Identification
- Generic Name
- Radotinib
- DrugBank Accession Number
- DB12323
- Background
Radotinib is under investigation for the treatment of Leukemia, Myelogenous, Chronic, BCR-ABL Positive.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Radotinib (DB12323)
- Weight
- Average: 530.515
Monoisotopic: 530.179041817 - Chemical Formula
- C27H21F3N8O
- Synonyms
- Radotinib
- External IDs
- IY5511
Pharmacology
- Indication
Radotinib is indicated for the treatment of different types of cancer, most notably Philadelphia chromosome-positive (Ph+) chronic myeloid leukemia (CML) with resistance or intolerance of other Bcr-Abl tyrosine-kinase inhibitors, such as patients resistant or intolerant to imatinib.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Not Available
- Mechanism of action
Philadelphia chromosome positive (Ph+) leukemia is driven by the constitutive enzymatic activity of the BCR-ABL1 fusion kinase. Tyrosine kinase inhibitors (TKIs) that block the activity of BCR-ABL1 are successfully used clinically to treat chronic myeloid leukemia (CML) and Philadelphia chromosome-positive acute lymphoblastic leukemia (Ph+ ALL).
Target Actions Organism ATyrosine-protein kinase ABL1 antagonistHumans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
radotinib shares the recently reported cardiovascular toxicity of nilotinib. Electrocardiographic abnormalities were recorded in 20% of all patients and some of them developed severe or even life-threatening coronary artery disease, QT prolongation, changes in left ventricular ejection fraction.
- 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 softwareAcetaminophen The serum concentration of Acetaminophen can be increased when it is combined with Radotinib. Carbimazole The therapeutic efficacy of Carbimazole can be decreased when used in combination with Radotinib. Follitropin The therapeutic efficacy of Follitropin can be decreased when used in combination with Radotinib. Levothyroxine The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Radotinib. Liothyronine The therapeutic efficacy of Liothyronine can be decreased when used in combination with Radotinib. Liotrix The therapeutic efficacy of Liotrix can be decreased when used in combination with Radotinib. Methimazole The therapeutic efficacy of Methimazole can be decreased when used in combination with Radotinib. Parathyroid hormone The therapeutic efficacy of Parathyroid hormone can be decreased when used in combination with Radotinib. Potassium Iodide The therapeutic efficacy of Potassium Iodide can be decreased when used in combination with Radotinib. Potassium perchlorate The therapeutic efficacy of Potassium perchlorate can be decreased when used in combination with Radotinib. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as benzanilides. These are aromatic compounds containing an anilide group in which the carboxamide group is substituted with a benzene ring. They have the general structure RNC(=O)R', where R,R'= benzene.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Anilides
- Direct Parent
- Benzanilides
- Alternative Parents
- Phenylimidazoles / Trifluoromethylbenzenes / Aminobenzoic acids and derivatives / p-Toluamides / Benzamides / Aniline and substituted anilines / Benzoyl derivatives / Aminopyrimidines and derivatives / Pyrazines / N-substituted imidazoles show 10 more
- Substituents
- 1-phenylimidazole / Alkyl fluoride / Alkyl halide / Amine / Amino acid or derivatives / Aminobenzoic acid or derivatives / Aminopyrimidine / Aniline or substituted anilines / Aromatic heteromonocyclic compound / Azacycle show 27 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- I284LJY110
- CAS number
- 926037-48-1
- InChI Key
- DUPWHXBITIZIKZ-UHFFFAOYSA-N
- InChI
- InChI=1S/C27H21F3N8O/c1-16-3-4-18(9-23(16)37-26-33-6-5-22(36-26)24-13-31-7-8-32-24)25(39)35-20-10-19(27(28,29)30)11-21(12-20)38-14-17(2)34-15-38/h3-15H,1-2H3,(H,35,39)(H,33,36,37)
- IUPAC Name
- 4-methyl-N-[3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl]-3-{[4-(pyrazin-2-yl)pyrimidin-2-yl]amino}benzamide
- SMILES
- CC1=CN(C=N1)C1=CC(NC(=O)C2=CC=C(C)C(NC3=NC=CC(=N3)C3=CN=CC=N3)=C2)=CC(=C1)C(F)(F)F
References
- General References
- Kim SH, Menon H, Jootar S, Saikia T, Kwak JY, Sohn SK, Park JS, Jeong SH, Kim HJ, Kim YK, Oh SJ, Kim H, Zang DY, Chung JS, Shin HJ, Do YR, Kim JA, Kim DY, Choi CW, Park S, Park HL, Lee GY, Cho DJ, Shin JS, Kim DW: Efficacy and safety of radotinib in chronic phase chronic myeloid leukemia patients with resistance or intolerance to BCR-ABL1 tyrosine kinase inhibitors. Haematologica. 2014 Jul;99(7):1191-6. doi: 10.3324/haematol.2013.096776. Epub 2014 Apr 4. [Article]
- O'Hare T, Zabriskie MS, Eiring AM, Deininger MW: Pushing the limits of targeted therapy in chronic myeloid leukaemia. Nat Rev Cancer. 2012 Jul 24;12(8):513-26. doi: 10.1038/nrc3317. [Article]
- Zabriskie MS, Vellore NA, Gantz KC, Deininger MW, O'Hare T: Radotinib is an effective inhibitor of native and kinase domain-mutant BCR-ABL1. Leukemia. 2015 Sep;29(9):1939-42. doi: 10.1038/leu.2015.42. Epub 2015 Feb 13. [Article]
- External Links
- PubChem Compound
- 16063245
- PubChem Substance
- 347828586
- ChemSpider
- 17222861
- ZINC
- ZINC000059749972
- Wikipedia
- Radotinib
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Active Not Recruiting Treatment Chronic Phase Chronic Myeloid Leukemia 1 3 Completed Treatment Bone marrow disorder / Hematologic Disease and Disorders / Leukemias / Myeloid Leukemias / Philadelphia Chromosome / Philadelphia Chromosome Positive (Ph+) Chronic Myeloid Leukemia (CML) 1 3 Recruiting Treatment Chronic Phase Chronic Myeloid Leukemia / CML, Refractory / Philadelphia Chromosome Positive (Ph+) Chronic Myeloid Leukemia (CML) 1 2 Recruiting Treatment Parkinson's Disease (PD) 1 2 Unknown Status Treatment Chronic Myelogenous Leukemia (CML) 1 1, 2 Completed Treatment Hematologic Disease and Disorders / Leukemias / Myeloid Leukemias / Philadelphia Chromosome / Philadelphia Chromosome Positive (Ph+) Chronic Myeloid Leukemia (CML) 1 Not Available Withdrawn Not Available Philadelphia Chromosome Positive (Ph+) Chronic Myeloid Leukemia (CML) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.00234 mg/mL ALOGPS logP 3.77 ALOGPS logP 4.53 Chemaxon logS -5.4 ALOGPS pKa (Strongest Acidic) 12.22 Chemaxon pKa (Strongest Basic) 6.29 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 7 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 110.51 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 150.32 m3·mol-1 Chemaxon Polarizability 52.47 Å3 Chemaxon Number of Rings 5 Chemaxon Bioavailability 1 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
Spectrum Spectrum Type Splash Key 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
- Yes
- Actions
- Antagonist
- General Function
- Syntaxin binding
- Specific Function
- Non-receptor tyrosine-protein kinase that plays a role in many key processes linked to cell growth and survival such as cytoskeleton remodeling in response to extracellular stimuli, cell motility a...
- Gene Name
- ABL1
- Uniprot ID
- P00519
- Uniprot Name
- Tyrosine-protein kinase ABL1
- Molecular Weight
- 122871.435 Da
References
- Kim SH, Menon H, Jootar S, Saikia T, Kwak JY, Sohn SK, Park JS, Jeong SH, Kim HJ, Kim YK, Oh SJ, Kim H, Zang DY, Chung JS, Shin HJ, Do YR, Kim JA, Kim DY, Choi CW, Park S, Park HL, Lee GY, Cho DJ, Shin JS, Kim DW: Efficacy and safety of radotinib in chronic phase chronic myeloid leukemia patients with resistance or intolerance to BCR-ABL1 tyrosine kinase inhibitors. Haematologica. 2014 Jul;99(7):1191-6. doi: 10.3324/haematol.2013.096776. Epub 2014 Apr 4. [Article]
Drug created at October 20, 2016 21:57 / Updated at February 21, 2021 18:53