Relugolix

Relugolix
Clinical data
Pronunciation	/ˌrɛlʊˈɡoʊlɪks/; RE-luu-GOH-liks
Trade names	Orgovyx, Relumina
Other names	RGX; RVT-601; TAK-385
AHFS/Drugs.com	Monograph
MedlinePlus	a621006
License data	US DailyMed: Relugolix;
Routes of; administration	By mouth
Drug class	GnRH antagonist
ATC code	L02BX04 (WHO) ; H01CC54 (WHO) (combination with estradiol and norethisterone);
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; US: ℞-only; EU: Rx-only;
Pharmacokinetic data
Protein binding	68–71%
Elimination half-life	36 to 65 hours
Excretion	Feces: 82%; Urine: 4%
Identifiers
	IUPAC name 1-[4-[1-[(2,6-difluorophenyl)methyl]-5-[(dimethylamino)methyl]-3-(6-methoxypyridazin-3-yl)-2,4-dioxothieno[2,3-d]pyrimidin-6-yl]phenyl]-3-methoxyurea;
CAS Number	737789-87-6;
PubChem CID	10348973;
IUPHAR/BPS	5586;
DrugBank	DB11853;
ChemSpider	8524431;
UNII	P76B05O5V6;
KEGG	D10888;
ChEMBL	ChEMBL1800159;
CompTox Dashboard (EPA)	DTXSID40224167 ;
Chemical and physical data
Formula	C29H27F2N7O5S
Molar mass	623.64 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CONC(=O)Nc1ccc(-c2sc3c(c2CN(C)C)c(=O)n(-c2ccc(OC)nn2)c(=O)n3Cc2c(F)cccc2F)cc1;
	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); Key:AOMXMOCNKJTRQP-UHFFFAOYSA-N;

Relugolix, sold under the brand names Orgovyx and Relumina among others, is a gonadotropin-releasing hormone antagonist (GnRH receptor antagonist) medication which is used in the treatment of prostate cancer, uterine fibroids and endometriosis.^[5]^[1]^[7]^[8] It is taken by mouth.^[1]^[7]

Side effects of relugolix include menstrual abnormalities, hot flashes, excessive sweating, headache, and decreased bone mineral density.^[7]^[1] Relugolix is a GnRH antagonist, or an antagonist of the gonadotropin-releasing hormone receptor.^[1] Unlike most other GnRH modulators, but similarly to elagolix (brand name Orilissa), relugolix is a non-peptide, small-molecule compound and is orally active.^[9]^[10]^[11] It suppresses sex hormone levels to the postmenopausal or castrate range in both women and men.^[1]^[12]^[5]

^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Barra F, Seca M, Della Corte L, Giampaolino P, Ferrero S (August 2019). "Relugolix for the treatment of uterine fibroids". Drugs of Today. 55 (8): 503–512. doi:10.1358/dot.2019.55.8.3020179. PMID 31461087. S2CID 201654739.
^ "Therapeutic Goods (Poisons Standard—June 2024) Instrument 2024". Federal Register of Legislation. 30 May 2024. Retrieved 10 June 2024.
^ "Notice: Multiple additions to the Prescription Drug List (PDL) [2023-12-22]". Health Canada. 22 December 2023. Retrieved 3 January 2024.
^ "Summary Basis of Decision (SBD) for Orgovyx". Health Canada. 16 February 2024. Retrieved 24 February 2024.
^ ^a ^b ^c "Orgovyx- relugolix tablet, film coated". DailyMed. Retrieved 25 May 2021.
^ Cite error: The named reference Orgovyx EPAR was invoked but never defined (see the help page).
^ ^a ^b ^c "Relumina (relugolix) Information" (PDF). ASKA Pharmaceutical (in Japanese). January 2019. Archived from the original (PDF) on 16 February 2019. Retrieved 16 February 2019.
^ "New endometriosis pill approved on NHS in England".
^ Miwa K, Hitaka T, Imada T, Sasaki S, Yoshimatsu M, Kusaka M, et al. (July 2011). "Discovery of 1-{4-[1-(2,6-difluorobenzyl)-5-[(dimethylamino)methyl]-3-(6-methoxypyridazin-3-yl)-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-6-yl]phenyl}-3-methoxyurea (TAK-385) as a potent, orally active, non-peptide antagonist of the human gonadotropin-releasing hormone receptor". Journal of Medicinal Chemistry. 54 (14): 4998–5012. doi:10.1021/jm200216q. PMID 21657270.
^ Nakata D, Masaki T, Tanaka A, Yoshimatsu M, Akinaga Y, Asada M, et al. (January 2014). "Suppression of the hypothalamic-pituitary-gonadal axis by TAK-385 (relugolix), a novel, investigational, orally active, small molecule gonadotropin-releasing hormone (GnRH) antagonist: studies in human GnRH receptor knock-in mice". European Journal of Pharmacology. 723: 167–174. doi:10.1016/j.ejphar.2013.12.001. PMID 24333551.
^ Cite error: The named reference pmid29232843 was invoked but never defined (see the help page).
^ Cite error: The named reference pmid26502357 was invoked but never defined (see the help page).

[pmid31461087-1] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Barra F, Seca M, Della Corte L, Giampaolino P, Ferrero S (August 2019). "Relugolix for the treatment of uterine fibroids". Drugs of Today. 55 (8): 503–512. doi:10.1358/dot.2019.55.8.3020179. PMID 31461087. S2CID 201654739.

[2] "Therapeutic Goods (Poisons Standard—June 2024) Instrument 2024". Federal Register of Legislation. 30 May 2024. Retrieved 10 June 2024.

[3] "Notice: Multiple additions to the Prescription Drug List (PDL) [2023-12-22]". Health Canada. 22 December 2023. Retrieved 3 January 2024.

[4] "Summary Basis of Decision (SBD) for Orgovyx". Health Canada. 16 February 2024. Retrieved 24 February 2024.

[Orgovyx_FDA_label-5] "Orgovyx- relugolix tablet, film coated". DailyMed. Retrieved 25 May 2021.

[Orgovyx_EPAR-6] Cite error: The named reference Orgovyx EPAR was invoked but never defined (see the help page).

[ReluminaInfo-7] "Relumina (relugolix) Information" (PDF). ASKA Pharmaceutical (in Japanese). January 2019. Archived from the original (PDF) on 16 February 2019. Retrieved 16 February 2019.

[:0-8] "New endometriosis pill approved on NHS in England".

[pmid21657270-9] Miwa K, Hitaka T, Imada T, Sasaki S, Yoshimatsu M, Kusaka M, et al. (July 2011). "Discovery of 1-{4-[1-(2,6-difluorobenzyl)-5-[(dimethylamino)methyl]-3-(6-methoxypyridazin-3-yl)-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-6-yl]phenyl}-3-methoxyurea (TAK-385) as a potent, orally active, non-peptide antagonist of the human gonadotropin-releasing hormone receptor". Journal of Medicinal Chemistry. 54 (14): 4998–5012. doi:10.1021/jm200216q. PMID 21657270.

[pmid24333551-10] Nakata D, Masaki T, Tanaka A, Yoshimatsu M, Akinaga Y, Asada M, et al. (January 2014). "Suppression of the hypothalamic-pituitary-gonadal axis by TAK-385 (relugolix), a novel, investigational, orally active, small molecule gonadotropin-releasing hormone (GnRH) antagonist: studies in human GnRH receptor knock-in mice". European Journal of Pharmacology. 723: 167–174. doi:10.1016/j.ejphar.2013.12.001. PMID 24333551.

[pmid29232843-11] Cite error: The named reference pmid29232843 was invoked but never defined (see the help page).

[pmid26502357-12] Cite error: The named reference pmid26502357 was invoked but never defined (see the help page).

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