Etrinabdione: Difference between revisions

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Created page with '{{Drugbox | IUPAC_name = 5-(benzylamino)-4-hydroxy-3-[(1R,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]-6-pentylcyclohexa-3,5-diene-1,2-dione | image = Etrinabdione_structure.png | CAS_number = 1818428-24-8 | ATC_prefix = | ATC_suffix = | PubChem = 118465221 | DrugBank = | ChemSpiderID = | C=28 | H=35 | N=1 | O=3 | smiles = CCCCCC1=C(C(=C(C(=O)C1=O)[C@@H]2C=C(CC[C@H]2C(=C)C)C)O)N...'
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Revision as of 02:35, 19 July 2023

Etrinabdione
Identifiers
  • 5-(benzylamino)-4-hydroxy-3-[(1R,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]-6-pentylcyclohexa-3,5-diene-1,2-dione
CAS Number
PubChem CID
Chemical and physical data
FormulaC28H35NO3
Molar mass433.592 g·mol−1
3D model (JSmol)
  • CCCCCC1=C(C(=C(C(=O)C1=O)[C@@H]2C=C(CC[C@H]2C(=C)C)C)O)NCC3=CC=CC=C3
  • InChI=1S/C28H35NO3/c1-5-6-8-13-22-25(29-17-20-11-9-7-10-12-20)27(31)24(28(32)26(22)30)23-16-19(4)14-15-21(23)18(2)3/h7,9-12,16,21,23,29,31H,2,5-6,8,13-15,17H2,1,3-4H3/t21-,23+/m0/s1
  • Key:CGGGAXJIRQSRPH-JTHBVZDNSA-N

Etrinabdione (VCE-​004.8, EHP-101) is a drug derived from cannabidiol which has potent antiinflammatory and neuroprotective effects. It acts as a dual agonist of CB2 and PPARγ and is in clinical trials for the treatment of scleroderma.[1][2][3][4][5][6][7][8][9]

See also

References

  1. ^ Navarrete C, Carrillo-Salinas F, Palomares B, Mecha M, Jiménez-Jiménez C, Mestre L, Feliú A, Bellido ML, Fiebich BL, Appendino G, Calzado MA, Guaza C, Muñoz E. Hypoxia mimetic activity of VCE-004.8, a cannabidiol quinone derivative: implications for multiple sclerosis therapy. J Neuroinflammation. 2018 Mar 1;15(1):64. doi:10.1186/s12974-018-1103-y PMID 29495967
  2. ^ García-Martín A, Garrido-Rodríguez M, Navarrete C, Del Río C, Bellido ML, Appendino G, Calzado MA, Muñoz E. EHP-101, an oral formulation of the cannabidiol aminoquinone VCE-004.8, alleviates bleomycin-induced skin and lung fibrosis. Biochem Pharmacol. 2018 Nov;157:304-313. doi:10.1016/j.bcp.2018.07.047 PMID 30076848
  3. ^ Palomares B, Ruiz-Pino F, Navarrete C, Velasco I, Sánchez-Garrido MA, Jimenez-Jimenez C, Pavicic C, Vazquez MJ, Appendino G, Bellido ML, Calzado MA, Tena-Sempere M, Muñoz E. VCE-004.8, A Multitarget Cannabinoquinone, Attenuates Adipogenesis and Prevents Diet-Induced Obesity. Sci Rep. 2018 Oct 31;8(1):16092. doi:10.1038/s41598-018-34259-0 PMID 30382123
  4. ^ García-Martín A, Garrido-Rodríguez M, Navarrete C, Caprioglio D, Palomares B, DeMesa J, Rollland A, Appendino G, Muñoz E. Cannabinoid derivatives acting as dual PPARγ/CB2 agonists as therapeutic agents for systemic sclerosis. Biochem Pharmacol. 2019 May;163:321-334. doi:10.1016/j.bcp.2019.02.029 PMID 30825431
  5. ^ Navarrete C, García-Martin A, Garrido-Rodríguez M, Mestre L, Feliú A, Guaza C, Calzado MA, Muñoz E. Effects of EHP-101 on inflammation and remyelination in murine models of Multiple sclerosis. Neurobiol Dis. 2020 Sep;143:104994. doi:10.1016/j.nbd.2020.104994 PMID 32599064
  6. ^ Burgaz S, García C, Gómez-Cañas M, Rolland A, Muñoz E, Fernández-Ruiz J. Neuroprotection with the Cannabidiol Quinone Derivative VCE-004.8 (EHP-101) against 6-Hydroxydopamine in Cell and Murine Models of Parkinson's Disease. Molecules. 2021 May 28;26(11):3245. doi:10.3390/molecules26113245 PMID 34071302
  7. ^ Caprioglio D, Mattoteia D, Taglialatela-Scafati O, Muñoz E, Appendino G. Cannabinoquinones: Synthesis and Biological Profile. Biomolecules. 2021 Jul 5;11(7):991. doi:10.3390/biom11070991 PMID 34356614
  8. ^ Navarrete C, García-Martín A, Correa-Sáez A, Prados ME, Fernández F, Pineda R, Mazzone M, Álvarez-Benito M, Calzado MA, Muñoz E. A cannabidiol aminoquinone derivative activates the PP2A/B55α/HIF pathway and shows protective effects in a murine model of traumatic brain injury. J Neuroinflammation. 2022 Jul 9;19(1):177. doi:10.1186/s12974-022-02540-9 PMID 35810304
  9. ^ Lavayen BP, Yang C, Larochelle J, Liu L, Tishko RJ, de Oliveira ACP, Muñoz E, Candelario-Jalil E. Neuroprotection by the cannabidiol aminoquinone VCE-004.8 in experimental ischemic stroke in mice. Neurochem Int. 2023 May;165:105508. doi:10.1016/j.neuint.2023.105508 PMID 36863495