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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
Structure of OLEANDRIN

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

HIDE SMILES / InChI

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

Description
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
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
Inhibition of 12-O-tetradecanoylphorbol-13-acetate-induced tumor promotion markers in CD-1 mouse skin by oleandrin.
2004 Mar 15
Determination of oleandrin in tissues and biological fluids by liquid chromatography-electrospray tandem mass spectrometry.
2005 Jun 1
Cardiac glycoside inhibits IL-8-induced biological responses by downregulating IL-8 receptors through altering membrane fluidity.
2006 Apr
Unexpectedly dangerous escargot stew: oleandrin poisoning through the alimentary chain.
2006 Nov-Dec
Oleandrin induces apoptosis in human, but not in murine cells: dephosphorylation of Akt, expression of FasL, and alteration of membrane fluidity.
2007 Mar
A fatal case of oleandrin poisoning.
2008 Aug 6
The prince and the pauper. A tale of anticancer targeted agents.
2008 Oct 23
Short-term exposure to oleandrin enhances responses to IL-8 by increasing cell surface IL-8 receptors.
2014 Jul
Patents

Sample Use Guides

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
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
by admin
on Sat Dec 16 04:16:09 GMT 2023
Edited
by admin
on Sat Dec 16 04:16:09 GMT 2023
Record UNII
II95UDU7I4
Record Status Validated (UNII)
Record Version
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Name Type Language
OLEANDRIN
MI   WHO-DD  
Common Name English
OLEANDRIN [MI]
Common Name English
CARD-20(22)-ENOLIDE, 16-(ACETYLOXY)-3-((2,6-DIDEOXY-3-O-METHYL-.ALPHA.-L-ARABINO-HEXOPYRANOSYL)OXY)-14-HYDROXY-, (3.BETA.,5.BETA.,16.BETA.)-
Common Name English
NSC-692219
Code English
ANVIRZEL
Brand Name English
Oleandrin [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C274
Created by admin on Sat Dec 16 04:16:10 GMT 2023 , Edited by admin on Sat Dec 16 04:16:10 GMT 2023
Code System Code Type Description
PUBCHEM
11541511
Created by admin on Sat Dec 16 04:16:10 GMT 2023 , Edited by admin on Sat Dec 16 04:16:10 GMT 2023
PRIMARY
MERCK INDEX
m8189
Created by admin on Sat Dec 16 04:16:10 GMT 2023 , Edited by admin on Sat Dec 16 04:16:10 GMT 2023
PRIMARY Merck Index
MESH
C021065
Created by admin on Sat Dec 16 04:16:10 GMT 2023 , Edited by admin on Sat Dec 16 04:16:10 GMT 2023
PRIMARY
FDA UNII
II95UDU7I4
Created by admin on Sat Dec 16 04:16:10 GMT 2023 , Edited by admin on Sat Dec 16 04:16:10 GMT 2023
PRIMARY
SMS_ID
100000080011
Created by admin on Sat Dec 16 04:16:10 GMT 2023 , Edited by admin on Sat Dec 16 04:16:10 GMT 2023
PRIMARY
EPA CompTox
DTXSID40861950
Created by admin on Sat Dec 16 04:16:10 GMT 2023 , Edited by admin on Sat Dec 16 04:16:10 GMT 2023
PRIMARY
CAS
465-16-7
Created by admin on Sat Dec 16 04:16:10 GMT 2023 , Edited by admin on Sat Dec 16 04:16:10 GMT 2023
PRIMARY
EVMPD
SUB14684MIG
Created by admin on Sat Dec 16 04:16:10 GMT 2023 , Edited by admin on Sat Dec 16 04:16:10 GMT 2023
PRIMARY
NCI_THESAURUS
C90586
Created by admin on Sat Dec 16 04:16:10 GMT 2023 , Edited by admin on Sat Dec 16 04:16:10 GMT 2023
PRIMARY
NSC
692219
Created by admin on Sat Dec 16 04:16:10 GMT 2023 , Edited by admin on Sat Dec 16 04:16:10 GMT 2023
PRIMARY
ECHA (EC/EINECS)
207-361-5
Created by admin on Sat Dec 16 04:16:10 GMT 2023 , Edited by admin on Sat Dec 16 04:16:10 GMT 2023
PRIMARY
WIKIPEDIA
OLEANDRIN
Created by admin on Sat Dec 16 04:16:10 GMT 2023 , Edited by admin on Sat Dec 16 04:16:10 GMT 2023
PRIMARY
DRUG CENTRAL
3399
Created by admin on Sat Dec 16 04:16:10 GMT 2023 , Edited by admin on Sat Dec 16 04:16:10 GMT 2023
PRIMARY
HSDB
3518
Created by admin on Sat Dec 16 04:16:10 GMT 2023 , Edited by admin on Sat Dec 16 04:16:10 GMT 2023
PRIMARY
DRUG BANK
DB12843
Created by admin on Sat Dec 16 04:16:10 GMT 2023 , Edited by admin on Sat Dec 16 04:16:10 GMT 2023
PRIMARY
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