Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C32H48O9 |
Molecular Weight | 576.7181 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 13 / 13 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]1(C[C@H](OC)[C@@H](O)[C@H](C)O1)O[C@H]2CC[C@@]3(C)[C@]([H])(CC[C@]4([H])[C@]3([H])CC[C@]5(C)[C@H]([C@H](C[C@]45O)OC(C)=O)C6=CC(=O)OC6)C2
InChI
InChIKey=JLPDBLFIVFSOCC-XYXFTTADSA-N
InChI=1S/C32H48O9/c1-17-29(35)24(37-5)14-27(39-17)41-21-8-10-30(3)20(13-21)6-7-23-22(30)9-11-31(4)28(19-12-26(34)38-16-19)25(40-18(2)33)15-32(23,31)36/h12,17,20-25,27-29,35-36H,6-11,13-16H2,1-5H3/t17-,20+,21-,22-,23+,24-,25-,27-,28-,29-,30-,31+,32-/m0/s1
Molecular Formula | C32H48O9 |
Molecular Weight | 576.7181 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 13 / 13 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/24347921Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/24172227 | https://www.ncbi.nlm.nih.gov/pubmed/21950737
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24347921
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/24172227 | https://www.ncbi.nlm.nih.gov/pubmed/21950737
Oleandrin is a toxic cardiac glycoside found in oleander (Nerium oleander L.). Along with neandrin it is primarily responsible for the toxicity of the sap of oleander. Oleandrin has been used for many years in China and Russia for its properties as a cardiac glycoside, for both suicidal and therapeutic purposes as in treatment of cardiac insufficiency. Because of its properties as a cardiac glycoside, oleandrin interferes in some essential processes within the cell, the most important of these being the inhibition of the Na-K ATPase. This protein enables the cell to exchange the cations Na+ and K+ between the intercellular and extracellular spaces by which, for instance, electronic signaling is made possible in nerve cells. Oleandrin binds to specific amino acids in the protein, causing it to lose its function. After depolarization of the cell in which Na+ flows into the cell, the Na+ cannot be transported back into the extracellular membrane, causing the sodium gradient to disappear. This gradient is the driving force for other transport proteins, such as the sodium-calcium exchanger, which plays an important role in cardiomyocytes. To make muscle contraction possible, a calcium influx from the extracellular fluid into the cell is crucial. After the muscle contraction, the calcium is normally pumped out of the cell and exchanged for sodium. When the sodium gradient is depleted, calcium cannot be pumped back and, as a consequence, accumulates in the cardiomyocyte. As a result of the high calcium concentration, actin and myosin filaments will bind stronger, unable to relax properly to make a new contraction possible. This may result in cardiac arrhythmias, in the worst case decreasing cardiac output and causing a shortage in oxygen supply in vital tissues. Apart from being a potent toxic compound, it may also be used in therapeutic ways. Both oleandrin and oleandrigenin, as well as their relatives, may be able to inhibit proliferation of tumor cells and stimulate their apoptosis as a result of the high concentration of intracellular calcium. In addition, it inhibits excretion of fibroblast growth factor 2 through membrane interaction and through inhibition of the Na,K-ATPase pump. However, there are no results from clinical testing on humans that support any use as a cancer treatment. Oleandrin has been reported to be lethal, but exact dosages are not fully documented. The fatal blood concentration of oleandrin has been estimated for humans to be approximately 20 ng/ml in decreased blood by extrapolation of intoxication symptoms. Symptoms present in poisoned animals include bloody diarrhea and colic, the latter especially in horses. Because the leaf itself is quite bitter, only starving animals will be likely to eat the plant. The lethal dosage for animals is estimated to be about 0.5 mg/kg.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2095186 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19894733 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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PubMed
Title | Date | PubMed |
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Inhibition of export of fibroblast growth factor-2 (FGF-2) from the prostate cancer cell lines PC3 and DU145 by Anvirzel and its cardiac glycoside component, oleandrin. | 2001 Aug 15 |
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Inhibition of 12-O-tetradecanoylphorbol-13-acetate-induced tumor promotion markers in CD-1 mouse skin by oleandrin. | 2004 Mar 15 |
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Determination of oleandrin in tissues and biological fluids by liquid chromatography-electrospray tandem mass spectrometry. | 2005 Jun 1 |
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Cardiac glycoside inhibits IL-8-induced biological responses by downregulating IL-8 receptors through altering membrane fluidity. | 2006 Apr |
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Unexpectedly dangerous escargot stew: oleandrin poisoning through the alimentary chain. | 2006 Nov-Dec |
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Oleandrin induces apoptosis in human, but not in murine cells: dephosphorylation of Akt, expression of FasL, and alteration of membrane fluidity. | 2007 Mar |
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A fatal case of oleandrin poisoning. | 2008 Aug 6 |
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The prince and the pauper. A tale of anticancer targeted agents. | 2008 Oct 23 |
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Short-term exposure to oleandrin enhances responses to IL-8 by increasing cell surface IL-8 receptors. | 2014 Jul |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21950737
Oleandrin (3 mg/kg, 100 lL) were administered to male CD1 mice i.p. in DMSO : PEG400 vehicle 25 : 75 v/v.
Route of Administration:
Intraperitoneal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19894733
Human pancreatic cancer cells (Panc-1, BxPC3, and Mia-Paca), human colon cancer cell lines (CaCO-2, DOD-1, HCT-116, HT29, RKO, and LST174), rodent melanoma B16 cells, human breast cancer cells (SUM149, MCF-7, and MDA231), human oral cancer cells (SCC9 and CAL-27), human ovarian cancer (ES3, TOV1120, and SKOV cells), and human non–small cell lung cancer (A549 and H1299 cells) were treated with various concentrations of oleandrin (1–500 nmol/L). After an additional 72 h, inhibition of cellular proliferation was assessed
Substance Class |
Chemical
Created
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admin
on
Edited
Sat Dec 16 04:16:09 GMT 2023
by
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on
Sat Dec 16 04:16:09 GMT 2023
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Record UNII |
II95UDU7I4
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Record Status |
Validated (UNII)
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Record Version |
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C274
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OLEANDRIN
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ACTIVE MOIETY |