radotinib   Click here for help

GtoPdb Ligand ID: 7814

Synonyms: IY-5511 | IY5511 | IY5511HCl | KB-146009 | Supect®
Approved drug
radotinib is an approved drug (South Korea (2012))
Compound class: Synthetic organic
Comment: This drug is approved only in South Korea, for the treatment of chronic myeloid leukemia (CML), where its trade name is Supect.
It is Example 5 in patent US7501424 [1]. The marketed formulation contains the hydrochloride salt..
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View more information in the IUPHAR Pharmacology Education Project: radotinib

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 8
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 109.99
Molecular weight 530.18
XLogP 3.77
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES Cc1ncn(c1)c1cc(NC(=O)c2ccc(c(c2)Nc2nccc(n2)c2nccnc2)C)cc(c1)C(F)(F)F
Isomeric SMILES Cc1ncn(c1)c1cc(NC(=O)c2ccc(c(c2)Nc2nccc(n2)c2nccnc2)C)cc(c1)C(F)(F)F
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)
InChI Key DUPWHXBITIZIKZ-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Kim D-Y, Cho D-J, Lee G-Y, Kim H-Y, Woo S-H, Kim Y-S, Lee S-A, Han B-C. 
4-methyl-N-(5-methylthiazol-2-yl)-3-(4-thiazol-2-yl-pyrimidin-2-ylamino)-benzamide; amidation; protein kinase inhibitor; water soluble; stability; anticancer; Chronic Myelogenous Leukemia; lung, gastric, colon, pancreatic, hepatoma, prostatic, breast, encephalophyma, bladder, cervical, lymphoma.
Patent number: US7501424. Assignee: Il-Yang Pharm. Co., Ltd. Priority date: 05/08/2005. Publication date: 10/03/2010.
2. Kim SH, Menon H, Jootar S, Saikia T, Kwak JY, Sohn SK, Park JS, Jeong SH, Kim HJ, Kim YK et al.. (2014)
Efficacy and safety of radotinib in chronic phase chronic myeloid leukemia patients with resistance or intolerance to BCR-ABL1 tyrosine kinase inhibitors.
Haematologica, 99 (7): 1191-6. [PMID:24705186]
3. Zabriskie MS, Vellore NA, Gantz KC, Deininger MW, O'Hare T. (2015)
Radotinib is an effective inhibitor of native and kinase domain-mutant BCR-ABL1.
Leukemia, 29 (9): 1939-42. [PMID:25676420]