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
Thumb
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.

Pharmacology
Reduce drug development failure rates
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Contraindications & Blackbox Warnings
Contraindications
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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.

TargetActionsOrganism
ADNA topoisomerase 2-alpha
inhibitor
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
Adverseeffects
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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
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Aldoxorubicin.
AmsacrineThe risk or severity of cardiotoxicity can be increased when Amsacrine is combined with Aldoxorubicin.
AnastrozoleThe risk or severity of cardiotoxicity can be increased when Anastrozole is combined with Aldoxorubicin.
Arsenic trioxideThe risk or severity of cardiotoxicity can be increased when Arsenic trioxide is combined with Aldoxorubicin.
BevacizumabThe risk or severity of cardiotoxicity can be increased when Bevacizumab is combined with Aldoxorubicin.
BleomycinThe risk or severity of cardiotoxicity can be increased when Bleomycin is combined with Aldoxorubicin.
BortezomibThe risk or severity of cardiotoxicity can be increased when Bortezomib is combined with Aldoxorubicin.
BusulfanThe risk or severity of cardiotoxicity can be increased when Busulfan is combined with Aldoxorubicin.
CabazitaxelThe risk or severity of cardiotoxicity can be increased when Aldoxorubicin is combined with Cabazitaxel.
CapecitabineThe risk or severity of cardiotoxicity can be increased when Capecitabine is combined with Aldoxorubicin.
Interactions
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Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Aldoxorubicin hydrochlorideS098K6HGD91361563-03-2NGKHWQPYPXRQTM-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
KEGG Drug
D10383
ChemSpider
7986464
ChEMBL
CHEMBL2107818
ZINC
ZINC000085540119
Wikipedia
Aldoxorubicin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentMetastatic, Locally Advanced, or Unresectable Soft Tissue Sarcoma1
2CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / HIV Positive / Kaposi’s sarcoma1
2CompletedTreatmentGlioblastoma Multiforme (GBM)1
2CompletedTreatmentPancreatic Adenocarcinoma (Ductal Adenocarcinoma)1
2RecruitingTreatmentMalignant Neoplasm of Pancreas1
2Unknown StatusTreatmentLocally Advanced Soft Tissue Sarcoma / Metastatic Soft Tissue Sarcoma / Unresectable Soft Tissue Sarcoma1
2Unknown StatusTreatmentMetastatic Small Cell Lung Cancer1
2WithdrawnTreatmentBreast Cancer (Triple Negative Breast Cancer (TNBC))1
2WithdrawnTreatmentNon-Small Cell Lung Carcinoma (NSCLC)1
2WithdrawnTreatmentPancreatic Metastatic Cancer1

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
PropertyValueSource
Water Solubility0.151 mg/mLALOGPS
logP1.26ALOGPS
logP0.71ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)8.2ChemAxon
pKa (Strongest Basic)9.39ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area267.84 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity189.86 m3·mol-1ChemAxon
Polarizability75.89 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Targets

Drugtargets2
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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
  1. 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