This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Identification
- Generic Name
- Aldoxorubicin
- DrugBank Accession Number
- DB06013
- Background
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
- Aldoxorubicin
- External IDs
- INNO-206
Pharmacology
- Indication
Investigated for use/treatment in solid tumors.
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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
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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 softwareAcetyldigitoxin 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. 
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- Not Available
Products
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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
- Affected organisms
- 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[C@](O)(C[C@@H]4O[C@H]4C[C@H](N)[C@H](O)[C@H](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 Glioblastoma Multiforme (GBM) 1 2 Completed Treatment Pancreatic Adenocarcinoma (Ductal Adenocarcinoma) 1 2 Recruiting Treatment Malignant Neoplasm of Pancreas 1 2 Unknown Status Treatment Locally Advanced Soft Tissue Sarcoma / Metastatic Soft Tissue Sarcoma / Unresectable Soft Tissue Sarcoma 1 2 Unknown Status Treatment Metastatic Small Cell Lung Cancer 1 2 Withdrawn Treatment Non-Small Cell Lung Carcinoma (NSCLC) 1 2 Withdrawn Treatment Pancreatic Metastatic Cancer 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
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- 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. [Article]
Drug created at November 18, 2007 18:29 / Updated at February 21, 2021 18:51