Relugolix | TAK-385 | CAS#737789-87-6 | LH-RH

MedKoo Cat#: 205919 | Name: Relugolix

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Relugolix, also known as TAK-385, is a luteinizing hormone-releasing hormone (LH-RH) receptor antagonist administered orally. Relugolix is a gonadotropin releasing hormone (GnRH) receptor antagonist that decreases serum estradiol and progesterone concentrations to postmenopausal levels. Relugolix is effective in inducing a dose-dependent decrease in menstrual blood loss.

Chemical Structure

Relugolix

CAS#737789-87-6

Theoretical Analysis

MedKoo Cat#: 205919

Name: Relugolix

CAS#: 737789-87-6

Chemical Formula: C29H27F2N7O5S

Exact Mass: 623.1762

Molecular Weight: 623.63

Elemental Analysis: C, 55.85; H, 4.36; F, 6.09; N, 15.72; O, 12.83; S, 5.14

Price and Availability

Size	Price	Availability
10mg	USD 150.00	Ready to ship
25mg	USD 250.00	Ready to ship
50mg	USD 450.00	Ready to ship
100mg	USD 750.00	Ready to ship
200mg	USD 1,350.00	Ready to ship
500mg	USD 2,850.00	Ready to ship

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

Synonym

TAK385; TAK-385; TAK 385; Relugolix.

IUPAC/Chemical Name

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

InChi Key

AOMXMOCNKJTRQP-UHFFFAOYSA-N

InChi Code

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)

SMILES Code

O=C(NOC)NC1=CC=C(C(S2)=C(CN(C)C)C(C(N3C4=NN=C(OC)C=C4)=O)=C2N(CC5=C(F)C=CC=C5F)C3=O)C=C1

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not soluble in water.

Shelf Life

>5 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#C9R12B27

QC Data

View QC data: current batch, Lot#C9R12B27

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Relugolix (TAK-385) is a potent, orally active, nonpeptidic gonadotropin-releasing hormone (GnRH) antagonist. Relugolix possesses high affinity and potent antagonistic activity for human receptor (binding IC50=0.33 nM) and monkey receptor (IC50=0.32 nM) compared with TAK-013 (HY-100209).

In vitro activity:

Relugolix showed potent in vitro human gonadotropin-releasing hormone antagonistic activity in the presence of fetal bovine serum without cytochrome P450 inhibition. Reference: J Med Chem. 2011 Jul 28;54(14):4998-5012. https://pubmed.ncbi.nlm.nih.gov/21657270/

In vivo activity:

Relugolix 40 mg in combination with estradiol 1 mg and norethindrone acetate 0.5 mg provided systemic estradiol concentrations within a range expected to minimize the risk of undesirable effects of hypoestrogenism associated with the administration of relugolix alone, which is associated with vasomotor symptoms and long-term bone mineral density loss. Reference: Clin Pharmacokinet. 2023 Jun 26. https://pubmed.ncbi.nlm.nih.gov/37365436/

	Solvent	mg/mL	mM
Solubility
	DMSO	20.0	32.10
	Ethanol	1.0	1.60

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 623.63 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Miwa K, Hitaka T, Imada T, Sasaki S, Yoshimatsu M, Kusaka M, Tanaka A, Nakata D, Furuya S, Endo S, Hamamura K, Kitazaki T. 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. J Med Chem. 2011 Jul 28;54(14):4998-5012. doi: 10.1021/jm200216q. Epub 2011 Jun 23. PMID: 21657270. 2. Komiya S, Tsuzuki-Nakao T, Asai Y, Inoue T, Morimoto Y, Okada H. The novel oral gonadotropin-releasing hormone receptor antagonist relugolix is a new option for controlled ovarian stimulation cycles. Reprod Med Biol. 2022 Feb 17;21(1):e12448. doi: 10.1002/rmb2.12448. PMID: 35386367; PMCID: PMC8967300. 3. Lukes A, Migoya E, Johnson B, Lee TY, Li Y, Arjona Ferreira JC. A Randomized Open-Label Study of Relugolix Alone or Relugolix Combination Therapy in Premenopausal Women. Clin Pharmacokinet. 2023 Jun 26. doi: 10.1007/s40262-023-01269-9. Epub ahead of print. PMID: 37365436. 4. Arjona Ferreira JC, Migoya E. Development of relugolix combination therapy as a medical treatment option for women with uterine fibroids or endometriosis. F S Rep. 2022 Nov 21;4(2 Suppl):73-82. doi: 10.1016/j.xfre.2022.11.010. PMID: 37223761; PMCID: PMC10201285.

In vitro protocol:

In vivo protocol:

1. Lukes A, Migoya E, Johnson B, Lee TY, Li Y, Arjona Ferreira JC. A Randomized Open-Label Study of Relugolix Alone or Relugolix Combination Therapy in Premenopausal Women. Clin Pharmacokinet. 2023 Jun 26. doi: 10.1007/s40262-023-01269-9. Epub ahead of print. PMID: 37365436. 2. Arjona Ferreira JC, Migoya E. Development of relugolix combination therapy as a medical treatment option for women with uterine fibroids or endometriosis. F S Rep. 2022 Nov 21;4(2 Suppl):73-82. doi: 10.1016/j.xfre.2022.11.010. PMID: 37223761; PMCID: PMC10201285.

1: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012–. Relugolix. 2023 May 28. PMID: 37335836. 2: Syed YY. Relugolix/Estradiol/Norethisterone (Norethindrone) Acetate: A Review in Symptomatic Uterine Fibroids. Drugs. 2022 Oct;82(15):1549-1556. doi: 10.1007/s40265-022-01790-4. Epub 2022 Nov 4. Erratum in: Drugs. 2022 Nov;82(17):1687. doi: 10.1007/s40265-022-01814-z. PMID: 36331779; PMCID: PMC9684252. 3: Sahu KK, Tripathi N, Agarwal N, Swami U. Relugolix in the management of prostate cancer. Expert Rev Anticancer Ther. 2022 Sep;22(9):891-902. doi: 10.1080/14737140.2022.2105209. Epub 2022 Jul 27. PMID: 35866612. 4: Shore ND, Saad F, Cookson MS, George DJ, Saltzstein DR, Tutrone R, Akaza H, Bossi A, van Veenhuyzen DF, Selby B, Fan X, Kang V, Walling J, Tombal B; HERO Study Investigators. Oral Relugolix for Androgen-Deprivation Therapy in Advanced Prostate Cancer. N Engl J Med. 2020 Jun 4;382(23):2187-2196. doi: 10.1056/NEJMoa2004325. Epub 2020 May 29. PMID: 32469183. 5: Al-Hendy A, Lukes AS, Poindexter AN 3rd, Venturella R, Villarroel C, Critchley HOD, Li Y, McKain L, Arjona Ferreira JC, Langenberg AGM, Wagman RB, Stewart EA. Treatment of Uterine Fibroid Symptoms with Relugolix Combination Therapy. N Engl J Med. 2021 Feb 18;384(7):630-642. doi: 10.1056/NEJMoa2008283. PMID: 33596357; PMCID: PMC8262231. 6: Al-Hendy A, Lukes AS, Poindexter AN 3rd, Venturella R, Villarroel C, McKain L, Li Y, Wagman RB, Stewart EA. Long-term Relugolix Combination Therapy for Symptomatic Uterine Leiomyomas. Obstet Gynecol. 2022 Dec 1;140(6):920-930. doi: 10.1097/AOG.0000000000004988. Epub 2022 Nov 2. PMID: 36357960; PMCID: PMC9665945. 7: Shirley M. Relugolix: A Review in Advanced Prostate Cancer. Target Oncol. 2023 Mar;18(2):295-302. doi: 10.1007/s11523-022-00944-4. Epub 2023 Jan 18. Erratum in: Target Oncol. 2023 Jul;18(4):637. doi: 10.1007/s11523-023-00977-3. PMID: 36652173; PMCID: PMC10198864. 8: Rocca ML, Palumbo AR, Lico D, Fiorenza A, Bitonti G, D'Agostino S, Gallo C, Di Carlo C, Zullo F, Venturella R. Relugolix for the treatment of uterine fibroids. Expert Opin Pharmacother. 2020 Oct;21(14):1667-1674. doi: 10.1080/14656566.2020.1787988. Epub 2020 Jul 17. PMID: 32674616. 9: Relugolix. Am J Health Syst Pharm. 2021 Apr 22;78(9):762-763. doi: 10.1093/ajhp/zxab036. PMID: 33704417. 10: Blair HA. Relugolix/Estradiol/Norethisterone Acetate: A Review in Endometriosis-Associated Pain. Drugs. 2024 Apr;84(4):449-457. doi: 10.1007/s40265-024-02018-3. Epub 2024 Apr 9. Erratum in: Drugs. 2024 May;84(5):623. doi: 10.1007/s40265-024-02050-3. PMID: 38592603; PMCID: PMC11127801. 11: Giudice LC, As-Sanie S, Arjona Ferreira JC, Becker CM, Abrao MS, Lessey BA, Brown E, Dynowski K, Wilk K, Li Y, Mathur V, Warsi QA, Wagman RB, Johnson NP. Once daily oral relugolix combination therapy versus placebo in patients with endometriosis-associated pain: two replicate phase 3, randomised, double-blind, studies (SPIRIT 1 and 2). Lancet. 2022 Jun 18;399(10343):2267-2279. doi: 10.1016/S0140-6736(22)00622-5. Erratum in: Lancet. 2022 Aug 27;400(10353):660. doi: 10.1016/S0140-6736(22)01581-1. PMID: 35717987. 12: Saad F, Shore ND. Relugolix: a novel androgen deprivation therapy for management of patients with advanced prostate cancer. Ther Adv Med Oncol. 2021 Mar 24;13:1758835921998586. doi: 10.1177/1758835921998586. PMID: 34408793; PMCID: PMC8366106. 13: Relugolix+estradiol+norethisterone for symptomatic uterine fibroids. Aust Prescr. 2024 Apr;47(2):68-69. doi: 10.18773/austprescr.2024.013. PMID: 38737374; PMCID: PMC11081736. 14: Harada T, Osuga Y, Suzuki Y, Fujisawa M, Fukui M, Kitawaki J. Relugolix, an oral gonadotropin-releasing hormone receptor antagonist, reduces endometriosis- associated pain compared with leuprorelin in Japanese women: a phase 3, randomized, double-blind, noninferiority study. Fertil Steril. 2022 Mar;117(3):583-592. doi: 10.1016/j.fertnstert.2021.11.013. Epub 2021 Dec 8. PMID: 34895700. 15: Tatenuma T, Miyamoto H. Profile of Relugolix in the Management of Advanced Hormone-Sensitive Prostate Cancer: Design, Development, and Place in Therapy. Drug Des Devel Ther. 2023 Aug 4;17:2325-2333. doi: 10.2147/DDDT.S373546. PMID: 37559910; PMCID: PMC10408655. 16: Rolla E. Endometriosis: advances and controversies in classification, pathogenesis, diagnosis, and treatment. F1000Res. 2019 Apr 23;8:F1000 Faculty Rev-529. doi: 10.12688/f1000research.14817.1. PMID: 31069056; PMCID: PMC6480968. 17: Becker CM, Johnson NP, As-Sanie S, Arjona Ferreira JC, Abrao MS, Wilk K, Imm SJ, Mathur V, Perry JS, Wagman RB, Giudice LC. Two-year efficacy and safety of relugolix combination therapy in women with endometriosis-associated pain: SPIRIT open-label extension study. Hum Reprod. 2024 Mar 1;39(3):526-537. doi: 10.1093/humrep/dead263. PMID: 38243752; PMCID: PMC10905503. 18: Venturella R, Rechberger T, Zatik J, Wagman RB, Zhu E, Rakov VG, Petraglia F. Relugolix combination therapy in European women with symptomatic uterine fibroids: a subgroup analysis from the randomized phase 3 LIBERTY pivotal trials. Gynecol Endocrinol. 2023 Aug 17;39(1):2249107. doi: 10.1080/09513590.2023.2249107. PMID: 37634528. 19: Giudice LC, As-Sanie S, Arjona Ferreira JC, Becker CM, Abrao MS, Lessey BA, Dynowski K, Wilk K, Li Y, Mathur V, Wagman RB, Johnson NP. A Plain Language Summary to learn about relugolix combination therapy for the treatment of pain associated with endometriosis. Pain Manag. 2023 Nov;13(11):631-640. doi: 10.2217/pmt-2023-0052. Epub 2023 Nov 20. PMID: 37982388. 20: Stewart EA, Lukes AS, Venturella R, Arjona Ferreira JC, Li Y, Hunsche E, Wagman RB, Al-Hendy A. Relugolix Combination Therapy for Uterine Leiomyoma- Associated Pain in the LIBERTY Randomized Trials. Obstet Gynecol. 2022 Jun 1;139(6):1070-1081. doi: 10.1097/AOG.0000000000004787. Epub 2022 May 2. Erratum in: Obstet Gynecol. 2022 Jul 01;140(1):138. doi: 10.1097/AOG.0000000000004858. PMID: 35675604.