GtoPdb is requesting financial support from commercial users. Please see our sustainability page for more information.

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
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
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
Click here for help

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/)

✖
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/)
No information available.
Summary of Clinical Use Click here for help
Crisugabalin (HSK-16149) is in clinical evaluations to determine safety and analgesic efficacy in combatting peripheral and central pain. The Chinese drug regulator (NMPA) approved crisugabalin (Simei Ning®) in May 2024, to treat diabetic peripheral neuropathic pain, and postherpetic neuralgia the month after.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT06422117 Efficacy and Safety of HSK16149 Capsule in the Treatment of Moderate and Severe Central Neuropathic Pain in China Phase 3 Interventional Haisco Pharmaceutical Group Co., Ltd.
NCT05890053 To Evaluate the Long-term Safety and Efficacy of HSK16149 in Chinese Patients With Peripheral Neuralgia Phase 3 Interventional Haisco Pharmaceutical Group Co., Ltd.
NCT06007066 HSK16149 for Perioperative Analgesia in Orthopedic Surgery Phase 2 Interventional Haisco Pharmaceutical Group Co., Ltd.
NCT04647773 To Evaluate the Efficacy and Safety of HSK16149 Capsule in Chinese Patients With Diabetic Peripheral Neuropathic Pain Phase 2/Phase 3 Interventional Haisco Pharmaceutical Group Co., Ltd. 2
NCT05140863 To Evaluate the Efficacy and Safety of HSK16149 Capsule in Chinese Patients With Postherpetic Neuralgia Phase 3 Interventional Haisco Pharmaceutical Group Co., Ltd. 3