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Dexanabinol

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Dexanabinol
Clinical data
ATC code
  • none
Identifiers
  • (6aS,10aS)-9-(Hydroxymethyl)-6,6-dimethyl-3-(2-methyloctan-2-yl)-6a,7,10,10a-tetrahydrobenzo[c]chromen-1-ol
CAS Number
PubChemCID
DrugBank
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.201.022Edit this at Wikidata
Chemical and physical data
FormulaC25H38O3
Molar mass386.576 g·mol−1
3D model (JSmol)
  • Oc2cc(cc1OC([C@H]3C/C=C(\C[C@@H]3c12)CO)(C)C)C(C)(C)CCCCCC
  • InChI=1S/C25H38O3/c1-6-7-8-9-12-24(2,3)18-14-21(27)23-19-13-17(16-26)10-11-20(19)25(4,5)28-22(23)15-18/h10,14-15,19-20,26-27H,6-9,11-13,16H2,1-5H3/t19-,20-/m0/s1 ☒N
  • Key:SSQJFGMEZBFMNV-PMACEKPBSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Dexanabinol (HU-211 orETS2101[1]) is asynthetic cannabinoid derivative in development by e-Therapeutics plc. It is the "unnatural"enantiomer of the potent cannabinoid agonistHU-210.[2] Unlike othercannabinoid derivatives, HU-211 does not act as acannabinoid receptor agonist, but instead as anNMDA antagonist.[3] It therefore does not produce cannabis-like effects, but isanticonvulsant andneuroprotective, 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 inclinical trials[7] and is currently undergoingPhase I trials for the treatment ofbrain cancer[8] and advanced solid tumors.[9]

Clinical trials

[edit]

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

[edit]

HU-211 is not listed in the schedules set out by theUnited Nations'Single Convention on Narcotic Drugs from 1961 nor theirConvention on Psychotropic Substances from 1971,[13] so the signatory countries to these international drug control treaties are not required by said treaties to control HU-211.

United States

[edit]

HU-211 is not listed in thelist of scheduled controlled substances in the USA.[14] It is therefore notscheduled at thefederal level in theUnited States, but it is possible that HU-211 could legally be considered ananalog of Delta-8-THC (one of the THC isomers which is in Schedule I under the designation of "Tetrahydrocannabinols"), and therefore sales orpossession could potentially be prosecuted under theFederal Analogue Act.[15]

HU-211 is a Schedule I controlled substance inAlabama.[16]

HU-211 is a Schedule Icontrolled substance in the state ofFlorida making it illegal to buy, sell, or possess in Florida.[17]

Effective January 1, 2016, HU-211 is a regulated drug in Vermont designated as a "Hallucinogenic Drug."[18]

See also

[edit]

References

[edit]
  1. ^"e-therapeutics Clinical Development Pipeline". Archived fromthe original on 2013-01-26. Retrieved2012-10-23.
  2. ^Pop E (September 2000). "Nonpsychotropic synthetic cannabinoids".Current Pharmaceutical Design.6 (13):1347–60.doi:10.2174/1381612003399446.PMID 10903397.
  3. ^Feigenbaum JJ, Bergmann F, Richmond SA, Mechoulam R, Nadler V, Kloog Y, Sokolovsky M (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.Bibcode:1989PNAS...86.9584F.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.doi:10.1080/01616412.1995.11740326.PMID 7477742.
  5. ^Darlington CL (October 2003). "Dexanabinol: a novel cannabinoid with neuroprotective properties".IDrugs.6 (10):976–9.PMID 14534855.
  6. ^Vink R, Nimmo AJ (January 2009)."Multifunctional drugs for head injury".Neurotherapeutics.6 (1):28–42.doi:10.1016/j.nurt.2008.10.036.PMC 5084254.PMID 19110197.
  7. ^Maas AI, Murray G, Henney H, Kassem N, Legrand V, Mangelus M, et al. (January 2006). "Efficacy and safety of dexanabinol in severe traumatic brain injury: results of a phase III randomised, placebo-controlled, clinical trial".The Lancet. Neurology.5 (1):38–45.doi:10.1016/S1474-4422(05)70253-2.PMID 16361021.S2CID 28268833.
  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. Archived fromthe original(PDF) on 5 February 2015.
  11. ^"Clinical Development Pipeline". Archived fromthe original on February 5, 2015. RetrievedFeb 5, 2015.
  12. ^"A Study of Dexanabinol in Combination With Chemotherapy in Patients With Advanced Tumours - Full Text View - ClinicalTrials.gov".clinicaltrials.gov. Retrieved2015-09-18.
  13. ^"UN International Drug Control Conventions". Archived fromthe original on 2014-03-17. Retrieved2016-08-07.
  14. ^"§1308.11 Schedule I." Archived fromthe original on 2009-08-27. Retrieved2014-12-17.
  15. ^Erowid Analog Law Vault : Federal Controlled Substance Analogue Act Summary
  16. ^"Alabama Senate Bill 333 - Controlled substances, Schedule I, additional synthetic controlled substances and analogue substances included in, trafficking in controlled substance analogues, requisite weight increased, Secs. 13A-12-231, 20-2-23 am'd". March 2014. Retrieved2 February 2017.
  17. ^Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL
  18. ^Vermont DOH - Regulated Drug Rule 2016 .PDF
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