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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
Structure of SCYLLO-INOSITOL

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-

HIDE SMILES / InChI

Description

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

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Palliative
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
13.7 μg/mL
1000 mg 2 times / day multiple, oral
SCYLLO-INOSITOL cerebrospinal fluid
Homo sapiens
6.5 μg/mL
2000 mg single, oral
SCYLLO-INOSITOL cerebrospinal fluid
Homo sapiens
39.8 μg/mL
1000 mg 2 times / day multiple, oral
SCYLLO-INOSITOL plasma
Homo sapiens
17.2 μg/mL
2000 mg single, oral
SCYLLO-INOSITOL plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
153 μg × h/mL
1000 mg 2 times / day multiple, oral
SCYLLO-INOSITOL cerebrospinal fluid
Homo sapiens
49.4 μg × h/mL
2000 mg single, oral
SCYLLO-INOSITOL cerebrospinal fluid
Homo sapiens
277 μg × h/mL
1000 mg 2 times / day multiple, oral
SCYLLO-INOSITOL plasma
Homo sapiens
98.9 μg × h/mL
2000 mg single, oral
SCYLLO-INOSITOL plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
26.2 h
1000 mg 2 times / day multiple, oral
SCYLLO-INOSITOL cerebrospinal fluid
Homo sapiens
62.6 h
1000 mg 2 times / day multiple, oral
SCYLLO-INOSITOL plasma
Homo sapiens

PubMed

Sample Use Guides

In Vivo Use Guide
ELND005 250 mg twice daily.
Route of Administration: Oral
In Vitro Use Guide
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.