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etripamil   Click here for help

GtoPdb Ligand ID: 14304

Synonyms: Cardamyst® | MSP-2017 | MSP2017
Approved drug
etripamil is an approved drug
Compound class: Synthetic organic
Comment: Etripamil (MSP-2017) acts as a fast-acting, short half-life L-type calcium-channel antagonist [1-2]. It is a structural analogue of verapamil.
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 0
Rotatable bonds 13
Topological polar surface area 71.79
Molecular weight 452.59
XLogP 3.56
No. Lipinski's rules broken 1

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 CC(C)[C@](CCCN(C)CCC1=CC=CC(=C1)C(=O)OC)(C#N)C2=CC=C(C(=C2)OC)OC
Isomeric SMILES CC(C)[C@](CCCN(C)CCC1=CC(=CC=C1)C(=O)OC)(C#N)C2=CC(=C(C=C2)OC)OC
InChI InChI=1S/C27H36N2O4/c1-20(2)27(19-28,23-11-12-24(31-4)25(18-23)32-5)14-8-15-29(3)16-13-21-9-7-10-22(17-21)26(30)33-6/h7,9-12,17-18,20H,8,13-16H2,1-6H3/t27-/m0/s1
InChI Key VAZNEHLGJGSQEL-MHZLTWQESA-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
Etripamil (MSP-2017; formulated as a nasal spray) was first approved by the US FDA in December 2025, treat episodes of paroxysmal supraventricular tachycardia.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT04072835 Safety Study of Etripamil Nasal Spray for Patients With Paroxysmal Supraventricular Tachycardia. NODE-303 Phase 3 Interventional Milestone Pharmaceuticals Inc.
NCT04467905 ReVeRA-201: Etripamil in Atrial Fibrillation, Phase 2 Phase 2 Interventional Milestone Pharmaceuticals Inc.
NCT06716021 ReVeRA-301: Etripamil in Atrial Fibrillation Phase 3 Phase 3 Interventional Milestone Pharmaceuticals Inc.
NCT02296190 Efficacy and Safety of Intranasal MSP-2017 (Etripamil) for the Conversion of PSVT to Sinus Rhythm Phase 2 Interventional Milestone Pharmaceuticals Inc. 3