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Details

Stereochemistry ABSOLUTE
Molecular Formula C8H15NO4
Molecular Weight 189.209
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CASTANOSPERMINE

SMILES

[H][C@]12[C@@H](O)CCN1C[C@H](O)[C@@H](O)[C@@H]2O

InChI

InChIKey=JDVVGAQPNNXQDW-TVNFTVLESA-N
InChI=1S/C8H15NO4/c10-4-1-2-9-3-5(11)7(12)8(13)6(4)9/h4-8,10-13H,1-3H2/t4-,5-,6+,7+,8+/m0/s1

HIDE SMILES / InChI

Description

Castanospermine (1,6,7,8-tetrahydroxyoctahydroindolizine) is an indolizine alkaloid first isolated from the seeds of Australian tree Castanospermum austral. Castanospermine is a potent inhibitor of some glucosidase enzymes and has antiviral, immunosuppressant and anti-inflammatory activity in vitro and in animal models. Castanospermine has been shown to be a potent inhibitor of almond emulsion β-glucosidase, and also to inhibit fungal β-xylosidase. Additionally, castanospermine may have the potential ability to inhibit syncytium formation between HIV-infected and CD4-expressing cells and may also interfere with infectivity. It has also been demonstrated that this agent inhibits inflammation at the level of leukocyte extravasation in rat models of experimental adjuvant-induced arthritis and autoimmune encephalomyelitis. Celgosivir, Castanospermine’s oral prodrug, is currently tested in clinical trials.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
19.0 µM [IC50]
127.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
400 mg loading dose and 200 mg bid
Route of Administration: Oral
In Vitro Use Guide
LoVo/Dx, W1PR, W1TR and A2780T1 cell lines were used for activity evaluation. The cells were seeded at 4x10^3 cells/well (200 μl) in 96-well culture plates and pre-incubated for 48 h. To examine the effect of BFA, CAS or chemotherapeutic drugs on cell survival, the cells were treated with increasing concentrations of BFA, CAS (Castanospermine, 10 μg/ml for LoVo/Dx, 50 μg/ml for W1PR and W1TR and 60 μg/ml for A2780T1 cells.) for 72 h. Subsequently, 10 μl of MTT labeling reagent was added to the medium (the final concentration of MTT was 0.5 mg/ml) for 4 h and 100 μl of the solubilized solution was then added to each well. After an overnight incubation, the absorbance was measured in a microplate reader at 570 nm with a reference wavelength of 720 nm.