Dopamantine

Not to be confused with Dopamine or N-Arachidonoyl dopamine.

Dopamantine
Clinical data
Other namesSCH-15507; Sch 15507; N-Adamantanoyl dopamine; NSC-172619
Identifiers
  • N-[2-(3,4-dihydroxyphenyl)ethyl]adamantane-1-carboxamide
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.049.707 Edit this at Wikidata
Chemical and physical data
FormulaC19H25NO3
Molar mass315.413 g·mol−1
3D model (JSmol)
  • C1C2CC3CC1CC(C2)(C3)C(=O)NCCC4=CC(=C(C=C4)O)O
  • InChI=1S/C19H25NO3/c21-16-2-1-12(8-17(16)22)3-4-20-18(23)19-9-13-5-14(10-19)7-15(6-13)11-19/h1-2,8,13-15,21-22H,3-7,9-11H2,(H,20,23)
  • Key:ZWKFENYDXISLGK-UHFFFAOYSA-N

Dopamantine (INNTooltip International Nonproprietary Name, USANTooltip United States Adopted Name; developmental code name SCH-15507; also known as N-adamantanoyl dopamine) is an antiparkinsonian drug of the adamantane group that developed for treatment of Parkinson's disease but was never marketed.[1][2][3][4][5][6] It was developed and studied in the 1970s and was said to have reached early clinical trials.[1][6][4]

Dopamantine combines elements of the chemical structures of clinically used adamantane antiparkinsonian agents like amantadine and dopamine or levodopa (L-DOPA) into a single molecule.[3][4] It is said to have been designed to help dopamine cross the blood–brain barrier via the lipophilic adamantane moiety.[5] The drug is said to share pharmacological effects with amantadine.[4] Another related compound is carmantadine, which is also an adamantane antiparkinsonian agent that was never marketed.[4][6]

References

  1. ^ a b Elks J (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 466. ISBN 978-1-4757-2085-3. Retrieved 13 August 2024.
  2. ^ Kovtun VY, Plakhotnik VM (1987). "Use of adamantanecarboxylic acid for the modification of drugs and biologically active compounds (review)". Pharmaceutical Chemistry Journal. 21 (8): 555–563. doi:10.1007/BF00759430. ISSN 0091-150X.
  3. ^ a b Kovalev IE (1977). "Biological activity of adamantane-containing substances". Pharmaceutical Chemistry Journal. 11 (3): 310–317. doi:10.1007/BF00781088. ISSN 0091-150X. Sometimes a combination of L-DOPA and amantadine is used [39]. Moreover, an original preparation has been created - 1-N-(3,4-dihydroxyphenetyl)-1-adamantanecarboxamide, with the brand name dopamantine (V) -- the structure of which combines both these agents [40]. The mechanism of the action of amantadine in parkinsonism is unclear. Some authors attempt to relate the antiparkinson effect to an influence on the metabolism of brain catecholamines [41].
  4. ^ a b c d e Vernier VG, du Pont EI (1974). "Chapter 3. Antiparkinsonism Drugs". Annual Reports in Medicinal Chemistry. Vol. 9. Elsevier. pp. 19–26. doi:10.1016/s0065-7743(08)61424-4. ISBN 978-0-12-040509-1. Carmantadine (VII, Sch 15427) is structurally related to amantadine33. It shares some of its pharmacological actions, was effective in a head-turning test34, and is in early clinical trials. Dopamantine (VIII) combined elements of both amantadine and dopamine in its structure, shares some pharmacological effects of amantadine and is in early clinical trials35.
  5. ^ a b Lamoureux G, Artavia G (2010). "Use of the adamantane structure in medicinal chemistry". Current Medicinal Chemistry. 17 (26): 2967–2978. doi:10.2174/092986710792065027. PMID 20858176. Dopamantine 4, the anti-Parkinson drug which has passed clinical trials, is also based on the ability of adamantane to change the distribution of a drug [10]. The conjugation of an adamantyl group as a "lipophilic carrier" allows poorly absorbed drugs to penetrate the BBB more readily and increase the concentration in the brain tissue.
  6. ^ a b c Barnett A, Goldstein J, Taber R, Fiedler E (January 1974). "Pharmacology of Dopamantine and Carmantadine, 2 Potential Antiparkinson Agents". Pharmacologist. 16 (2): 205–.