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zuranolone   Click here for help

GtoPdb Ligand ID: 12858

Synonyms: compound 3 [PMID: 28753313] | SAGE-217 | SAGE217 | Zurzuvae®
Approved drug
zuranolone is an approved drug (FDA (2023))
Compound class: Synthetic organic
Comment: Zuranolone (SAGE-217) is a novel, rapid-acting, oral antipsychotic [1]. It is a neuroactive steroid that acts as a positive allosteric modulator of synaptic and extrasynaptic GABAA receptors [2,4].
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 5
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 76.69
Molecular weight 409.57
XLogP 5.61
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 C[C@]1(CC[C@H]2[C@H](CC[C@@H]3[C@@H]2CC[C@@]4(C)[C@H]3CC[C@@H]4C(=O)CN5C=C(C#N)C=N5)C1)O
Isomeric SMILES C[C@]1(CC[C@H]2[C@@H](C1)CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@H]4C(=O)CN5C=C(C=N5)C#N)C)O
InChI InChI=1S/C25H35N3O2/c1-24(30)9-7-18-17(11-24)3-4-20-19(18)8-10-25(2)21(20)5-6-22(25)23(29)15-28-14-16(12-26)13-27-28/h13-14,17-22,30H,3-11,15H2,1-2H3/t17-,18+,19-,20-,21+,22-,24-,25+/m1/s1
InChI Key HARRKNSQXBRBGZ-GVKWWOCJSA-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
The FDA approved zuranolone as a treatment option for postpartum depression in August 2023 [3].
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT02978326 A Study to Evaluate SAGE-217 in Participants With Severe Postpartum Depression Phase 3 Interventional Sage Therapeutics
NCT04442490 A Study to Evaluate the Efficacy of Sage-217 in the Treatment of Adult Participants With Major Depressive Disorder (MDD) Phase 3 Interventional Sage Therapeutics
NCT02978781 A Study to Evaluate SAGE-217 in Participants With Essential Tremor Phase 2 Interventional Sage Therapeutics
NCT04442503 A Study to Evaluate the Efficacy and Safety of SAGE-217 in Participants With Severe Postpartum Depression (PPD) Phase 3 Interventional Sage Therapeutics 3