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
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
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/27509020 | https://www.ncbi.nlm.nih.gov/pubmed/19649930 | https://www.ncbi.nlm.nih.gov/pubmed/26794905https://www.ncbi.nlm.nih.gov/pubmed/3881759Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/27986123 | https://www.ncbi.nlm.nih.gov/pubmed/15994763 | https://www.ncbi.nlm.nih.gov/pubmed/3300654
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27509020 | https://www.ncbi.nlm.nih.gov/pubmed/19649930 | https://www.ncbi.nlm.nih.gov/pubmed/26794905https://www.ncbi.nlm.nih.gov/pubmed/3881759
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/27986123 | https://www.ncbi.nlm.nih.gov/pubmed/15994763 | https://www.ncbi.nlm.nih.gov/pubmed/3300654
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3881759
Curator's Comment: Known to be CNS penetrant in rats. Human data not available.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL3761 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23363020 |
19.0 µM [IC50] | ||
Target ID: Alpha-glucosidase I Sources: https://www.ncbi.nlm.nih.gov/pubmed/7986008 |
127.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Glycosylation and the cystic fibrosis transmembrane conductance regulator. | 2001 |
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Synthesis of polyhydroxyindolizidines from 5,6-dihydro-2H-pyran-2-one. | 2001 Dec 7 |
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Interferon-gamma increases the expression of glycosylated CD95 in B-leukemic cells: an inducible model to study the role of glycosylation in CD95-signalling and trafficking. | 2002 Apr 21 |
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Biosynthesis and processing of Spodoptera frugiperda alpha-mannosidase III. | 2002 Jun |
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Inhibition of bacterial alpha-glucosidases by castanospermine in pure cultures and activated sludge. | 2002 Jun |
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Selection of a high-energy bioactive conformation of a sulfonium-ion glycosidase inhibitor by the enzyme glucoamylase G2. | 2003 May 14 |
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The cargo receptor ERGIC-53 is a target of the unfolded protein response. | 2003 May 16 |
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Indolizidine and quinolizidine alkaloids. | 2004 Oct |
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Synthesis of 1-deoxy-1-hydroxymethyl- and 1-deoxy-1-epi-hydroxymethyl castanospermine as new potential immunomodulating agents. | 2007 Nov 1 |
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Vinylogous Mukaiyama aldol reactions with 4-oxy-2-trimethylsilyloxypyrroles: relevance to castanospermine synthesis. | 2007 Nov 3 |
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A divergent asymmetric approach to aza-spiropyran derivative and (1S,8aR)-1-hydroxyindolizidine. | 2007 Nov 8 |
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Role of receptor polymorphism and glycosylation in syncytium induction and host range variation of ecotropic mouse gammaretroviruses. | 2008 Jan 10 |
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The comparative pathology of the glycosidase inhibitors swainsonine, castanospermine, and calystegines A3, B2, and C1 in mice. | 2008 Jul |
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Divergence of catalytic mechanism within a glycosidase family provides insight into evolution of carbohydrate metabolism by human gut flora. | 2008 Oct 20 |
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Tetrapisispora phaffii killer toxin is a highly specific beta-glucanase that disrupts the integrity of the yeast cell wall. | 2009 Oct 27 |
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Single chain variable fragment against nicastrin inhibits the gamma-secretase activity. | 2009 Oct 9 |
|
A new synthetic access to bicyclic polyhydroxylated alkaloid analogues from pyranosides. | 2010 Jun 7 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27509020
400 mg loading dose and 200 mg bid
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26985570
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.
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625381
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27860
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m3166
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CASTANOSPERMINE
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54445
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DTXSID601026043
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DB01816
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ACTIVE MOIETY
PRODRUG (METABOLITE ACTIVE)