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
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PubMed
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.