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Aldoxorubicin
This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Identification
- Name
- Aldoxorubicin
- Accession Number
- DB06013
- Description
Aldoxorubicin, an antineoplastic agents, is an albumin-binding prodrug of doxorubicin.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Aldoxorubicin (DB06013)
- Weight
- Average: 750.758
Monoisotopic: 750.274837428 - Chemical Formula
- C37H42N4O13
- Synonyms
- Not Available
- External IDs
- INNO-206
Pharmacology
- Indication
Investigated for use/treatment in solid tumors.
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
- Not Available
- Mechanism of action
INNO-206 is the (6-Maleimidocaproyl) hydrazone of doxorubicin. INNO-206 is a prodrug of doxorubicin that binds endogenous albumin after administration. The bound doxorubicin is released in the acidic environment of the tumor cell through cleavage of an acid sensitive linker. In preclinical models, INNO-206 was superior to doxorubicin with regard to antitumor efficacy and toxicity.
Target Actions Organism ADNA topoisomerase 2-alpha inhibitorHumans - 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
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
- Not Available
- Affected organisms
- 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 Unlock Additional DataAcetyldigitoxin Acetyldigitoxin may decrease the cardiotoxic activities of Aldoxorubicin. Amsacrine The risk or severity of cardiotoxicity can be increased when Amsacrine is combined with Aldoxorubicin. Anastrozole The risk or severity of cardiotoxicity can be increased when Anastrozole is combined with Aldoxorubicin. Arsenic trioxide The risk or severity of cardiotoxicity can be increased when Arsenic trioxide is combined with Aldoxorubicin. Bevacizumab The risk or severity of cardiotoxicity can be increased when Bevacizumab is combined with Aldoxorubicin. Bleomycin The risk or severity of cardiotoxicity can be increased when Bleomycin is combined with Aldoxorubicin. Bortezomib The risk or severity of cardiotoxicity can be increased when Bortezomib is combined with Aldoxorubicin. Busulfan The risk or severity of cardiotoxicity can be increased when Busulfan is combined with Aldoxorubicin. Cabazitaxel The risk or severity of cardiotoxicity can be increased when Aldoxorubicin is combined with Cabazitaxel. Capecitabine The risk or severity of cardiotoxicity can be increased when Capecitabine is combined with Aldoxorubicin. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Not Available
Products
- Product Ingredients
Ingredient UNII CAS InChI Key Aldoxorubicin hydrochloride S098K6HGD9 1361563-03-2 NGKHWQPYPXRQTM-UKFSEGPMSA-N
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as anthracyclines. These are polyketides containing a tetracenequinone ring structure with a sugar attached by glycosidic linkage.
- Kingdom
- Organic compounds
- Super Class
- Phenylpropanoids and polyketides
- Class
- Anthracyclines
- Sub Class
- Not Available
- Direct Parent
- Anthracyclines
- Alternative Parents
- Tetracenequinones / Aminoglycosides / Anthraquinones / Hexoses / O-glycosyl compounds / Tetralins / Aryl ketones / Anisoles / Maleimides / Alkyl aryl ethers show 19 more
- Substituents
- 1,2-aminoalcohol / 1,4-anthraquinone / 9,10-anthraquinone / Acetal / Alcohol / Aldehyde / Alkyl aryl ether / Amine / Amino acid or derivatives / Amino saccharide show 41 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
Chemical Identifiers
- UNII
- C28MV4IM0B
- CAS number
- 1361644-26-9
- InChI Key
- OBMJQRLIQQTJLR-USGQOSEYSA-N
- InChI
- InChI=1S/C37H42N4O13/c1-17-32(46)20(38)13-27(53-17)54-22-15-37(51,23(16-42)39-40-24(43)9-4-3-5-12-41-25(44)10-11-26(41)45)14-19-29(22)36(50)31-30(34(19)48)33(47)18-7-6-8-21(52-2)28(18)35(31)49/h6-8,10-11,17,20,22,27,32,42,46,48,50-51H,3-5,9,12-16,38H2,1-2H3,(H,40,43)/b39-23+/t17-,20-,22-,27-,32+,37-/m0/s1
- IUPAC Name
- N'-[(1E)-1-[(2S,4S)-4-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-2-yl]-2-hydroxyethylidene]-6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanehydrazide
- SMILES
- COC1=C2C(=O)C3=C(O)C4=C(C[[email protected]](O)(C[[email protected]@H]4O[[email protected]]4C[[email protected]](N)[[email protected]](O)[[email protected]](C)O4)C(\CO)=N\NC(=O)CCCCCN4C(=O)C=CC4=O)C(O)=C3C(=O)C2=CC=C1
References
- General References
- Not Available
- External Links
- KEGG Drug
- D10383
- ChemSpider
- 7986464
- ChEMBL
- CHEMBL2107818
- ZINC
- ZINC000085540119
- Wikipedia
- Aldoxorubicin
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Completed Treatment Metastatic, Locally Advanced or Unresectable Soft Tissue Sarcoma 1 2 Completed Treatment Acquired Immune Deficiency Syndrome (AIDS) / HIV Positive / Kaposi’s sarcoma 1 2 Completed Treatment Glioblastomas 1 2 Completed Treatment Pancreatic Ductal Adenocarcinoma 1 2 Recruiting Treatment Malignant Neoplasm of Pancreas 1 2 Recruiting Treatment Metastatic Small Cell Lung Cancer 1 2 Unknown Status Treatment Locally Advanced Soft Tissue Sarcoma / Metastatic Soft Tissue Sarcoma / Unresectable Soft Tissue Sarcoma 1 2 Withdrawn Treatment Non-Small Cell Lung Carcinoma (NSCLC) 1 2 Withdrawn Treatment Pancreatic Cancer Metastatic 1 2 Withdrawn Treatment Small Cell Lung Cancer (SCLC) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.151 mg/mL ALOGPS logP 1.26 ALOGPS logP 0.71 ChemAxon logS -3.7 ALOGPS pKa (Strongest Acidic) 8.2 ChemAxon pKa (Strongest Basic) 9.39 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 15 ChemAxon Hydrogen Donor Count 7 ChemAxon Polar Surface Area 267.84 Å2 ChemAxon Rotatable Bond Count 12 ChemAxon Refractivity 189.86 m3·mol-1 ChemAxon Polarizability 75.89 Å3 ChemAxon Number of Rings 6 ChemAxon Bioavailability 0 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
- Not Available
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Ubiquitin binding
- Specific Function
- Control of topological states of DNA by transient breakage and subsequent rejoining of DNA strands. Topoisomerase II makes double-strand breaks. Essential during mitosis and meiosis for proper segr...
- Gene Name
- TOP2A
- Uniprot ID
- P11388
- Uniprot Name
- DNA topoisomerase 2-alpha
- Molecular Weight
- 174383.88 Da
References
- Chawla SP, Chua VS, Hendifar AF, Quon DV, Soman N, Sankhala KK, Wieland DS, Levitt DJ: A phase 1B/2 study of aldoxorubicin in patients with soft tissue sarcoma. Cancer. 2015 Feb 15;121(4):570-9. doi: 10.1002/cncr.29081. Epub 2014 Oct 13. [PubMed:25312684]
Drug created on November 18, 2007 11:29 / Updated on June 12, 2020 10:52
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