Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C6H12O6 |
| Molecular Weight | 180.1559 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 6 / 6 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O
InChI
InChIKey=CDAISMWEOUEBRE-CDRYSYESSA-N
InChI=1S/C6H12O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-12H/t1-,2-,3+,4+,5-,6-
Scyllo-inositol (ELND005) is an inositol isoform. Inositol is a derivative of cyclohexane with six hydroxyl groups, making it a polyol. It also is known as a sugar alcohol, having exactly the same molecular formula as glucose or other hexoses. Scyllo-inositol (ELND005) is a naturally occurring plant sugar alcohol found most abundantly in the coconut palm. It appears to accumulate in a number of human tissues and biofluids through dietary consumption. It has traditionally been considered to be a B vitamin although it has an uncertain status as a vitamin and a deficiency syndrome has not been identified in man. Although scyllo-inositol (ELND005) at pharmacologic doses may alter myo-inositol levels and indirectly affect phosphatidyl-inositol signaling, its main effects are thought to be binding and inhibition of beta-amyloid 42 peptide aggregation and formation of beta-amyloid fibrils. In transgenic animals, scyllo-inositol (ELND005) reduced brain beta-amyloid concentrations and plaque burden, preserved synaptic density, and improved learning deficits. Scyllo-inositol (ELND005) also appears to neutralize toxic effects of beta-amyloid oligomers, including amelioration of oligomer-induced synaptic loss, long-term potentiation inhibition, and memory deficits. Scyllo-inositol (ELND005) is an attractive candidate as a potential disease-modifying oral treatment for Alzheimer disease.
CNS Activity
Originator
Curator's Comment: In 1858 Staedeler and Frerichs reported the isolation of a substance from organs of the shark Scylluim canicula and the skates Raja batis and clavata which they named 'Scyllit' and described as having many similarities to the previously discovered myo-inositol. The compound was definitely related to myo-inositol by Muller in 1907 and has come to be known as scylloinositol (PMID 318234).
Approval Year
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
39.8 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27121673/ |
1000 mg 2 times / day multiple, oral dose: 1000 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
SCYLLO-INOSITOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
17.2 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27121673/ |
2000 mg single, oral dose: 2000 mg route of administration: Oral experiment type: SINGLE co-administered: |
SCYLLO-INOSITOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
|
6.5 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27121673/ |
2000 mg single, oral dose: 2000 mg route of administration: Oral experiment type: SINGLE co-administered: |
SCYLLO-INOSITOL cerebrospinal fluid | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
13.7 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27121673/ |
1000 mg 2 times / day multiple, oral dose: 1000 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
SCYLLO-INOSITOL cerebrospinal fluid | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
277 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27121673/ |
1000 mg 2 times / day multiple, oral dose: 1000 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
SCYLLO-INOSITOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
98.9 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27121673/ |
2000 mg single, oral dose: 2000 mg route of administration: Oral experiment type: SINGLE co-administered: |
SCYLLO-INOSITOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
|
49.4 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27121673/ |
2000 mg single, oral dose: 2000 mg route of administration: Oral experiment type: SINGLE co-administered: |
SCYLLO-INOSITOL cerebrospinal fluid | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
153 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27121673/ |
1000 mg 2 times / day multiple, oral dose: 1000 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
SCYLLO-INOSITOL cerebrospinal fluid | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
62.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27121673/ |
1000 mg 2 times / day multiple, oral dose: 1000 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
SCYLLO-INOSITOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
26.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27121673/ |
1000 mg 2 times / day multiple, oral dose: 1000 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
SCYLLO-INOSITOL cerebrospinal fluid | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Inositol phosphates from barley low-phytate grain mutants analysed by metal-dye detection HPLC and NMR. | 2001-03-01 |
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| Characterization and mapping of the 12 kDa FK506-binding protein (FKBP12)-binding site on different isoforms of the ryanodine receptor and of the inositol 1,4,5-trisphosphate receptor. | 2001-03-01 |
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| Evidence that 2-aminoethyl diphenylborate is a novel inhibitor of store-operated Ca2+ channels in liver cells, and acts through a mechanism which does not involve inositol trisphosphate receptors. | 2001-03-01 |
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| Regulation of slow wave frequency by IP(3)-sensitive calcium release in the murine small intestine. | 2001-03 |
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| Desensitization of angiotensin II: effect on [Ca2+]i, inositol triphosphate, and prolactin in pituitary cells. | 2001-03 |
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| Muscarinic stimulation increases basal Ca(2+) and inhibits spontaneous Ca(2+) transients in murine colonic myocytes. | 2001-03 |
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| Progesterone treatment abolishes exogenously expressed ionic currents in Xenopus oocytes. | 2001-03 |
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| Integrin mobilizes intracellular Ca(2+) in renal vascular smooth muscle cells. | 2001-03 |
|
| Intracellular calcium dynamics and membrane conductance changes evoked by Deiters' cell purinoceptor activation in the organ of Corti. | 2001-03 |
|
| Multiple effects of caffeine on Ca2+ release and influx in human B lymphocytes. | 2001-03 |
|
| Role of the ENTH domain in phosphatidylinositol-4,5-bisphosphate binding and endocytosis. | 2001-02-09 |
|
| Melanocortin receptor-mediated mobilization of intracellular free calcium in HEK293 cells. | 2001-02-07 |
|
| 1,10-Phenanthroline inhibits glycosylphosphatidylinositol anchoring by preventing phosphoethanolamine addition to glycosylphosphatidylinositol anchor precursors. | 2001-02-06 |
|
| Crucial role of type 1, but not type 3, inositol 1,4,5-trisphosphate (IP(3)) receptors in IP(3)-induced Ca(2+) release, capacitative Ca(2+) entry, and proliferation of A7r5 vascular smooth muscle cells. | 2001-02-02 |
|
| Inositol 1,4,5-trisphosphate receptor isoform expression in mouse pancreatic islets: effects of carbachol. | 2001-02-01 |
|
| A two-state receptor model for the interaction between angiotensin II type 1 receptors and non-peptide antagonists. | 2001-02-01 |
|
| Sarcoplasmic/endoplasmic-reticulum-Ca2+-ATPase-mediated Ca2+ reuptake, and not Ins(1,4,5)P3 receptor inactivation, prevents the activation of macroscopic Ca2+ release-activated Ca2+ current in the presence of physiological Ca2+ buffer in rat basophilic leukaemia-1 cells. | 2001-02-01 |
|
| Role of Ins(1,4,5)P3, cADP-ribose and nicotinic acid-adenine dinucleotide phosphate in Ca2+ signalling in mouse submandibular acinar cells. | 2001-02-01 |
|
| Nicotinic acid-adenine dinucleotide phosphate (NAADP) elicits specific microsomal Ca2+ release from mammalian cells. | 2001-02-01 |
|
| Calcium currents and arrhythmias: insights from molecular biology. | 2001-02-01 |
|
| Injection of a sperm extract triggers egg activation in the newt Cynops pyrrhogaster. | 2001-02-01 |
|
| Rac and phosphatidylinositol 3-kinase regulate the protein kinase B in Fc epsilon RI signaling in RBL 2H3 mast cells. | 2001-02-01 |
|
| The endoplasmic reticulum is a glucose-modulated high-affinity sink for Ca2+ in mouse pancreatic beta-cells. | 2001-02-01 |
|
| Inositol-1,4,5-trisphosphate-binding proteins controlling the phototransduction cascade of invertebrate visual cells. | 2001-02 |
|
| Human platelets bind and degrade 2-arachidonoylglycerol, which activates these cells through a cannabinoid receptor. | 2001-02 |
|
| Clinical usefulness of measuring urinary polyol excretion by gas-chromatography/mass-spectrometry in type 2 diabetes to assess polyol pathway activity. | 2001-02 |
|
| 2-Aminoethoxydiphenyl borate affects the inositol 1,4,5-trisphosphate receptor, the intracellular Ca2+ pump and the non-specific Ca2+ leak from the non-mitochondrial Ca2+ stores in permeabilized A7r5 cells. | 2001-02 |
|
| Voltage dependence of the [Ca2+](i) oscillations system, in the Mg2+ -stimulated oocyte of the prawn Palaemon serratus. | 2001-02 |
|
| Regulation of thromboxane receptor (TP) phosphorylation by protein phosphatase 1 (PP1) and PP2A. | 2001-02 |
|
| Signaling mechanisms for the selective vasoconstrictor effect of norbormide on the rat small arteries. | 2001-02 |
|
| Requirement for Ca2+ signaling in the mechanism of thrombin-induced increase in endothelial permeability. | 2001-02 |
|
| PTH and PTH-related peptide enhance steroid secretion from human adrenocortical cells. | 2001-02 |
|
| Brain proton magnetic resonance spectroscopy and imaging in children exposed to cocaine in utero. | 2001-02 |
|
| Human angiotensin II type 1 receptor isoforms encoded by messenger RNA splice variants are functionally distinct. | 2001-02 |
|
| Adenosine triphosphate-evoked cytosolic calcium oscillations in human granulosa-luteal cells: role of protein kinase C. | 2001-02 |
|
| Quantitative short echo time proton magnetic resonance spectroscopic imaging study of malformations of cortical development causing epilepsy. | 2001-02 |
|
| Crystal structure and catalytic mechanism of the MJ0109 gene product: a bifunctional enzyme with inositol monophosphatase and fructose 1,6-bisphosphatase activities. | 2001-01-23 |
|
| Inhibition of CaT1 channel activity by a noncompetitive IP3 antagonist. | 2001-01-12 |
|
| Structure elucidation of sphingolipids from the mycopathogen Sporothrix schenckii: identification of novel glycosylinositol phosphorylceramides with core manalpha1-->6Ins linkage. | 2001-01-12 |
|
| The antidepressant activity of inositol in the forced swim test involves 5-HT(2) receptors. | 2001-01-08 |
|
| Alternative splice variants of hTrp4 differentially interact with the C-terminal portion of the inositol 1,4,5-trisphosphate receptors. | 2001-01-05 |
|
| The effects of inositol treatment in animal models of psychiatric disorders. | 2001-01 |
|
| Traumatic injury of cultured astrocytes alters inositol (1,4,5)-trisphosphate-mediated signaling. | 2001-01 |
|
| Polymeric IgA binding to the human pIgR elicits intracellular signalling, but fails to stimulate pIgR-transcytosis. | 2001-01 |
|
| Novel effects of 5,8,11-eicosatriynoic acid, a lipoxygenase inhibitor, on Ca2+ mobilization in Madin Darby canine kidney cells. | 2001-01 |
|
| Saccharin activates cation conductance via inositol 1,4,5-trisphosphate production in a subset of isolated rod taste cells in the frog. | 2001-01 |
|
| Effects of extracellular nucleotides and nucleosides on prostate carcinoma cells. | 2001-01 |
|
| Chlorpromazine inhibits store-operated calcium entry and subsequent noradrenaline secretion in PC12 cells. | 2001-01 |
|
| Intercellular Ca2+ wave propagation through gap-junctional Ca2+ diffusion: a theoretical study. | 2001-01 |
|
| Differential neuronal localizations and dynamics of phosphorylated and unphosphorylated type 1 inositol 1,4,5-trisphosphate receptors. | 2001 |
Patents
Sample Use Guides
In toxicity assays when amyloid beta 40 was preincubated in the presence of epi- and scyllo-inositol, these mixtures increased the cell survival of PC-12 rat pheochromocytoma cells from 56 to 93% and 83%, respectively. Preincubation of amyloid beta 42 with epi- and scyllo-inositol increased cell survival from 54 to 89% and 83%, respectively. In contrast, chiro-inositol preincubation did not rescue PC-12 rat pheochromocytoma cells from either amyloid beta 40- or amyloid beta 42-induced toxicity with neuritic dystrophy similar to amyloid beta treatment alone.
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NCI_THESAURUS |
C1509
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1VS4X81277
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488-59-5
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C122987
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10642
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DTXSID50905091
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SCYLLO-INOSITOL
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SUB177828
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DB03106
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100000163522
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ACTIVE MOIETY
