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
Structure for Amonafide (DB05022)
- Weight
- Average: 283.3251
Monoisotopic: 283.132076803 - Chemical Formula
- C16H17N3O2
- Synonyms
- Amonafide
- External IDs
- NSC-308847
Pharmacology
- Indication
Investigated for use/treatment in breast cancer, ovarian cancer, and prostate cancer.
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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.
Target Actions Organism UDNA topoisomerase 2-alpha Not Available Humans UDNA topoisomerase 2-beta Not Available 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
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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 softwareAmbroxol The risk or severity of methemoglobinemia can be increased when Amonafide is combined with Ambroxol. Articaine The risk or severity of methemoglobinemia can be increased when Amonafide is combined with Articaine. Benzocaine The risk or severity of methemoglobinemia can be increased when Amonafide is combined with Benzocaine. Benzyl alcohol The risk or severity of methemoglobinemia can be increased when Amonafide is combined with Benzyl alcohol. Bupivacaine The risk or severity of methemoglobinemia can be increased when Amonafide is combined with Bupivacaine. Butacaine The risk or severity of methemoglobinemia can be increased when Amonafide is combined with Butacaine. Butamben The risk or severity of methemoglobinemia can be increased when Amonafide is combined with Butamben. Capsaicin The risk or severity of methemoglobinemia can be increased when Amonafide is combined with Capsaicin. Chloroprocaine The risk or severity of methemoglobinemia can be increased when Amonafide is combined with Chloroprocaine. Cinchocaine The risk or severity of methemoglobinemia can be increased when Amonafide is combined with Cinchocaine. 
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- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Amonafide L-malate LI06Q37TEG 618863-54-0 Not 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
- External Links
- Human Metabolome Database
- HMDB0248346
- PubChem Compound
- 50515
- PubChem Substance
- 175426932
- ChemSpider
- 45804
- BindingDB
- 50033894
- 1440270
- ChEBI
- 94661
- ChEMBL
- CHEMBL428676
- ZINC
- ZINC000004214836
- Wikipedia
- Amonafide
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Unknown Status Treatment Secondary Acute Myeloid Leukemia (Secondary AML, sAML) 1 2 Completed Treatment Acute Myeloid Leukemia 1 2 Unknown Status Treatment Acute Myeloid Leukemia 1 1, 2 Completed Treatment Prostate Cancer 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 0.764 mg/mL ALOGPS logP 0.9 ALOGPS logP 1.1 Chemaxon logS -2.6 ALOGPS pKa (Strongest Basic) 8.52 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 66.64 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 83.38 m3·mol-1 Chemaxon Polarizability 30.1 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9784 Blood Brain Barrier + 0.9724 Caco-2 permeable + 0.6097 P-glycoprotein substrate Substrate 0.7806 P-glycoprotein inhibitor I Non-inhibitor 0.7457 P-glycoprotein inhibitor II Non-inhibitor 0.7632 Renal organic cation transporter Non-inhibitor 0.5063 CYP450 2C9 substrate Non-substrate 0.8545 CYP450 2D6 substrate Non-substrate 0.557 CYP450 3A4 substrate Substrate 0.705 CYP450 1A2 substrate Inhibitor 0.8204 CYP450 2C9 inhibitor Non-inhibitor 0.8706 CYP450 2D6 inhibitor Non-inhibitor 0.8765 CYP450 2C19 inhibitor Non-inhibitor 0.8722 CYP450 3A4 inhibitor Non-inhibitor 0.8756 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8379 Ames test Non AMES toxic 0.5244 Carcinogenicity Non-carcinogens 0.9172 Biodegradation Not ready biodegradable 0.9847 Rat acute toxicity 2.4943 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.895 hERG inhibition (predictor II) Inhibitor 0.6327
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- 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
- 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