Etrinabdione
Chemical compound
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Chemical and physical data | |
Formula | C28H35NO3 |
Molar mass | 433.592 g·mol−1 |
3D model (JSmol) |
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Etrinabdione (VCE-004.8, EHP-101) is a drug structurally related to cannabidiol and HU-331 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
- HU-331
- HU-336
- HUF-101
References
- ^ Navarrete C, Carrillo-Salinas F, Palomares B, Mecha M, Jiménez-Jiménez C, Mestre L, et al. (March 2018). "Hypoxia mimetic activity of VCE-004.8, a cannabidiol quinone derivative: implications for multiple sclerosis therapy". Journal of Neuroinflammation. 15 (1): 64. doi:10.1186/s12974-018-1103-y. PMC 5831753. PMID 29495967.
- ^ García-Martín A, Garrido-Rodríguez M, Navarrete C, Del Río C, Bellido ML, Appendino G, et al. (November 2018). "EHP-101, an oral formulation of the cannabidiol aminoquinone VCE-004.8, alleviates bleomycin-induced skin and lung fibrosis". Biochemical Pharmacology. 157: 304–313. doi:10.1016/j.bcp.2018.07.047. PMID 30076848. S2CID 51921018.
- ^ Palomares B, Ruiz-Pino F, Navarrete C, Velasco I, Sánchez-Garrido MA, Jimenez-Jimenez C, et al. (October 2018). "VCE-004.8, A Multitarget Cannabinoquinone, Attenuates Adipogenesis and Prevents Diet-Induced Obesity". Scientific Reports. 8 (1): 16092. Bibcode:2018NatSR...816092P. doi:10.1038/s41598-018-34259-0. PMC 6208444. PMID 30382123.
- ^ García-Martín A, Garrido-Rodríguez M, Navarrete C, Caprioglio D, Palomares B, DeMesa J, et al. (May 2019). "Cannabinoid derivatives acting as dual PPARγ/CB2 agonists as therapeutic agents for systemic sclerosis". Biochemical Pharmacology. 163: 321–334. doi:10.1016/j.bcp.2019.02.029. PMID 30825431. S2CID 73492817.
- ^ Navarrete C, García-Martin A, Garrido-Rodríguez M, Mestre L, Feliú A, Guaza C, et al. (September 2020). "Effects of EHP-101 on inflammation and remyelination in murine models of Multiple sclerosis". Neurobiology of Disease. 143: 104994. doi:10.1016/j.nbd.2020.104994. hdl:10261/219645. PMID 32599064. S2CID 220075831.
- ^ Burgaz S, García C, Gómez-Cañas M, Rolland A, Muñoz E, Fernández-Ruiz J (May 2021). "Neuroprotection with the Cannabidiol Quinone Derivative VCE-004.8 (EHP-101) against 6-Hydroxydopamine in Cell and Murine Models of Parkinson's Disease". Molecules. 26 (11): 3245. doi:10.3390/molecules26113245. PMC 8198479. PMID 34071302.
- ^ Caprioglio D, Mattoteia D, Taglialatela-Scafati O, Muñoz E, Appendino G (July 2021). "Cannabinoquinones: Synthesis and Biological Profile". Biomolecules. 11 (7): 991. doi:10.3390/biom11070991. PMC 8301883. PMID 34356614.
- ^ Navarrete C, García-Martín A, Correa-Sáez A, Prados ME, Fernández F, Pineda R, et al. (July 2022). "A cannabidiol aminoquinone derivative activates the PP2A/B55α/HIF pathway and shows protective effects in a murine model of traumatic brain injury". Journal of Neuroinflammation. 19 (1): 177. doi:10.1186/s12974-022-02540-9. PMC 9270745. PMID 35810304.
- ^ Lavayen BP, Yang C, Larochelle J, Liu L, Tishko RJ, de Oliveira AC, et al. (May 2023). "Neuroprotection by the cannabidiol aminoquinone VCE-004.8 in experimental ischemic stroke in mice". Neurochemistry International. 165: 105508. doi:10.1016/j.neuint.2023.105508. PMID 36863495. S2CID 257235882.
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Cannabinoids
(comparison)
Cannabibutols |
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Cannabichromenes | |
Cannabicyclols |
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Cannabidiols | |
Cannabielsoins |
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Cannabigerols | |
Cannabiphorols |
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Cannabinols | |
Cannabitriols |
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Cannabivarins |
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Delta-8-tetrahydrocannabinols |
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Delta-9-tetrahydrocannabinols | |
Delta-10-Tetrahydrocannabinols | |
Miscellaneous cannabinoids |
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Active metabolites |
- Arachidonoyl ethanolamide (AEA; anandamide)
- 2-Arachidonoylglycerol (2-AG)
- 2-Arachidonyl glyceryl ether (2-AGE; noladin ether)
- 2-Oleoylglycerol (2-OG)
- N-Arachidonoyl dopamine (NADA)
- N-Arachidonylglycine (NAGly)
- 2-Arachidonoyl lysophosphatidylinositol (2-ALPI)
- N-Arachidonoyl serotonin (AA-5-HT)
- Docosatetraenoylethanolamide (DEA)
- Lysophosphatidylinositol (LPI)
- Oleamide
- Oleoylethanolamide (OEA)
- Palmitoylethanolamide (PEA)
- RVD-Hpα
- Stearoylethanolamide (SEA)
- O-Arachidonoyl ethanolamine (O-AEA; virodhamine)
cannabinoid
receptor
agonists /
neocannabinoids
enhancers
(inactivation inhibitors)
- 4-Nonylphenylboronic acid
- AM-404
- Arachidonoyl serotonin
- Arvanil
- BIA 10-2474
- Biochanin A
- CAY-10401
- CAY-10429
- Genistein
- Guineesine
- IDFP
- JNJ 1661010
- JNJ-42165279
- JZL184
- JZL195
- Kaempferol
- LY-2183240
- MK-4409
- O-1624
- O-2093
- Oleoylethanolamide (OEA)
- Olvanil
- Palmitoylethanolamide (PEA)
- PF-04457845
- PF-622
- PF-750
- PF-3845
- PHOP
- URB-447
- URB-597
- URB-602
- URB-754
- VDM-11
(antagonists/inverse
agonists/antibodies)
- AM-251
- AM-281
- AM-630
- AM-1387
- AM-4113
- AM-6527
- AM-6545
- BML-190
- Brizantin (Бризантин)
- CAY-10508
- CB-25
- CB-52
- CB-86
- Dietressa (Диетресса)
- Drinabant (AVE1625)
- Hemopressin
- Ibipinabant (SLV319)
- JTE-907
- LH-21
- LY-320,135
- MDA-77
- MJ-15
- MK-9470
- NESS-0327
- NIDA-41020
- O-606
- O-1184
- O-1248
- O-1918
- O-2050
- O-2654
- Otenabant (CP-945,598)
- PF-514273
- PipISB
- PSB-SB-487
- Rimonabant (SR141716)
- Rosonabant (E-6776)
- SR-144,528
- Surinabant (SR147778)
- Taranabant (MK-0364)
- TM-38837
- VCHSR
- See also: Cannabinoid receptor modulators (cannabinoids by pharmacology)
- List of: AM cannabinoids
- JWH cannabinoids
- Designer drugs § Synthetic cannabimimetics
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