troriluzole   Click here for help

GtoPdb Ligand ID: 11375

Synonyms: BHV-4157 | BHV-4157a | BHV4157 | BHV4157a | FC-4157 | trigriluzole
Compound class: Synthetic organic
Comment: Troriluzole (BHV-4157) is a prodrug of the voltage-dependent calcium channel blocker riluzole. Chemically it is riluzole conjugated to a tripeptide carrier (IUPAC sequence H-Gly-Gly-Sar-Unk, where Unk = the riluzole component), and the active moiety is released by peptidases in vivo. The prodrug is more stable than riluzole and is suitable for once-daily dosing.
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 CDK toolkit. 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 3
Rotatable bonds 11
Topological polar surface area 154.89
Molecular weight 419.09
XLogP -0.27
No. Lipinski's rules broken 0
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.

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Canonical SMILES NCC(=O)NCC(=O)N(CC(=O)Nc1nc2c(s1)cc(cc2)OC(F)(F)F)C
Isomeric SMILES NCC(=O)NCC(=O)N(CC(=O)Nc1nc2c(s1)cc(cc2)OC(F)(F)F)C
InChI InChI=1S/C15H16F3N5O4S/c1-23(13(26)6-20-11(24)5-19)7-12(25)22-14-21-9-3-2-8(4-10(9)28-14)27-15(16,17)18/h2-4H,5-7,19H2,1H3,(H,20,24)(H,21,22,25)
InChI Key YBZSGIWIPOUSHY-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Is prodrug? Yes
Active form riluzole
International Nonproprietary Names Click here for help
INN number INN
10784 troriluzole
Synonyms Click here for help
BHV-4157 | BHV-4157a | BHV4157 | BHV4157a | FC-4157 | trigriluzole
Database Links Click here for help
CAS Registry No. 1926203-09-9 (source: WHO INN record)
ChEMBL Ligand CHEMBL4297586
DrugBank Ligand DB15079
GtoPdb PubChem SID 440816744
PubChem CID 121488186
Search Google for chemical match using the InChIKey YBZSGIWIPOUSHY-UHFFFAOYSA-N
Search Google for chemicals with the same backbone YBZSGIWIPOUSHY
Search PubMed clinical trials troriluzole
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UniChem Compound Search for chemical match using the InChIKey YBZSGIWIPOUSHY-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey YBZSGIWIPOUSHY-UHFFFAOYSA-N