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词条 Mesocarb
释义

  1. Chemistry

  2. Preparation

  3. References

{{Drugbox
| verifiedrevid = 444178004
| IUPAC_name = 5-(Phenylcarbamoylimino)-3-(1-phenylpropan-2-yl)-5H-1,2,3-oxadiazol-3-ium-2-ide
| image = Sidnocarb.svg
| width = 260
| tradename =
| legal_CA = Schedule III
| legal_UK = Class C
| legal_DE = Anlage II
| legal_status =
| routes_of_administration = Oral
| metabolism = hepatic
| elimination_half-life =
| excretion = renal
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 34262-84-5
| ATC_prefix = none
| PubChem = 71932
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 16736988
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = UMT8MP2NDU
| C=18 | H=18 | N=4 | O=2
| molecular_weight = 322.36 g/mol
| smiles = O=C(\=C1/C=[N+](\\[N-]O1)C(C)Cc2ccccc2)Nc3ccccc3
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C18H18N4O2/c1-14(12-15-8-4-2-5-9-15)22-13-17(24-21-22)20-18(23)19-16-10-6-3-7-11-16/h2-11,13-14H,12H2,1H3,(H,19,23)/b20-17+
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = DMHQLXUFCQSQQQ-LVZFUZTISA-N
}}Mesocarb (brand names Sidnocarb, Sydnocarb) is a drug that is currently being developed for Parkinson's disease.[1]

The drug was originally developed in the USSR in the 1970s [2][3] for a variety of indications including asthenia, apathy, adynamia and some clinical aspects of depression and schizophrenia.[4][5] Mesocarb was used for counteracting the sedative effects of benzodiazepine drugs,[6] increasing workload capacity and cardiovascular function,[7] treatment of ADHD and hyperactivity in children,[8][9] as a nootropic,[10] and as a drug to enhance resistance to extremely cold temperatures.[11][12] It is also listed as having antidepressant and anticonvulsant properties.

The drug has been found to act as a selective dopamine reuptake inhibitor by blocking the actions of the dopamine transporter (DAT),[13][14] and lacks the dopamine release characteristic of stimulants such as dextroamphetamine.[15][16][17] It was the most selective DAT inhibitor amongst an array of other DAT inhibitors to which it was compared.[14]

Mesocarb was sold in Russia as 5 milligram tablets under the brand name Sydnocarb. Hydroxylated metabolites can be detected in urine for up to 10 days after consumption.[18]

The drug is almost unknown in the western world and is neither used in medicine or studied scientifically to any great extent outside Russia and other countries in the former Soviet Union. It has however been added to the list of drugs under international control and is illegal in most countries, despite its multiple therapeutic applications and reported lack of significant abuse potential.[19]

Mesocarb had erroneously been referred to as a prodrug of amphetamine[20] but this was based on older literature that relied on gas chromatography as an analytical method. Subsequently, with the advent of mass spectroscopy, it has been shown that presence of amphetamine in prior studies was an artifact of gas chromatography method.[21] More recent studies using mass spectroscopy show that negligible levels of amphetamine are released from mesocarb metabolism.[18]

Chemistry

Mesocarb is a mesoionic sydnone imine. It has the amphetamine-backbone present, except that the RN has a complicated imine side-chain present.

Preparation

References

1. ^{{cite web|title=Melior Discovery Announces Spinout of Melior Pharmaceuticals II, LLC.|url=https://www.businesswire.com/news/home/20160510005485/en/Melior-Discovery-Announces-Spinout-Melior-Pharmaceuticals-II}}
2. ^GB Patent 1262830 - NOVEL SYDNONIMINE DERIVATIVE
3. ^{{cite journal |author1=Anokhina IP |author2=Zabrodin GD |author3=Svirinovskiĭ IaE |title=[Характеристика центрального действия сиднокарба] |language=Russian |journal=Zh Nevropatol Psikhiatr Im S S Korsakova |volume=74 |issue=4 |pages=594–602 |year=1974 |pmid=4825943 |trans-title=Characteristics of the central action of sidnocarb |issn=1997-7298}}
4. ^{{cite journal |vauthors=Rudenko GM, Altshuler RA |title=Peculiarities of clinical activity and pharmacokinetics of sydnocarb (sydnocarbum), an original psychostimulant |journal= Agressologie |volume=20 |issue=D |pages=265–70 |year=1979 |pmid=45391 |url= |doi=}}
5. ^{{cite journal |vauthors=Witkin JM, Savtchenko N, Mashkovsky M, etal |title=Behavioral, toxic, and neurochemical effects of sydnocarb, a novel psychomotor stimulant: comparisons with methamphetamine |journal=J Pharmacol Exp Ther |volume=288 |issue=3 |pages=1298–310 |date=1 March 1999|pmid=10027871 |url=http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=10027871 }}
6. ^{{cite journal |vauthors=Valueva LN, Tozhanova NM |title=[Коррекция мезокарбом побочного действия транквилизаторов бензодиазепинового ряда] |language=Russian |journal=Zh Nevropatol Psikhiatr Im S S Korsakova |volume=82 |issue=8 |pages=92–7 |year=1982 |pmid=6127851 |trans-title=Sidnocarb correction of the adverse effects of benzodiazepine tranquilizers}}
7. ^{{cite journal |vauthors=Vinar O, Klein DF, Potter WZ, Gause EM |title=A survey of psychotropic medications not available in the United States |journal=Neuropsychopharmacology |volume=5 |issue=4 |pages=201–17 |date=December 1991|pmid=1804161 }}
8. ^{{cite journal |author1=Turova NF |author2=Misionzhnik EIu |author3=Ermolina LA |author4=Aziavchik AV |author5=Krasov VA |title=[Экскреция моноаминов, их предшественников и метаболитов при гиперактивном синдроме у детей с интеллектуальной недостаточностью] |language=Russian |journal=Vopr Med Khim. |volume=34 |issue=1 |pages=47–50 |year=1988 |pmid=3369126 |trans-title=Excretion of monoamines, their precursors and metabolites in the hyperactivity syndrome in mentally defective children }}
9. ^{{cite journal |author=Krasov VA |title=[Лечение мезокарбом детей младшего школьного возраста с гипердинамическим синдромом] |language=Russian |journal=Zh Nevropatol Psikhiatr Im S S Korsakova |volume=88 |issue=8 |pages=97–101 |year=1988 |pmid=3195293 |trans-title=Sidnocarb treatment of young schoolchildren with the hyperdynamic syndrome }}
10. ^{{cite journal |author1=Ganiev MM |author2=Kharlamov AN |author3=Raevskiĭ KS |author4=Guseĭnov DIa |title=[Effect of sidnocarb on learning and memory] |language=Russian |journal=Biull Eksp Biol Med |volume=104 |issue=10 |pages=453–4 |date=October 1987|pmid=3676468 |trans-title=Effect of sidnocarb on learning and memory }}
11. ^{{cite journal |vauthors=Barer AS, Lakota NG, Ostrovskaia GZ, Shashkov VS |title=[Фармакологическая коррекция холодовых воздействий на человека] |language=Russian |journal=Kosm Biol Aviakosm Med |volume=22 |issue=6 |pages=66–73 |date=Nov–Dec 1988 |pmid=2906380 |trans-title=Pharmacologic correction of the effect of cold on man }}
12. ^{{cite journal |vauthors=Levina MN, Badyshtov BA, Gan'shina TS |title=[Thermoprotector properties of a combination of sydnocarb with ladasten] |language=Russian |journal=Eksp Klin Farmakol |volume=69 |issue=1 |pages=71–3 |year=2006 |pmid=16579065 |trans-title=Thermoprotector properties of a combination of sydnocarb with ladasten }}
13. ^{{cite journal | vauthors = Erdö SL, Kiss B, Rosdy B | title = Inhibition of dopamine uptake by a new psychostimulant mesocarb (Sydnocarb) | journal = Pol J Pharmacol Pharm | volume = 33 | issue = 2 | pages = 141–7 | year = 1981 | pmid = 7312716 | doi = | url = }}
14. ^1 {{Cite journal|last=Gruner|first=John A.|last2=Mathiasen|first2=Joanne R.|last3=Flood|first3=Dorothy G.|last4=Gasior|first4=Maciej|date=May 2011|title=Characterization of pharmacological and wake-promoting properties of the dopaminergic stimulant sydnocarb in rats|journal=The Journal of Pharmacology and Experimental Therapeutics|volume=337|issue=2|pages=380–390|doi=10.1124/jpet.111.178947|issn=1521-0103|pmid=21300706}}
15. ^{{cite journal |vauthors=Afanas'ev II, Anderzhanova EA, Kudrin VS, Rayevsky KS |title=Effects of amphetamine and sydnocarb on dopamine release and free radical generation in rat striatum |journal=Pharmacol Biochem Behav |volume=69 |issue=3–4 |pages=653–8 |year=2001 |pmid=11509228 |url=http://linkinghub.elsevier.com/retrieve/pii/S0091-3057(01)00574-3 |doi=10.1016/S0091-3057(01)00574-3}}
16. ^{{cite journal |doi=10.1111/j.1749-6632.2000.tb05191.x |vauthors=Anderzhanova EA, Afanas'ev II, Kudrin VS, Rayevsky KS |title=Effect of d-amphetamine and sydnocarb on the extracellular level of dopamine, 3,4-dihydroxyphenylacetic acid, and hydroxyl radicals generation in rat striatum |journal=Ann N Y Acad Sci |volume=914 |pages=137–45 |date=September 2000|pmid=11085316 |url=http://www.blackwell-synergy.com/openurl?genre=article&sid=nlm:pubmed&issn=0077-8923&date=2000&volume=914&spage=137}}
17. ^{{cite journal |vauthors=Gainetdinov RR, Sotnikova TD, Grekhova TV, Rayevsky KS |title=Effects of a psychostimulant drug sydnocarb on rat brain dopaminergic transmission in vivo |journal=Eur J Pharmacol |volume=340 |issue=1 |pages=53–8 |date=December 1997|pmid=9527506 |url=http://linkinghub.elsevier.com/retrieve/pii/S0014-2999(97)01407-6 |doi=10.1016/S0014-2999(97)01407-6}}
18. ^1 {{cite journal | vauthors = Shpak AV, Appolonova SA, Semenov VA | title = Validation of liquid chromatography-electrospray ionization ion trap mass spectrometry method for the determination of mesocarb in human plasma and urine | journal = J Chromatogr Sci | volume = 43 | issue = 1 | pages = 11–21 | year = 2005 | pmid = 15808002 | doi = 10.1093/chromsci/43.1.11| url = }}
19. ^{{cite journal |vauthors=Rudenko GM, Altshuler RA |title=[Experimental and clinical study of Sydnocarb] |language=Russian |journal=Hung Pharmacotherapy |volume=124 |issue= |pages=150–4 |year=1978}}
20. ^{{cite book|author1=Reinhard Dettmeyer|author2=Marcel A. Verhoff|author3=Harald F. Schütz|title=Forensic Medicine: Fundamentals and Perspectives|url=https://books.google.com/books?id=yHHABAAAQBAJ&pg=PA519|date=9 October 2013|publisher=Springer Science & Business Media|isbn=978-3-642-38818-7|pages=519–}}
21. ^{{Cite journal|last=Appolonova|first=Svetlana S.|last2=Shpak|first2=Alexey V.|last3=Semenov|first3=Vitaliy|date=2004|title=Liquid chromatography-electrospray ionization ion trap mass spectrometry for analysis of mesocarp and its metabolites in human urine|journal=Journal of Chromatography B|volume=800|issue=|pages=281–289|pmid=14698267|doi=10.1016/j.jchromb.2003.10.071}}
{{Stimulants}}{{ADHD pharmacotherapies}}{{Monoamine reuptake inhibitors}}

7 : Dopamine reuptake inhibitors|Oxadiazoles|Prodrugs|Russian drugs|Stimulants|Ureas|Drugs in the Soviet Union
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