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
Structure for Oleandrin (DB12843)
- Weight
- Average: 576.727
Monoisotopic: 576.329833126 - Chemical Formula
- C32H48O9
- Synonyms
- Anvirzel
- Oleandrina
- External IDs
- NSC-692219
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UMatrix metalloproteinase-9 inhibitordownregulatorHumans U72 kDa type IV collagenase inhibitordownregulatorHumans UApoptosis regulator Bcl-2 downregulatorHumans UBeta-nerve growth factor inhibitorHumans UCaspase-3 regulatorHumans UCaspase-8 regulatorHumans UEphrin type-B receptor 2 activatorHumans UInterleukin-8 inhibitorHumans UNuclear factor kappa-light-chain-enhancer of activated B cells inhibitorHumans UPro-epidermal growth factor inhibitorHumans USerine/threonine-protein kinase mTOR downregulatorHumans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAcebutolol Acebutolol may increase the bradycardic activities of Oleandrin. Acetylsalicylic acid The serum concentration of Oleandrin can be decreased when it is combined with Acetylsalicylic acid. Alfacalcidol The risk or severity of ventricular arrhythmias and Cardiac Arrhythmia can be increased when Alfacalcidol is combined with Oleandrin. Amikacin The risk or severity of adverse effects can be increased when Amikacin is combined with Oleandrin. Amiloride Amiloride may decrease the excretion rate of Oleandrin which could result in a higher serum level. Aminosalicylic acid The serum concentration of Oleandrin can be decreased when it is combined with Aminosalicylic acid. Amiodarone The serum concentration of Oleandrin can be increased when it is combined with Amiodarone. Amlodipine The serum concentration of Oleandrin can be increased when it is combined with Amlodipine. Amodiaquine The serum concentration of Oleandrin can be increased when it is combined with Amodiaquine. Amphotericin B The risk or severity of adverse effects can be increased when Amphotericin B is combined with Oleandrin. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - 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
- External Links
- PubChem Compound
- 11541511
- PubChem Substance
- 347829006
- ChemSpider
- 9716290
- ChEBI
- 59030
- ChEMBL
- CHEMBL1075789
- ZINC
- ZINC000008214621
- Wikipedia
- Oleandrin
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 1 Withdrawn Treatment Chemotherapeutic Agent Toxicity / Lung Cancer 1
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
Property Value Source Water Solubility 0.00299 mg/mL ALOGPS logP 2.1 ALOGPS logP 2.95 Chemaxon logS -5.3 ALOGPS pKa (Strongest Acidic) 6.82 Chemaxon pKa (Strongest Basic) -3.2 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 7 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 120.75 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 148.45 m3·mol-1 Chemaxon Polarizability 63.2 Å3 Chemaxon Number of Rings 6 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- InhibitorDownregulator
- 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
- 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
- InhibitorDownregulator
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
Unknown
Inhibitor
References
- 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
- 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
- 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