crisugabalin   Click here for help

GtoPdb Ligand ID: 13764

Synonyms: HSK-16149 | HSK16149
Approved drug
crisugabalin is an approved drug
Compound class: Synthetic organic
Comment: Crisugabalin (HSK-16149) is a gabapentinoid that binds to the α2-δ subunits of voltage-gated calcium channels (encoded by the CACNA2D1 and CACNA2D2 genes), with some selectivity for the α2-δ1 channel complex [1]. It was designed for analgesic potential in chronic pain conditions.
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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Click here for structure editor
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 2
Rotatable bonds 3
Topological polar surface area 63.32
Molecular weight 209.29
XLogP 2.17
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 C1C[C@@H]2[C@@H]3C[C@H]1C[C@@H]3[C@@]2(CC(=O)O)CN
Isomeric SMILES C1C[C@@H]2[C@@H]3C[C@H]1C[C@@H]3[C@@]2(CC(=O)O)CN
InChI InChI=1S/C12H19NO2/c13-6-12(5-11(14)15)9-2-1-7-3-8(9)10(12)4-7/h7-10H,1-6,13H2,(H,14,15)/t7-,8-,9+,10-,12-/m0/s1
InChI Key WCEFMBSFXJUREW-LIJGXYGRSA-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. China NMPA (2024)
International Nonproprietary Names Click here for help
INN number INN
12414 crisugabalin
Synonyms Click here for help
HSK-16149 | HSK16149
Database Links Click here for help
CAS Registry No. 2209104-84-5 (source: PubChem)
ChEMBL Ligand CHEMBL5314958
DrugBank Ligand DB19300
GtoPdb PubChem SID 507750397
PubChem CID 139300919
Search Google for chemical match using the InChIKey WCEFMBSFXJUREW-LIJGXYGRSA-N
Search Google for chemicals with the same backbone WCEFMBSFXJUREW
Search PubMed clinical trials crisugabalin
Search PubMed titles crisugabalin
Search PubMed titles/abstracts crisugabalin
UniChem Compound Search for chemical match using the InChIKey WCEFMBSFXJUREW-LIJGXYGRSA-N
UniChem Connectivity Search for chemical match using the InChIKey WCEFMBSFXJUREW-LIJGXYGRSA-N