tirasemtiv   Click here for help

GtoPdb Ligand ID: 8280

Synonyms: CK-2017357
PDB Ligand
Compound class: Synthetic organic
Comment: Tirasemtiv acts as an activator of the fast skeletal muscle (type II) troponin complex [4]. The compound is being investigated as a potential treatment for diseases and conditions associated with aging, muscle weakness and wasting or neuromuscular dysfunction [4] (e.g. amyotrophic lateral sclerosis [5], myasthenia gravis and claudication [2]). In clinical trial tirasemtiv was not well tolerated, and this was likely a contributory factor to its lack of significant efficacy.

tirasemtiv 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 3
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 63.57
Molecular weight 230.12
XLogP 1.74
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 CCC(n1c(=O)[nH]c2c1nc(C#C)cn2)CC
Isomeric SMILES CCC(n1c(=O)[nH]c2c1nc(C#C)cn2)CC
InChI InChI=1S/C12H14N4O/c1-4-8-7-13-10-11(14-8)16(12(17)15-10)9(5-2)6-3/h1,7,9H,5-6H2,2-3H3,(H,13,15,17)
InChI Key RSQGZEAXODVTOL-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/)
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
5-ethynyl-3-pentan-3-yl-1H-imidazo[4,5-b]pyrazin-2-one
International Nonproprietary Names Click here for help
INN number INN
9555 tirasemtiv
Synonyms Click here for help
CK-2017357
Database Links Click here for help
CAS Registry No. 1005491-15-3
ChEMBL Ligand CHEMBL3039529
GtoPdb PubChem SID 252166492
PubChem CID 23729157
RCSB PDB Ligand W97
Search Google for chemical match using the InChIKey RSQGZEAXODVTOL-UHFFFAOYSA-N
Search Google for chemicals with the same backbone RSQGZEAXODVTOL
Search PubMed clinical trials tirasemtiv
Search PubMed titles tirasemtiv
Search PubMed titles/abstracts tirasemtiv
UniChem Compound Search for chemical match using the InChIKey RSQGZEAXODVTOL-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey RSQGZEAXODVTOL-UHFFFAOYSA-N

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MedChemExpress
Tirasemtiv (links to external site)
Cat. No. HY-15964