relugolix   Click here for help

GtoPdb Ligand ID: 5586

Synonyms: Orgovyx® | Ryeqo® (relugolix-estradiol-norethisterone acetate) | TAK 385 | TAK-385
Approved drug
relugolix is an approved drug (FDA (2020), EMA (2021))
Compound class: Synthetic organic
Comment: Relugolix (TAK-385) is a non-peptide, orally active GnRH receptor antagonist [1]. Administration suppresses the hypothalamic-pituitary-gonadal axis. In males this causes chemical castration.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 2
Rotatable bonds 11
Topological polar surface area 160.33
Molecular weight 623.18
XLogP 4.28
No. Lipinski's rules broken 0
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Canonical SMILES CONC(=O)Nc1ccc(cc1)c1sc2c(c1CN(C)C)c(=O)n(c(=O)n2Cc1c(F)cccc1F)c1ccc(nn1)OC
Isomeric SMILES CONC(=O)Nc1ccc(cc1)c1sc2c(c1CN(C)C)c(=O)n(c(=O)n2Cc1c(F)cccc1F)c1ccc(nn1)OC
InChI InChI=1S/C29H27F2N7O5S/c1-36(2)14-19-24-26(39)38(22-12-13-23(42-3)34-33-22)29(41)37(15-18-20(30)6-5-7-21(18)31)27(24)44-25(19)16-8-10-17(11-9-16)32-28(40)35-43-4/h5-13H,14-15H2,1-4H3,(H2,32,35,40)
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Summary of Clinical Use Click here for help
Relugolix (TAK-385) was evaluated in several Phase 3 clinical trials. In women it was progressed as a therapy for endometriosis related pain and heavy menstrual bleeding associated with uterine fibroids. In males it was evaluated in prostate cancer. Click here to view's full list of registered TAK-385 trials. In December 2020, the FDA approved relugolix as the first oral GnRH receptor antagonist-based treatment for advanced prostate cancer. In July 2021 the EMA approved the combination drug Ryeqo® (relugolix+estradiol+norethisterone acetate) as a treatment for leiomyoma. The EMA authorised use of single agent relugolix for treatment of prostatic neoplasms in 2022.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Administration of TAK-385 suppresses the hypothalamic-pituitary-gonadal axis [1]. In males this causes chemical castration (testosterone suppression) and this action has potential for treating hormone sensitive prostate cancer.