This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Oleandrin
DrugBank Accession Number
DB12843
Background

Oleandrin has been used in trials studying the treatment of Lung Cancer and Chemotherapeutic Agent Toxicity.

Type
Small Molecule
Groups
Experimental, Investigational
Structure
Weight
Average: 576.727
Monoisotopic: 576.329833126
Chemical Formula
C32H48O9
Synonyms
  • Anvirzel
  • Oleandrina
External IDs
  • NSC-692219

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UMatrix metalloproteinase-9
inhibitor
downregulator
Humans
U72 kDa type IV collagenase
inhibitor
downregulator
Humans
UApoptosis regulator Bcl-2
downregulator
Humans
UBeta-nerve growth factor
inhibitor
Humans
UCaspase-3
regulator
Humans
UCaspase-8
regulator
Humans
UEphrin type-B receptor 2
activator
Humans
UInterleukin-8
inhibitor
Humans
UNuclear factor kappa-light-chain-enhancer of activated B cells
inhibitor
Humans
UPro-epidermal growth factor
inhibitor
Humans
USerine/threonine-protein kinase mTOR
downregulator
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcebutololAcebutolol may increase the bradycardic activities of Oleandrin.
Acetylsalicylic acidThe serum concentration of Oleandrin can be decreased when it is combined with Acetylsalicylic acid.
AlfacalcidolThe risk or severity of ventricular arrhythmias and Cardiac Arrhythmia can be increased when Alfacalcidol is combined with Oleandrin.
AmikacinThe risk or severity of adverse effects can be increased when Amikacin is combined with Oleandrin.
AmilorideAmiloride may decrease the excretion rate of Oleandrin which could result in a higher serum level.
Aminosalicylic acidThe serum concentration of Oleandrin can be decreased when it is combined with Aminosalicylic acid.
AmiodaroneThe serum concentration of Oleandrin can be increased when it is combined with Amiodarone.
AmlodipineThe serum concentration of Oleandrin can be increased when it is combined with Amlodipine.
AmodiaquineThe serum concentration of Oleandrin can be increased when it is combined with Amodiaquine.
Amphotericin BThe risk or severity of adverse effects can be increased when Amphotericin B is combined with Oleandrin.
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Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as cardenolide glycosides and derivatives. These are compounds containing a carbohydrate glycosidically bound to the cardenolide moiety.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Steroid lactones
Direct Parent
Cardenolide glycosides and derivatives
Alternative Parents
Steroidal glycosides / Steroid esters / 14-hydroxysteroids / Hexoses / O-glycosyl compounds / Oxanes / Butenolides / Dicarboxylic acids and derivatives / Tertiary alcohols / Enoate esters
show 9 more
Substituents
14-hydroxysteroid / 2-furanone / Acetal / Alcohol / Aliphatic heteropolycyclic compound / Alpha,beta-unsaturated carboxylic ester / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Cardanolide-glycoside
show 23 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
steroid ester, steroid saponin, 14beta-hydroxy steroid, cardenolide glycoside (CHEBI:59030)
Affected organisms
Not Available

Chemical Identifiers

UNII
II95UDU7I4
CAS number
465-16-7
InChI Key
JLPDBLFIVFSOCC-XYXFTTADSA-N
InChI
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
IUPAC Name
(1S,2S,5S,7R,10R,11S,13S,14R,15R)-11-hydroxy-5-{[(2R,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-2,15-dimethyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-13-yl acetate
SMILES
CO[C@H]1C[C@H](O[C@H]2CC[C@@]3(C)[C@H](CC[C@@H]4[C@@H]3CC[C@]3(C)[C@H]([C@H](C[C@]43O)OC(C)=O)C3=CC(=O)OC3)C2)O[C@@H](C)[C@@H]1O

References

General References
Not Available
PubChem Compound
11541511
PubChem Substance
347829006
ChemSpider
9716290
ChEBI
59030
ChEMBL
CHEMBL1075789
ZINC
ZINC000008214621
Wikipedia
Oleandrin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1WithdrawnTreatmentChemotherapeutic Agent Toxicity / Lung Cancers1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00299 mg/mLALOGPS
logP2.1ALOGPS
logP2.95ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)6.82ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area120.75 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity148.45 m3·mol-1ChemAxon
Polarizability63.2 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

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insights and accelerate drug research.
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Downregulator
General Function
Zinc ion binding
Specific Function
May play an essential role in local proteolysis of the extracellular matrix and in leukocyte migration. Could play a role in bone osteoclastic resorption. Cleaves KiSS1 at a Gly-|-Leu bond. Cleaves...
Gene Name
MMP9
Uniprot ID
P14780
Uniprot Name
Matrix metalloproteinase-9
Molecular Weight
78457.51 Da
References
  1. Ma Y, Zhu B, Liu X, Yu H, Yong L, Liu X, Shao J, Liu Z: Inhibition of oleandrin on the proliferation show and invasion of osteosarcoma cells in vitro by suppressing Wnt/beta-catenin signaling pathway. J Exp Clin Cancer Res. 2015 Oct 6;34:115. doi: 10.1186/s13046-015-0232-8. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Downregulator
General Function
Zinc ion binding
Specific Function
Ubiquitinous metalloproteinase that is involved in diverse functions such as remodeling of the vasculature, angiogenesis, tissue repair, tumor invasion, inflammation, and atherosclerotic plaque rup...
Gene Name
MMP2
Uniprot ID
P08253
Uniprot Name
72 kDa type IV collagenase
Molecular Weight
73881.695 Da
References
  1. Ma Y, Zhu B, Liu X, Yu H, Yong L, Liu X, Shao J, Liu Z: Inhibition of oleandrin on the proliferation show and invasion of osteosarcoma cells in vitro by suppressing Wnt/beta-catenin signaling pathway. J Exp Clin Cancer Res. 2015 Oct 6;34:115. doi: 10.1186/s13046-015-0232-8. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Downregulator
General Function
Ubiquitin protein ligase binding
Specific Function
Suppresses apoptosis in a variety of cell systems including factor-dependent lymphohematopoietic and neural cells. Regulates cell death by controlling the mitochondrial membrane permeability. Appea...
Gene Name
BCL2
Uniprot ID
P10415
Uniprot Name
Apoptosis regulator Bcl-2
Molecular Weight
26265.66 Da
References
  1. Ma Y, Zhu B, Yong L, Song C, Liu X, Yu H, Wang P, Liu Z, Liu X: Regulation of Intrinsic and Extrinsic Apoptotic Pathways in Osteosarcoma Cells Following Oleandrin Treatment. Int J Mol Sci. 2016 Nov 23;17(11). pii: ijms17111950. doi: 10.3390/ijms17111950. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Receptor signaling protein activity
Specific Function
Nerve growth factor is important for the development and maintenance of the sympathetic and sensory nervous systems. Extracellular ligand for the NTRK1 and NGFR receptors, activates cellular signal...
Gene Name
NGF
Uniprot ID
P01138
Uniprot Name
Beta-nerve growth factor
Molecular Weight
26958.53 Da
References
  1. Manna SK, Sreenivasan Y, Sarkar A: Cardiac glycoside inhibits IL-8-induced biological responses by downregulating IL-8 receptors through altering membrane fluidity. J Cell Physiol. 2006 Apr;207(1):195-207. doi: 10.1002/jcp.20555. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Regulator
General Function
Phospholipase a2 activator activity
Specific Function
Involved in the activation cascade of caspases responsible for apoptosis execution. At the onset of apoptosis it proteolytically cleaves poly(ADP-ribose) polymerase (PARP) at a '216-Asp-|-Gly-217' ...
Gene Name
CASP3
Uniprot ID
P42574
Uniprot Name
Caspase-3
Molecular Weight
31607.58 Da
References
  1. Ma Y, Zhu B, Yong L, Song C, Liu X, Yu H, Wang P, Liu Z, Liu X: Regulation of Intrinsic and Extrinsic Apoptotic Pathways in Osteosarcoma Cells Following Oleandrin Treatment. Int J Mol Sci. 2016 Nov 23;17(11). pii: ijms17111950. doi: 10.3390/ijms17111950. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Regulator
General Function
Ubiquitin protein ligase binding
Specific Function
Most upstream protease of the activation cascade of caspases responsible for the TNFRSF6/FAS mediated and TNFRSF1A induced cell death. Binding to the adapter molecule FADD recruits it to either rec...
Gene Name
CASP8
Uniprot ID
Q14790
Uniprot Name
Caspase-8
Molecular Weight
55390.53 Da
References
  1. Ma Y, Zhu B, Yong L, Song C, Liu X, Yu H, Wang P, Liu Z, Liu X: Regulation of Intrinsic and Extrinsic Apoptotic Pathways in Osteosarcoma Cells Following Oleandrin Treatment. Int J Mol Sci. 2016 Nov 23;17(11). pii: ijms17111950. doi: 10.3390/ijms17111950. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Activator
General Function
Transmembrane-ephrin receptor activity
Specific Function
Receptor tyrosine kinase which binds promiscuously transmembrane ephrin-B family ligands residing on adjacent cells, leading to contact-dependent bidirectional signaling into neighboring cells. The...
Gene Name
EPHB2
Uniprot ID
P29323
Uniprot Name
Ephrin type-B receptor 2
Molecular Weight
117491.74 Da
References
  1. Terzioglu-Usak S, Nalli A, Elibol B, Ozek E, Hatiboglu MA: Anvirzel(TM)regulates cell death through inhibiting GSK-3 activity in human U87 glioma cells. Neurol Res. 2020 Jan;42(1):68-75. doi: 10.1080/01616412.2019.1709744. Epub 2020 Jan 3. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Interleukin-8 receptor binding
Specific Function
IL-8 is a chemotactic factor that attracts neutrophils, basophils, and T-cells, but not monocytes. It is also involved in neutrophil activation. It is released from several cell types in response t...
Gene Name
CXCL8
Uniprot ID
P10145
Uniprot Name
Interleukin-8
Molecular Weight
11097.98 Da
References
  1. Manna SK, Sreenivasan Y, Sarkar A: Cardiac glycoside inhibits IL-8-induced biological responses by downregulating IL-8 receptors through altering membrane fluidity. J Cell Physiol. 2006 Apr;207(1):195-207. doi: 10.1002/jcp.20555. [Article]
9. Nuclear factor kappa-light-chain-enhancer of activated B cells
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
References
  1. 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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Transmembrane receptor protein tyrosine kinase activator activity
Specific Function
EGF stimulates the growth of various epidermal and epithelial tissues in vivo and in vitro and of some fibroblasts in cell culture. Magnesiotropic hormone that stimulates magnesium reabsorption in ...
Gene Name
EGF
Uniprot ID
P01133
Uniprot Name
Pro-epidermal growth factor
Molecular Weight
133993.12 Da
References
  1. Manna SK, Sreenivasan Y, Sarkar A: Cardiac glycoside inhibits IL-8-induced biological responses by downregulating IL-8 receptors through altering membrane fluidity. J Cell Physiol. 2006 Apr;207(1):195-207. doi: 10.1002/jcp.20555. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Downregulator
General Function
Tfiiic-class transcription factor binding
Specific Function
Serine/threonine protein kinase which is a central regulator of cellular metabolism, growth and survival in response to hormones, growth factors, nutrients, energy and stress signals. MTOR directly...
Gene Name
MTOR
Uniprot ID
P42345
Uniprot Name
Serine/threonine-protein kinase mTOR
Molecular Weight
288889.05 Da
References
  1. Roth MT, Cardin DB, Borazanci EH, Steinbach M, Picozzi VJ, Rosemury A, Wadlow RC, Newman RA, Berlin J: A Phase II, Single-Arm, Open-Label, Bayesian Adaptive Efficacy and Safety Study of PBI-05204 in Patients with Stage IV Metastatic Pancreatic Adenocarcinoma. Oncologist. 2020 Oct;25(10):e1446-e1450. doi: 10.1634/theoncologist.2020-0440. Epub 2020 Jul 2. [Article]

Drug created at October 21, 2016 00:39 / Updated at June 28, 2022 19:53