linzagolix   Click here for help

GtoPdb Ligand ID: 12283

Synonyms: KLH-2109 | KLH2109 | OBE-2109 | OBE2109 | Yselty®
Approved drug
linzagolix is an approved drug (EMA (2022))
Compound class: Synthetic organic
Comment: Linzagolix (KLH-2109) is an orally bioavailable gonadotropin-releasing hormone (GnRH) receptor antagonist [5]. It was developed for potential to downregulate the hypothalamic pituitary-gonadal axis to inhibit the driving force of LH and FSH on estrogen release, as a mechanism to combat the symptoms associated with endometriosis [6], heavy menstrual bleeding or uterine fibroids [1,4].
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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

linzagolix is commercially available from our sponsors

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 4
Hydrogen bond donors 2
Rotatable bonds 7
Topological polar surface area 147.57
Molecular weight 508.06
XLogP 3.96
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
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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 COc1cc(F)c(cc1OCc1c(OC)ccc(c1F)F)n1c(=O)[nH]c2c(c1=O)c(sc2)C(=O)O
Isomeric SMILES COc1c(c(c(cc1)F)F)COc1c(cc(c(c1)n1c(=O)c2c(scc2[nH]c1=O)C(=O)O)F)OC
InChI InChI=1S/C22H15F3N2O7S/c1-32-14-4-3-10(23)18(25)9(14)7-34-16-6-13(11(24)5-15(16)33-2)27-20(28)17-12(26-22(27)31)8-35-19(17)21(29)30/h3-6,8H,7H2,1-2H3,(H,26,31)(H,29,30)
InChI Key BMAAMIIYNNPHAB-UHFFFAOYSA-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. de Lange ME, Huirne JAF. (2022)
Linzagolix: an oral gonadotropin-releasing hormone receptor antagonist treatment for uterine fibroid-associated heavy menstrual bleeding.
Lancet, 400 (10356): 866-867. [PMID:36116467]
2. Donnez J, Taylor HS, Stewart EA, Bradley L, Marsh E, Archer D, Al-Hendy A, Petraglia F, Watts N, Gotteland JP et al.. (2022)
Linzagolix with and without hormonal add-back therapy for the treatment of symptomatic uterine fibroids: two randomised, placebo-controlled, phase 3 trials.
Lancet, 400 (10356): 896-907. [PMID:36116480]
3. Keam SJ. (2022)
Linzagolix: First Approval.
Drugs, 82 (12): 1317-1325. [PMID:35997940]
4. Niaz R, Saeed M, Khan H, Ali MA, Irshad A, Faiz M, Irshad A, Fatima F, Tunio SA, Aiman W. (2022)
Efficacy and Safety of Oral GnRh Antagonists in Patients With Uterine Fibroids: A Systematic Review.
J Obstet Gynaecol Can, 44 (12): 1279-1288. [PMID:36368594]
5. Tezuka M, Tamai Y, Kuramochi Y, Kobayashi K, Fushimi N, Kiguchi S. (2022)
Pharmacological characterization of linzagolix, a novel, orally active, non-peptide antagonist of gonadotropin-releasing hormone receptors.
Clin Exp Pharmacol Physiol, 49 (10): 1082-1093. [PMID:35690889]
6. Yan H, Shi J, Li X, Dai Y, Wu Y, Zhang J, Gu Z, Zhang C, Leng J. (2022)
Oral gonadotropin-releasing hormone antagonists for treating endometriosis-associated pain: a systematic review and network meta-analysis.
Fertil Steril, 118 (6): 1102-1116. [PMID:36283862]