lusutrombopag   Click here for help

GtoPdb Ligand ID: 10032

Synonyms: Mulpleta® | S-888711 | S888711
Approved drug
lusutrombopag is an approved drug (Japan (2015), FDA (2018), EMA (2019))
Compound class: Synthetic organic
Comment: Lusutrombopag is an orally bioavailable, nonpeptidyl, small molecule thrombopoietin (TPO) receptor agonist [4] that was developed by Shionogi in Japan. It was the second TPO receptor agonist to receive FDA approval in 2018 (avatrombopag was the first).
Lusutrombopag demonstrates antibacterial activity in vitro with potential to be repurposed as a treatment for infections caused by drug-resistant Enterococcus spp. [3].

lusutrombopag is commercially available from our sponsors

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 6
Hydrogen bond donors 2
Rotatable bonds 14
Topological polar surface area 125.99
Molecular weight 590.14
XLogP 7.78
No. Lipinski's rules broken 2

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 CCCCCCOC(c1cccc(c1OC)c1csc(n1)NC(=O)c1cc(Cl)c(c(c1)Cl)C=C(C(=O)O)C)C
Isomeric SMILES CCCCCCO[C@H](c1cccc(c1OC)c1csc(n1)NC(=O)c1cc(Cl)c(c(c1)Cl)/C=C(/C(=O)O)\C)C
InChI InChI=1S/C29H32Cl2N2O5S/c1-5-6-7-8-12-38-18(3)20-10-9-11-21(26(20)37-4)25-16-39-29(32-25)33-27(34)19-14-23(30)22(24(31)15-19)13-17(2)28(35)36/h9-11,13-16,18H,5-8,12H2,1-4H3,(H,35,36)(H,32,33,34)/b17-13+/t18-/m0/s1
InChI Key NOZIJMHMKORZBA-KJCUYJGMSA-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. FDA. 
Lusutrombopag; FDA Approved Drug Products.
Accessed on 01/08/2018. Modified on 01/08/2018. Drugs@FDA, https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=BasicSearch.process
2. Kim ES. (2016)
Lusutrombopag: First Global Approval.
Drugs, 76 (1): 155-8. [PMID:26666417]
3. She P, Li L, Yang Y, Zhou L, Huang G, Xiao D, Wu Y. (2024)
Lusutrombopag as a Repurposing Drug in Combination with Aminoglycosides against Vancomycin-Resistant Enterococcus.
ACS Infect Dis, 10 (4): 1327-1338. [PMID:38567846]
4. Yoshida H, Yamada H, Nogami W, Dohi K, Kurino-Yamada T, Sugiyama K, Takahashi K, Gahara Y, Kitaura M, Hasegawa M et al.. (2018)
Development of a new knock-in mouse model and evaluation of pharmacological activities of lusutrombopag, a novel, nonpeptidyl small-molecule agonist of the human thrombopoietin receptor c-Mpl.
Exp Hematol, 59: 30-39.e2. [PMID:29274361]