Dexanabinol

Dexanabinol
Systematic (IUPAC) name
(6aS,10aS)-9-(Hydroxymethyl)- 6,6-dimethyl- 3-(2-methyloctan-2-yl)- 6a,7,10,10a-tetrahydrobenzo [c]chromen-1-ol
Identifiers
CAS Number 112924-45-5 YesY
ATC code none
PubChem CID 107778
ChemSpider 96934 N
UNII R6VT8U5372 YesY
Chemical data
Formula C25H38O3
Molar mass 386.567 g/mol
 NYesY (what is this?)  (verify)

Dexanabinol (HU-211 or ETS2101[1]) is a synthetic cannabinoid derivative in development by e-Therapeutics plc. It is the "unnatural" enantiomer of the potent cannabinoid agonist HU-210.[2] Unlike other cannabinoid derivatives, HU-211 does not act as a cannabinoid receptor agonist, but instead has NMDA antagonist effects.[3] It therefore does not produce cannabis-like effects, but is anticonvulsant and neuroprotective, and is widely used in scientific research as well as currently being studied for applications such as treating head injury, stroke, or cancer.[4][5][6] It was shown to be safe in clinical trials[7] and is currently undergoing Phase I trials for the treatment of brain cancer[8] and advanced solid tumors.[9]

Clinical Trials

Dexanabinol has been studied in IV administration and oral dosing.[10] e-Therapeutics is evaluating the compound in clinical trials for brain and solid cancers.[11] Phase II studies are planned based on the results of the current trials.

A phase 1b study for hepatocellular carcinoma and pancreatic cancer was started in 2015.[12]

Legal status

United States

HU-211 is not scheduled at the federal level in the United States.[13]

Florida

"HU-211 ((6aS,10aS)-9-(Hydroxymethyl)-6,6-dimethyl-3-(2-methyloctan-2-yl)-6a,7,10,10a-tetrahydrobenzo[c]chromen-1-ol)" is a Schedule I controlled substance in the state of Florida making it illegal to buy, sell, or possess in Florida.[14]

References

  1. ↑ e-therapeutics Clinical Development Pipeline
  2. ↑ Pop E (September 2000). "Nonpsychotropic synthetic cannabinoids". Current Pharmaceutical Design 6 (13): 1347–60. doi:10.2174/1381612003399446. PMID 10903397.
  3. ↑ Feigenbaum JJ; et al. (December 1989). "Nonpsychotropic cannabinoid acts as a functional N-methyl-D-aspartate receptor blocker". Proceedings of the National Academy of Sciences of the United States of America 86 (23): 9584–7. doi:10.1073/pnas.86.23.9584. PMC 298542. PMID 2556719.
  4. ↑ Biegon A; Joseph AB (August 1995). "Development of HU-211 as a neuroprotectant for ischemic brain damage". Neurological Research 17 (4): 275–80. PMID 7477742.
  5. ↑ Darlington CL (October 2003). "Dexanabinol: a novel cannabinoid with neuroprotective properties". IDrugs : the Investigational Drugs Journal 6 (10): 976–9. PMID 14534855.
  6. ↑ Vink R; Nimmo AJ (January 2009). "Multifunctional drugs for head injury". Neurotherapeutics : the Journal of the American Society for Experimental NeuroTherapeutics 6 (1): 28–42. doi:10.1016/j.nurt.2008.10.036. PMID 19110197.
  7. ↑ Maas AI; et al. (January 2006). "Efficacy and safety of dexanabinol in severe traumatic brain injury: results of a phase III randomised, placebo-controlled, clinical trial". Lancet Neurol 5 (1): 38–45. doi:10.1016/S1474-4422(05)70253-2. PMID 16361021.
  8. ↑ University of California, San Diego "Synthetic Cannabinoid May Be Used as Brain Cancer Treatment". (28 September 2012) Laboratory Equipment. Retrieved 28 September 2012.
  9. ↑ "A Phase 1 Study of Dexanabinol in Patients With Advanced Solid Tumours". ClinicalTrials.gov. NIH. January 26, 2015.
  10. ↑ "e-Therapeutics Reports Progress in ETS2101 Phase 1a and Oral Dosing Studies" (PDF). 18 December 2014.
  11. ↑ "Clinical Development Pipeline". Retrieved Feb 5, 2015.
  12. ↑ "A Study of Dexanabinol in Combination With Chemotherapy in Patients With Advanced Tumours - Full Text View - ClinicalTrials.gov". clinicaltrials.gov. Retrieved 2015-09-18.
  13. ↑ 21 CFR — SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I.
  14. ↑ Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL


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