Relugolix

Base Information

• Chemical Name: Relugolix
• CAS No.: 737789-87-6
• Molecular Formula: C29H27F2N7O5S
• Molecular Weight: 623.63
• European Community (EC) Number: 864-997-1
• UNII: P76B05O5V6
• DSSTox Substance ID: DTXSID40224167
• Wikipedia: Relugolix
• Wikidata: Q21099000
• NCI Thesaurus Code: C114498
• RXCUI: 2472778
• Pharos Ligand ID: N973NW8VMJYN
• Metabolomics Workbench ID: 152943
• ChEMBL ID: CHEMBL1800159
• Mol file: 737789-87-6.mol

Synonyms: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;orgovyx;relugolix;TAK 385;TAK-385;TAK385

Chemical Property of Relugolix

Chemical Property:

• Melting Point: 228 °C (decomp)(Solv: ethyl acetate (141-78-6); tetrahydrofuran (109-99-9))
• PKA: 13.17±0.70(Predicted)
• PSA: 182.86000
• Density: 1.442±0.06 g/cm3(Predicted)
• LogP: 3.69890
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 9
• Exact Mass: 623.17624448
• Heavy Atom Count: 44
• Complexity: 1010

Purity/Quality:

99% ^*data from raw suppliers

Relugolix(TAK-385) >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antineoplastic Agents
• 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
• Recent ClinicalTrials: A Multi-Center, Prospective, Observational Study of Patients Being Treated With ORGOVYX
• Recent EU Clinical Trials: An International Phase 3 Double-Blind, Placebo-controlled, Randomized Withdrawal Study of Relugolix Co-administered with Estradiol and Norethindrone Acetate in Women with Heavy Menstrual Bleeding Associated with Uterine Fibroids
• Recent NIPH Clinical Trials: MyLacRstudy
• Description: Relugolix (TAK-385)?is a potent, orally active, nonpeptidic?gonadotropin-releasing hormone (GnRH)?antagonist. It 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). Relugolix is used for the study of sex-hormone-dependent diseases, such as including endometriosis, uterine fibroids and prostate cancer et al.
• Uses: Relugolix is a highly selective, oral, nonpeptide GnRH antagonist being investigated as a possible prostate cancer treatment
• Clinical Use: Relugolix was first approved in Japan in 2019, under the brand name Relumina, for the symptomatic treatment of uterine fibroids, and more recently by the United States' FDA in 2020, under the brand name Orgovyx, for the treatment of advanced prostate cancer. Relugolix has also been studied in the symptomatic treatment of endometriosis.

Technology Process of Relugolix

There total 78 articles about Relugolix which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.89%

C33H37F2N7O6S → TAK-385 (737789-87-6)

Guidance literature:

With sodium methylate; In tetrahydrofuran; methanol; at 60 ℃; for 2h;

Reference yield: 93.0%

C32H35F2N7O6S → TAK-385 (737789-87-6)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃;

Reference yield: 92.36%

1-(2,6-difluorobenzyl)-5-((dimethylamino)methyl)-3-(6-methoxypyridazin-3-yl)-6-(4-aminophenyl)thiophene[2,3-d]pyrimidine-2,4(1H,3H)-dione (1589503-93-4) + phenyl N-methoxy carbamate (85989-62-4) → TAK-385 (737789-87-6)

Guidance literature:

With triethylamine; In toluene; at 75 ℃; for 20h;

upstream raw materials:

2-((ethoxycarbonyl)amino)-4-methyl-5-(4-nitrophenyl)thiophene-3-carboxylic acid ethyl ester

2-((2,6-difluorobenzyl)(ethoxycarbonyl)amino)-4-methyl-5-(4-nitrophenyl)thiophene-3-carboxylic acid ethyl ester

4-(bromomethyl)-2-((2,6-difluorobenzyl)(ethoxycarbonyl)amino)-5-(4-nitrophenyl)thiophene-3-carboxylic acid ethyl ester

ethyl 2-[(2,6-difluorobenzyl)(ethoxycarbonyl)amino]-4-{[(2-methoxyethyl)(methyl)amino]methyl}-5-(4-nitrophenyl)thiophene-3-carboxylate