scyllo-Inositol

scyllo-Inositol is one of the stereoisomers of inositol. It is also known as scyllitol, cocositol, quercinitol, and 1,3,5/2,4,6-hexahydroxycyclohexane. scyllo-Inositol is a naturally occurring plant sugar alcohol found most abundantly in the coconut palm.[2]

scyllo-Inositol
Names
IUPAC name
scyllo-Inositol[1]
Systematic IUPAC name
(1r,2r,3r,4r,5r,6r)-Cyclohexane-1,2,3,4,5,6-hexol
Other names
Scyllitol; Cocositol; Quercinitol; AZD 103; 1,3,5/2,4,6-Hexahydroxycyclohexane; scyllo-Cyclohexanehexol
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.113.358
EC Number
  • 610-437-4
UNII
  • InChI=1S/C6H12O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-12H/t1-,2-,3+,4+,5-,6- ☒N
    Key: CDAISMWEOUEBRE-CDRYSYESSA-N ☒N
  • InChI=1/C6H12O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-12H/t1-,2-,3+,4+,5-,6-
    Key: CDAISMWEOUEBRE-CDRYSYESBJ
  • O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O
Properties
C6H12O6
Molar mass 180.156 g·mol−1
Appearance White crystalline solid
Melting point 348.5 to 350 °C (659.3 to 662.0 °F; 621.6 to 623.1 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Biological effects

Researchers at the University of Toronto have found that scyllo-inositol can block the development of amyloid-beta (Aβ) plaques in the brains of transgenic mice.[3] scyllo-Inositol also reversed memory deficits, reduced the formation of Aβ plaques, and alleviated other symptoms that are associated with the accumulation of Aβ proteins in these mice.[4]

Researchers at the Harvard Medical School-affiliated McLean Hospital identified that chronic users of anabolic steroids had statistically significantly lower levels of brain scyllo-inositol levels as compared to non-users.[5]

Clinical evaluation

scyllo-Inositol is under investigation by Transition Therapeutics as a disease-modifying therapy for Alzheimer's disease under the designation AZD-103. A patent was issued on April 21, 2009 (U.S. Patent 7,521,481) claiming the use of scyllo-inositol for treating Alzheimer's disease.[6] scyllo-Inositol is undergoing clinical investigation as an orally-administered therapeutic agent for the treatment of mild to moderate Alzheimer's disease. It has received fast track designation from the U.S. Food and Drug Administration. Transition has partnered with Elan Corporation on the development of the compound under the designation ELND005. ELND005 is currently in a Phase 2 clinical study, which completed enrollment in October 2008. The study is a randomized, double-blind, placebo-controlled, dose-ranging, safety and efficacy study in approximately 353 patients with mild to moderate Alzheimer's disease. The planned treatment period for each patient is approximately 18 months.

In December 2009, Elan and Transition jointly reported that the study has been modified so that only the 250 mg twice daily dose will be continued because of greater rates of adverse events, including 9 deaths, in the higher dose groups (1000 mg and 2000 mg dosed twice daily).[7] Although the clinical trial helped establish the safety profile, the removal of the higher dose groups reduced the power of the study to establish efficacy.[8]

See also

References
  1. International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 1415. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
  2. Scyllitol, Dr. Duke's Phytochemical and Ethnobotanical Databases
  3. Aβ Busters and Other Ploys Show Promise for Treating Neurodegeneration
  4. McLaurin, Joanne; Kierstead, Meredith E.; Brown, Mary E.; Hawkes, Cheryl A.; Lambermon, Mark H L.; Phinney, Amie L.; Darabie, Audrey A.; Cousins, Julian E.; French, Janet E.; Lan, Melissa F.; Chen, Fusheng; Wong, Sydney S N.; Mount, Howard T J.; Fraser, Paul E.; Westaway, David; George-Hyslop, Peter St (July 2006). "Cyclohexanehexol inhibitors of Abeta aggregation prevent and reverse Alzheimer phenotype in a mouse model". Nature Medicine. 12 (7): 801–8. doi:10.1038/nm1423. PMID 16767098. S2CID 24478093.
  5. "Brain Imaging Study Suggests Long-Term Steroid Use Can Lead to Significant Brain Structural and Functional Abnormalities | McLean Hospital". www.mcleanhospital.org. Retrieved 2019-09-20.
  6. Elan and Transition Therapeutics Receive Key Patent for Alzheimer's Disease Treatment with ELND005 Archived 2013-01-22 at archive.today
  7. Elan and Transition Therapeutics Announce Modifications to ELND005 Phase II Clinical Trials in Alzheimer's Disease
  8. Ma K, Thomason LA, McLaurin J (2012). "Scyllo-Inositol, Preclinical, and Clinical Data for Alzheimer's Disease". scyllo-Inositol, preclinical, and clinical data for Alzheimer's disease. Advances in Pharmacology. Vol. 64. pp. 177–212. doi:10.1016/B978-0-12-394816-8.00006-4. ISBN 9780123948168. PMID 22840748.
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