elinzanetant   Click here for help

GtoPdb Ligand ID: 12691

Synonyms: BAY-3427080 | BAY3427080 | Compound A [WO2021094247A1] | Example 34 [WO2007028654A1] | NT-814 | NT814
Compound class: Synthetic organic
Comment: Elinzanetant (BAY3427080) is a dual NK1R/NK3R antagonist [2]. It was initially developed for use in the treatment of psychotic disorders [1], but has subsequently been repositioned to manage vasomotor symptoms of the menopause.
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 CDK toolkit. 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 7
Hydrogen bond donors 1
Rotatable bonds 9
Topological polar surface area 68.61
Molecular weight 668.65
XLogP 2.98
No. Lipinski's rules broken 1
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.

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Canonical SMILES CC1=C(C=CC(=C1)F)C2=CC(=NC=C2N(C)C(=O)C(C)(C)C3=CC(=CC(=C3)C(F)(F)F)C(F)(F)F)N4C[C@H]5COCCN5C[C@H]4CO
Isomeric SMILES CC1=C(C=CC(=C1)F)C2=CC(=NC=C2N(C)C(=O)C(C)(C)C3=CC(=CC(=C3)C(F)(F)F)C(F)(F)F)N4C[C@H]5COCCN5C[C@H]4CO
InChI InChI=1S/C33H35F7N4O3/c1-19-9-23(34)5-6-26(19)27-13-29(44-16-25-18-47-8-7-43(25)15-24(44)17-45)41-14-28(27)42(4)30(46)31(2,3)20-10-21(32(35,36)37)12-22(11-20)33(38,39)40/h5-6,9-14,24-25,45H,7-8,15-18H2,1-4H3/t24-,25-/m0/s1
InChI Key DWRIJNIPBUFCQS-DQEYMECFSA-N
References
1. Alvaro G, Andreotti D, Belvedere S, Di Fabro R, Falchi A, Giovannini R. (2007)
Pyridine derivatives and their use in the treatment of psychotic disorders.
Patent number: WO2007028654A1. Assignee: Smithkline Beecham Corporation. Priority date: 07/09/2006. Publication date: 15/03/2007.
2. Schleusner M, Ghizzoni M, Lawrence R. (2021)
New chemical process for making 6-chloro-4-(4-fluoro-2-methylphenyl)pyridin-3-amine a key intermediate of nt-814.
Patent number: WO2021094247A1. Assignee: KaNDy Therapeutics Limited. Priority date: 09/11/2020. Publication date: 20/05/2021.
3. Simon JA, Anderson RA, Ballantyne E, Bolognese J, Caetano C, Joffe H, Kerr M, Panay N, Seitz C, Seymore S et al.. (2023)
Efficacy and safety of elinzanetant, a selective neurokinin-1,3 receptor antagonist for vasomotor symptoms: a dose-finding clinical trial (SWITCH-1).
Menopause, 30 (3): 239-246. [PMID:36720081]
4. Trower M, Anderson RA, Ballantyne E, Joffe H, Kerr M, Pawsey S. (2020)
Effects of NT-814, a dual neurokinin 1 and 3 receptor antagonist, on vasomotor symptoms in postmenopausal women: a placebo-controlled, randomized trial.
Menopause, 27 (5): 498-505. [PMID:32068688]