Oleandrin
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MedKoo CAT#: 202070

CAS#: 465-16-7

Description: Oleandrin, also known as PBI-05204 , is a lipid soluble cardiac glycoside with potential antineoplastic activity. Upon administration, oleandrin specifically binds to and inhibits the alpha3 subunit of the Na/K-ATPase pump in human cancer cells. This may inhibit the phosphorylation of Akt, upregulate MAPK, inhibit NF-kb activation and inhibit FGF-2 export and may downregulate mTOR thereby inhibiting p70S6K and S6 protein expression. All of this may lead to an induction of apoptosis.


Chemical Structure

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Oleandrin
CAS# 465-16-7

Theoretical Analysis

MedKoo Cat#: 202070
Name: Oleandrin
CAS#: 465-16-7
Chemical Formula: C32H48O9
Exact Mass: 576.32983
Molecular Weight: 576.72
Elemental Analysis: C, 66.64; H, 8.39; O, 24.97

Price and Availability

Size Price Availability Quantity
100.0mg USD 2950.0 2 Weeks
200.0mg USD 3950.0 2 Weeks
500.0mg USD 4950.0 2 Weeks
1.0g USD 5950.0 2 Weeks
2.0g USD 9850.0 2 Weeks
Bulk inquiry

Synonym: PBI05204; PBI 05204; PBI-05204; Oleandrin

IUPAC/Chemical Name: (3S,5R,9S,10S,13R,14S,16S)-14-hydroxy-3-(((2R,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-10,13-dimethyl-17-(5-oxo-2,5-dihydrofuran-3-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-16-yl acetate

InChi Key: JLPDBLFIVFSOCC-YBKPGLTNSA-N

InChi Code: 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

SMILES Code: CC(O[C@H]1C[C@]2(O)C3CC[C@]4([H])C[C@@H](O[C@H]5C[C@H](OC)[C@@H](O)[C@H](C)O5)CC[C@]4(C)[C@@]3([H])CC[C@]2(C)C1C6=CC(OC6)=O)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 576.72 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Van Kanegan MJ, He DN, Dunn DE, Yang P, Newman RA, West AE, Lo DC. BDNF mediates neuroprotection against oxygen-glucose deprivation by the cardiac glycoside oleandrin. J Neurosci. 2014 Jan 15;34(3):963-8. doi: 10.1523/JNEUROSCI.2700-13.2014. PubMed PMID: 24431454; PubMed Central PMCID: PMC3891971.

2: Dasgupta A, Welsh KJ, Hwang SA, Johnson M, Actor JK. Bidirectional (negative/positive) interference of oleandrin and oleander extract on a relatively new Loci digoxin assay using Vista 1500 analyzer. J Clin Lab Anal. 2014 Jan;28(1):16-20. doi: 10.1002/jcla.21637. Epub 2013 Dec 27. PubMed PMID: 24375780.

3: Kumar A, De T, Mishra A, Mishra AK. Oleandrin: A cardiac glycosides with potent cytotoxicity. Pharmacogn Rev. 2013 Jul;7(14):131-9. doi: 10.4103/0973-7847.120512. Review. PubMed PMID: 24347921; PubMed Central PMCID: PMC3841991.

4: Raviprakash N, Manna SK. Short-term exposure to oleandrin enhances responses to IL-8 by increasing cell surface IL-8 receptors. Br J Pharmacol. 2014 Jul;171(14):3339-51. doi: 10.1111/bph.12493. PubMed PMID: 24172227; PubMed Central PMCID: PMC4105924.

5: Retraction note: Oleandrin-mediated expression of Fas potentiates apoptosis in tumor cells. J Clin Immunol. 2013 Jul;33(5):1031. doi: 10.1007/s10875-013-9884-3. PubMed PMID: 23553607.

6: Singh S, Shenoy S, Nehete PN, Yang P, Nehete B, Fontenot D, Yang G, Newman RA, Sastry KJ. Nerium oleander derived cardiac glycoside oleandrin is a novel inhibitor of HIV infectivity. Fitoterapia. 2013 Jan;84:32-9. doi: 10.1016/j.fitote.2012.10.017. Epub 2012 Nov 2. PubMed PMID: 23127567.

7: Yang P, Cartwright C, Efuet E, Hamilton SR, Wistuba II, Menter D, Addington C, Shureiqi I, Newman RA. Cellular location and expression of Na+, K+ -ATPase α subunits affect the anti-proliferative activity of oleandrin. Mol Carcinog. 2014 Apr;53(4):253-63. doi: 10.1002/mc.21968. Epub 2012 Oct 16. PubMed PMID: 23073998.

8: Dunn DE, He DN, Yang P, Johansen M, Newman RA, Lo DC. In vitro and in vivo neuroprotective activity of the cardiac glycoside oleandrin from Nerium oleander in brain slice-based stroke models. J Neurochem. 2011 Nov;119(4):805-14. doi: 10.1111/j.1471-4159.2011.07439.x. Epub 2011 Sep 26. PubMed PMID: 21950737.

9: Lin Y, Ho DH, Newman RA. Human tumor cell sensitivity to oleandrin is dependent on relative expression of Na+, K+ -ATPase subunitst. J Exp Ther Oncol. 2010;8(4):271-86. PubMed PMID: 21222360.

10: Yang P, Menter DG, Cartwright C, Chan D, Dixon S, Suraokar M, Mendoza G, Llansa N, Newman RA. Oleandrin-mediated inhibition of human tumor cell proliferation: importance of Na,K-ATPase alpha subunits as drug targets. Mol Cancer Ther. 2009 Aug;8(8):2319-28. doi: 10.1158/1535-7163.MCT-08-1085. Epub 2009 Aug 11. PubMed PMID: 19671733.

Oleandrin

100.0mg / USD 2950.0


Additional Information

 
Application: Detection in biological specimens
Oleander extracts have been used as an instrument for both suicidal and homicidal poisonings. Oleandrin, the primary active constituent, may be quantified in serum, whole blood or urine to confirm a diagnosis of poisoning in hospitalized patients or to assist in the forensic investigation of a case of fatal overdosage. Most commercial immunoassays for digoxin or digitoxin will cross-react with the oleander glycosides and will suffice for clinical monitoring purposes, but forensic scientists generally rely on instrumental techniques such as liquid chromatography-mass spectrometry (Source: http://en.wikipedia.org/wiki/Oleandrin ).