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Moehs Relugolix

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Also known as: 737789-87-6, Tak-385, Orgovyx, Tak 385, 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, Chembl1800159

Molecular Formula

C₂₉H₂₇F₂N₇O₅S

Molecular Weight

623.6 g/mol

InChI Key

AOMXMOCNKJTRQP-UHFFFAOYSA-N

FDA UNII

P76B05O5V6

Relugolix is an orally available, non-peptide gonadotropin-releasing hormone (GnRH or luteinizing hormone-releasing hormone (LHRH)) antagonist, with potential antineoplastic activity. Relugolix competitively binds to and blocks the GnRH receptor in the anterior pituitary gland, which both prevents GnRH binding to the GnRH receptor and inhibits the secretion and release of both luteinizing hormone (LH) and follicle stimulating hormone (FSH). In males, the inhibition of LH secretion prevents the release of testosterone from Leydig cells in the testes. Since testosterone is required to sustain prostate growth, reducing testosterone levels may inhibit hormone-dependent prostate cancer cell proliferation.

Relugolix is a Gonadotropin Releasing Hormone Receptor Antagonist. The mechanism of action of relugolix is as a Gonadotropin Releasing Hormone Receptor Antagonist, and Cytochrome P450 3A Inducer, and Cytochrome P450 2B6 Inducer, and Breast Cancer Resistance Protein Inhibitor, and P-Glycoprotein Inhibitor. The physiologic effect of relugolix is by means of Decreased GnRH Secretion.

1 2D Structure

Relugolix

2 Identification

2.1 Computed Descriptors

2.1.1 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

2.1.2 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)

2.1.3 InChI Key

AOMXMOCNKJTRQP-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CN(C)CC1=C(SC2=C1C(=O)N(C(=O)N2CC3=C(C=CC=C3F)F)C4=NN=C(C=C4)OC)C5=CC=C(C=C5)NC(=O)NOC

2.2 Other Identifiers

2.2.1 UNII

P76B05O5V6

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 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

2. Orgovyx

3. Tak 385

4. Tak-385

5. Tak385

2.3.2 Depositor-Supplied Synonyms

1. 737789-87-6

2. Tak-385

3. Orgovyx

4. Tak 385

5. 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

6. Chembl1800159

7. P76b05o5v6

8. 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

9. Urea, N-(4-(1-((2,6-difluorophenyl)methyl)-5-((dimethylamino)methyl)-1,2,3,4-tetrahydro-3-(6-methoxy-3-pyridazinyl)-2,4-dioxothieno(2,3-d)pyrimidin-6-yl)phenyl)-n'-methoxy-

10. Relugolix [usan:inn]

11. Unii-p76b05o5v6

12. Tak385

13. Tak-385/tak385

14. Relugolix (jan/inn)

15. Relugolix [inn]

16. Relugolix [jan]

17. Relugolix(tak-385)

18. Relugolix [usan]

19. Relugolix [who-dd]

20. Schembl778416

21. Gtpl5586

22. Relugolix [orange Book]

23. C29h27f2n7o5s

24. Dtxsid40224167

25. Rvt-601

26. Amy27916

27. Bcp21587

28. Ex-a1083

29. Myfembree Component Relugolix

30. Tak-385; Rvt-601

31. Bdbm50347982

32. Mfcd25976856

33. S5808

34. Zinc43206033

35. Cs-5917

36. Db11853

37. Relugolix Component Of Myfembree

38. Sb16721

39. Ac-35863

40. Bs-18032

41. Hy-16474

42. N-(4-(1-((2,6-difluorophenyl)methyl)-5-((dimethylamino)methyl)-1,2,3,4-tetrahydro-3-(6-methoxy-3-pyridazinyl)-2,4-dioxothieno(2,3-d)pyrimidin-6-yl)phenyl)-n'-methoxyurea

43. D10888

44. A857822

45. Ryeqo (relugolix-estradiol-norethisterone Acetate)

46. Q21099000

47. 1-(4-(1-((2,6-difluorophenyl)methyl)-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

48. 1-[4-[1-[(2,6-difluorophenyl)methyl]-5-(dimethylaminomethyl)-3-(6-methoxypyridazin-3-yl)-2,4-dioxothieno[4,5-e]pyrimidin-6-yl]phenyl]-3-methoxyurea

49. 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;relugolix

50. 1-{4-[1-(2,6-difluorobenzyl)-5-dimethylaminomethyl-3-(6-methoxypyridazin-3-yl)-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-6-yl]phenyl}-3-methoxyurea

2.4 Create Date

2006-10-25

3 Chemical and Physical Properties

Molecular Formula	C₂₉H₂₇F₂N₇O₅S
Molecular Weight	623.6 g/mol
XLogP3	3.2
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	11
Rotatable Bond Count	9
Exact Mass	623.17624448 g/mol
Monoisotopic Mass	623.17624448 g/mol
Topological Polar Surface Area	158 Å²
Heavy Atom Count	44
Formal Charge	0
Complexity	1010
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Relugolix is indicated for the treatment of adult patients with advanced prostate cancer. In a combination product with [estradiol] and [norethindrone], relugolix is indicated for the once-daily treatment for the management of heavy menstrual bleeding associated with uterine fibroids in premenopausal women.

Orgovyx is indicated for the treatment of adult patients with advanced hormone-sensitive prostate cancer .

5 Pharmacology and Biochemistry

5.1 Pharmacology

Approximately 56% of patients achieved castrate-level testosterone concentrations (<50 ng/dL) by day 4 of therapy and 97% of patients maintain these levels through 48 weeks of therapy. Relugolix requires once-daily oral administration to maintain the desired testosterone concentrations. Androgen deprivation therapies may prolong the QTc interval and should therefore be used with caution in patients having a high baseline risk of QTc prolongation, such as those with electrolyte abnormalities, congestive heart failure, or using other medications known to prolong the QTc interval. Based on its mechanism of action and data from animal studies, relugolix may result in fetal harm if administered to pregnant females - male patients with female partners should be advised to use effective contraception throughout therapy and for 2 weeks following cessation of therapy to prevent inadvertent fetal exposure.

5.2 MeSH Pharmacological Classification

Androgen Antagonists

Compounds which inhibit or antagonize the biosynthesis or actions of androgens. (See all compounds classified as Androgen Antagonists.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

RELUGOLIX

5.3.2 FDA UNII

P76B05O5V6

5.3.3 Pharmacological Classes

Cytochrome P450 2B6 Inducers [MoA]; Cytochrome P450 3A Inducers [MoA]; Decreased GnRH Secretion [PE]; Gonadotropin Releasing Hormone Receptor Antagonist [EPC]; Gonadotropin Releasing Hormone Receptor Antagonists [MoA]; P-Glycoprotein Inhibitors [MoA]; Breast Cancer Resistance Protein Inhibitors [MoA]

5.4 ATC Code

L02BX

L - Antineoplastic and immunomodulating agents

L02 - Endocrine therapy

L02B - Hormone antagonists and related agents

L02BX - Other hormone antagonists and related agents

L02BX04 - Relugolix

5.5 Absorption, Distribution and Excretion

Absorption

The C_max and AUC of orally-administered relugolix increase proportionally following single doses - in contrast, with repeat dosing the AUC remains proportional to the dose while the C_max increases greater than proportionally to the dose. Following the administration of 120mg once daily, the steady-state AUC and C_max of relugolix were 407 ( 168) ng.hr/mL and 70 ( 65) ng/mL, respectively. The absolute oral bioavailability of relugolix is approximately 12% and the median T_max following oral administration is 2.25 hours.

Route of Elimination

Approximately 81% of an orally administered dose was recovered in the feces, of which 4.2% was unchanged parent drug, while 4.1% of the dose was recovered in the urine, of which 2.2% remained unchanged.

Clearance

The average renal clearance of relugolix is 8 L/h with a total clearance of 26.4 L/h.

5.6 Metabolism/Metabolites

Relugolix is metabolized mainly by the CYP3A subfamily of P450 enzymes, with a smaller contribution by CYP2C8.

5.7 Biological Half-Life

The average effective half-life of relugolix is 25 hours, while the average terminal elimination half-life is 60.8 hours.

5.8 Mechanism of Action

The pathogenesis and progression of prostate cancer appear driven, at least in part, by the effects of testosterone. Androgen deprivation has been demonstrated to result in cell death and tumor regression in many well-differentiated prostate cancer cell lines - for this reason, androgen deprivation therapy (ADT) has become a standard in the treatment of prostate cancer, particularly in advanced disease. Testosterone production in males is carried out in the Leydig cells of testes and is stimulated by luteinizing hormone (LH), which itself is produced in the pituitary gland following the binding of gonadotropin-releasing hormone (GnRH) to corresponding GnRH receptors. Relugolix is a competitive antagonist of these GnRH receptors, thereby decreasing the release of LH and, ultimately, testosterone.

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