobutane 1-Phenyl-2-(piperidin-1-yl)pentan-3-one 1-Methylamino-1-(3,4-methylenedioxyphenyl)propane 2-Fuoroamphetamine 2-Fuoromethamphetamine 2-OH-PEA 2-Phenyl-3-aminobutane 2-Phenyl-3-methylaminobutane 2,3-MDA 3-Fuoroamphetamine 3-Fluoroethamphetamine 3-Fluoromethcathinone 3-Methoxyamphetamine 3-Methylamphetamine 3,4-DMMC 4-BMC 4-CMC 4-Ethylamphetamine 4-Fluoroamphetamine 4-Fluoromethamphetamine 4-MA 4-Methylbuphedrone 4-Methylcathinone 4-MMA 4-Methylpentedrone 4-MTA 6-FNE AL-1095 Alfetamine a-Ethylphenethylamine Amfecloral Amfepentorex Amfepramone Amidephrine 2-Amino-1,2-dihydronaphthalene 2-Aminoindane 5-(2-Aminopropyl)indole 2-Aminotetralin Acridorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Arbutamine β-Methylphenethylamine β-Phenylmethamphetamine Benfluorex Benzedrone Benzphetamine BDB BOH 3-Benzhydrylmorpholine BPAP Buphedrone Bupropion Butylone Camfetamine Cathine Cathinone Chlorphentermine Cilobamine Cinnamedrine Clenbuterol Clobenzorex Cloforex Clortermine Cypenamine D-Deprenyl Denopamine Dimethoxyamphetamine Dimethylamphetamine Dimethylcathinone Dobutamine DOPA (Dextrodopa, Levodopa) Dopamine Dopexamine Droxidopa EBDB Ephedrine Epinephrine Epinine Etafedrine Ethcathinone Ethylnorepinephrine Ethylone Etilamfetamine Etilefrine Famprofazone Fencamfamine Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Feprosidnine Flephedrone Fludorex Formetorex Furfenorex Gepefrine Hexapradol Hexedrone HMMA Hordenine 4-Hydroxyamphetamine 5-Iodo-2-aminoindane Ibopamine IMP Indanylamphetamine Iofetamine Isoetarine Isoethcathinone Isoprenaline L-Deprenyl (Selegiline) Lefetamine Lisdexamfetamine Lophophine MBDB MDA MDBU MDEA MDMA MDMPEA MDOH MDPR MDPEA Mefenorex Mephedrone Mephentermine Metanephrine Metaraminol Mesocarb Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxamine Methoxyphenamine MMA Methcathinone Methedrone Methoxyphenamine Methylenedioxycathinone Methylone Mexedrone MMDA MMDMA MMMA Morforex N,alpha-Diethylphenylethylamine N-Benzyl-1-phenethylamine N-Ethylbuphedrone N-Ethylhexedrone N,N-Dimethylphenethylamine Naphthylamphetamine Nisoxetine Norepinephrine Norfenefrine Norfenfluramine Normetanephrine L-Norpseudoephedrine Octopamine (drug) Orciprenaline Ortetamine Oxifentorex Oxilofrine PBA PCA PCMA PHA Pentorex Pentedrone Pentylone Phenatine Phenpromethamine Phentermine Phenylalanine Phenylephrine Phenylpropanolamine Pholedrine PIA PMA PMEA PMMA PPAP Phthalimidopropiophenone Prenylamine Propylamphetamine Pseudoephedrine Ropinirole Salbutamol (Levosalbutamol) Sibutramine Synephrine Theodrenaline Tiflorex Tranylcypromine Tyramine Tyrosine Xylopropamine Zylofuramine

Phenylmorpholines	3-Fluorophenmetrazine Fenbutrazate Fenmetramide G-130 Manifaxine Morazone Morforex Oxaflozane PD-128,907 Phendimetrazine Phenmetrazine 2-Phenyl-3,6-dimethylmorpholine Pseudophenmetrazine Radafaxine

Piperazines	2C-B-BZP 3C-PEP BZP CM156 DBL-583 GBR-12783 GBR-12935 GBR-13069 GBR-13098 GBR-13119 MeOPP MBZP Vanoxerine

Piperidines	1-Benzyl-4-(2-(diphenylmethoxy)ethyl)piperidine 1-(3,4-Dichlorophenyl)-1-(piperidin-2-yl)butane 2-Benzylpiperidine 2-Methyl-3-phenylpiperidine 3-Chloromethylphenidate 3,4-Dichloromethylphenidate 4-Benzylpiperidine 4-Fluoromethylphenidate 4-Methylmethylphenidate Desoxypipradrol Difemetorex Diphenylpyraline Ethylnaphthidate Ethylphenidate Methylnaphthidate Isopropylphenidate Methylphenidate (Dexmethylphenidate) N-Methyl-3β-propyl-4β-(4-chlorophenyl)piperidine Nocaine Phacetoperane Pipradrol Propylphenidate SCH-5472

Pyrrolidines	2-Diphenylmethylpyrrolidine 5-DBFPV α-PPP α-PBP α-PHP α-PVP α-PVT Diphenylprolinol DMPVP FPOP FPVP MDPPP MDPBP MPBP MPHP MPPP MOPVP MOPPP Indapyrophenidone MDPV Naphyrone PEP Picilorex Prolintane Pyrovalerone

Racetams	Oxiracetam Phenylpiracetam Phenylpiracetam hydrazide

Tropanes	3-CPMT 3'-Chloro-3a-(diphenylmethoxy)tropane 4-fluorotropacocaine 4'-Fluorococaine AHN-1055 Altropane (IACFT) Brasofensine CFT (WIN 35,428) β-CIT (RTI-55) Cocaethylene Cocaine Dichloropane (RTI-111) Difluoropine FE-β-CPPIT FP-β-CPPIT Ioflupane (¹²³I) Norcocaine PIT PTT RTI-31 RTI-32 RTI-51 RTI-105 RTI-112 RTI-113 RTI-117 RTI-120 RTI-121 (IPCIT) RTI-126 RTI-150 RTI-154 RTI-171 RTI-177 RTI-183 RTI-193 RTI-194 RTI-199 RTI-202 RTI-204 RTI-229 RTI-241 RTI-336 RTI-354 RTI-371 RTI-386 Salicylmethylecgonine Tesofensine Troparil (β-CPT, WIN 35,065-2) Tropoxane WF-23 WF-33 WF-60

Tryptamines	4-HO-αMT 4-Methyl-αET 4-Methyl-αMT 5-Chloro-αMT 5-Fluoro-αMT 5-MeO-αET 5-MeO-αMT 5-MeO-DIPT 6-Fluoro-αMT 7-Methyl-αET αET αMT

Others	2-MDP 2-Phenylcyclohexylamine 3,3-Diphenylcyclobutanamine Amfonelic acid Amineptine Amiphenazole Atipamezole Atomoxetine Bemegride Benzydamine BTQ BTS 74,398 Centanafadine Ciclazindol Clofenciclan Cropropamide Crotetamide D-161 Diclofensine Dimethocaine Efaroxan Etamivan Fenisorex Fenpentadiol Gamfexine Gilutensin GSK1360707F GYKI-52895 Hexacyclonate Idazoxan Indanorex Indatraline JNJ-7925476 Lazabemide Leptacline Lomevactone LR-5182 Mazindol Meclofenoxate Medifoxamine Mefexamide Methamnetamine Methastyridone Methiopropamine Naphthylaminopropane Nefopam Nikethamide Nomifensine O-2172 Oxaprotiline PNU-99,194 PRC200-SS Rasagiline Rauwolscine Rubidium chloride Setazindol Tametraline Tandamine Thiopropamine Thiothinone Trazium UH-232 Yohimbine

ATC code: N06B

Adrenergic receptor modulators

α₁

Agonists 6-FNE Amidephrine Anisodine Buspirone Cirazoline Corbadrine Dexisometheptene Dipivefrine Dopamine Droxidopa (L-DOPS) Ephedrine Epinephrine Etilefrine Etilevodopa Ethylnorepinephrine Indanidine Isometheptene L-DOPA (levodopa) L-Phenylalanine L-Tyrosine Melevodopa Metaraminol Methoxamine Methyldopa Midodrine Naphazoline Norepinephrine Octopamine (drug) Oxymetazoline Phenylephrine Phenylpropanolamine Pseudoephedrine Synephrine Tetryzoline Tiamenidine XP21279 Xylometazoline

Antagonists Abanoquil Adimolol Ajmalicine Alfuzosin Amosulalol Anisodamine Arotinolol Atiprosin Atypical antipsychotics (e.g., clozapine, olanzapine, quetiapine, risperidone) Benoxathian Buflomedil Bunazosin Carvedilol Corynanthine Dapiprazole Domesticine Doxazosin Ergolines (e.g., ergotamine, dihydroergotamine, lisuride, terguride) Etoperidone Eugenodilol Fenspiride Hydroxyzine Indoramin Ketanserin L-765,314 Labetalol mCPP Mepiprazole Metazosin Monatepil Moxisylyte Naftopidil Nantenine Nefazodone Neldazosin Niaprazine Nicergoline Niguldipine Pardoprunox Pelanserin Phendioxan Phenoxybenzamine Phentolamine Piperoxan Prazosin Quinazosin Ritanserin Silodosin Spiperone Talipexole Tamsulosin Terazosin Tiodazosin Tolazoline Trazodone Tetracyclic antidepressants (e.g., amoxapine, maprotiline, mianserin) Tricyclic antidepressants (e.g., amitriptyline, clomipramine, doxepin, imipramine, trimipramine) Trimazosin Typical antipsychotics (e.g., chlorpromazine, fluphenazine, loxapine, thioridazine) Urapidil WB-4101 Zolertine

α₂

Agonists (R)-3-Nitrobiphenyline 4-NEMD 6-FNE Amitraz Apraclonidine Brimonidine Cannabivarin Clonidine Corbadrine Detomidine Dexmedetomidine Dihydroergotamine Dipivefrine Dopamine Droxidopa (L-DOPS) Etilevodopa Ephedrine Ergotamine Epinephrine Etilefrine Ethylnorepinephrine Guanabenz Guanfacine Guanoxabenz L-DOPA (levodopa) L-Phenylalanine L-Tyrosine Lofexidine Medetomidine Melevodopa Methyldopa Mivazerol Naphazoline Norepinephrine Oxymetazoline Phenylpropanolamine Piperoxan Pseudoephedrine Rilmenidine Romifidine Talipexole Tetrahydrozoline Tiamenidine Tizanidine Tolonidine Urapidil XP21279 Xylazine Xylometazoline

Antagonists 1-PP Adimolol Aptazapine Atipamezole Atypical antipsychotics (e.g., asenapine, clozapine, lurasidone, paliperidone, quetiapine, risperidone, zotepine) Azapirones (e.g., buspirone, tandospirone) BRL-44408 Buflomedil Cirazoline Efaroxan Esmirtazapine Fenmetozole Fluparoxan Idazoxan mCPP Mianserin Mirtazapine NAN-190 Olanzapine Pardoprunox Phentolamine Phenoxybenzamine Piperoxan Piribedil Rauwolscine Rotigotine SB-269970 Setiptiline Spiroxatrine Sunepitron Tolazoline Typical antipsychotics (e.g., chlorpromazine, fluphenazine, loxapine, thioridazine) Yohimbine

Agonists Abediterol Alifedrine Amibegron Arbutamine Arformoterol Arotinolol BAAM Bambuterol Befunolol Bitolterol Broxaterol Buphenine Carbuterol Carmoterol Cimaterol Clenbuterol Corbadrine Denopamine Dipivefrine Dobutamine Dopamine Dopexamine Droxidopa (L-DOPS) Ephedrine Epinephrine Etafedrine Etilefrine Etilevodopa Ethylnorepinephrine Fenoterol Formoterol Hexoprenaline Higenamine Indacaterol Isoetarine Isoprenaline Isoxsuprine L-DOPA (levodopa) L-Phenylalanine L-Tyrosine Levosalbutamol Mabuterol Melevodopa Methoxyphenamine Methyldopa Mirabegron Norepinephrine Orciprenaline Oxyfedrine PF-610355 Phenylpropanolamine Pirbuterol Prenalterol Ractopamine Procaterol Pseudoephedrine Reproterol Rimiterol Ritodrine Salbutamol Salmeterol Solabegron Terbutaline Tretoquinol Tulobuterol Vilanterol Xamoterol XP21279 Zilpaterol Zinterol

Antagonists Acebutolol Adaprolol Adimolol Afurolol Alprenolol Alprenoxime Amosulalol Ancarolol Arnolol Arotinolol Atenolol Befunolol Betaxolol Bevantolol Bisoprolol Bopindolol Bornaprolol Brefonalol Bucindolol Bucumolol Bufetolol Bufuralol Bunitrolol Bunolol Bupranolol Butaxamine Butidrine Butofilolol Capsinolol Carazolol Carpindolol Carteolol Carvedilol Celiprolol Cetamolol Cicloprolol Cinamolol Cloranolol Cyanopindolol Dalbraminol Dexpropranolol Diacetolol Dichloroisoprenaline Dihydroalprenolol Dilevalol Diprafenone Draquinolol Ecastolol Epanolol Ericolol Ersentilide Esatenolol Esprolol Eugenodilol Exaprolol Falintolol Flestolol Flusoxolol Hydroxycarteolol Hydroxytertatolol ICI-118,551 Idropranolol Indenolol Indopanolol Iodocyanopindolol Iprocrolol Isoxaprolol Isamoltane Labetalol Landiolol Levobetaxolol Levobunolol Levomoprolol Medroxalol Mepindolol Metipranolol Metoprolol Moprolol Nadolol Nadoxolol Nebivolol Nifenalol Nipradilol Oxprenolol Pacrinolol Pafenolol Pamatolol Pargolol Penbutolol Pindolol Practolol Primidolol Procinolol Pronethalol Propafenone Propranolol Ridazolol Ronactolol Soquinolol Sotalol Spirendolol SR 59230A Sulfinalol Talinolol Tazolol Tertatolol Tienoxolol Tilisolol Timolol Tiprenolol Tolamolol Toliprolol Xibenolol Xipranolol

See also: Dopaminergics

Melatonergics

Serotonergics

Monoamine reuptake and release modulators

Monoamine metabolism modulators

Monoamine neurotoxins

Nitric oxide signaling modulators

Forms

Targets

sGC	Activators: Cinaciguat (BAY 58-2667) Riociguat (BAY 63-2521) Inhibitors: ODQ

NO donors
(prodrugs)

Nitrates: Diethylene glycol dinitrate (DEGDN)
Erythritol tetranitrate (ETN)
Ethylene glycol dinitrate (EGDN; nitroglycol)
Isosorbide mononitrate (ISMN)
Isosorbide dinitrate (ISDN)
Itramin tosilate
Mannitol hexanitrate
Naproxcinod (nitronaproxen; AZD-3582, HCT-3012)
NCX-466
NCX-2216
NCX-4016
NCX 4040
NCX-4215
Nicorandil
Nipradilol (K-351)
Nitrate (NO−
3)
Nitroatorvastatin (NCX-6560)
Nitroflurbiprofen (HCT-1026)
Nitrofluvastatin
Nitroglycerin (glyceryl trinitrate (GTN))
Nitropravastatin (NCX-6550)
Pentaerithrityl tetranitrate (PETN)
Propatylnitrate
Propylene glycol dinitrate (PGDN)
Sodium trioxodinitrate (Angeli's salt)
Tenitramine
Trolnitrate

Nitroso compounds/nitrites: Nitrite (NO−
2); O-Nitroso compounds (alkyl nitrites): Amyl nitrite (isoamyl nitrite, isopentyl nitrite)
Cyclohexyl nitrite
Ethyl nitrite
Hexyl nitrite
Isobutyl nitrite (2-methylpropyl nitrite)
Isopropyl nitrite
Methyl nitrite
n-Butyl nitrite
Pentyl nitrite
tert-Butyl nitrite; S-Nitroso compounds (thionitrites): LA810
S-Nitrosoalbumin (SNALB)
S-Nitrosated AR545C
S-Nitroso-N-acetylcysteine (SNAC)
S-Nitroso-N-acetylpenicillamine (SNAP)
S-Nitroso-N-valerylpenicillamine (SNVP)
S-Nitrosocaptopril (SNO-Cap)
S-Nitrosocysteine (SNC, CysNO, SNO-Cys)
S-Nitrosodiclofenac
S-Nitrosoglutathione (GSNO, SNOG)
SNO-t-PA
SNO-vWF; N-Nitroso compounds (e.g., nitrosamines): SIN-1A

Nitrosyl compounds: Metal nitrosyl complexes: Roussin's black salt
Roussin's red salt
Sodium nitroprusside (SNP)

NONOates (diazeniumdiolates): Diethylamine/NO (DEA/NO)
Diethylenetriamine/NO (DETA/NO)
GLO/NO
JS-K
Methylamine hexamethylene methylamine/NO (MAHMA/NO)
PROLI/NO
Spermine/NO (SPER/NO)
V-PYRRO/NO

Heterocyclic compounds: Furoxans: Furoxan
REC15/2739; Sydnonimines: Feprosidnine
Linsidomine (SIN-1)
Molsidomine (SIN-10)
Sydnonimine

Unsorted: CXL-1427
FK-409
FR144220
FR146881
N-Acetyl-N-acetoxy-4-chlorobenzenesulfonamide

Enzyme
(inhibitors)

NOS

nNOS	3-Bromo-7-nitroindazole 3-Chloroindazole 3-Chloro-5-nitroindazole 5-Nitroindazole 6-Nitroindazole 7-Nitroindazole A-84643 Aminoguanidine (pimagedine) ARL-17477 Indazole N⁵-(1-Iminoethyl)-L-ornithine (L-NIO) N^ω-Methyl-L-arginine (L-NMA) N^ω-Propyl-L-arginine (L-NPA) Nitroarginine (NNA, NOARG) Pentamidine isethionate TRIM

iNOS	1-Amino-2-hydroxyguanidine 2-Ethylaminoguanidine 2-Iminopiperidine 1400W AEITU Aminoguanidine (pimagedine) AMT AR-C 102222 BYK-191023 Canavanine Cindunistat (SD-6010) EITU IPTU MITU N⁵-(1-Iminoethyl)-L-ornithine (L-NIO) N⁶-(1-Iminoethyl)-L-lysine (L-NIL) N^ω-Methyl-L-arginine (L-NMA) Ronopterin (VAS-203) TRIM

eNOS	Aminoguanidine (pimagedine) N⁵-(1-Iminoethyl)-L-ornithine (L-NIO) N^ω-Methyl-L-arginine (L-NMA) Nitroarginine (NNA, NOARG)

Unsorted	Asymmetric dimethylarginine (ADMA) CKD-712 Guanidinoethyldisulfide (GED) GW-273629 Indospicine KD-7040 Nitroarginine methyl ester (NAME) NCX-456 NXN-462 ONO-1714 VAS-2381

Arginase

ABH
N^ω-Hydroxy-L-arginine (NOHA)

CAMK

Calmidazolium
W-7

Others

Precursors: L-Arginine
N^ω-Hydroxy-L-arginine (NOHA)

Cofactors: NADPH
FAD
FMN
Heme
BH₄
CaM
O₂
Ca²⁺

Indirect/downstream NO modulators: ACE inhibitors/AT-II receptor antagonists (e.g., captopril, losartan)
ET_B receptor antagonists (e.g., bosentan)
L-Type calcium channel blockers (e.g., dihydropyridines: nifedipine)
Nebivolol (beta blocker)
PDE5 inhibitors (e.g., sildenafil)
Statins (e.g., simvastatin)

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