lasmiditan   Click here for help

GtoPdb Ligand ID: 3928

Synonyms: COL-144 | LY573144 | Reyvow®
Approved drug PDB Ligand
lasmiditan is an approved drug (FDA (2019), EMA (2022))
Compound class: Synthetic organic
Comment: Lasmiditan is a potent and selective 5-HT1F receptor agonist that was developed by Eli Lilly [2], as an alternative to triptan drugs for the treatment of migraine. 5-HT1F selectivity is reported to eliminate the vasoconstrictor properties of triptans (mediated via 5-HT1B/1D receptor agonism) that contraindicate their use in patients with coronary artery disease [3].
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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
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 5
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 62.3
Molecular weight 377.14
XLogP 2.98
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 CN1CCC(CC1)C(=O)c1cccc(n1)NC(=O)c1c(F)cc(cc1F)F
Isomeric SMILES CN1CCC(CC1)C(=O)c1cccc(n1)NC(=O)c1c(F)cc(cc1F)F
InChI InChI=1S/C19H18F3N3O2/c1-25-7-5-11(6-8-25)18(26)15-3-2-4-16(23-15)24-19(27)17-13(21)9-12(20)10-14(17)22/h2-4,9-11H,5-8H2,1H3,(H,23,24,27)
InChI Key XEDHVZKDSYZQBF-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
Approved drug? Yes. FDA (2019)  |  EMA (2022)
IUPAC Name Click here for help
2,4,6-trifluoro-N-[6-(1-methylpiperidine-4-carbonyl)pyridin-2-yl]benzamide
International Nonproprietary Names Click here for help
INN number INN
9176 lasmiditan
Synonyms Click here for help
COL-144 | LY573144 | Reyvow®
Database Links Click here for help
Specialist databases
GPCRdb Ligand lasmiditan
Other databases
CAS Registry No. 439239-90-4 (source: Scifinder)
ChEMBL Ligand CHEMBL3039520
DrugCentral Ligand 5351
GtoPdb PubChem SID 178100757
PubChem CID 11610526
RCSB PDB Ligand 05X
Search Google for chemical match using the InChIKey XEDHVZKDSYZQBF-UHFFFAOYSA-N
Search Google for chemicals with the same backbone XEDHVZKDSYZQBF
Search PubMed clinical trials lasmiditan
Search PubMed titles lasmiditan
Search PubMed titles/abstracts lasmiditan
UniChem Compound Search for chemical match using the InChIKey XEDHVZKDSYZQBF-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey XEDHVZKDSYZQBF-UHFFFAOYSA-N
Wikipedia Lasmiditan