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{{DISPLAYTITLE:''scyllo''-Inositol}}
{{DISPLAYTITLE:''scyllo''-Inositol}}
{{Chembox
{{Chembox
| Verifiedfields = changed
| verifiedrevid = 428259682
| Watchedfields = changed
| verifiedrevid = 439020881
| ImageFile = Scyllo-inositol.svg
| ImageFile = Scyllo-inositol.svg
| ImageSize = 200px
| ImageSize =
| Name = ''scyllo''-Inositol
| Name = ''scyllo''-Inositol
| IUPACName = ''scyllo''-Inositol<ref>{{cite book |author=[[International Union of Pure and Applied Chemistry]] |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=[[Royal Society of Chemistry|The Royal Society of Chemistry]] |pages=1415 |doi=10.1039/9781849733069 |isbn=978-0-85404-182-4}}</ref>
| IUPACName = (1''R'',2''R'',3''R'',4''R'',5''R'',6''R'')-Cyclohexane-1,2,3,4,5,6-hexaol
| SystematicName = (1''r'',2''r'',3''r'',4''r'',5''r'',6''r'')-Cyclohexane-1,2,3,4,5,6-hexol
| OtherNames = Scyllitol; Cocositol; Quercinitol; AZD 103; 1,3,5/2,4,6-Hexahydroxycyclohexane; ''scyllo''-Cyclohexanehexol
| OtherNames = Scyllitol; Cocositol; Quercinitol; AZD 103; 1,3,5/2,4,6-Hexahydroxycyclohexane; ''scyllo''-Cyclohexanehexol
| Section1 = {{Chembox Identifiers
|Section1={{Chembox Identifiers
| IUPHAR_ligand = 4649
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 488-59-5
| CASNo = 488-59-5
| EINECS = 610-437-4
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 1VS4X81277
| PubChem =
| PubChem =
| SMILES = O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O
| SMILES = O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 10254646
| InChI = 1/C6H12O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-12H/t1-,2-,3+,4+,5-,6-
| InChIKey = CDAISMWEOUEBRE-CDRYSYESBJ
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C6H12O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-12H/t1-,2-,3+,4+,5-,6-
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = CDAISMWEOUEBRE-CDRYSYESSA-N
}}
}}
| Section2 = {{Chembox Properties
|Section2={{Chembox Properties
| C=6|H=12|O=6
| C=6 | H=12 | O=6
| Appearance = White crystalline solid
| Appearance = White crystalline solid
| Density =
| Density =
| MeltingPt = 348.5-350 °C
| MeltingPtC = 348.5 to 350
| MeltingPt_notes =
| BoilingPt =
| BoilingPt =
| Solubility = }}
| Solubility = }}
| Section3 = {{Chembox Hazards
|Section3={{Chembox Hazards
| MainHazards =
| MainHazards =
| FlashPt =
| FlashPt =
| Autoignition = }}
| AutoignitionPt =
}}
}}
}}


'''''scyllo''-Inositol''' is one of the [[stereoisomer]]s 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]].<ref>[http://www.ars-grin.gov/cgi-bin/duke/chemical.pl?SCYLLITOL Scyllitol], Dr. Duke's Phytochemical and Ethnobotanical Databases</ref>
'''''scyllo''-Inositol''' is one of the [[stereoisomer]]s 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 [[coconut palm]].<ref>[http://www.ars-grin.gov/cgi-bin/duke/chemical.pl?SCYLLITOL Scyllitol], Dr. Duke's Phytochemical and Ethnobotanical Databases</ref>


== Biological effects ==
== 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.<ref>[http://www.alzforum.org/new/detail.asp?id=1414 Aβ Busters and Other Ploys Show Promise for Treating Neurodegeneration]</ref> ''scyllo''-Inositol also reversed memory deficits, reduced the formation of Aβ [[Senile plaques|plaques]], and alleviated other symptoms that are associated with the accumulation of Aβ proteins in these mice.<ref>{{cite journal | pmid = 16767098 | doi=10.1038/nm1423 | volume=12 | issue=7 | title=Cyclohexanehexol inhibitors of Abeta aggregation prevent and reverse Alzheimer phenotype in a mouse model | year=2006 | month=July | pages=801–8}}</ref>
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]].<ref>[http://www.alzforum.org/new/detail.asp?id=1414 Aβ Busters and Other Ploys Show Promise for Treating Neurodegeneration]</ref> ''scyllo''-Inositol also reversed [[Memory deficit|memory deficits]], and alleviated other symptoms associated with the accumulation of Aβ proteins in these mice.<ref>{{cite journal | pmid = 16767098 | doi=10.1038/nm1423 | volume=12 | issue=7 | title=Cyclohexanehexol inhibitors of Abeta aggregation prevent and reverse Alzheimer phenotype in a mouse model |date=July 2006 | pages=801–8| last1=McLaurin | first1=Joanne | last2=Kierstead | first2=Meredith E. | last3=Brown | first3=Mary E. | last4=Hawkes | first4=Cheryl A. | last5=Lambermon | first5=Mark H L. | last6=Phinney | first6=Amie L. | last7=Darabie | first7=Audrey A. | last8=Cousins | first8=Julian E. | last9=French | first9=Janet E. | last10=Lan | first10=Melissa F. | last11=Chen | first11=Fusheng | last12=Wong | first12=Sydney S N. | last13=Mount | first13=Howard T J. | last14=Fraser | first14=Paul E. | last15=Westaway | first15=David | last16=George-Hyslop | first16=Peter St | journal=Nature Medicine | s2cid=24478093 }}</ref>

Researchers at the [[Harvard Medical School]]-affiliated [[McLean Hospital]] found that chronic users of [[Anabolic steroid|anabolic steroids]] had lower levels of brain ''scyllo''-Inositol levels than non-users.<ref>{{Cite journal |last=Kaufman |first=Marc J. |last2=Janes |first2=Amy C. |last3=Hudson |first3=James I. |last4=Brennan |first4=Brian P. |last5=Kanayama |first5=Gen |last6=Kerrigan |first6=Andrew R. |last7=Jensen |first7=J. Eric |last8=Pope |first8=Harrison G. |date=2015-07-01 |title=Brain and cognition abnormalities in long-term anabolic-androgenic steroid users |url=https://pubmed.ncbi.nlm.nih.gov/25986964/ |journal=Drug and Alcohol Dependence |volume=152 |pages=47–56 |doi=10.1016/j.drugalcdep.2015.04.023 |issn=1879-0046 |pmc=4458166 |pmid=25986964}}</ref>


== Clinical evaluation ==
== Clinical evaluation ==
{{Out of date|date=June 2024|reason=The result of the 2009 clinical trial is not reported}}
''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 (US patent number 7,521,481) claiming the use of ''scyllo''-inositol for treating Alzheimer's disease.<ref>[http://newsroom.elan.com/phoenix.zhtml?c=88326&p=irol-newsArticle&ID=1279660&highlight=ELND005 Elan and Transition Therapeutics Receive Key Patent for Alzheimer's Disease Treatment with ELND005]</ref> ''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 [[FDA Fast Track Development Program|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.
''scyllo''-Inositol was investigated 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 ({{US patent|7521481}}) claiming the use of ''scyllo''-inositol for treating Alzheimer's disease.<ref>[http://newsroom.elan.com/phoenix.zhtml?c=88326&p=irol-newsArticle&ID=1279660&highlight=ELND005 Elan and Transition Therapeutics Receive Key Patent for Alzheimer's Disease Treatment with ELND005] {{webarchive|url=https://archive.today/20130122001730/http://newsroom.elan.com/phoenix.zhtml?c=88326&p=irol-newsArticle&ID=1279660&highlight=ELND005 |date=2013-01-22 }}</ref> ''scyllo''-Inositol underwent clinical investigation as an orally-administered therapeutic agent for the treatment of mild to moderate Alzheimer's disease. It had received [[FDA Fast Track Development Program|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 was in a [[Phases of clinical research|Phase 2 clinical study]], which completed enrollment in October 2008. The study was a randomized, double-blind, placebo-controlled, dose-ranging, safety and efficacy study in approximately 353 patients with mild to moderate [[Alzheimer's disease|Alzheimer's]] disease. The planned treatment period for each patient was 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).<ref>[http://finance.yahoo.com/news/Elan-and-Transition-bw-2610034367.html?x=0&.v=1 Elan and Transition Therapeutics Announce Modifications to ELND005 Phase II Clinical Trials in Alzheimer's Disease]</ref>
In December 2009, Elan and Transition jointly reported that the study has been modified so that only the 250&nbsp;mg twice daily dose will be continued because of greater rates of adverse events, including 9 deaths, in the higher dose groups (1000&nbsp;mg and 2000&nbsp;mg dosed twice daily).<ref>[https://finance.yahoo.com/news/Elan-and-Transition-bw-2610034367.html?x=0&.v=1 Elan and Transition Therapeutics Announce Modifications to ELND005 Phase II Clinical Trials in Alzheimer's Disease]</ref> 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.<ref>{{cite book | vauthors=Ma K, Thomason LA, McLaurin J | title=''scyllo''-Inositol, preclinical, and clinical data for Alzheimer's disease | chapter=Scyllo-Inositol, Preclinical, and Clinical Data for Alzheimer's Disease | series=Advances in Pharmacology | volume=64 | year=2012 | pages=177–212 | doi = 10.1016/B978-0-12-394816-8.00006-4 | pmid=22840748| isbn=9780123948168 }}</ref>


== External Links ==
==See also==
*[[allo-Inositol|''allo''-Inositol]]
[http://www.alzforum.org/drg/drc/detail.asp?id=130 Drugs In Clinical Trials - ELND005]
*[[cis-Inositol|''cis''-Inositol]]
*[[D-chiro-Inositol|<small>D</small>-''chiro''-Inositol]]
*[[epi-Inositol|''epi''-Inositol]]
*[[L-chiro-Inositol|<small>L</small>-''chiro''-Inositol]]
*[[muco-Inositol|''muco''-Inositol]]
*[[neo-Inositol|''neo''-Inositol]]


==References==
==References==
{{reflist}}
{{reflist}}

==External links==
* [http://www.alzforum.org/drg/drc/detail.asp?id=130 Drugs In Clinical Trials - ELND005] [https://web.archive.org/web/20231226004006/https://www.alzforum.org/therapeutics/elnd005?id=130 archived] 25-12-2023


{{DEFAULTSORT:Inositol, scyllo-}}
{{DEFAULTSORT:Inositol, scyllo-}}
[[Category:inositol]]
[[Category:Inositol]]