Mesocarb

Mesocarb
Clinical data
Trade namesSidnocarb, Sydnocarb, Synocarb
Other namesFensidnimine; Pharmaneocarb; Sydnocarbum; MLR-1017; N-Phenylcarbamoyl-3-(β-phenylisopropyl)sydnonimine; 3-(β-Phenylisopropyl)-N-phenylcarbamoylsydnonimine
Routes of
administration		Oral
Drug classAtypical dopamine reuptake inhibitor
ATC code
  • None
Legal status
Legal status
  • BR: Class B1 (Psychoactive drugs)[1]
  • CA: Schedule III
  • DE: Anlage II (Authorized trade only, not prescriptible)
  • UK: Class C
  • US: Schedule I
Pharmacokinetic data
MetabolismHepatic
ExcretionRenal
Identifiers
IUPAC name
  • 5-(Phenylcarbamoylimino)-3-(1-phenylpropan-2-yl)-5H-1,2,3-oxadiazol-3-ium-2-ide
CAS Number
PubChem CID
PubChem SID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC18H18N4O2
Molar mass322.368 g·mol−1
3D model (JSmol)
SMILES
  • O=C(\N=C1/C=[N+](\[N-]O1)C(C)Cc2ccccc2)Nc3ccccc3
InChI
  • InChI=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+ Y
  • Key:DMHQLXUFCQSQQQ-LVZFUZTISA-N Y
  (verify)

Mesocarb, sold under the brand name Sidnocarb or Sydnocarb and known by the developmental code name MLR-1017, is a psychostimulant medication which has been used in the treatment of psychiatric disorders and for a number of other indications in the Soviet Union and Russia.[2][3][4][5] It is currently under development for the treatment of Parkinson's disease and sleep disorders.[6][7] It is taken by mouth.

The drug is a selective dopamine reuptake inhibitor (DRI).[8][9][10][11] It is an unusual and unique DRI, acting as a negative allosteric modulator and non-competitive inhibitor of the dopamine transporter (DAT).[8][9][10] Chemically, mesocarb contains amphetamine within its structure but has been modified and extended at the amine with a sydnone imine-containing moiety.[12][2][3]

Mesocarb was first described by 1971.[2][13][14][11] It was used as a pharmaceutical drug until 2008.[15] In 2021, its nature as a DAT allosteric modulator was reported.[8][9][10] As of February 2023, mesocarb was in phase 1 clinical trials for Parkinson's disease.[7] The active enantiomer, armesocarb, is also being developed.[16]

  1. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  2. ^ a b c Elks J (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 774. ISBN 978-1-4757-2085-3. Retrieved 16 September 2024.
  3. ^ a b Schweizerischer Apotheker-Verein (2000). Index Nominum 2000: International Drug Directory. Index nominum. Medpharm Scientific Publishers. p. 655. ISBN 978-3-88763-075-1. Retrieved 16 September 2024.
  4. ^ Froestl W, Pfeifer A, Muhs A (2013). "Cognitive enhancers (nootropics). Part 3: drugs interacting with targets other than receptors or enzymes. disease-modifying drugs" (PDF). J Alzheimers Dis. 34 (1): 1–114. doi:10.3233/JAD-121729. PMID 23186990. MLR-1017 (mesocarb, sydnocarb, sidnocarb, Melior Pharmaceuticals, Exton, PA) (Fig. 4) is a dopamine transporter inhibitor for the potential treatment of ADHD and levodopa-induced side effects in PD. The drug was previously launched in Russia [271, 272] (Thomson Reuters Pharma, update of April 12, 2012).
  5. ^ Macolino-Kane CM, Ciallella JR, Lipinski CA, Reaume AG (14 July 2017). "Phenotypic Screening". Drug Repositioning (PDF). Frontiers in Neurotherapeutics. Boca Raton: CRC Press. p. 121–145. doi:10.4324/9781315373669-7. ISBN 978-1-315-37366-9.
  6. ^ "Melior Discovery Announces Spinout of Melior Pharmaceuticals II, LLC". 10 May 2016.
  7. ^ a b "MLR-1017 - Melior Pharmaceuticals". AdisInsight. 28 February 2023. Retrieved 16 September 2024.
  8. ^ a b c Cite error: The named reference NepalDasReith2023 was invoked but never defined (see the help page).
  9. ^ a b c Cite error: The named reference NguyenChengLee2024 was invoked but never defined (see the help page).
  10. ^ a b c Cite error: The named reference AggarwalChengSalvino2021 was invoked but never defined (see the help page).
  11. ^ a b Cite error: The named reference ErdöKissRosdy1981 was invoked but never defined (see the help page).
  12. ^ "Mesocarb". PubChem. Retrieved 16 September 2024.
  13. ^ Cite error: The named reference AnokhinaZabrodinSvirinovskiĭ1974 was invoked but never defined (see the help page).
  14. ^ Cite error: The named reference PolgárVereczkeyCzira1978 was invoked but never defined (see the help page).
  15. ^ Adhera Therapeutics (7 June 2021). "Adhera Therapeutics Signs Letter of Intent with Melior Pharmaceuticals II to Acquire a New Class of Drug for Parkinson's Disease". GlobeNewswire News Room. Retrieved 25 September 2024. Armesocarb is the active pharmaceutical ingredient (API) of the racemic mixture mesocarb, a highly selective dopamine reuptake inhibitor first approved in the former Soviet Union in 1971 and marketed for select psychiatric and central nervous system (CNS) indications until 2008. At that time, which coincided with the Great Recession, the Russian manufacturer discontinued operations for business reasons unrelated to the compound itself.
  16. ^ Cite error: The named reference AdisInsight-Armesocarb was invoked but never defined (see the help page).
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