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Aldoxorubicin

Targets (1)Biointeractions (1)

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

Type

Small Molecule

Groups

Investigational

Description

Aldoxorubicin, an antineoplastic agents, is an albumin-binding prodrug of doxorubicin.

Structure

Similar Structures

Synonyms

Not Available

External IDs

INNO-206

Product Ingredients

Ingredient	UNII	CAS	InChI Key
Aldoxorubicin hydrochloride	S098K6HGD9	1361563-03-2	NGKHWQPYPXRQTM-UKFSEGPMSA-N

Categories

UNII

C28MV4IM0B

CAS number

1361644-26-9

Weight

Average: 750.758
Monoisotopic: 750.274837428

Chemical Formula

C₃₇H₄₂N₄O₁₃

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

Pharmacology

Indication

Investigated for use/treatment in solid tumors.

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	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

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 Data
Acetyldigitoxin	Acetyldigitoxin may decrease the cardiotoxic activities of Aldoxorubicin.
Acetyldigoxin	Acetyldigoxin 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.

Additional Data Available

Extended Description

Extended description of the mechanism of action and particular properties of each drug interaction.

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Severity

A severity rating for each drug interaction, from minor to major.

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Evidence Level

A rating for the strength of the evidence supporting each drug interaction.

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Action

An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions

Not Available

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
1	Completed	Treatment	Advanced Solid Tumors	2
1	Completed	Treatment	Malignant Solid Tumours	1
1	Completed	Treatment	Metastatic Solid Tumors	1
1, 2	Active Not Recruiting	Treatment	Malignant Neoplasm of Pancreas	2
1, 2	Active Not Recruiting	Treatment	MCRC / Metastatic Colorectal Cancer (MCRC)	1
1, 2	Active Not Recruiting	Treatment	Squamous Cell Carcinoma (SCC)	1
1, 2	Active Not Recruiting	Treatment	Triple Negative Breast Cancer (TNBC)	1
1, 2	Recruiting	Treatment	Metastatic, Locally Advanced, or Unresectable Soft Tissue Sarcoma	1
1, 2	Withdrawn	Treatment	Chordomas / Unresectable Malignant Neoplasm	1
1, 2	Withdrawn	Treatment	Hepatocellular Carcinoma Non-resectable / Recurrent Hepatocellular Carcinoma	1
2	Completed	Treatment	Acquired Immune Deficiency Syndrome (AIDS) / HIV test positive / Kaposi s Sarcoma (KS)	1
2	Completed	Treatment	Glioblastomas	1
2	Completed	Treatment	Pancreatic Ductal Adenocarcinoma	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	Lung Cancer Non-Small Cell Cancer (NSCLC)	1
2	Withdrawn	Treatment	Pancreatic Cancer Metastatic	1
2	Withdrawn	Treatment	Small Cell Lung Cancer (SCLC)	1
2	Withdrawn	Treatment	Triple Negative Breast Cancer (TNBC)	1
3	Completed	Treatment	Metastatic, Locally Advanced or Unresectable Soft Tissue Sarcoma	1
Not Available	No Longer Available	Not Available	Sarcomas	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

Taxonomy

Classification: Not classified

Targets

Details1. DNA topoisomerase 2-alpha

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 March 01, 2020 23:57

Aldoxorubicin

Identification

Structure for Aldoxorubicin (DB06013)

Pharmacology

Interactions

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Taxonomy

Targets

References