merigolix   Click here for help

GtoPdb Ligand ID: 12394

Synonyms: example 2-13 [US9481684B2] | Formula 1 [US20220002312A1] | NCE403 | SKI2670 | TU-2670 | TU2670
Compound class: Synthetic organic
Comment: This is the chemical structure for the gonadotrophin releasing hormone (GnRH) receptor antagonist merigolix [2-3]. GnGHR antagonists are used to treat a range of sex hormone-related diseases. Evidence gathered online suggests that merigolix is likely to be TiumBio's clinical lead TU2670. an oral, small molecule GnGHR antagonist that's being developed as a treatment for endometriosis.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
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 7
Hydrogen bond donors 2
Rotatable bonds 14
Topological polar surface area 118.94
Molecular weight 752.24
XLogP 5.99
No. Lipinski's rules broken 2

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 OC(=O)CCCN[C@H](c1ccccc1)Cn1c(=O)n(Cc2c(F)cccc2C(F)(F)F)c2c(c1=O)C1(CCN(CC1)Cc1ccc(o1)C(F)(F)F)OC2
Isomeric SMILES C1CN(CCC21c1c(CO2)n(c(=O)n(c1=O)C[C@@H](c1ccccc1)NCCCC(=O)O)Cc1c(cccc1F)C(F)(F)F)Cc1ccc(o1)C(F)(F)F
InChI InChI=1S/C36H35F7N4O6/c37-26-9-4-8-25(35(38,39)40)24(26)19-46-28-21-52-34(13-16-45(17-14-34)18-23-11-12-29(53-23)36(41,42)43)31(28)32(50)47(33(46)51)20-27(22-6-2-1-3-7-22)44-15-5-10-30(48)49/h1-4,6-9,11-12,27,44H,5,10,13-21H2,(H,48,49)/t27-/m0/s1
InChI Key LJPSGSMPGVITHK-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/)
References
1. Han S, Cho YS, Yoon SK, Lim KS, Cho SH, Kim J, Choe S, Jung J, Ghim JL, Choi S et al.. (2021)
First-in-Human, Double-Blind, Randomized Controlled Trial of an Oral Dose of GnRH Antagonist TU2670 in Healthy Women.
Journal of clinical endocrinology and metabolism, 106 (3): e1111-e1120. DOI: 10.1210/clinem/dgaa939 [PMID:33347565]
2. Kim S-M, Kim J-S, Lee M, Lee S-Y, Lee B-Y, Shin Y-A, Park E, Lee JA, Han M-Y, Ahn J et al.. (2016)
Gonadotropin releasing hormone receptor antagonists, method for the preparation thereof and pharmaceutical composition comprising the same.
Patent number: US9481684B2. Assignee: Tiumbio Co Ltd. Priority date: 28/02/2013. Publication date: 01/11/2016.
3. Kim SM, Yoo T, Lee SY, Kim EJ, Lee SM, Lee MH, Han MY, Jung SH, Choi JH, Ryu KH et al.. (2015)
Effect of SKI2670, a novel, orally active, non-peptide GnRH antagonist, on hypothalamic-pituitary-gonadal axis.
Life Sci, 139: 166-74. [PMID:26321528]