sovesudil   Click here for help

GtoPdb Ligand ID: 10695

Synonyms: AMA 0076 | AMA-0076 | AMA0076 | compound 18 [PMID: 24119557] | PHP-201 | PHP201
Compound class: Synthetic organic
Comment: Sovesudil (compound 18 [PMID: 24119557]) is a Rho-associated, coiled coil containing protein kinase (ROCK) inhibitor from Amakem Therapeutics [1]. It contains a carboxylic ester moiety that is intended to facilitate rapid inactivation by esterases in vivo, as a mechanism to reduce systemic or local ROCK-associated side effects. This approach of exploiting designed metabolic inactivation is used to produce so-called 'soft' drugs. Compound 18's chemical structure matches that submitted to the WHO for INN sovesudil. Compound 18 is intended as an intraocular pressure (IOP)-lowering agent, and is expected to be devoid of the systemic blood pressure lowering side effect that is associated with systemic exposure to fasudil and therefore precludes fasudil's use in non-cardiovascular indications [2]. It is also expected to cause less local hyperemia than older ROCK inhibitor chemotypes. See our entry for compound 8 [PMID: 25898023], which is another soft ROCK inhibitor from Amakem Therapeutics.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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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 9
Topological polar surface area 94.31
Molecular weight 407.16
XLogP 3.68
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 CCCOC(=O)c1cccc(c1)c1cc(ccc1CN)C(=O)Nc1ccncc1F
Isomeric SMILES CCCOC(=O)c1cccc(c1)c1cc(ccc1CN)C(=O)Nc1ccncc1F
InChI InChI=1S/C23H22FN3O3/c1-2-10-30-23(29)17-5-3-4-15(11-17)19-12-16(6-7-18(19)13-25)22(28)27-21-8-9-26-14-20(21)24/h3-9,11-12,14H,2,10,13,25H2,1H3,(H,26,27,28)
InChI Key PNWBYIFLWUCWKS-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
propyl 3-[2-(aminomethyl)-5-[(3-fluoropyridin-4-yl)carbamoyl]phenyl]benzoate
International Nonproprietary Names Click here for help
INN number INN
11203 sovesudil
Synonyms Click here for help
AMA 0076 | AMA-0076 | AMA0076 | compound 18 [PMID: 24119557] | PHP-201 | PHP201
Database Links Click here for help
BindingDB Ligand 50442825
ChEMBL Ligand CHEMBL2440750
GtoPdb PubChem SID 404859142
PubChem CID 68245749
Search Google for chemical match using the InChIKey PNWBYIFLWUCWKS-UHFFFAOYSA-N
Search Google for chemicals with the same backbone PNWBYIFLWUCWKS
Search PubMed clinical trials sovesudil
Search PubMed titles sovesudil
Search PubMed titles/abstracts sovesudil
UniChem Compound Search for chemical match using the InChIKey PNWBYIFLWUCWKS-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey PNWBYIFLWUCWKS-UHFFFAOYSA-N

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MedChemExpress
Sovesudil (links to external site)
Cat. No. HY-109191