NAV

Amonafide

Identification

Generic Name
Amonafide
DrugBank Accession Number
DB05022
Background

Amonafide is a substance that is being studied in the treatment of cancer. It belongs to the families of drugs called topoisomerase inhibitors and intercalating agents.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 283.3251
Monoisotopic: 283.132076803
Chemical Formula
C16H17N3O2
Synonyms
  • Amonafide
External IDs
  • NSC-308847
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Pharmacology

Indication

Investigated for use/treatment in breast cancer, ovarian cancer, and prostate cancer.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action

Amonafide is a DNA intercalating agent and inhibitor of topoisomerase II that has been extensively studied in patients with malignant solid tumors. Amonafide has also been studied in patients with AML.

TargetActionsOrganism
UDNA topoisomerase 2-alphaNot AvailableHumans
UDNA topoisomerase 2-betaNot AvailableHumans
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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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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
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interactions in your software
AmbroxolThe risk or severity of methemoglobinemia can be increased when Amonafide is combined with Ambroxol.
ArticaineThe risk or severity of methemoglobinemia can be increased when Amonafide is combined with Articaine.
BenzocaineThe risk or severity of methemoglobinemia can be increased when Amonafide is combined with Benzocaine.
Benzyl alcoholThe risk or severity of methemoglobinemia can be increased when Amonafide is combined with Benzyl alcohol.
BupivacaineThe risk or severity of methemoglobinemia can be increased when Amonafide is combined with Bupivacaine.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Amonafide L-malateLI06Q37TEG618863-54-0Not applicable
International/Other Brands
Quinamed

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as isoquinolones and derivatives. These are aromatic polycyclic compounds containing a ketone bearing isoquinoline moiety.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Isoquinolines and derivatives
Sub Class
Isoquinolones and derivatives
Direct Parent
Isoquinolones and derivatives
Alternative Parents
Naphthalenes / N-substituted carboxylic acid imides / Trialkylamines / Amino acids and derivatives / Azacyclic compounds / Primary amines / Organopnictogen compounds / Organooxygen compounds / Organic oxides / Hydrocarbon derivatives
Substituents
Amine / Amino acid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carboxylic acid derivative / Carboxylic acid imide / Carboxylic acid imide, n-substituted / Hydrocarbon derivative / Isoquinolone
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
1Q8D39N37L
CAS number
69408-81-7
InChI Key
UPALIKSFLSVKIS-UHFFFAOYSA-N
InChI
InChI=1S/C16H17N3O2/c1-18(2)6-7-19-15(20)12-5-3-4-10-8-11(17)9-13(14(10)12)16(19)21/h3-5,8-9H,6-7,17H2,1-2H3
IUPAC Name
11-amino-3-[2-(dimethylamino)ethyl]-3-azatricyclo[7.3.1.0^{5,13}]trideca-1(13),5,7,9,11-pentaene-2,4-dione
SMILES
CN(C)CCN1C(=O)C2=CC=CC3=CC(N)=CC(C1=O)=C23

References

General References
Not Available
Human Metabolome Database
HMDB0248346
PubChem Compound
50515
PubChem Substance
175426932
ChemSpider
45804
BindingDB
50033894
RxNav
1440270
ChEBI
94661
ChEMBL
CHEMBL428676
ZINC
ZINC000004214836
Wikipedia
Amonafide

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
3Unknown StatusTreatmentSecondary Acute Myeloid Leukemia (Secondary AML, sAML)1
2CompletedTreatmentAcute Myeloid Leukemia1
2Unknown StatusTreatmentAcute Myeloid Leukemia1
1, 2CompletedTreatmentProstate 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 Solubility0.764 mg/mLALOGPS
logP0.9ALOGPS
logP1.1Chemaxon
logS-2.6ALOGPS
pKa (Strongest Basic)8.52Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area66.64 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity83.38 m3·mol-1Chemaxon
Polarizability30.1 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9784
Blood Brain Barrier+0.9724
Caco-2 permeable+0.6097
P-glycoprotein substrateSubstrate0.7806
P-glycoprotein inhibitor INon-inhibitor0.7457
P-glycoprotein inhibitor IINon-inhibitor0.7632
Renal organic cation transporterNon-inhibitor0.5063
CYP450 2C9 substrateNon-substrate0.8545
CYP450 2D6 substrateNon-substrate0.557
CYP450 3A4 substrateSubstrate0.705
CYP450 1A2 substrateInhibitor0.8204
CYP450 2C9 inhibitorNon-inhibitor0.8706
CYP450 2D6 inhibitorNon-inhibitor0.8765
CYP450 2C19 inhibitorNon-inhibitor0.8722
CYP450 3A4 inhibitorNon-inhibitor0.8756
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8379
Ames testNon AMES toxic0.5244
CarcinogenicityNon-carcinogens0.9172
BiodegradationNot ready biodegradable0.9847
Rat acute toxicity2.4943 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.895
hERG inhibition (predictor II)Inhibitor0.6327
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0a4i-9150000000-e561ab18a08e16bfcc6d
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0019-0090000000-af7e6129e0f5126bb9e1
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0290000000-43ac2381918f3c0d92e1
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0090000000-d4e4fe1e375498fafaa8
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-1920000000-0ff0c7ca080740092905
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0090000000-a612051b81e86dcde365
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-01ox-6290000000-7afd234ec8511a08c07f
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-172.6792703
predicted
DarkChem Lite v0.1.0
[M-H]-167.1323
predicted
DeepCCS 1.0 (2019)
[M+H]+173.3433703
predicted
DarkChem Lite v0.1.0
[M+H]+169.4903
predicted
DeepCCS 1.0 (2019)
[M+Na]+172.9275703
predicted
DarkChem Lite v0.1.0
[M+Na]+175.58345
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. DNA topoisomerase 2-alpha
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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
Details2. DNA topoisomerase 2-beta
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Protein kinase c binding
Specific Function
Control of topological states of DNA by transient breakage and subsequent rejoining of DNA strands. Topoisomerase II makes double-strand breaks.
Gene Name
TOP2B
Uniprot ID
Q02880
Uniprot Name
DNA topoisomerase 2-beta
Molecular Weight
183265.825 Da

Drug created at October 21, 2007 22:23 / Updated at December 13, 2022 10:46