WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H205919
CAS#: 737789-87-6
Description: Relugolix, also known as TAK-385, is a luteinizing hormone-releasing hormone (LH-RH) receptor antagonist administered orally.
Hodoodo Cat#: H205919
Name: Relugolix
CAS#: 737789-87-6
Chemical Formula: C29H27F2N7O5S
Exact Mass: 623.18
Molecular Weight: 623.630
Elemental Analysis: C, 55.85; H, 4.36; F, 6.09; N, 15.72; O, 12.83; S, 5.14
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:
| 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 | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 20.0 | 32.10 | |
| Ethanol | 1.0 | 1.60 |
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: | 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. |
| 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: 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. Epub 2011 Jun 23. PubMed PMID: 21657270.
